Photophysicochemical behaviour of phenoxy propanoic acid functionalised zinc phthalocyanines when grafted onto iron oxide and silica nanoparticles: Effects in photodynamic antimicrobial chemotherapy
- Dube, Edith, Soy, Rodath, Shumba, Mumyaradzi, Nyokong, Tebello
- Authors: Dube, Edith , Soy, Rodath , Shumba, Mumyaradzi , Nyokong, Tebello
- Date: 2021
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/185465 , vital:44389 , xlink:href="https://doi.org/10.1016/j.jlumin.2021.117939"
- Description: This work reports on the covalent linkage of (3-aminopropyl)triethoxysilane (APTES) functionalised iron oxide (IONPs–APTES) and silica (SiNPs–APTES) nanoparticles with zinc(II) tetra–([3–(4–phenoxy) propanoic acid) phthalocyanine] (1) and zinc(II) mono–([3–(4–phenoxy) propanoic acid) phthalocyanine (2) via an amide bond to form the conjugates, 1–IONPs-APTES, 1–SiNPs–APTES, 2-IONPs-APTES and 2-SiNPs-APTES). The photophysicochemical behaviour of the conjugates was investigated. These were characterized by a decrease in the fluorescence quantum yields and lifetimes, and an increase in the triplet quantum yield and singlet oxygen quantum yield when compared to complex 1 and 2 alone. The conjugates to IONPs-APTES displayed higher ΦT than those of SiNPs-APTES probably due to the heavy atom effect of iron compared to silica and the high loading capacity of the relatively smaller iron oxide NPs, however, there was no significant difference in the ΦΔ values of 2-IONPs-APTES (ΦΔ=0.59) and 2-SiNPs-APTES (ΦΔ=0.58), suggesting that the energy transfer process between the excited triplet state of 2-IONPs-APTES and ground state molecular oxygen was not effective. Photodynamic antimicrobial chemotherapy (PACT) studies showed that linkage of Pcs to NPs improves their photoinactivation capability against Staphylococcus aureus and Escherichia coli. IONPs-APTES and its conjugates generally displayed the highest log reductions than SiNPs-APTES and its conjugates except for studies after 75 min of irradiation for S. Aureus where the log reductions are the same. 2-IONP-APTES was recovered using a magnet after each photodegradation cycle and its stability after 3 cycles confirmed re-usability.
- Full Text:
- Date Issued: 2021
- Authors: Dube, Edith , Soy, Rodath , Shumba, Mumyaradzi , Nyokong, Tebello
- Date: 2021
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/185465 , vital:44389 , xlink:href="https://doi.org/10.1016/j.jlumin.2021.117939"
- Description: This work reports on the covalent linkage of (3-aminopropyl)triethoxysilane (APTES) functionalised iron oxide (IONPs–APTES) and silica (SiNPs–APTES) nanoparticles with zinc(II) tetra–([3–(4–phenoxy) propanoic acid) phthalocyanine] (1) and zinc(II) mono–([3–(4–phenoxy) propanoic acid) phthalocyanine (2) via an amide bond to form the conjugates, 1–IONPs-APTES, 1–SiNPs–APTES, 2-IONPs-APTES and 2-SiNPs-APTES). The photophysicochemical behaviour of the conjugates was investigated. These were characterized by a decrease in the fluorescence quantum yields and lifetimes, and an increase in the triplet quantum yield and singlet oxygen quantum yield when compared to complex 1 and 2 alone. The conjugates to IONPs-APTES displayed higher ΦT than those of SiNPs-APTES probably due to the heavy atom effect of iron compared to silica and the high loading capacity of the relatively smaller iron oxide NPs, however, there was no significant difference in the ΦΔ values of 2-IONPs-APTES (ΦΔ=0.59) and 2-SiNPs-APTES (ΦΔ=0.58), suggesting that the energy transfer process between the excited triplet state of 2-IONPs-APTES and ground state molecular oxygen was not effective. Photodynamic antimicrobial chemotherapy (PACT) studies showed that linkage of Pcs to NPs improves their photoinactivation capability against Staphylococcus aureus and Escherichia coli. IONPs-APTES and its conjugates generally displayed the highest log reductions than SiNPs-APTES and its conjugates except for studies after 75 min of irradiation for S. Aureus where the log reductions are the same. 2-IONP-APTES was recovered using a magnet after each photodegradation cycle and its stability after 3 cycles confirmed re-usability.
- Full Text:
- Date Issued: 2021
Effect of gold nanoparticle shape on the photophysicochemical properties of sulphur containing metallophthalocyanines
- Dube, Edith, Nyokong, Tebello
- Authors: Dube, Edith , Nyokong, Tebello
- Date: 2019
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187048 , vital:44559 , xlink:href="https://doi.org/10.1016/j.molstruc.2018.12.091"
- Description: In this work tetrakise[(thiopheneethoxy) phthalocyaninato] zinc(II) (1), tetrakise[(thiopheneethoxy) phthalocyaninato] indium (II) chloride (2), tetrakis [(benzo [d]thiazol-2-yl phenoxy) phthalocyaninato] zinc(II) (3), and tetrakis [(benzo [d]thiazol-2-yl phenoxy)phthalocyaninato] indium (II) chloride (4) were linked to both gold nanospheres (AuNSs) and gold nanotriangles (AuNTs) via Au-S and Au-N (the latter for complexes 3 and 4 only) self assembly. The photophysicochemical behaviour of complexes and their conjugates were studied. The conjugates yielded improved triplet and singlet quantum yields, with nanospheres displaying better properties than nanotriangles. The conjugates with a benzothiazole phenoxy substituent also yielded better properties than their thiophene ethoxy counterpart. These conjugates especially those with a benzothiazole phenoxy substituent have potential as photosensitisers for photodynamic therapy applications.
- Full Text:
- Date Issued: 2019
- Authors: Dube, Edith , Nyokong, Tebello
- Date: 2019
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187048 , vital:44559 , xlink:href="https://doi.org/10.1016/j.molstruc.2018.12.091"
- Description: In this work tetrakise[(thiopheneethoxy) phthalocyaninato] zinc(II) (1), tetrakise[(thiopheneethoxy) phthalocyaninato] indium (II) chloride (2), tetrakis [(benzo [d]thiazol-2-yl phenoxy) phthalocyaninato] zinc(II) (3), and tetrakis [(benzo [d]thiazol-2-yl phenoxy)phthalocyaninato] indium (II) chloride (4) were linked to both gold nanospheres (AuNSs) and gold nanotriangles (AuNTs) via Au-S and Au-N (the latter for complexes 3 and 4 only) self assembly. The photophysicochemical behaviour of complexes and their conjugates were studied. The conjugates yielded improved triplet and singlet quantum yields, with nanospheres displaying better properties than nanotriangles. The conjugates with a benzothiazole phenoxy substituent also yielded better properties than their thiophene ethoxy counterpart. These conjugates especially those with a benzothiazole phenoxy substituent have potential as photosensitisers for photodynamic therapy applications.
- Full Text:
- Date Issued: 2019
Effect of gold nanoparticles shape and size on the photophysicochemical behaviour of symmetric and asymmetric zinc phthalocyanines
- Dube, Edith, Nyokong, Tebello
- Authors: Dube, Edith , Nyokong, Tebello
- Date: 2019
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187569 , vital:44672 , xlink:href="https://doi.org/10.1016/j.jlumin.2018.09.063"
- Description: Glutathione (GSH) capped Au nanotriangles (AuNTs–GSH) and nanospheres (AuNSs–GSH) are covalently linked to symmetric Zn phthalocyanine (ZnPc) substituted with phenoxy propanoic acid substituents only (complex 1) and two asymmetric ZnPc, each containing one phenoxy propanoic acid and three benzothiazole phenoxy moieties (complex 2), and one phenoxy propanoic acid and no other ligands (complex 3). The photophysicochemical behaviour of Pc complexes and their conjugates were studied. All conjugates displayed improved triplet and singlet oxygen quantum yields with decreases in fluorescence quantum yields compared to their respective Pc complexes. The conjugates of asymmetric complexes 2 and 3, afforded much higher triplet and singlet oxygen quantum yields compared to the symmetric complex 1, and could serve as good candidates for photodynamic therapy
- Full Text:
- Date Issued: 2019
- Authors: Dube, Edith , Nyokong, Tebello
- Date: 2019
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187569 , vital:44672 , xlink:href="https://doi.org/10.1016/j.jlumin.2018.09.063"
- Description: Glutathione (GSH) capped Au nanotriangles (AuNTs–GSH) and nanospheres (AuNSs–GSH) are covalently linked to symmetric Zn phthalocyanine (ZnPc) substituted with phenoxy propanoic acid substituents only (complex 1) and two asymmetric ZnPc, each containing one phenoxy propanoic acid and three benzothiazole phenoxy moieties (complex 2), and one phenoxy propanoic acid and no other ligands (complex 3). The photophysicochemical behaviour of Pc complexes and their conjugates were studied. All conjugates displayed improved triplet and singlet oxygen quantum yields with decreases in fluorescence quantum yields compared to their respective Pc complexes. The conjugates of asymmetric complexes 2 and 3, afforded much higher triplet and singlet oxygen quantum yields compared to the symmetric complex 1, and could serve as good candidates for photodynamic therapy
- Full Text:
- Date Issued: 2019
Photophysicochemical and photodynamic therapy properties of metallophthalocyanines linked to gold speckled silica nanoparticles
- Dube, Edith, Oluwole, David O, Niemuwa, Nwaji, Prinsloo, Earl, Nyokong, Tebello
- Authors: Dube, Edith , Oluwole, David O , Niemuwa, Nwaji , Prinsloo, Earl , Nyokong, Tebello
- Date: 2019
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187472 , vital:44657 , xlink:href="https://doi.org/10.1016/j.pdpdt.2019.01.019"
- Description: This work reports on the linkage of 2(3),9(10),16(17),23(24) tetrakis [(benzo[d]thiazol-2-yl phenoxy) phthalocyaninato] zinc(II) (1) and indium(III) chloride (2) to gold speckled silica (GSS) nanoparticles via gold to sulphur (Au-S) and gold to nitrogen (Au-N) self-assembly to form the conjugates: 1-GSS and 2-GSS. The formed conjugates were characterized using microscopic and spectroscopic techniques, and the photophysicochemical properties and photodynamic therapy (PDT) activity against human breast adenocarcinoma cell line (MCF-7 cells) were studied. The conjugates afforded decrease in fluorescence quantum yields with corresponding increase in triplet and singlet oxygen quantum yields when compared to phthalocyanines alone. Singlet oxygen is cytotoxic to cancer cells hence it is important for PDT. The in vitro dark toxicity of complex 2 and 2-GSS against MCF–7 cells showed ≥93% viable cells within concentration ranges of 10–160 μg/mL. 2–GSS showed enhanced PDT activity with less than 50% viable cells at 80 μg/mL as compared to 2 and GSS alone which showed > 60% viable cells within 10–160 μg/mL. The observed improvements in the PDT activity of 2-GSS could be attributed to the high singlet oxygen generation of 2-GSS compared to 2 alone in addition to the phototoxicity of GSS.
- Full Text:
- Date Issued: 2019
- Authors: Dube, Edith , Oluwole, David O , Niemuwa, Nwaji , Prinsloo, Earl , Nyokong, Tebello
- Date: 2019
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187472 , vital:44657 , xlink:href="https://doi.org/10.1016/j.pdpdt.2019.01.019"
- Description: This work reports on the linkage of 2(3),9(10),16(17),23(24) tetrakis [(benzo[d]thiazol-2-yl phenoxy) phthalocyaninato] zinc(II) (1) and indium(III) chloride (2) to gold speckled silica (GSS) nanoparticles via gold to sulphur (Au-S) and gold to nitrogen (Au-N) self-assembly to form the conjugates: 1-GSS and 2-GSS. The formed conjugates were characterized using microscopic and spectroscopic techniques, and the photophysicochemical properties and photodynamic therapy (PDT) activity against human breast adenocarcinoma cell line (MCF-7 cells) were studied. The conjugates afforded decrease in fluorescence quantum yields with corresponding increase in triplet and singlet oxygen quantum yields when compared to phthalocyanines alone. Singlet oxygen is cytotoxic to cancer cells hence it is important for PDT. The in vitro dark toxicity of complex 2 and 2-GSS against MCF–7 cells showed ≥93% viable cells within concentration ranges of 10–160 μg/mL. 2–GSS showed enhanced PDT activity with less than 50% viable cells at 80 μg/mL as compared to 2 and GSS alone which showed > 60% viable cells within 10–160 μg/mL. The observed improvements in the PDT activity of 2-GSS could be attributed to the high singlet oxygen generation of 2-GSS compared to 2 alone in addition to the phototoxicity of GSS.
- Full Text:
- Date Issued: 2019
Physicochemical properties and photodynamic therapy activities of indium and zinc phthalocyanine-nanoparticle conjugates
- Authors: Dube, Edith
- Date: 2019
- Subjects: Indium , Zinc , Phthalocyanines , Breast -- Cancer -- Photochemotherapy , Nanoparticles
- Language: English
- Type: text , Thesis , Doctoral , PhD
- Identifier: http://hdl.handle.net/10962/76506 , vital:30589
- Description: The syntheses and characterization of symmetric and asymmetric Pcs functionalized at the peripheral position are reported. The Pcs contain either zinc or indium as central metals and have carboxyphenoxy, phenoxy propanoic acid, benzothiazole phenoxy, thiophine ethoxy or di-O-isopropylidene-α-D-glucopyranose as ring substituents. The Pcs were linked to NPs via an amide bond or through self-assembly. The photophysics and photochemistry of the Pcs were assessed when alone and with conjugates. All the studied Pcs showed good photophysicochemical behaviour with relatively high triplet and singlet oxygen quantum yields corresponding to their low fluorescence quantum yield. The Pcs with indium in their central cavity exhibited higher triplet and singlet oxygen quantum yields in comparison to their zinc counterparts due to the heavy–atom effect obtained from the former. Asymmetrical Pcs displayed higher triplet and singlet oxygen quantum yields than their symmetrical counterparts. The triplet quantum yield, generally increased on linkage to nanoparticles (NPs) due to the heavy–atom effect of gold and silver in NPs. The conjugates to gold nanospheres yielded higher triplet and singlet quantum yields than their gold nanotriangles counterparts due to the higher loading by the former probably encouraged by their relatively small particle size. The in vitro dark cytotoxicity and photodynamic therapy of selected Pc complexes and conjugates against MCF-7 cells was tested. All studied Pc complexes and conjugates showed minimum dark toxicity making them applicable for PDT. All complexes displayed poor phototoxicity with >50Îll viability at concentrations≤ 160μg/mL, however the conjugates showed<50% cell viabilityatconcentrations≤ 160μg/mLprobably due to the enhanced singlet oxygen quantum yield. The findings from this work show the importance of linking photosensitises such as phthalocyanines to metal nanoparticles for the enhancement ofsinglet oxygen quantum yield and ultimately the photodynamic effect.
- Full Text:
- Date Issued: 2019
- Authors: Dube, Edith
- Date: 2019
- Subjects: Indium , Zinc , Phthalocyanines , Breast -- Cancer -- Photochemotherapy , Nanoparticles
- Language: English
- Type: text , Thesis , Doctoral , PhD
- Identifier: http://hdl.handle.net/10962/76506 , vital:30589
- Description: The syntheses and characterization of symmetric and asymmetric Pcs functionalized at the peripheral position are reported. The Pcs contain either zinc or indium as central metals and have carboxyphenoxy, phenoxy propanoic acid, benzothiazole phenoxy, thiophine ethoxy or di-O-isopropylidene-α-D-glucopyranose as ring substituents. The Pcs were linked to NPs via an amide bond or through self-assembly. The photophysics and photochemistry of the Pcs were assessed when alone and with conjugates. All the studied Pcs showed good photophysicochemical behaviour with relatively high triplet and singlet oxygen quantum yields corresponding to their low fluorescence quantum yield. The Pcs with indium in their central cavity exhibited higher triplet and singlet oxygen quantum yields in comparison to their zinc counterparts due to the heavy–atom effect obtained from the former. Asymmetrical Pcs displayed higher triplet and singlet oxygen quantum yields than their symmetrical counterparts. The triplet quantum yield, generally increased on linkage to nanoparticles (NPs) due to the heavy–atom effect of gold and silver in NPs. The conjugates to gold nanospheres yielded higher triplet and singlet quantum yields than their gold nanotriangles counterparts due to the higher loading by the former probably encouraged by their relatively small particle size. The in vitro dark cytotoxicity and photodynamic therapy of selected Pc complexes and conjugates against MCF-7 cells was tested. All studied Pc complexes and conjugates showed minimum dark toxicity making them applicable for PDT. All complexes displayed poor phototoxicity with >50Îll viability at concentrations≤ 160μg/mL, however the conjugates showed<50% cell viabilityatconcentrations≤ 160μg/mLprobably due to the enhanced singlet oxygen quantum yield. The findings from this work show the importance of linking photosensitises such as phthalocyanines to metal nanoparticles for the enhancement ofsinglet oxygen quantum yield and ultimately the photodynamic effect.
- Full Text:
- Date Issued: 2019
A gold–chitosan composite with low symmetry zinc phthalocyanine for enhanced singlet oxygen generation and improved photodynamic therapy activity
- Dube, Edith, Oluwole, David O, Prinsloo, Earl, Nyokong, Tebello
- Authors: Dube, Edith , Oluwole, David O , Prinsloo, Earl , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/233397 , vital:50087 , xlink:href="https://doi.org/10.1039/C8NJ00801A"
- Description: Novel zinc(II) 3-(4-((3,17,23-tris(4-(benzo[d]thiazol-2-yl)phenoxy)phthalocyanine-9-yl)oxy)phenyl)propanoic acid (complex 3) was synthesised. Complex 3 was subsequently reacted with gold nanoparticles (AuNPs), chitosan (CT) and a gold–chitosan (AuCT) hybrid to form 3-AuNPs, 3-CT and 3-AuCT, respectively. The conjugates afforded a decrease in fluorescence quantum yield with a corresponding increase in the triplet and singlet quantum yields compared to complex 3. The in vitro dark cytotoxicity and photodynamic therapy activity (PDT) of complex 3 and 3-AuCT composites were investigated against epithelial breast cancer cells (MCF-7) with both the samples showing minimum dark cytotoxicity. They both accounted for a cell viability of ≥90% at a concentration of ≤59.2 μg mL−1. 3-AuCT showed better PDT activity (compared to 3 alone) with less than 50% viable cells at a concentration of ≥29.6 μg mL−1 making it potentially applicable for PDT. On the other hand, AuCT displayed some activity against cancer cells, probably due to photothermal activity since gold is a light absorber, however it had more than 50% viable cells at a concentration of ≤59.2 μg mL−1.
- Full Text:
- Date Issued: 2018
- Authors: Dube, Edith , Oluwole, David O , Prinsloo, Earl , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/233397 , vital:50087 , xlink:href="https://doi.org/10.1039/C8NJ00801A"
- Description: Novel zinc(II) 3-(4-((3,17,23-tris(4-(benzo[d]thiazol-2-yl)phenoxy)phthalocyanine-9-yl)oxy)phenyl)propanoic acid (complex 3) was synthesised. Complex 3 was subsequently reacted with gold nanoparticles (AuNPs), chitosan (CT) and a gold–chitosan (AuCT) hybrid to form 3-AuNPs, 3-CT and 3-AuCT, respectively. The conjugates afforded a decrease in fluorescence quantum yield with a corresponding increase in the triplet and singlet quantum yields compared to complex 3. The in vitro dark cytotoxicity and photodynamic therapy activity (PDT) of complex 3 and 3-AuCT composites were investigated against epithelial breast cancer cells (MCF-7) with both the samples showing minimum dark cytotoxicity. They both accounted for a cell viability of ≥90% at a concentration of ≤59.2 μg mL−1. 3-AuCT showed better PDT activity (compared to 3 alone) with less than 50% viable cells at a concentration of ≥29.6 μg mL−1 making it potentially applicable for PDT. On the other hand, AuCT displayed some activity against cancer cells, probably due to photothermal activity since gold is a light absorber, however it had more than 50% viable cells at a concentration of ≤59.2 μg mL−1.
- 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
Improved Photophysical and Photochemical Properties of Thiopheneethoxy Substituted Metallophthalocyanines on Immobilization onto Gold‐speckled Silica Nanoparticles
- Dube, Edith, Oluwole, David O, Nyokong, Tebello
- Authors: Dube, Edith , Oluwole, David O , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187699 , vital:44688 , xlink:href="https://doi.org/10.1111/php.12879"
- Description: This work reports on the synthesis of tetrakis-[(thiophineethoxy) phthalocyaninato] indium(II) chloride (3). The photophysical behavior of complex 3 was compared to that of the Zn derivative (tetrakis-[(thiophineethoxy) phthalocyaninato] zinc(II) (complex 2)). The compounds were interacted with gold-speckled silica (GSS) nanoparticles via Au–S self assembly to afford the conjugates (2–GSS and 3–GSS). The photophysicochemical behavior of the compounds and their conjugates were assessed. The conjugates afforded a decrease in fluorescence quantum yields and lifetimes with improved triplet and singlet oxygen quantum yields in comparison with complexes 2 and 3 alone. The complexes and their conjugates could serve as good candidates for photodynamic therapy.
- Full Text:
- Date Issued: 2018
- Authors: Dube, Edith , Oluwole, David O , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187699 , vital:44688 , xlink:href="https://doi.org/10.1111/php.12879"
- Description: This work reports on the synthesis of tetrakis-[(thiophineethoxy) phthalocyaninato] indium(II) chloride (3). The photophysical behavior of complex 3 was compared to that of the Zn derivative (tetrakis-[(thiophineethoxy) phthalocyaninato] zinc(II) (complex 2)). The compounds were interacted with gold-speckled silica (GSS) nanoparticles via Au–S self assembly to afford the conjugates (2–GSS and 3–GSS). The photophysicochemical behavior of the compounds and their conjugates were assessed. The conjugates afforded a decrease in fluorescence quantum yields and lifetimes with improved triplet and singlet oxygen quantum yields in comparison with complexes 2 and 3 alone. The complexes and their conjugates could serve as good candidates for photodynamic therapy.
- Full Text:
- Date Issued: 2018
Novel nano-dyad of homoleptic sandwich-type phthalocyanines with nitrogen doped graphene quantum dots for nonlinear optics
- Oluwole, David O, Nwaji, Njemuwa, Nene, Lindokuhle C, Mokone, Lesedi, Dube, Edith, Nyokong, Tebello
- Authors: Oluwole, David O , Nwaji, Njemuwa , Nene, Lindokuhle C , Mokone, Lesedi , Dube, Edith , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/233386 , vital:50086 , xlink:href="https://doi.org/10.1039/C8NJ01707G"
- Description: The syntheses of neodymium(III) 2,9,16,23-tetrakis-(2,6-di-tert-butyl-4-methylphenoxy)phthalocyanine (2), bis europium(III) 2,9,16,23-tetrakis-(2,6-di-tert-butyl-4-methylphenoxy)phthalocyanine (3), bis dysprosium(III) 2,9,16,23-tetrakis-(2,6-di-tert-butyl-4-methylphenoxy)phthalocyanine (4) and their conjugated analogues with nitrogen doped quantum dots (NGQDs) are reported herein. The optical nonlinearity of the sandwich-type phthalocyanine complexes and their conjugates with NGQDs were studied in dimethyl sulfoxide using the open aperture Z-scan technique at an excitation wavelength of 532 nm with a 10 ns pulse. The nonlinear absorption coefficient (βeff) value of the samples ranges from 15 cm GW−1 to 89.6 cm GW−1. Complex 4 and its conjugates afforded a strong optical limiting behaviour compared to the other samples. These fabricated complexes and their conjugates with NGQDs could serve as a plausible nonlinear optical (NLO) material due to their fascinating NLO properties.
- Full Text:
- Date Issued: 2018
- Authors: Oluwole, David O , Nwaji, Njemuwa , Nene, Lindokuhle C , Mokone, Lesedi , Dube, Edith , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/233386 , vital:50086 , xlink:href="https://doi.org/10.1039/C8NJ01707G"
- Description: The syntheses of neodymium(III) 2,9,16,23-tetrakis-(2,6-di-tert-butyl-4-methylphenoxy)phthalocyanine (2), bis europium(III) 2,9,16,23-tetrakis-(2,6-di-tert-butyl-4-methylphenoxy)phthalocyanine (3), bis dysprosium(III) 2,9,16,23-tetrakis-(2,6-di-tert-butyl-4-methylphenoxy)phthalocyanine (4) and their conjugated analogues with nitrogen doped quantum dots (NGQDs) are reported herein. The optical nonlinearity of the sandwich-type phthalocyanine complexes and their conjugates with NGQDs were studied in dimethyl sulfoxide using the open aperture Z-scan technique at an excitation wavelength of 532 nm with a 10 ns pulse. The nonlinear absorption coefficient (βeff) value of the samples ranges from 15 cm GW−1 to 89.6 cm GW−1. Complex 4 and its conjugates afforded a strong optical limiting behaviour compared to the other samples. These fabricated complexes and their conjugates with NGQDs could serve as a plausible nonlinear optical (NLO) material due to their fascinating NLO properties.
- 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
The photophysicochemical behavior of symmetric and asymmetric zinc phthalocyanines, surface assembled onto gold nanotriangles
- Dube, Edith, Nwaji, Njemuwa, Mack, John, Nyokong, Tebello
- Authors: Dube, Edith , Nwaji, Njemuwa , Mack, John , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/233310 , vital:50079 , xlink:href="https://doi.org/10.1039/C8NJ02746C"
- Description: The synthesis of a novel asymmetric phthalocyanine, (4-(4-(benzo[d]thiazol-2-yl)phenoxy)-2,10,17-tris(4-(2-carboxyethyl)phenoxy)phthalocyaninatol)zinc(II), complex 3, is reported. Complex 3 together with the previously reported complexes tetrakis[(benzo[d]thiazol-2-yl phenoxy)phthalocyaninato]zinc(II) (4) and 3-(4-((3,17,23-tris(4-(benzo[d]thiazol-2-yl)phenoxy)phthalocyaninatol)oxy)phenyl)propanoic acid zinc(II) (5), were linked to gold nanotriangles (AuNTs) through S–Au/Au–N self-assembly to afford the conjugates (3-AuNTs, 4-AuNTs and 5-AuNTs). The photophysicochemical behaviour of the complexes and their conjugates were studied. The asymmetric complexes 3 and 5, displayed improved triplet and singlet oxygen quantum yields compared to the symmetric complex 4, while all conjugates displayed improved triplet and singlet oxygen quantum yields compared to their respective complexes alone. The complexes and their conjugates could serve as good candidates for photodynamic therapy.
- Full Text:
- Date Issued: 2018
- Authors: Dube, Edith , Nwaji, Njemuwa , Mack, John , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/233310 , vital:50079 , xlink:href="https://doi.org/10.1039/C8NJ02746C"
- Description: The synthesis of a novel asymmetric phthalocyanine, (4-(4-(benzo[d]thiazol-2-yl)phenoxy)-2,10,17-tris(4-(2-carboxyethyl)phenoxy)phthalocyaninatol)zinc(II), complex 3, is reported. Complex 3 together with the previously reported complexes tetrakis[(benzo[d]thiazol-2-yl phenoxy)phthalocyaninato]zinc(II) (4) and 3-(4-((3,17,23-tris(4-(benzo[d]thiazol-2-yl)phenoxy)phthalocyaninatol)oxy)phenyl)propanoic acid zinc(II) (5), were linked to gold nanotriangles (AuNTs) through S–Au/Au–N self-assembly to afford the conjugates (3-AuNTs, 4-AuNTs and 5-AuNTs). The photophysicochemical behaviour of the complexes and their conjugates were studied. The asymmetric complexes 3 and 5, displayed improved triplet and singlet oxygen quantum yields compared to the symmetric complex 4, while all conjugates displayed improved triplet and singlet oxygen quantum yields compared to their respective complexes alone. The complexes and their conjugates could serve as good candidates for photodynamic therapy.
- Full Text:
- Date Issued: 2018
Investigation of photophysicochemical properties of zinc phthalocyanines conjugated to metallic nanoparticles
- Dube, Edith, Nwaji, Njemuwa, Oluwole, David O, Mack, John, Nyokong, Tebello
- Authors: Dube, Edith , Nwaji, Njemuwa , Oluwole, David O , Mack, John , Nyokong, Tebello
- Date: 2017
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/233425 , vital:50089 , xlink:href="https://doi.org/10.1016/j.jphotochem.2017.09.020"
- Description: The syntheses of zinc(II) tetra–[3–(4–phenoxy) (propanoic acid) phthalocyanine] (2) and zinc(II) mono–[3–(4–phenoxy) (propanoic acid) phthalocyanine (3) are reported in this work. Compounds 2 and 3 were covalently linked to glutathione capped silver (AgNPs–GSH), gold (AuNPs–GSH) and silver-gold alloy (Ag3Au1NPs–GSH) nanoparticles (NPs) via an amide bond formation to afford the conjugates: 2–AgNPs–GSH, 3–AgNPs–GSH, 2–AuNPs–GSH, 3–AuNPs–GSH, 2-Ag3Au1NPs–GSH and 3-Ag3Au1NPs–GSH. The photophysicochemical behaviours of the compounds and their conjugates with NPs were assessed in solution. The conjugates afforded a decrease in fluorescence quantum yields and lifetimes with improved triplet quantum yields in comparison to the compounds. Accordingly, the AgNPs and AuNPs conjugates with the compounds afforded high singlet quantum yields. On the contrary, the conjugates of the alloy afforded decreased singlet quantum yields probably due to the screening effect. The compounds and their conjugates with NPs could serve as a viable and efficacious photosensitizer for photodynamic therapy.
- Full Text:
- Date Issued: 2017
- Authors: Dube, Edith , Nwaji, Njemuwa , Oluwole, David O , Mack, John , Nyokong, Tebello
- Date: 2017
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/233425 , vital:50089 , xlink:href="https://doi.org/10.1016/j.jphotochem.2017.09.020"
- Description: The syntheses of zinc(II) tetra–[3–(4–phenoxy) (propanoic acid) phthalocyanine] (2) and zinc(II) mono–[3–(4–phenoxy) (propanoic acid) phthalocyanine (3) are reported in this work. Compounds 2 and 3 were covalently linked to glutathione capped silver (AgNPs–GSH), gold (AuNPs–GSH) and silver-gold alloy (Ag3Au1NPs–GSH) nanoparticles (NPs) via an amide bond formation to afford the conjugates: 2–AgNPs–GSH, 3–AgNPs–GSH, 2–AuNPs–GSH, 3–AuNPs–GSH, 2-Ag3Au1NPs–GSH and 3-Ag3Au1NPs–GSH. The photophysicochemical behaviours of the compounds and their conjugates with NPs were assessed in solution. The conjugates afforded a decrease in fluorescence quantum yields and lifetimes with improved triplet quantum yields in comparison to the compounds. Accordingly, the AgNPs and AuNPs conjugates with the compounds afforded high singlet quantum yields. On the contrary, the conjugates of the alloy afforded decreased singlet quantum yields probably due to the screening effect. The compounds and their conjugates with NPs could serve as a viable and efficacious photosensitizer for photodynamic therapy.
- Full Text:
- Date Issued: 2017
Photophysicochemical behaviour of anionic indium phthalocyanine when grafted onto AgxAuy and porous silica nanoparticles
- Dube, Edith, Oluwole, David O, Nyokong, Tebello
- Authors: Dube, Edith , Oluwole, David O , Nyokong, Tebello
- Date: 2017
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/188899 , vital:44796 , xlink:href="https://doi.org/10.1016/j.jlumin.2017.05.071"
- Description: This work reports on the synthesis of glutathione functionalised Ag3Au1 (Ag rich alloy, denoted as AgAu) and Ag1Au3 (Au rich alloy – denoted as AuAg) nano alloys as well as aminopropyl triethoxylsilane capped Ag1Au3 doped silica nanoparticles (NPs). The NPs were covalently linked to indium(III) chloride 2,9(10),16(17),23(24)–tetra–(3–carboxyphenoxy)phthalocyanine (1) via amide bond to form 1–AgAuNPs–GSH and 1–AuAgNPs–GSH. The AgAuNPs were also doped into aminopropyl triethoxylsilane (APTES) silica NPs (SiNPs-APTES) followed by linkage to complex 1 to form 1–AgAu-SiNPs–APTES. The photophysicochemical behaviour of complex 1 and its nanoconjugates were investigated. Decrease in the fluorescence quantum yields and lifetimes was observed in the conjugates in comparison to 1 alone. The singlet oxygen quantum yield for 1–AgAuNPs–GSH and 1–AuAgNPs–GSH decreased probably due to the screening effect caused by the NPs, while that of 1–AgAu-SiNPs–APTES increased in dimethylsulfoxide probably due to the permeability of the porous silica matrix to molecular oxygen.
- Full Text:
- Date Issued: 2017
- Authors: Dube, Edith , Oluwole, David O , Nyokong, Tebello
- Date: 2017
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/188899 , vital:44796 , xlink:href="https://doi.org/10.1016/j.jlumin.2017.05.071"
- Description: This work reports on the synthesis of glutathione functionalised Ag3Au1 (Ag rich alloy, denoted as AgAu) and Ag1Au3 (Au rich alloy – denoted as AuAg) nano alloys as well as aminopropyl triethoxylsilane capped Ag1Au3 doped silica nanoparticles (NPs). The NPs were covalently linked to indium(III) chloride 2,9(10),16(17),23(24)–tetra–(3–carboxyphenoxy)phthalocyanine (1) via amide bond to form 1–AgAuNPs–GSH and 1–AuAgNPs–GSH. The AgAuNPs were also doped into aminopropyl triethoxylsilane (APTES) silica NPs (SiNPs-APTES) followed by linkage to complex 1 to form 1–AgAu-SiNPs–APTES. The photophysicochemical behaviour of complex 1 and its nanoconjugates were investigated. Decrease in the fluorescence quantum yields and lifetimes was observed in the conjugates in comparison to 1 alone. The singlet oxygen quantum yield for 1–AgAuNPs–GSH and 1–AuAgNPs–GSH decreased probably due to the screening effect caused by the NPs, while that of 1–AgAu-SiNPs–APTES increased in dimethylsulfoxide probably due to the permeability of the porous silica matrix to molecular oxygen.
- Full Text:
- Date Issued: 2017
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