Low-Symmetry Phthalocyanines Bearing Carboxy-Groups
- Bunin, Dmitry A, Ndebele, Nobuhle, Martynov, Alexander G, Mack, John, Gorbunova, Yulia G, Nyokong, Tebello
- Authors: Bunin, Dmitry A , Ndebele, Nobuhle , Martynov, Alexander G , Mack, John , Gorbunova, Yulia G , Nyokong, Tebello
- Date: 2022
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/231262 , vital:49870 , xlink:href="https://doi.org/10.3390/molecules27020524" "
- Description: The synthesis and characterization of A3B-type phthalocyanines, ZnPc1–4, bearing bulky 2,6-diisopropylphenoxy-groups or chlorine atoms on isoindoline units “A” and either one or two carboxylic anchors on isoindoline unit “B” are reported. A comparison of molecular modelling with the conventional time dependent—density functional theory (TD-DFT) approach and its simplified sTD-DFT approximation provides further evidence that the latter method accurately reproduces the key trends in the spectral properties, providing colossal savings in computer time for quite large molecules. This demonstrates that it is a valuable tool for guiding the rational design of new phthalocyanines for practical applications.
- Full Text:
- Authors: Bunin, Dmitry A , Ndebele, Nobuhle , Martynov, Alexander G , Mack, John , Gorbunova, Yulia G , Nyokong, Tebello
- Date: 2022
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/231262 , vital:49870 , xlink:href="https://doi.org/10.3390/molecules27020524" "
- Description: The synthesis and characterization of A3B-type phthalocyanines, ZnPc1–4, bearing bulky 2,6-diisopropylphenoxy-groups or chlorine atoms on isoindoline units “A” and either one or two carboxylic anchors on isoindoline unit “B” are reported. A comparison of molecular modelling with the conventional time dependent—density functional theory (TD-DFT) approach and its simplified sTD-DFT approximation provides further evidence that the latter method accurately reproduces the key trends in the spectral properties, providing colossal savings in computer time for quite large molecules. This demonstrates that it is a valuable tool for guiding the rational design of new phthalocyanines for practical applications.
- Full Text:
Photodynamic therapy activity of 5, 10, 15-tris (5-bromo-2-thienyl), 20 (phenylcarboxy) porphyrin conjugated to graphene quantum dot against MCF-7 breast cancer cells
- Makola, Lekgowa Collen, Nwahahra, Nnamdi, Managa, Muthumuni, Nyokong, Tebello
- Authors: Makola, Lekgowa Collen , Nwahahra, Nnamdi , Managa, Muthumuni , Nyokong, Tebello
- Date: 2022
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/300244 , vital:57909 , xlink:href="https://doi.org/10.1080/00958972.2022.2087515"
- Description: A novel 5,10,15-tris(5-bromo-2-thienyl),20(phenylcarboxy)porphyrin and its gallium derivative have been synthesized and fully characterized by various spectroscopic techniques and their respective photophysical and photochemical properties, such as the singlet oxygen quantum yield (ΦΔ), fluorescence quantum yield (ΦF) and triplet lifetime (τT) were determined. The complexes were conjugated to PEI_GQDs resulting is stable conjugates, owing to strong π–π stacking interaction between the PEI_GQDs and the porphyrins. PDT studies were carried out on these nanoconjugates and results obtained indicated they are suitable candidates for further in-depth PDT studies.
- Full Text:
- Authors: Makola, Lekgowa Collen , Nwahahra, Nnamdi , Managa, Muthumuni , Nyokong, Tebello
- Date: 2022
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/300244 , vital:57909 , xlink:href="https://doi.org/10.1080/00958972.2022.2087515"
- Description: A novel 5,10,15-tris(5-bromo-2-thienyl),20(phenylcarboxy)porphyrin and its gallium derivative have been synthesized and fully characterized by various spectroscopic techniques and their respective photophysical and photochemical properties, such as the singlet oxygen quantum yield (ΦΔ), fluorescence quantum yield (ΦF) and triplet lifetime (τT) were determined. The complexes were conjugated to PEI_GQDs resulting is stable conjugates, owing to strong π–π stacking interaction between the PEI_GQDs and the porphyrins. PDT studies were carried out on these nanoconjugates and results obtained indicated they are suitable candidates for further in-depth PDT studies.
- Full Text:
Electrocatalytic Activity of Cobalt Phthalocyanines Revisited: Effect of the Number of Oxygen Atoms and Conjugation to Carbon Nanomaterials
- Ndebele, Nobuhle, Mgidlana, Sithi, Nyokong, Tebello
- Authors: Ndebele, Nobuhle , Mgidlana, Sithi , Nyokong, Tebello
- Date: 2021
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/185700 , vital:44416 , xlink:href="https://doi.org/10.1007/s12678-021-00670-x"
- Description: The synthesis and characterization of tetrakis[4(4-acetlyphenoxy)phthalocyanato] cobalt (II) (1) are presented. Complex 1 together with the reported tetrakis dimethyl 5-(phenoxy)-isophthalatephthalocyaninato] cobalt (II) (2) are conjugated to carbon-based nanomaterials: graphene quantum dots (GQDs) and single-walled carbon nanotubes (SWCNTs) via π-π stacking, taking advantage of the π electrons on the graphitic structure of the nanomaterial as well as on the aromatic rings of the Co phthalocyanines (CoPcs). The electrocatalytic behaviour of the CoPcs, GQDs, SWCNTs and their respective conjugates towards the electrochemical oxidation of catechol was studied. The electrocatalytic probes were drop-dried onto the electrode surface of the glassy carbon electrode (GCE). The electrochemical oxidation of catechol was studied using cyclic voltammetry, electrochemical impedance spectroscopy and chronoamperometry. Complex 2 when linked to GQDs gave the lowest oxidation peak potentials of 0.33 V. Low catechol detection limits (LOD) of 0.057 µM was obtained for complex 2 with SWCNT. Thus, complex 2 containing more oxygen atoms outperformed complex 1 with less oxygen atoms. The CoPcs on their own showed moderate electrocatalytic behaviour, hence showing the importance of conjugating them to the carbon nanomaterials. SWCNT-based electrodes performed better than GQDs, and an improvement in the LoDs, sensitivity and the catalytic rate was observed upon conjugation.
- Full Text:
- Authors: Ndebele, Nobuhle , Mgidlana, Sithi , Nyokong, Tebello
- Date: 2021
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/185700 , vital:44416 , xlink:href="https://doi.org/10.1007/s12678-021-00670-x"
- Description: The synthesis and characterization of tetrakis[4(4-acetlyphenoxy)phthalocyanato] cobalt (II) (1) are presented. Complex 1 together with the reported tetrakis dimethyl 5-(phenoxy)-isophthalatephthalocyaninato] cobalt (II) (2) are conjugated to carbon-based nanomaterials: graphene quantum dots (GQDs) and single-walled carbon nanotubes (SWCNTs) via π-π stacking, taking advantage of the π electrons on the graphitic structure of the nanomaterial as well as on the aromatic rings of the Co phthalocyanines (CoPcs). The electrocatalytic behaviour of the CoPcs, GQDs, SWCNTs and their respective conjugates towards the electrochemical oxidation of catechol was studied. The electrocatalytic probes were drop-dried onto the electrode surface of the glassy carbon electrode (GCE). The electrochemical oxidation of catechol was studied using cyclic voltammetry, electrochemical impedance spectroscopy and chronoamperometry. Complex 2 when linked to GQDs gave the lowest oxidation peak potentials of 0.33 V. Low catechol detection limits (LOD) of 0.057 µM was obtained for complex 2 with SWCNT. Thus, complex 2 containing more oxygen atoms outperformed complex 1 with less oxygen atoms. The CoPcs on their own showed moderate electrocatalytic behaviour, hence showing the importance of conjugating them to the carbon nanomaterials. SWCNT-based electrodes performed better than GQDs, and an improvement in the LoDs, sensitivity and the catalytic rate was observed upon conjugation.
- Full Text:
Photodynamic antimicrobial action of asymmetrical porphyrins functionalized silver-detonation nanodiamonds nanoplatforms for the suppression of Staphylococcus aureus planktonic cells and biofilms
- Openda, Yolande I, Ngoy, Bokolombe P, Nyokong, Tebello
- Authors: Openda, Yolande I , Ngoy, Bokolombe P , Nyokong, Tebello
- Date: 2021
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/190544 , vital:45004 , xlink:href="https://doi.org/10.3389/fchem.2021.628316"
- Description: New asymmetrical porphyrin derivatives containing a p-hydroxyphenyl moiety and p-acetylphenyl moieties along with their functionalized silver-detonation nanodiamonds nanohybrids were characterized and their photophysicochemical properties were established. The study provides evidence that the metalated porphyrin derivatives were red-shifted in absorption wavelength and possessed high singlet oxygen quantum yield comparative to the unmetalated core, thus making them suitable agents for photodynamic antimicrobial chemotherapy. As a result of conjugation to detonation nanodiamonds and silver nanoparticles, these compounds proved to be more effective as they exhibited stronger antibacterial and anti-biofilm activities on the multi-drug resistant S. aureus strain due to synergetic effect, compared to Ps alone. This suggests that the newly prepared nanohybrids could be used as a potential antimicrobial agent in the treatment of biofilms caused by S. aureus strain.
- Full Text:
- Authors: Openda, Yolande I , Ngoy, Bokolombe P , Nyokong, Tebello
- Date: 2021
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/190544 , vital:45004 , xlink:href="https://doi.org/10.3389/fchem.2021.628316"
- Description: New asymmetrical porphyrin derivatives containing a p-hydroxyphenyl moiety and p-acetylphenyl moieties along with their functionalized silver-detonation nanodiamonds nanohybrids were characterized and their photophysicochemical properties were established. The study provides evidence that the metalated porphyrin derivatives were red-shifted in absorption wavelength and possessed high singlet oxygen quantum yield comparative to the unmetalated core, thus making them suitable agents for photodynamic antimicrobial chemotherapy. As a result of conjugation to detonation nanodiamonds and silver nanoparticles, these compounds proved to be more effective as they exhibited stronger antibacterial and anti-biofilm activities on the multi-drug resistant S. aureus strain due to synergetic effect, compared to Ps alone. This suggests that the newly prepared nanohybrids could be used as a potential antimicrobial agent in the treatment of biofilms caused by S. aureus strain.
- Full Text:
Photodynamic antimicrobial chemotherapy of asymmetric porphyrin-silver conjugates towards photoinactivation of Staphylococcus aureus
- Shabangu, Samuel M, Babu, Balaji, Soy, Rodah C, Managa, Muthumuni, Sekhosana, Kutloano E, Nyokong, Tebello
- Authors: Shabangu, Samuel M , Babu, Balaji , Soy, Rodah C , Managa, Muthumuni , Sekhosana, Kutloano E , Nyokong, Tebello
- Date: 2020
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/186536 , vital:44509 , xlink:href="https://doi.org/10.1080/00958972.2020.1739273"
- Description: Asymmetric mono-carboxy-porphyrins, (5-(4-carboxyphenyl)10,15, 20-tris(pentafluorophenyl)porphyrinato zinc(II) (1), 5-(4- carboxyphenyl)10,15,20-triphenylporphyrinato zinc(II) (2) and 5-(4- carboxyphenyl)10,15,20-tris(2-thienyl)porphyrinato zinc(II) (3), were linked to Ag nanoparticles (AgNPs) through amide bonds and selfassembly (the latter only for 3). The porphyrins and conjugates were used for photodynamic antimicrobial chemotherapy (PACT) against Staphylococcus aureus. PACT uses singlet oxygen for antimicrobial activity. Complex 3 and its conjugates had higher singlet oxygen quantum yields and higher log reduction when compared with the rest of the porphyrins and corresponding conjugates. These high log reductions for 3 and its conjugate were attributed to the presence of sulfur groups whereby there was more interaction with the bacterial membrane.
- Full Text:
- Authors: Shabangu, Samuel M , Babu, Balaji , Soy, Rodah C , Managa, Muthumuni , Sekhosana, Kutloano E , Nyokong, Tebello
- Date: 2020
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/186536 , vital:44509 , xlink:href="https://doi.org/10.1080/00958972.2020.1739273"
- Description: Asymmetric mono-carboxy-porphyrins, (5-(4-carboxyphenyl)10,15, 20-tris(pentafluorophenyl)porphyrinato zinc(II) (1), 5-(4- carboxyphenyl)10,15,20-triphenylporphyrinato zinc(II) (2) and 5-(4- carboxyphenyl)10,15,20-tris(2-thienyl)porphyrinato zinc(II) (3), were linked to Ag nanoparticles (AgNPs) through amide bonds and selfassembly (the latter only for 3). The porphyrins and conjugates were used for photodynamic antimicrobial chemotherapy (PACT) against Staphylococcus aureus. PACT uses singlet oxygen for antimicrobial activity. Complex 3 and its conjugates had higher singlet oxygen quantum yields and higher log reduction when compared with the rest of the porphyrins and corresponding conjugates. These high log reductions for 3 and its conjugate were attributed to the presence of sulfur groups whereby there was more interaction with the bacterial membrane.
- Full Text:
Characterization and physicochemical studies of the conjugates of graphene quantum dots with differently charged zinc phthalocyanines
- Matshitse, Refilwe, Sekhosana, Kutloana E, Achadu, Ojodomo John, Nyokong, Tebello
- Authors: Matshitse, Refilwe , Sekhosana, Kutloana E , Achadu, Ojodomo John , Nyokong, Tebello
- Date: 2017
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/189227 , vital:44829 , xlink:href="https://doi.org/10.1080/00958972.2017.1387652"
- Description: Unsubstituted zinc phthalocyanine (ZnPc), 2,9,16,23-tetrakis[4-(N-methylpyridyloxy)]-phthalocyanine (ZnTPPcQ) and Zn tetrasulfo phthalocyanine (ZnTSPc) were non-covalently (electrostatic and/or π–π interaction) attached to graphene quantum dots (GQDs) to form GQDs-Pc nanoconjugates. Relative to Pcs alone, the presence of GQDs improved the triplet quantum yields with the following values: GQDs-ZnPc (0.73), GQDs-ZnTPPcQ (0.76) and GQDs-ZnTSPc (0.67). Respective Förster resonance energy transfer (FRET) efficiencies were calculated to be 0.81, 0.80 and 0.28. However, singlet oxygen generating abilities of the as-synthesized nanoconjugates were relatively low due to the screening effect of GQDs and quenching in water. This study shows that, the type of Pc, loading and solvent used are among the vital properties to consider when constructing GQD-nanoconjugate systems with optimal triplet quantum yield properties and investigation of their physicochemical properties.
- Full Text:
- Authors: Matshitse, Refilwe , Sekhosana, Kutloana E , Achadu, Ojodomo John , Nyokong, Tebello
- Date: 2017
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/189227 , vital:44829 , xlink:href="https://doi.org/10.1080/00958972.2017.1387652"
- Description: Unsubstituted zinc phthalocyanine (ZnPc), 2,9,16,23-tetrakis[4-(N-methylpyridyloxy)]-phthalocyanine (ZnTPPcQ) and Zn tetrasulfo phthalocyanine (ZnTSPc) were non-covalently (electrostatic and/or π–π interaction) attached to graphene quantum dots (GQDs) to form GQDs-Pc nanoconjugates. Relative to Pcs alone, the presence of GQDs improved the triplet quantum yields with the following values: GQDs-ZnPc (0.73), GQDs-ZnTPPcQ (0.76) and GQDs-ZnTSPc (0.67). Respective Förster resonance energy transfer (FRET) efficiencies were calculated to be 0.81, 0.80 and 0.28. However, singlet oxygen generating abilities of the as-synthesized nanoconjugates were relatively low due to the screening effect of GQDs and quenching in water. This study shows that, the type of Pc, loading and solvent used are among the vital properties to consider when constructing GQD-nanoconjugate systems with optimal triplet quantum yield properties and investigation of their physicochemical properties.
- Full Text:
Effects of covalent versus non-covalent interactions on the electrocatalytic behavior of tetracarboxyphenoxyphthalocyanine in the presence of multi-walled carbon nanotubes
- Shumba, Munyaradzi S, Nyokong, Tebello
- Authors: Shumba, Munyaradzi S , Nyokong, Tebello
- Date: 2017
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/188271 , vital:44740 , xlink:href="https://doi.org/10.1080/00958972.2017.1303679"
- Description: Tetracarboxyphenoxy phthalocyanine was covalently linked to multi-walled carbon nanotubes and the conjugate was used for modification of glassy carbon electrodes for the detection of hydrogen peroxide. The electrocatalytic behavior was examined by cyclic voltammetry, square wave voltammetry, and rotating disk electrode. The results show that covalent linking is attractive in terms of high detecting currents, low overpotential, and high catalytic rate constants. Very low detection limits were observed with CoTCPhPc-DAMN-MWCNT(linked)-GCE at 0.33 nM. The resulting catalytic rate constant was 1.1 × 103 M−1s−1.
- Full Text:
- Authors: Shumba, Munyaradzi S , Nyokong, Tebello
- Date: 2017
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/188271 , vital:44740 , xlink:href="https://doi.org/10.1080/00958972.2017.1303679"
- Description: Tetracarboxyphenoxy phthalocyanine was covalently linked to multi-walled carbon nanotubes and the conjugate was used for modification of glassy carbon electrodes for the detection of hydrogen peroxide. The electrocatalytic behavior was examined by cyclic voltammetry, square wave voltammetry, and rotating disk electrode. The results show that covalent linking is attractive in terms of high detecting currents, low overpotential, and high catalytic rate constants. Very low detection limits were observed with CoTCPhPc-DAMN-MWCNT(linked)-GCE at 0.33 nM. The resulting catalytic rate constant was 1.1 × 103 M−1s−1.
- Full Text:
Effects of pluronic silica nanoparticles on the photophysical and photodynamic therapy behavior of triphenyl-p-phenoxy benzoic acid metalloporphyrins
- Managa, Muthumuni, Britton, Jonathan, Prinsloo, Earl, Nyokong, Tebello
- Authors: Managa, Muthumuni , Britton, Jonathan , Prinsloo, Earl , Nyokong, Tebello
- Date: 2016
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/239698 , vital:50756 , xlink:href="https://doi.org/10.1080/00958972.2016.1236372"
- Description: 5, 10, 15, Triphenyl-20-p-phenoxy benzoic acid porphyrins (P) containing Zn (ZnP), Ga (GaP), and Si (SiP) were synthesized and conjugated to pluronic-silica (PluS) nanoparticles (NPs) where the fluorescence and singlet oxygen generating behavior of the porphyrins were investigated. The highest singlet oxygen quantum yield (ΦΔ) was obtained for ZnP. When the porphyrins were conjugated to the PluS NPs, the ΦΔ was quenched and fluorescence was enhanced. The pore size of the NPs upon conjugation decreased from 18.9 nm for PluS NPs to 2.4 nm (for ZnP as an example) as determined by applying the Brunauer–Emmett–Teller method. The porphyrin complexes and their conjugates were tested for their photodynamic therapy (PDT) activity on MCF-7 breast cancer cells. It was found that ZnP and its conjugate showed the highest PDT activity. The p > 0.05 indicated that ZnP is significantly different than GaP and SiP.
- Full Text:
- Authors: Managa, Muthumuni , Britton, Jonathan , Prinsloo, Earl , Nyokong, Tebello
- Date: 2016
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/239698 , vital:50756 , xlink:href="https://doi.org/10.1080/00958972.2016.1236372"
- Description: 5, 10, 15, Triphenyl-20-p-phenoxy benzoic acid porphyrins (P) containing Zn (ZnP), Ga (GaP), and Si (SiP) were synthesized and conjugated to pluronic-silica (PluS) nanoparticles (NPs) where the fluorescence and singlet oxygen generating behavior of the porphyrins were investigated. The highest singlet oxygen quantum yield (ΦΔ) was obtained for ZnP. When the porphyrins were conjugated to the PluS NPs, the ΦΔ was quenched and fluorescence was enhanced. The pore size of the NPs upon conjugation decreased from 18.9 nm for PluS NPs to 2.4 nm (for ZnP as an example) as determined by applying the Brunauer–Emmett–Teller method. The porphyrin complexes and their conjugates were tested for their photodynamic therapy (PDT) activity on MCF-7 breast cancer cells. It was found that ZnP and its conjugate showed the highest PDT activity. The p > 0.05 indicated that ZnP is significantly different than GaP and SiP.
- Full Text:
- «
- ‹
- 1
- ›
- »