Effect of doping vs covalent linking of a low symmetry zinc phthalocyanine to silica nanoparticles on singlet oxygen production
- Peteni, Siwaphiwe, Nyokong, Tebello
- Authors: Peteni, Siwaphiwe , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187873 , vital:44705 , xlink:href="https://doi.org/10.1016/j.ica.2018.06.029"
- Description: Tris[(4-(pyridin-4-ylthio)-2-thio-4-methylthiazol-5-yl)acetic acid phthalocyaninato] zinc (II) (3) was covalently linked to and doped onto SiNPs. An increase in triplet quantum yields for 3-SiNPs (linked) with decreasing lifetimes was observed. For 3-SiNPs (doped) there was a decrease in both the triplet quantum yield and lifetimes when compared to 3 alone. There was an increase in singlet oxygen quantum yields for 3-SiNPs (linked) compared to 3 from 0.67 to 0.80, while there was a decrease for 3-SiNPs (doped) to 0.25.
- Full Text:
- Date Issued: 2018
- Authors: Peteni, Siwaphiwe , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187873 , vital:44705 , xlink:href="https://doi.org/10.1016/j.ica.2018.06.029"
- Description: Tris[(4-(pyridin-4-ylthio)-2-thio-4-methylthiazol-5-yl)acetic acid phthalocyaninato] zinc (II) (3) was covalently linked to and doped onto SiNPs. An increase in triplet quantum yields for 3-SiNPs (linked) with decreasing lifetimes was observed. For 3-SiNPs (doped) there was a decrease in both the triplet quantum yield and lifetimes when compared to 3 alone. There was an increase in singlet oxygen quantum yields for 3-SiNPs (linked) compared to 3 from 0.67 to 0.80, while there was a decrease for 3-SiNPs (doped) to 0.25.
- Full Text:
- Date Issued: 2018
In-situ synthesis of gold nanoparticles on graphene quantum dots-phthalocyanine nanoplatforms: First description of the photophysical and surface enhanced Raman scattering behaviour
- Nwahara, Nnamdi, Achadu, Ojodomo John, Nyokong, Tebello
- Authors: Nwahara, Nnamdi , Achadu, Ojodomo John , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187638 , vital:44682 , xlink:href="https://doi.org/10.1016/j.jphotochem.2018.04.011"
- Description: Owing to the need for new low-dimensional molecular assemblies with tailored electronic properties, the current study presents a facile approach for the synthesis and assembly of gold nanoparticles (AuNPs) onto functional graphene quantum dots (GQDs)-phthalocyanines (Pcs) arrays and the investigation of their photophysical and surface enhanced Raman scattering (SERS) properties. The GQDs were functionalized with L-glutathione (GSH) (to form GQDs@GSH) in order to assist coupling to the low symmetry Zn tris–(tert–butyl) mono carboxyphenoxy (propionic acid) phthalocyanine (complex 1) to form 1@GQDs. The affinity of gold (Au) to sulphur (S) was exploited for the assembly of the AuNPs onto 1@GQDs platform to form 1@GQDs-AuNPs. Transmission electron microscopic investigations confirmed the formation of monodispersed, spherical Pc/GQDs@GSH/AuNPs hybrids. The nanocomposite displayed high triplet quantum yields, which translated into high singlet oxygen quantum yield as high as 87%. Furthermore, the formed composites demonstrated strong surface enhanced Raman scattering (SERS) properties with an unprecedented intrinsic maximal enhancement factor of more than 30-fold. These nanostructures also retain more than 90% of their original SERS intensities after a week of storage, displaying superb stability under ambient conditions. These results highlight the remarkable potential of this composite as a unique Raman-based PDT dosimetric agent.
- Full Text:
- Date Issued: 2018
- Authors: Nwahara, Nnamdi , Achadu, Ojodomo John , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187638 , vital:44682 , xlink:href="https://doi.org/10.1016/j.jphotochem.2018.04.011"
- Description: Owing to the need for new low-dimensional molecular assemblies with tailored electronic properties, the current study presents a facile approach for the synthesis and assembly of gold nanoparticles (AuNPs) onto functional graphene quantum dots (GQDs)-phthalocyanines (Pcs) arrays and the investigation of their photophysical and surface enhanced Raman scattering (SERS) properties. The GQDs were functionalized with L-glutathione (GSH) (to form GQDs@GSH) in order to assist coupling to the low symmetry Zn tris–(tert–butyl) mono carboxyphenoxy (propionic acid) phthalocyanine (complex 1) to form 1@GQDs. The affinity of gold (Au) to sulphur (S) was exploited for the assembly of the AuNPs onto 1@GQDs platform to form 1@GQDs-AuNPs. Transmission electron microscopic investigations confirmed the formation of monodispersed, spherical Pc/GQDs@GSH/AuNPs hybrids. The nanocomposite displayed high triplet quantum yields, which translated into high singlet oxygen quantum yield as high as 87%. Furthermore, the formed composites demonstrated strong surface enhanced Raman scattering (SERS) properties with an unprecedented intrinsic maximal enhancement factor of more than 30-fold. These nanostructures also retain more than 90% of their original SERS intensities after a week of storage, displaying superb stability under ambient conditions. These results highlight the remarkable potential of this composite as a unique Raman-based PDT dosimetric agent.
- Full Text:
- Date Issued: 2018
Glycosylated zinc phthalocyanine-gold nanoparticle conjugates for photodynamic therapy
- Dube, Edith, Oluwole, David O, Nwaji, Njemuwa, Nyokong, Tebello
- Authors: Dube, Edith , Oluwole, David O , Nwaji, Njemuwa , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/234524 , vital:50205 , xlink:href="https://doi.org/10.1016/j.saa.2018.05.081"
- Description: In this work, we report on the synthesis of tris-[(2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-5-yl)methoxy)-2-(4-benzo[d]thiazol-2-ylphenoxyphthalocyaninato] zinc(II) (complex 3) and its linkage to gold nanoparticles (AuNPs) of different shapes through S-Au/N-Au self-assembly. The conjugates of complex 3 (with both gold nanorods (AuNR) and nanospheres (AuNS)), displayed decreased fluorescence quantum yield with corresponding improved triplet and singlet quantum yields compared to complex 3 alone, however 3-AuNR showed improved properties than 3-AuNS. Complex 3 showed relatively low in vitro dark cytotoxicity against the epithelial breast cancer cells with cell survival ≥ 85% at concentration ≤ 160 μg/mL but afforded reduced photodynamic therapy activity which may be due to aggregation. 3-AuNR afforded superior PDT activity with more than 50% viable cells at concentration ≥ 40 μg/mL in comparison to 3-AuNS with more than 50% viable cells at concentration ≥ 80 μg/mL. The superior activity of 3-AuNR is attributed to the photothermal therapy effect since nanorods absorb more light at 680 nm than nanospheres.
- Full Text:
- Date Issued: 2018
- Authors: Dube, Edith , Oluwole, David O , Nwaji, Njemuwa , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/234524 , vital:50205 , xlink:href="https://doi.org/10.1016/j.saa.2018.05.081"
- Description: In this work, we report on the synthesis of tris-[(2,2,7,7-tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-5-yl)methoxy)-2-(4-benzo[d]thiazol-2-ylphenoxyphthalocyaninato] zinc(II) (complex 3) and its linkage to gold nanoparticles (AuNPs) of different shapes through S-Au/N-Au self-assembly. The conjugates of complex 3 (with both gold nanorods (AuNR) and nanospheres (AuNS)), displayed decreased fluorescence quantum yield with corresponding improved triplet and singlet quantum yields compared to complex 3 alone, however 3-AuNR showed improved properties than 3-AuNS. Complex 3 showed relatively low in vitro dark cytotoxicity against the epithelial breast cancer cells with cell survival ≥ 85% at concentration ≤ 160 μg/mL but afforded reduced photodynamic therapy activity which may be due to aggregation. 3-AuNR afforded superior PDT activity with more than 50% viable cells at concentration ≥ 40 μg/mL in comparison to 3-AuNS with more than 50% viable cells at concentration ≥ 80 μg/mL. The superior activity of 3-AuNR is attributed to the photothermal therapy effect since nanorods absorb more light at 680 nm than nanospheres.
- Full Text:
- Date Issued: 2018
Low symmetric metallophthalocyanine modified electrode via click chemistry for simultaneous detection of heavy metals
- Fomo, Gertrude, Nwaji, Njemuwa, Nyokong, Tebello
- Authors: Fomo, Gertrude , Nwaji, Njemuwa , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187914 , vital:44709 , xlink:href="https://doi.org/10.1016/j.jelechem.2018.02.016"
- Description: Beside different methods and materials used to develop electrochemical sensors, the modification of the electrode using click reaction based on metallophthalocyanine (MPc) compounds are shown to improve the stability and sensitivity of the sensor. This work reported the development of electrochemical sensor for mercury (II), Lead (II), copper (II) and cadmium (II) ions detection based on the synthesized novel low symmetry alkyne terminated cobalt Phthalocyanine (CoPc) derivative. Differential pulse stripping voltammetry (DPSV) technique was employed for the first time in simultaneous determination of trace levels of the above metal ions using modified glassy carbon electrode (GCE) via click chemistry. Under the optimum experimental conditions, the anodic peak current is proportional to the concentrations of metal ions over a wide range of 0 to 0.1 mM with nanolevel detection limit of 81.94, 327.71, 55.87 and 347.06 nM and the sensitivity of 866.23 ± 5.48, 215.82 ± 2.16, 1979.48 ± 11.47 and 204.50 ± 1.10 μA/mM for Hg(II), Cu(II), Pb(II) and Cd(II), respectively. The selectivity of the clicked-CoPc modified GCE toward Hg(II), Cu(II), Pb(II), Cd(II) present no interference from these metals ions. The fabricated electrochemical sensor exhibited very good electrochemical properties such as good reproducibility, stability, reusability and is suitable for the detection of heavy metal ions in tap water in our laboratory.
- Full Text:
- Date Issued: 2018
- Authors: Fomo, Gertrude , Nwaji, Njemuwa , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187914 , vital:44709 , xlink:href="https://doi.org/10.1016/j.jelechem.2018.02.016"
- Description: Beside different methods and materials used to develop electrochemical sensors, the modification of the electrode using click reaction based on metallophthalocyanine (MPc) compounds are shown to improve the stability and sensitivity of the sensor. This work reported the development of electrochemical sensor for mercury (II), Lead (II), copper (II) and cadmium (II) ions detection based on the synthesized novel low symmetry alkyne terminated cobalt Phthalocyanine (CoPc) derivative. Differential pulse stripping voltammetry (DPSV) technique was employed for the first time in simultaneous determination of trace levels of the above metal ions using modified glassy carbon electrode (GCE) via click chemistry. Under the optimum experimental conditions, the anodic peak current is proportional to the concentrations of metal ions over a wide range of 0 to 0.1 mM with nanolevel detection limit of 81.94, 327.71, 55.87 and 347.06 nM and the sensitivity of 866.23 ± 5.48, 215.82 ± 2.16, 1979.48 ± 11.47 and 204.50 ± 1.10 μA/mM for Hg(II), Cu(II), Pb(II) and Cd(II), respectively. The selectivity of the clicked-CoPc modified GCE toward Hg(II), Cu(II), Pb(II), Cd(II) present no interference from these metals ions. The fabricated electrochemical sensor exhibited very good electrochemical properties such as good reproducibility, stability, reusability and is suitable for the detection of heavy metal ions in tap water in our laboratory.
- Full Text:
- Date Issued: 2018
Photophysicochemical behaviour and antimicrobial properties of monocarboxy Mg (II) and Al (III) phthalocyanine-magnetite conjugates
- Idowu, Mopelola A I, Xego, Solami, Arslanoglu, Yasin, Mark, John, Antunes, Edith M, Nyokong, Tebello
- Authors: Idowu, Mopelola A I , Xego, Solami , Arslanoglu, Yasin , Mark, John , Antunes, Edith M , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/188205 , vital:44734 , xlink:href="https://doi.org/10.1016/j.saa.2017.12.052"
- Description: Asymmetric Mg (II) or Al (III) phthalocyanine (containing a COOH group and 3-pyridylsulfanyl units) was conjugated via an amide bond to amino functionalized magnetic nanoparticle (AIMN) to form MgPc-AIMN or AlPc-AIMN conjugate, and characterized. The photophysicochemical behaviour of the phthalocyanine–AIMN conjugates was investigated and compared to the asymmetric Pcs and to the simple mixture of Pc with AIMNs without a chemical bond, (MPc-AIMN (mixed)). The directed covalent linkage of AIMNs to the asymmetrical metallopthalocyanines afforded improvements in the singlet oxygen (ФΔ) and triplet state quantum yield (ФT) as well as singlet oxygen lifetimes for the MPcs–AIMN-linked conjugates compared to MPc-AIMN (mixed) and MPcs alone. The asymmetric phthalocyanines and their conjugates showed effective antimicrobial activity against Escherichia coli bacteria under illumination.
- Full Text:
- Date Issued: 2018
- Authors: Idowu, Mopelola A I , Xego, Solami , Arslanoglu, Yasin , Mark, John , Antunes, Edith M , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/188205 , vital:44734 , xlink:href="https://doi.org/10.1016/j.saa.2017.12.052"
- Description: Asymmetric Mg (II) or Al (III) phthalocyanine (containing a COOH group and 3-pyridylsulfanyl units) was conjugated via an amide bond to amino functionalized magnetic nanoparticle (AIMN) to form MgPc-AIMN or AlPc-AIMN conjugate, and characterized. The photophysicochemical behaviour of the phthalocyanine–AIMN conjugates was investigated and compared to the asymmetric Pcs and to the simple mixture of Pc with AIMNs without a chemical bond, (MPc-AIMN (mixed)). The directed covalent linkage of AIMNs to the asymmetrical metallopthalocyanines afforded improvements in the singlet oxygen (ФΔ) and triplet state quantum yield (ФT) as well as singlet oxygen lifetimes for the MPcs–AIMN-linked conjugates compared to MPc-AIMN (mixed) and MPcs alone. The asymmetric phthalocyanines and their conjugates showed effective antimicrobial activity against Escherichia coli bacteria under illumination.
- Full Text:
- Date Issued: 2018
Synthesis, photophysicochemical and photodynamic antimicrobial chemotherapy studies of indium pyridyl phthalocyanines: Charge versus bridging atom
- Sindelo, Azole, Nyokong, Tebello
- Authors: Sindelo, Azole , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187650 , vital:44683 , xlink:href="https://doi.org/10.1016/j.ica.2018.02.020"
- Description: 2(3), 9(10), 16(17), 23(24)-Octapyridylsulfanyl phthalocyaninato chloroindium(III) (complex 1a) and its quaternized derivative 2(3), 9(10), 16(17), 23(24)-octamethylpyridylsulfanyl phthalocyaninato chloroindium (III) (complex 1b) were synthesised. The triplet quantum yields were 0.53 and 0.48 while the singlet oxygen quantum yields were 0.46 and 0.33 in DMF for 1a and 1b, respectively. The photodynamic antimicrobial chemotherapy (PACT) activity of 1b (containing 8 positive charges) was compared to those of 9(10),16(17),23(24)-tri-N-methyl-4-pyridylsulfanyl-2(3)-(4-aminophenoxy) phthalocyaninato chloro indium(III) triiodide (2) (containing 3 positive charges) and 2-[4-(N-Methylpyridyloxy) phthalocyaninato] chloroindium (III) iodide (3) (containing 4 positive charges). Complex 1b gave log reductions of 4.21, 8.30 and 3.21 for Gram(−) E. coli, Gram(+) S. aureus and C. albicans, respectively. When comparing 1b, 2 and 3, the largest log reductions for E. coli were obtained for complex 3 containing four positive charges hence showing it is not always the charge that determines the PACT activity, but the bridging atom in the phthalocyanine plays a role.
- Full Text:
- Date Issued: 2018
- Authors: Sindelo, Azole , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187650 , vital:44683 , xlink:href="https://doi.org/10.1016/j.ica.2018.02.020"
- Description: 2(3), 9(10), 16(17), 23(24)-Octapyridylsulfanyl phthalocyaninato chloroindium(III) (complex 1a) and its quaternized derivative 2(3), 9(10), 16(17), 23(24)-octamethylpyridylsulfanyl phthalocyaninato chloroindium (III) (complex 1b) were synthesised. The triplet quantum yields were 0.53 and 0.48 while the singlet oxygen quantum yields were 0.46 and 0.33 in DMF for 1a and 1b, respectively. The photodynamic antimicrobial chemotherapy (PACT) activity of 1b (containing 8 positive charges) was compared to those of 9(10),16(17),23(24)-tri-N-methyl-4-pyridylsulfanyl-2(3)-(4-aminophenoxy) phthalocyaninato chloro indium(III) triiodide (2) (containing 3 positive charges) and 2-[4-(N-Methylpyridyloxy) phthalocyaninato] chloroindium (III) iodide (3) (containing 4 positive charges). Complex 1b gave log reductions of 4.21, 8.30 and 3.21 for Gram(−) E. coli, Gram(+) S. aureus and C. albicans, respectively. When comparing 1b, 2 and 3, the largest log reductions for E. coli were obtained for complex 3 containing four positive charges hence showing it is not always the charge that determines the PACT activity, but the bridging atom in the phthalocyanine plays a role.
- Full Text:
- Date Issued: 2018
Optimizing phthalocyanine based dye-sensitized solar cells: The role of reduced graphene oxide
- Chindeka, Francis, Mashazi, Philani N, Britton, Jonathan, Fomo, Gertrude, Oluwole, David O, Sindelo, Azole, Nyokong, Tebello
- Authors: Chindeka, Francis , Mashazi, Philani N , Britton, Jonathan , Fomo, Gertrude , Oluwole, David O , Sindelo, Azole , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187770 , vital:44695 , xlink:href="https://doi.org/10.1016/j.synthmet.2018.10.021"
- Description: Dye-sensitized solar cells (DSSC) were fabricated by incorporating graphene materials as catalysts at the counter electrode. Platinum was also used as a catalyst for comparison purposes. Different phthalocyanines: hydroxyl indium tetracarboxyphenoxy phthalocyanine (1), chloro indium octacarboxy phthalocyanine (2) and dibenzoic acid silicon phthalocyanine (3) were used as dyes. Complex 3 gave the highest power conversion efficiency (η) of 3.19% when using nitrogen doped reduced graphene oxide nanosheets (NrGONS) as a catalyst at the counter electrode, and TiO2 containing rGONS at the anode. The value is close to 3.8% obtained when using Pt catalyst instead of NrGONS at the cathode, thus confirming that NrGONS is a promising candidate to replace the more expensive Pt. The study also shows that placing rGONS on both the anode and cathode improves efficiency.
- Full Text:
- Date Issued: 2018
- Authors: Chindeka, Francis , Mashazi, Philani N , Britton, Jonathan , Fomo, Gertrude , Oluwole, David O , Sindelo, Azole , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187770 , vital:44695 , xlink:href="https://doi.org/10.1016/j.synthmet.2018.10.021"
- Description: Dye-sensitized solar cells (DSSC) were fabricated by incorporating graphene materials as catalysts at the counter electrode. Platinum was also used as a catalyst for comparison purposes. Different phthalocyanines: hydroxyl indium tetracarboxyphenoxy phthalocyanine (1), chloro indium octacarboxy phthalocyanine (2) and dibenzoic acid silicon phthalocyanine (3) were used as dyes. Complex 3 gave the highest power conversion efficiency (η) of 3.19% when using nitrogen doped reduced graphene oxide nanosheets (NrGONS) as a catalyst at the counter electrode, and TiO2 containing rGONS at the anode. The value is close to 3.8% obtained when using Pt catalyst instead of NrGONS at the cathode, thus confirming that NrGONS is a promising candidate to replace the more expensive Pt. The study also shows that placing rGONS on both the anode and cathode improves efficiency.
- Full Text:
- Date Issued: 2018
Incorporation of metal free and Ga 5, 10, 15, 20-tetrakis (4-bromophenyl) porphyrin into Pluronic F127-folic acid micelles
- Managa, Muthumuni, Ngoy, Bucolome P, Mafukidze, Donovan M, Nyokong, Tebello
- Authors: Managa, Muthumuni , Ngoy, Bucolome P , Mafukidze, Donovan M , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/233256 , vital:50073 , xlink:href="https://doi.org/10.1016/j.jlumin.2017.09.045"
- Description: ClGa 5,10,15,20-Tetrakis (4-bromophenyl) porphyrinato (ClGaTBrPP) and its metal free derivative were successfully synthesized and incorporated into Pluronic F127 polymeric micelles that has been conjugated to folic acid (FA) to form ClGaTBrPP-F127-FA (or H2TBrPP-F127-FA). For comparison, ClGaTBrPP-F127 and H2TBrPP-F127 (without FA) were also formed. The singlet oxygen quantum yield for ClGaTBrPP-F127-FA was higher (ΦΔ = 0.44) than that of H2TBrPP-F127-FA (ΦΔ = 0.37), due to the heavy atom effect of Ga in the former which encourages intersystem crossing to the triplet state. The same applies to ClGaTBrPP-F127 (ΦΔ = 0.47) and H2TBrPP-F127 (ΦΔ = 0.41). Thus, ΦΔ values decreased in the presence of FA, but still high enough for practical application of the nanodrug system. The binding constants Kb were determined to be 1.08 × 104 M−1, 2.51 × 105 M−1, 1.52 × 103 and 2.68 × 103 for H2TBrPP+F127-FA, ClGaTBrPP+F127-FA, ClGaTBrPP-F127 and H2TBrPP-F127, respectively. The Kp values were determined in biphasic octanol and water system.
- Full Text:
- Date Issued: 2018
- Authors: Managa, Muthumuni , Ngoy, Bucolome P , Mafukidze, Donovan M , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/233256 , vital:50073 , xlink:href="https://doi.org/10.1016/j.jlumin.2017.09.045"
- Description: ClGa 5,10,15,20-Tetrakis (4-bromophenyl) porphyrinato (ClGaTBrPP) and its metal free derivative were successfully synthesized and incorporated into Pluronic F127 polymeric micelles that has been conjugated to folic acid (FA) to form ClGaTBrPP-F127-FA (or H2TBrPP-F127-FA). For comparison, ClGaTBrPP-F127 and H2TBrPP-F127 (without FA) were also formed. The singlet oxygen quantum yield for ClGaTBrPP-F127-FA was higher (ΦΔ = 0.44) than that of H2TBrPP-F127-FA (ΦΔ = 0.37), due to the heavy atom effect of Ga in the former which encourages intersystem crossing to the triplet state. The same applies to ClGaTBrPP-F127 (ΦΔ = 0.47) and H2TBrPP-F127 (ΦΔ = 0.41). Thus, ΦΔ values decreased in the presence of FA, but still high enough for practical application of the nanodrug system. The binding constants Kb were determined to be 1.08 × 104 M−1, 2.51 × 105 M−1, 1.52 × 103 and 2.68 × 103 for H2TBrPP+F127-FA, ClGaTBrPP+F127-FA, ClGaTBrPP-F127 and H2TBrPP-F127, respectively. The Kp values were determined in biphasic octanol and water system.
- Full Text:
- Date Issued: 2018
Physicochemical properties of water soluble unsymmetrical phthalocyanine-folic acid conjugates
- Matlou, Gauta G, Kobayashi, Nagao, Kimura, Mutsumi, Nyokong, Tebello
- Authors: Matlou, Gauta G , Kobayashi, Nagao , Kimura, Mutsumi , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/233240 , vital:50071 , xlink:href="https://doi.org/10.1016/j.dyepig.2017.10.030"
- Description: This work reports on the successful chemical linkage of folic acid (FA) to Zn mono carboxyphenoxy phthalocyanine (1) and Zn mono carboxyphenoxy tri–(tert–butyl) phthalocyanine (2). The amide bond linkage of FA to phthalocyanine (Pc) is achieved for the first time through the FA-NH2 and Pc-COOH and confirmed using FTIR, MS, elemental analysis and NMR. The linked conjugates were found to be water soluble compared to the physical mixtures of FA and Pc, which allowed for studies of singlet oxygen in water. The Pc-FA linked conjugates (1-FA and 2-FA) were found to be singlet oxygen generators with the following singlet oxygen quantum yields: 1-FA = 0.61 and 2-FA = 0.47 in DMSO and 1-FA = 0.17 and 2-FA = 0.12 in water.
- Full Text:
- Date Issued: 2018
- Authors: Matlou, Gauta G , Kobayashi, Nagao , Kimura, Mutsumi , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/233240 , vital:50071 , xlink:href="https://doi.org/10.1016/j.dyepig.2017.10.030"
- Description: This work reports on the successful chemical linkage of folic acid (FA) to Zn mono carboxyphenoxy phthalocyanine (1) and Zn mono carboxyphenoxy tri–(tert–butyl) phthalocyanine (2). The amide bond linkage of FA to phthalocyanine (Pc) is achieved for the first time through the FA-NH2 and Pc-COOH and confirmed using FTIR, MS, elemental analysis and NMR. The linked conjugates were found to be water soluble compared to the physical mixtures of FA and Pc, which allowed for studies of singlet oxygen in water. The Pc-FA linked conjugates (1-FA and 2-FA) were found to be singlet oxygen generators with the following singlet oxygen quantum yields: 1-FA = 0.61 and 2-FA = 0.47 in DMSO and 1-FA = 0.17 and 2-FA = 0.12 in water.
- Full Text:
- Date Issued: 2018
Photophysical studies of graphene quantum dots-Pyrene-derivatized porphyrins conjugates when encapsulated within Pluronic F127 micelles
- Managa, Muthumuni, Achadu, Ojodomo John, Nyokong, Tebello
- Authors: Managa, Muthumuni , Achadu, Ojodomo John , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187971 , vital:44714 , xlink:href="https://doi.org/10.1016/j.dyepig.2017.09.031"
- Description: Pyrene-derivatized H2, GaCl, and Zn porphyrins were immobilized on graphene quantum dots (GQDs) to form (GQDs-H2TPrP, GQDs-GaClTPrP, and GQDs-ZnTPrP) conjugates through the π-π stacking interaction method followed by encapsulating into Pluronic F127 micelles to form (GQDs-H2TPrP + F127, GQDs-GaClTPrP + F127, and GQDs-ZnTPrP + F127). Spectroscopic evidence shows that the resultant conjugates were stable due to the strong π-π stacking interaction between the GQDs and the porphyrins. The fluorescence and singlet oxygen generating behaviour of the porphyrins were investigated following incorporation. GQDs-GaClTPrP + F127 showed highest values of the binding constant (Kb). The Stern-Volmer constant (Ksv) for GQDs-ZnTPrP + F127 were the highest compared to other porphyrins derivatives.
- Full Text:
- Date Issued: 2018
- Authors: Managa, Muthumuni , Achadu, Ojodomo John , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187971 , vital:44714 , xlink:href="https://doi.org/10.1016/j.dyepig.2017.09.031"
- Description: Pyrene-derivatized H2, GaCl, and Zn porphyrins were immobilized on graphene quantum dots (GQDs) to form (GQDs-H2TPrP, GQDs-GaClTPrP, and GQDs-ZnTPrP) conjugates through the π-π stacking interaction method followed by encapsulating into Pluronic F127 micelles to form (GQDs-H2TPrP + F127, GQDs-GaClTPrP + F127, and GQDs-ZnTPrP + F127). Spectroscopic evidence shows that the resultant conjugates were stable due to the strong π-π stacking interaction between the GQDs and the porphyrins. The fluorescence and singlet oxygen generating behaviour of the porphyrins were investigated following incorporation. GQDs-GaClTPrP + F127 showed highest values of the binding constant (Kb). The Stern-Volmer constant (Ksv) for GQDs-ZnTPrP + F127 were the highest compared to other porphyrins derivatives.
- Full Text:
- Date Issued: 2018
In-situ synthesis of gold nanoparticles on graphene quantum dots-phthalocyanine nanoplatforms: First description of the photophysical and surface enhanced Raman scattering behaviour
- Nwahara, Nnamdi, Achadu, Ojodomo John, Nyokong, Tebello
- Authors: Nwahara, Nnamdi , Achadu, Ojodomo John , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/188183 , vital:44730 , xlink:href="https://doi.org/10.1016/j.jphotochem.2018.04.011"
- Description: Owing to the need for new low-dimensional molecular assemblies with tailored electronic properties, the current study presents a facile approach for the synthesis and assembly of gold nanoparticles (AuNPs) onto functional graphene quantum dots (GQDs)-phthalocyanines (Pcs) arrays and the investigation of their photophysical and surface enhanced Raman scattering (SERS) properties. The GQDs were functionalized with L-glutathione (GSH) (to form GQDs@GSH) in order to assist coupling to the low symmetry Zn tris–(tert–butyl) mono carboxyphenoxy (propionic acid) phthalocyanine (complex 1) to form 1@GQDs. The affinity of gold (Au) to sulphur (S) was exploited for the assembly of the AuNPs onto 1@GQDs platform to form 1@GQDs-AuNPs. Transmission electron microscopic investigations confirmed the formation of monodispersed, spherical Pc/GQDs@GSH/AuNPs hybrids. The nanocomposite displayed high triplet quantum yields, which translated into high singlet oxygen quantum yield as high as 87%. Furthermore, the formed composites demonstrated strong surface enhanced Raman scattering (SERS) properties with an unprecedented intrinsic maximal enhancement factor of more than 30-fold. These nanostructures also retain more than 90% of their original SERS intensities after a week of storage, displaying superb stability under ambient conditions. These results highlight the remarkable potential of this composite as a unique Raman-based PDT dosimetric agent.
- Full Text:
- Date Issued: 2018
- Authors: Nwahara, Nnamdi , Achadu, Ojodomo John , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/188183 , vital:44730 , xlink:href="https://doi.org/10.1016/j.jphotochem.2018.04.011"
- Description: Owing to the need for new low-dimensional molecular assemblies with tailored electronic properties, the current study presents a facile approach for the synthesis and assembly of gold nanoparticles (AuNPs) onto functional graphene quantum dots (GQDs)-phthalocyanines (Pcs) arrays and the investigation of their photophysical and surface enhanced Raman scattering (SERS) properties. The GQDs were functionalized with L-glutathione (GSH) (to form GQDs@GSH) in order to assist coupling to the low symmetry Zn tris–(tert–butyl) mono carboxyphenoxy (propionic acid) phthalocyanine (complex 1) to form 1@GQDs. The affinity of gold (Au) to sulphur (S) was exploited for the assembly of the AuNPs onto 1@GQDs platform to form 1@GQDs-AuNPs. Transmission electron microscopic investigations confirmed the formation of monodispersed, spherical Pc/GQDs@GSH/AuNPs hybrids. The nanocomposite displayed high triplet quantum yields, which translated into high singlet oxygen quantum yield as high as 87%. Furthermore, the formed composites demonstrated strong surface enhanced Raman scattering (SERS) properties with an unprecedented intrinsic maximal enhancement factor of more than 30-fold. These nanostructures also retain more than 90% of their original SERS intensities after a week of storage, displaying superb stability under ambient conditions. These results highlight the remarkable potential of this composite as a unique Raman-based PDT dosimetric agent.
- Full Text:
- Date Issued: 2018
Optical nonlinearity of pentadecylphenoxyl substituted sandwich–type metallophthalocyanines in the presence of Ag–CdSeTe/ZnTeSe nanocrystals: Effects of conjugation and central metals
- Oluwole, David O, Nyokong, Tebello
- Authors: Oluwole, David O , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187899 , vital:44708 , xlink:href="https://doi.org/10.1016/j.dyepig.2018.01.009"
- Description: Novel pentadecylphenoxyl substituted homoleptic sandwich–type metallophthalocyanines: bis (complexes 2 and 4 containing Eu and Dy, respectively) and tris (complexes 3 and 5 containing Eu and Dy, respectively) 2,9,16,23–tetrakis–(3–pentadecylphenoxyl) phthalocyanines and cadmium based (Ag–CdSeTe/ZnTeSe) nanocrystals (NCs) were synthesized. The nonlinear optical (NLO) behavior of the metallophthalocyanines and their composites with NCs were investigated using the open aperture Z–scan technique at excitation wavelength of 532 nm with 10 ns pulse. All of the samples exhibited interesting NLO attributes: among all the sandwich–type complexes, complex 5 afforded the most efficient NLO features accounting for large nonlinear absorption coefficient (βeff) value of 3500 cm/GW and limiting threshold (Ilim) value of 0.43 J cm−2. Overall, the composites of the triple decker sandwich–type complexes with Ag–CdSeTe/ZnTeSe yielded the best NLO characteristics with 3 and 5 accounting for the largest βeff value of 5500 cm/GW and Ilim value of 0.09 J cm−2. The synthesized complexes and their composites with NCs could be viable and efficient NLO absorber due to their interesting NLO activities.
- Full Text:
- Date Issued: 2018
- Authors: Oluwole, David O , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187899 , vital:44708 , xlink:href="https://doi.org/10.1016/j.dyepig.2018.01.009"
- Description: Novel pentadecylphenoxyl substituted homoleptic sandwich–type metallophthalocyanines: bis (complexes 2 and 4 containing Eu and Dy, respectively) and tris (complexes 3 and 5 containing Eu and Dy, respectively) 2,9,16,23–tetrakis–(3–pentadecylphenoxyl) phthalocyanines and cadmium based (Ag–CdSeTe/ZnTeSe) nanocrystals (NCs) were synthesized. The nonlinear optical (NLO) behavior of the metallophthalocyanines and their composites with NCs were investigated using the open aperture Z–scan technique at excitation wavelength of 532 nm with 10 ns pulse. All of the samples exhibited interesting NLO attributes: among all the sandwich–type complexes, complex 5 afforded the most efficient NLO features accounting for large nonlinear absorption coefficient (βeff) value of 3500 cm/GW and limiting threshold (Ilim) value of 0.43 J cm−2. Overall, the composites of the triple decker sandwich–type complexes with Ag–CdSeTe/ZnTeSe yielded the best NLO characteristics with 3 and 5 accounting for the largest βeff value of 5500 cm/GW and Ilim value of 0.09 J cm−2. The synthesized complexes and their composites with NCs could be viable and efficient NLO absorber due to their interesting NLO activities.
- Full Text:
- Date Issued: 2018
Evaluation of the photophysicochemical properties and photodynamic therapy activity of nanoconjugates of zinc phthalocyanine linked to glutathione capped Au and Au3Ag1 nanoparticles
- Oluwole, David O, Manoto, Sello L, Malabi, Rudzani, Maphanga, Charles, Ombinda-Lemboumba, Saturnin, Mthunzi-Kufa, Patience, Nyokong, Tebello
- Authors: Oluwole, David O , Manoto, Sello L , Malabi, Rudzani , Maphanga, Charles , Ombinda-Lemboumba, Saturnin , Mthunzi-Kufa, Patience , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/237886 , vital:50563 , xlink:href="https://doi.org/10.1016/j.dyepig.2017.11.019"
- Description: We report on the synthesis of glutathione capped gold (AuNPs–GSH) and gold–silver (Au3Ag1NPs–GSH) nanoparticles and their covalent attachment to Zn monocarboxyphenoxy phthalocyanine (1) via amide bond formation. The photophysicochemical properties and photodynamic therapy (PDT) activity of the complex and its nanoconjugates were assessed. The conjugates afforded improved triplet and singlet oxygen quantum yield as well as PDT activity (except for 1-Au3Ag1NPs which afforded decreased activity) in comparison to complex 1.
- Full Text:
- Date Issued: 2018
- Authors: Oluwole, David O , Manoto, Sello L , Malabi, Rudzani , Maphanga, Charles , Ombinda-Lemboumba, Saturnin , Mthunzi-Kufa, Patience , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/237886 , vital:50563 , xlink:href="https://doi.org/10.1016/j.dyepig.2017.11.019"
- Description: We report on the synthesis of glutathione capped gold (AuNPs–GSH) and gold–silver (Au3Ag1NPs–GSH) nanoparticles and their covalent attachment to Zn monocarboxyphenoxy phthalocyanine (1) via amide bond formation. The photophysicochemical properties and photodynamic therapy (PDT) activity of the complex and its nanoconjugates were assessed. The conjugates afforded improved triplet and singlet oxygen quantum yield as well as PDT activity (except for 1-Au3Ag1NPs which afforded decreased activity) in comparison to complex 1.
- Full Text:
- Date Issued: 2018
Effect of nature of nanoparticles on the photophysicochemical properties of asymmetrically substituted Zn phthalocyanines
- Magadla, Aviwe, Oluwole, David O, Britton, Jonathan, Nyokong, Tebello
- Authors: Magadla, Aviwe , Oluwole, David O , Britton, Jonathan , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/234539 , vital:50206 , xlink:href="https://doi.org/10.1016/j.ica.2018.06.043"
- Description: In this work, low symmetry Zn mono caffeic acid tri-tert butyl (1) and Zn monocarboxyphenoxy tri-(tert-butylphenoxyl) (2) phthalocyanines (Pcs) were covalently linked to amino (using glutathione, GSH, or 3-aminopropyl)triethoxysilane, APTES) functionalised nanoparticles. The nanoparticles are represented as: AgNPs-GSH, SiNPs-APTES, Fe3O4-Ag-SiNPs-APTES and Fe3O4-AgNPs-GSH). The photophysical and photochemical behaviour of the complexes 1 and 2 and their conjugates with nanoparticles were investigated in dimethyl sulfoxide. The conjugates of the Pc complexes with the NPs afforded increase in triplet quantum yields with corresponding decrease in fluorescence quantum yield compared to the Pc complexes alone. The conjugates of 1-AgNPs-GSH, 2-SiNPs-APTES and 2-Fe3O4-Ag-SiNPs-APTES showed higher singlet oxygen quantum yield values as compared to the Pc complexes alone.
- Full Text:
- Date Issued: 2018
- Authors: Magadla, Aviwe , Oluwole, David O , Britton, Jonathan , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/234539 , vital:50206 , xlink:href="https://doi.org/10.1016/j.ica.2018.06.043"
- Description: In this work, low symmetry Zn mono caffeic acid tri-tert butyl (1) and Zn monocarboxyphenoxy tri-(tert-butylphenoxyl) (2) phthalocyanines (Pcs) were covalently linked to amino (using glutathione, GSH, or 3-aminopropyl)triethoxysilane, APTES) functionalised nanoparticles. The nanoparticles are represented as: AgNPs-GSH, SiNPs-APTES, Fe3O4-Ag-SiNPs-APTES and Fe3O4-AgNPs-GSH). The photophysical and photochemical behaviour of the complexes 1 and 2 and their conjugates with nanoparticles were investigated in dimethyl sulfoxide. The conjugates of the Pc complexes with the NPs afforded increase in triplet quantum yields with corresponding decrease in fluorescence quantum yield compared to the Pc complexes alone. The conjugates of 1-AgNPs-GSH, 2-SiNPs-APTES and 2-Fe3O4-Ag-SiNPs-APTES showed higher singlet oxygen quantum yield values as compared to the Pc complexes alone.
- Full Text:
- Date Issued: 2018
Porphyrin dimers with a bridging chiral amide-bonded benzo-moiety
- Liang, Xu, Qin, Mingfeng, Zhou, Lin, Liu, Tingting, Li, Minzhi, Mack, John, Ndebele, Nobuhle, Nyokong, Tebello, Zhu, Weihua
- Authors: Liang, Xu , Qin, Mingfeng , Zhou, Lin , Liu, Tingting , Li, Minzhi , Mack, John , Ndebele, Nobuhle , Nyokong, Tebello , Zhu, Weihua
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/233433 , vital:50090 , xlink:href="https://doi.org/10.1016/j.dyepig.2018.02.043"
- Description: The facile synthesis and characterization of four porphyrin dimers which introduced stereomeric centers with chiral amide-bonded para- and meta-disubstituted benzo-moiety is reported. Trends in the electronic structures and optical and redox properties are analyzed through a comparison with theoretical calculations to explore the effect of positional isomerism of the bridging benzene rings.
- Full Text:
- Date Issued: 2018
- Authors: Liang, Xu , Qin, Mingfeng , Zhou, Lin , Liu, Tingting , Li, Minzhi , Mack, John , Ndebele, Nobuhle , Nyokong, Tebello , Zhu, Weihua
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/233433 , vital:50090 , xlink:href="https://doi.org/10.1016/j.dyepig.2018.02.043"
- Description: The facile synthesis and characterization of four porphyrin dimers which introduced stereomeric centers with chiral amide-bonded para- and meta-disubstituted benzo-moiety is reported. Trends in the electronic structures and optical and redox properties are analyzed through a comparison with theoretical calculations to explore the effect of positional isomerism of the bridging benzene rings.
- Full Text:
- Date Issued: 2018
Effects of Pluronic F127 micelles as delivering agents on the vitro dark toxicity and photodynamic therapy activity of carboxy and pyrene substituted porphyrins
- Managa, Muthumuni, Britton, Jonathan, Prinsloo, Earl, Nyokong, Tebello
- Authors: Managa, Muthumuni , Britton, Jonathan , Prinsloo, Earl , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/234439 , vital:50196 , xlink:href="https://doi.org/10.1016/j.poly.2018.06.031"
- Description: Metal free, Zn and ClGa containing carboxyphenoxy and phenoxy groups (complexes 1) and pyrene groups (complexes 2) were synthesized and embedded into Pluronic F127 micelles (represented as F127). Dark toxicity and photodynamic therapy activities of the embedded porphyrins were successfully studied on MCF-7 breast cancer cells. Dark toxicity showed more than 80% cell viability for all complexes. It was found that 1-Zn + F127 showed better photodynamic therapy activity compared to 1-H2 + F127, and 1-ClGa + F127, corresponding to the high partition coefficient for the Zn porphyrin derivatives. The same applies to 2-Zn + F127 compared to 2-H2 + F127, 2-ClGa + F127. 1-ClGa and 1-Zn were also linked to Pluronic F127 silica nanoparticles. PDT activities for embedded 1-ClGa + F127 and 1-Zn + F127 were much higher than when linked to Pluronic silica nanoparticles (PluS NPs), showing the importance of loading of porphyrins into Pluronic F127 as a drug delivering agent rather than linking. PDT studies at the highest concentration of 60 µg/ml showed decrease in cell viability down to 15.9% for 2-Zn + F127. The Kp was determined in biphasic octanol and water system.
- Full Text:
- Date Issued: 2018
- Authors: Managa, Muthumuni , Britton, Jonathan , Prinsloo, Earl , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/234439 , vital:50196 , xlink:href="https://doi.org/10.1016/j.poly.2018.06.031"
- Description: Metal free, Zn and ClGa containing carboxyphenoxy and phenoxy groups (complexes 1) and pyrene groups (complexes 2) were synthesized and embedded into Pluronic F127 micelles (represented as F127). Dark toxicity and photodynamic therapy activities of the embedded porphyrins were successfully studied on MCF-7 breast cancer cells. Dark toxicity showed more than 80% cell viability for all complexes. It was found that 1-Zn + F127 showed better photodynamic therapy activity compared to 1-H2 + F127, and 1-ClGa + F127, corresponding to the high partition coefficient for the Zn porphyrin derivatives. The same applies to 2-Zn + F127 compared to 2-H2 + F127, 2-ClGa + F127. 1-ClGa and 1-Zn were also linked to Pluronic F127 silica nanoparticles. PDT activities for embedded 1-ClGa + F127 and 1-Zn + F127 were much higher than when linked to Pluronic silica nanoparticles (PluS NPs), showing the importance of loading of porphyrins into Pluronic F127 as a drug delivering agent rather than linking. PDT studies at the highest concentration of 60 µg/ml showed decrease in cell viability down to 15.9% for 2-Zn + F127. The Kp was determined in biphasic octanol and water system.
- Full Text:
- Date Issued: 2018
Photophysicochemical properties and photodynamic therapy activity of highly water-soluble Zn (II) phthalocyanines
- Oluwole, David O, Sari, Fatma Aslihan, Prinsloo, Earl, Dube, Edith, Yuzer, Abdulcelil, Nyokong, Tebello, Ince, Mine
- Authors: Oluwole, David O , Sari, Fatma Aslihan , Prinsloo, Earl , Dube, Edith , Yuzer, Abdulcelil , Nyokong, Tebello , Ince, Mine
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/234507 , vital:50203 , xlink:href="https://doi.org/10.1016/j.saa.2018.05.090"
- Description: The syntheses of two zinc(II) phthalocyanines (ZnPcs) having either imidazole (ZnPc 1) or pyridiloxy (ZnPc 2) moieties as their macrocycle substituents are reported. Quaternization of the ZnPcs with methyl iodide afforded water soluble cationic phthalocyanines. The photophysical, photochemical properties and photodynamic therapy (PDT) activity of the ZnPcs were studied in solution. The fluorescence quantum yield and lifetime of ZnPc 1 were higher as compared to ZnPc 2. ZnPc 2 afforded higher triplet state (ΦT) and singlet oxygen quantum yields (ΦΔ) in comparison to ZnPc 1. The PDT activity of ZnPcs was investigated against human breast adenocarcinoma cells (MCF–7). The two compounds afforded a very minimal in vitro dark cytotoxicity with 85% viable cells at concentration ≤80 μM. On irradiation of the cells having the ZnPcs, ≥50% cell death was recorded for ZnPc 1 which was also evidenced by the cells photo–micrograph.
- Full Text:
- Date Issued: 2018
- Authors: Oluwole, David O , Sari, Fatma Aslihan , Prinsloo, Earl , Dube, Edith , Yuzer, Abdulcelil , Nyokong, Tebello , Ince, Mine
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/234507 , vital:50203 , xlink:href="https://doi.org/10.1016/j.saa.2018.05.090"
- Description: The syntheses of two zinc(II) phthalocyanines (ZnPcs) having either imidazole (ZnPc 1) or pyridiloxy (ZnPc 2) moieties as their macrocycle substituents are reported. Quaternization of the ZnPcs with methyl iodide afforded water soluble cationic phthalocyanines. The photophysical, photochemical properties and photodynamic therapy (PDT) activity of the ZnPcs were studied in solution. The fluorescence quantum yield and lifetime of ZnPc 1 were higher as compared to ZnPc 2. ZnPc 2 afforded higher triplet state (ΦT) and singlet oxygen quantum yields (ΦΔ) in comparison to ZnPc 1. The PDT activity of ZnPcs was investigated against human breast adenocarcinoma cells (MCF–7). The two compounds afforded a very minimal in vitro dark cytotoxicity with 85% viable cells at concentration ≤80 μM. On irradiation of the cells having the ZnPcs, ≥50% cell death was recorded for ZnPc 1 which was also evidenced by the cells photo–micrograph.
- Full Text:
- Date Issued: 2018
Photodynamic therapy activity of zinc phthalocyanine linked to folic acid and magnetic nanoparticles
- Matlou, Gauta G, Oluwole, David O, Prinsloo, Earl, Nyokong, Tebello
- Authors: Matlou, Gauta G , Oluwole, David O , Prinsloo, Earl , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/234429 , vital:50195 , xlink:href="https://doi.org/10.1016/j.jphotobiol.2018.07.025"
- Description: In this work, the photodynamic therapy (PDT) activities (using human carcinoma adherent MCF-7 cells) of zinc phthalocyanine derivatives: complexes 1 (Zn mono cinnamic acid phthalocyanine) and 2 (zinc mono carboxyphenoxy phthalocyanine) when covalently linked to folic acid (FA) and amine functionalized magnetic nanoparticles (AMNPs) are reported. The covalent linkage of asymmetric zinc cinnamic acid Pc (1) to FA (1-FA) through an amide bond is reported for the first time. Complex 1 is insoluble in water, but upon linkage to FA, (to form 1-FA) the molecule become water soluble, hence the UV–Vis spectrum and singlet oxygen quantum yield for 1-FA were also done in water since water solubility is essential for biological applications. The reported 2-FA is also water soluble. Linking complexes 1 and 2 to FA and AMNPs decreased the dark toxicity of 1 and 2 on MCF-7 cells. Pc-FA (1-FA and 2-FA) conjugates had better singlet oxygen quantum yields (Φ∆) in DMSO as compared to Pc-AMNPs (1-AMNPs and 2-AMNPs). The water- soluble 1-FA and 2-FA also achieved a better photodynamic therapy (PDT) activity as compared to 1-AMNPs and 2-AMNPs. Folic acid targeting on the tumor cells may have also facilitated better bioavailability of 1-FA and 2-FA and improved PDT activity on MCF-7 cells over AMNPs carriers.
- Full Text:
- Date Issued: 2018
Photodynamic therapy activity of zinc phthalocyanine linked to folic acid and magnetic nanoparticles
- Authors: Matlou, Gauta G , Oluwole, David O , Prinsloo, Earl , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/234429 , vital:50195 , xlink:href="https://doi.org/10.1016/j.jphotobiol.2018.07.025"
- Description: In this work, the photodynamic therapy (PDT) activities (using human carcinoma adherent MCF-7 cells) of zinc phthalocyanine derivatives: complexes 1 (Zn mono cinnamic acid phthalocyanine) and 2 (zinc mono carboxyphenoxy phthalocyanine) when covalently linked to folic acid (FA) and amine functionalized magnetic nanoparticles (AMNPs) are reported. The covalent linkage of asymmetric zinc cinnamic acid Pc (1) to FA (1-FA) through an amide bond is reported for the first time. Complex 1 is insoluble in water, but upon linkage to FA, (to form 1-FA) the molecule become water soluble, hence the UV–Vis spectrum and singlet oxygen quantum yield for 1-FA were also done in water since water solubility is essential for biological applications. The reported 2-FA is also water soluble. Linking complexes 1 and 2 to FA and AMNPs decreased the dark toxicity of 1 and 2 on MCF-7 cells. Pc-FA (1-FA and 2-FA) conjugates had better singlet oxygen quantum yields (Φ∆) in DMSO as compared to Pc-AMNPs (1-AMNPs and 2-AMNPs). The water- soluble 1-FA and 2-FA also achieved a better photodynamic therapy (PDT) activity as compared to 1-AMNPs and 2-AMNPs. Folic acid targeting on the tumor cells may have also facilitated better bioavailability of 1-FA and 2-FA and improved PDT activity on MCF-7 cells over AMNPs carriers.
- Full Text:
- Date Issued: 2018
Effect of number of positive charges on the photophysical and photodynamic therapy activities of quarternary benzothiazole substituted zinc phthalocyanine
- Matshitse, Refilwe, Nwaji, Njemuwa, Mananga, Muthumuni, Prinsloo, Earl, Nyokong, Tebello
- Authors: Matshitse, Refilwe , Nwaji, Njemuwa , Mananga, Muthumuni , Prinsloo, Earl , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187819 , vital:44700 , xlink:href="https://doi.org/10.1016/j.jphotochem.2018.08.033"
- Description: The synthesis, photophysicochemical and photodynamic therapy (PDT) activity of quaternary benzothiazole substituted zinc phthalocyanine (2, containing two charges, and 3, containing four charges) are reported in this work. Furthermore, the activity of the synthesized complex was compared to non-quaternary derivative (1). Higher triplet and singlet oxygen quantum yields of 0.92 and 0.85, respectively, for quaternized complexes 2 and 3 compared to complex 1 alone. Complexes 1, 2 and 3 showed relatively no dark toxicity against the epithelial breast cancer cells with cell survival of above 90 ± 3%. The quaternary derivatives (2 and 3) showed superior PDT activity with 30% or less of viable cells at concentration of 50.0 μg/mL in comparison to complex 1 alone which further lay credence to the importance of quaternization in the enhancement of PDT activity.
- Full Text:
- Date Issued: 2018
- Authors: Matshitse, Refilwe , Nwaji, Njemuwa , Mananga, Muthumuni , Prinsloo, Earl , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187819 , vital:44700 , xlink:href="https://doi.org/10.1016/j.jphotochem.2018.08.033"
- Description: The synthesis, photophysicochemical and photodynamic therapy (PDT) activity of quaternary benzothiazole substituted zinc phthalocyanine (2, containing two charges, and 3, containing four charges) are reported in this work. Furthermore, the activity of the synthesized complex was compared to non-quaternary derivative (1). Higher triplet and singlet oxygen quantum yields of 0.92 and 0.85, respectively, for quaternized complexes 2 and 3 compared to complex 1 alone. Complexes 1, 2 and 3 showed relatively no dark toxicity against the epithelial breast cancer cells with cell survival of above 90 ± 3%. The quaternary derivatives (2 and 3) showed superior PDT activity with 30% or less of viable cells at concentration of 50.0 μg/mL in comparison to complex 1 alone which further lay credence to the importance of quaternization in the enhancement of PDT activity.
- Full Text:
- Date Issued: 2018
Optical limiting properties of 3, 5-dipyrenylvinyleneBODIPY dyes at 532 nm
- Kubheka, Gugu, Sanusi, Kayode, Mack, John, Nyokong, Tebello
- Authors: Kubheka, Gugu , Sanusi, Kayode , Mack, John , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/237938 , vital:50567 , xlink:href="https://doi.org/10.1016/j.saa.2017.10.021"
- Description: The optical limiting (OL) properties of 3,5-dipyrenylvinyleneBODIPY dyes that contain both electron withdrawing and donating moieties have been investigated by using the z-scan technique at 532 nm in the nanosecond pulse range. The extension of the π-conjugation at the 3,5-positions with pyrenylvinylene groups results in a ca. 200 nm red shift of the main BODIPY spectral band to ca. 700 nm, so there is relatively weak absorbance at 532 nm under ambient light conditions. Reverse saturable absorbance (RSA) profiles are observed in response to incident pulsed laser light that is consistent with a two photon absorption-assisted excited state absorption (ESA) mechanism in CH2Cl2 solution and when the dyes are embedded in poly(bisphenol carbonate A) (PBC) polymer thin films. This demonstrates that 3,5-divinyleneBODIPY dyes are potentially suitable for use in OL applications, since limiting threshold fluence (Ilim) values of below 0.95 J cm−2 are observed when thin films are prepared.
- Full Text:
- Date Issued: 2018
- Authors: Kubheka, Gugu , Sanusi, Kayode , Mack, John , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/237938 , vital:50567 , xlink:href="https://doi.org/10.1016/j.saa.2017.10.021"
- Description: The optical limiting (OL) properties of 3,5-dipyrenylvinyleneBODIPY dyes that contain both electron withdrawing and donating moieties have been investigated by using the z-scan technique at 532 nm in the nanosecond pulse range. The extension of the π-conjugation at the 3,5-positions with pyrenylvinylene groups results in a ca. 200 nm red shift of the main BODIPY spectral band to ca. 700 nm, so there is relatively weak absorbance at 532 nm under ambient light conditions. Reverse saturable absorbance (RSA) profiles are observed in response to incident pulsed laser light that is consistent with a two photon absorption-assisted excited state absorption (ESA) mechanism in CH2Cl2 solution and when the dyes are embedded in poly(bisphenol carbonate A) (PBC) polymer thin films. This demonstrates that 3,5-divinyleneBODIPY dyes are potentially suitable for use in OL applications, since limiting threshold fluence (Ilim) values of below 0.95 J cm−2 are observed when thin films are prepared.
- Full Text:
- Date Issued: 2018