A comparative study of the photophysicochemical and photodynamic activity properties of meso-4-methylthiophenyl functionalized Sn (IV) tetraarylporphyrins and triarylcorroles
- Dingiswayo, Somila, Babu, Balaji, Prinsloo, Earl, Mack, John, Nyokong, Tebello
- Authors: Dingiswayo, Somila , Babu, Balaji , Prinsloo, Earl , Mack, John , Nyokong, Tebello
- Date: 2020
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/186157 , vital:44469 , xlink:href="https://doi.org/10.1142/S1088424620500273"
- Description: Tin(IV) complexes of a 4-methylthiophenyl functionalized porphyrin (1-Sn) and its corrole analogue (2-Sn) were synthesized so that their photophysicochemical properties and photodynamic activities against MCF-7 breast cancer cells could be compared. Singlet oxygen luminescence studies revealed that 1-Sn and 2-Sn have comparable ΦΔΦΔ values in DMF of 0.59 and 0.60, respectively, while the IC5050 values after irradiation of MCF-7 cells for 30 min with a Thorlabs 625 nm LED (432 J · cm−2)−2) were determined to be 12.4 and 8.9 μμM. The results demonstrate that the cellular uptake of 2-Sn and its molar absorptivity at the irradiation wavelength play a crucial role during in vitro cytotoxicity studies.
- Full Text:
- Date Issued: 2020
- Authors: Dingiswayo, Somila , Babu, Balaji , Prinsloo, Earl , Mack, John , Nyokong, Tebello
- Date: 2020
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/186157 , vital:44469 , xlink:href="https://doi.org/10.1142/S1088424620500273"
- Description: Tin(IV) complexes of a 4-methylthiophenyl functionalized porphyrin (1-Sn) and its corrole analogue (2-Sn) were synthesized so that their photophysicochemical properties and photodynamic activities against MCF-7 breast cancer cells could be compared. Singlet oxygen luminescence studies revealed that 1-Sn and 2-Sn have comparable ΦΔΦΔ values in DMF of 0.59 and 0.60, respectively, while the IC5050 values after irradiation of MCF-7 cells for 30 min with a Thorlabs 625 nm LED (432 J · cm−2)−2) were determined to be 12.4 and 8.9 μμM. The results demonstrate that the cellular uptake of 2-Sn and its molar absorptivity at the irradiation wavelength play a crucial role during in vitro cytotoxicity studies.
- Full Text:
- Date Issued: 2020
An octabrominated Sn (iv) tetraisopropylporphyrin as a photosensitizer dye for singlet oxygen biomedical applications
- Babu, Balaji, Mack, John, Nyokong, Tebello
- Authors: Babu, Balaji , Mack, John , Nyokong, Tebello
- Date: 2020
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/186679 , vital:44524 , xlink:href="https://doi.org/10.1039/D0DT01915A"
- Description: Two novel Sn(IV) tetraisopropylphenylporphyrins have been synthesized to explore the effect of octabromination at the β-pyrrole positions on their photophysical properties and photodynamic activity. The lower energy Q band of an octabrominated complex lies at 675 nm well within the therapeutic window. The octabrominated dye has a relatively high singlet oxygen quantum yield of 0.78 in DMF and exhibits favorable photodynamic activity against MCF-7 cells with an IC50 value of 10.7 μM and a 5.74 log reduction value (5 μM) towards S. aureus under illumination at 660 nm for 60 min with a Thorlabs M660L3 LED (280 mW cm−2).
- Full Text:
- Date Issued: 2020
- Authors: Babu, Balaji , Mack, John , Nyokong, Tebello
- Date: 2020
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/186679 , vital:44524 , xlink:href="https://doi.org/10.1039/D0DT01915A"
- Description: Two novel Sn(IV) tetraisopropylphenylporphyrins have been synthesized to explore the effect of octabromination at the β-pyrrole positions on their photophysical properties and photodynamic activity. The lower energy Q band of an octabrominated complex lies at 675 nm well within the therapeutic window. The octabrominated dye has a relatively high singlet oxygen quantum yield of 0.78 in DMF and exhibits favorable photodynamic activity against MCF-7 cells with an IC50 value of 10.7 μM and a 5.74 log reduction value (5 μM) towards S. aureus under illumination at 660 nm for 60 min with a Thorlabs M660L3 LED (280 mW cm−2).
- Full Text:
- Date Issued: 2020
Non-aggregated lipophilic water-soluble tin porphyrins as photosensitizers for photodynamic therapy and photodynamic antimicrobial chemotherapy:
- Babu, Balaji, Soy, Rodah C, Mack, John, Nyokong, Tebello
- Authors: Babu, Balaji , Soy, Rodah C , Mack, John , Nyokong, Tebello
- Date: 2020
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/158241 , vital:40165 , DOI: 10.1039/d0nj01564d
- Description: Two readily synthesized water-soluble Sn(IV) porphyrins have been prepared with quaternized pyridyl nitrogens and 2-naphthalato trans-axial ligands. Methyl and hexyl groups were attached to the quaternized nitrogens to form lipophilic dyes with high singlet oxygen quantum yields (ca. 0.90) and unusually long triplet state lifetimes. The dyes exhibit good photodynamic activity against MCF-7 cells with IC50 values of 14.3 and 8.5 μM, respectively. The hexyl quaternized dye exhibited a 9.69 log reduction value (0.5 μM) towards S. aureus under illumination for 90 min (250 mW cm−2). The results demonstrate that this set of structural modification strategies for photosensitizer dyes merits further in depth study.
- Full Text:
- Date Issued: 2020
- Authors: Babu, Balaji , Soy, Rodah C , Mack, John , Nyokong, Tebello
- Date: 2020
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/158241 , vital:40165 , DOI: 10.1039/d0nj01564d
- Description: Two readily synthesized water-soluble Sn(IV) porphyrins have been prepared with quaternized pyridyl nitrogens and 2-naphthalato trans-axial ligands. Methyl and hexyl groups were attached to the quaternized nitrogens to form lipophilic dyes with high singlet oxygen quantum yields (ca. 0.90) and unusually long triplet state lifetimes. The dyes exhibit good photodynamic activity against MCF-7 cells with IC50 values of 14.3 and 8.5 μM, respectively. The hexyl quaternized dye exhibited a 9.69 log reduction value (0.5 μM) towards S. aureus under illumination for 90 min (250 mW cm−2). The results demonstrate that this set of structural modification strategies for photosensitizer dyes merits further in depth study.
- Full Text:
- Date Issued: 2020
Photodynamic activity of 2, 6-diiodo-3, 5-dithienylvinyleneBODIPYs and their folate-functionalized chitosan-coated Pluronic® F-127 micelles on MCF-7 breast cancer cells
- Molupe, Nthabeleng, Babu, Balaji, Oluwole, David O, Prinsloo, Earl, Gai, Lizhi, Shen, Zhen, Mack, John, Nyokong, Tebello
- Authors: Molupe, Nthabeleng , Babu, Balaji , Oluwole, David O , Prinsloo, Earl , Gai, Lizhi , Shen, Zhen , Mack, John , Nyokong, Tebello
- Date: 2020
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/186222 , vital:44474 , xlink:href="https://doi.org/10.1142/S1088424619501773"
- Description: A 2,6-diiodo-3,5-dithienylvinyleneBODIPY dye was prepared and encapsulated with folate-chitosan capped Pluronic®® F-127 to provide drug delivery systems for photodynamic therapy (PDT). Moderately enhanced singlet oxygen quantum yields were observed for the dye encapsulation complexes in water. The in vitro dark cytotoxicity and photodynamic activity were investigated on the human breast adenocarcinoma (MCF-7) cell line. Minimal dark cytotoxicity was observed for the BODIPY dyes in 5% DMSO and when encapsulated in folate-functionalized chitosan-coated Pluronic®® F-127 micelles, since the cell viability values are consistently greater than 80% over the 0-40 μg⋅mL−1μg⋅mL−1 concentration range. Upon irradiation of the samples, significant cytocidal activity was observed for the encapsulation complex of a 2,6-diiodo-8-dimethylaminophenyl-3,5-dithienylvinyleneBODIPY dye with less than 50% viable cells observed at concentrations ≥20μg⋅mL−1≥20μg⋅mL−1.
- Full Text:
- Date Issued: 2020
- Authors: Molupe, Nthabeleng , Babu, Balaji , Oluwole, David O , Prinsloo, Earl , Gai, Lizhi , Shen, Zhen , Mack, John , Nyokong, Tebello
- Date: 2020
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/186222 , vital:44474 , xlink:href="https://doi.org/10.1142/S1088424619501773"
- Description: A 2,6-diiodo-3,5-dithienylvinyleneBODIPY dye was prepared and encapsulated with folate-chitosan capped Pluronic®® F-127 to provide drug delivery systems for photodynamic therapy (PDT). Moderately enhanced singlet oxygen quantum yields were observed for the dye encapsulation complexes in water. The in vitro dark cytotoxicity and photodynamic activity were investigated on the human breast adenocarcinoma (MCF-7) cell line. Minimal dark cytotoxicity was observed for the BODIPY dyes in 5% DMSO and when encapsulated in folate-functionalized chitosan-coated Pluronic®® F-127 micelles, since the cell viability values are consistently greater than 80% over the 0-40 μg⋅mL−1μg⋅mL−1 concentration range. Upon irradiation of the samples, significant cytocidal activity was observed for the encapsulation complex of a 2,6-diiodo-8-dimethylaminophenyl-3,5-dithienylvinyleneBODIPY dye with less than 50% viable cells observed at concentrations ≥20μg⋅mL−1≥20μg⋅mL−1.
- Full Text:
- Date Issued: 2020
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:
- Date Issued: 2020
- 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:
- Date Issued: 2020
Sn (iv) N-confused porphyrins as photosensitizer dyes for photodynamic therapy in the near IR region
- Babu, Balaji, Mack, John, Nyokong, Tebello
- Authors: Babu, Balaji , Mack, John , Nyokong, Tebello
- Date: 2020
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/186648 , vital:44521 , xlink:href="https://doi.org/10.1039/D0DT03296D"
- Description: The utility of Sn(IV) N-confused porphyrin (SnNCP) for use as photosensitizer dyes in photodynamic therapy is investigated. SnNCP has an unusually high singlet oxygen quantum yield of 0.72 in DMSO. IC50 values of 1.6 and 12.8 μM were obtained against MCF-7 cells upon irradiation with 660 and 780 nm LEDs.
- Full Text:
- Date Issued: 2020
Sn (iv) N-confused porphyrins as photosensitizer dyes for photodynamic therapy in the near IR region
- Authors: Babu, Balaji , Mack, John , Nyokong, Tebello
- Date: 2020
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/186648 , vital:44521 , xlink:href="https://doi.org/10.1039/D0DT03296D"
- Description: The utility of Sn(IV) N-confused porphyrin (SnNCP) for use as photosensitizer dyes in photodynamic therapy is investigated. SnNCP has an unusually high singlet oxygen quantum yield of 0.72 in DMSO. IC50 values of 1.6 and 12.8 μM were obtained against MCF-7 cells upon irradiation with 660 and 780 nm LEDs.
- Full Text:
- Date Issued: 2020
Susceptibility of Staphylococcus aureus to porphyrin-silver nanoparticle mediated photodynamic antimicrobial chemotherapy
- Shabangu, Samuel M, Babu, Balaji, Soy, Rodah C, Ovim, James, Amuhaya, Edith K, Nyokong, Tebello
- Authors: Shabangu, Samuel M , Babu, Balaji , Soy, Rodah C , Ovim, James , Amuhaya, Edith K , Nyokong, Tebello
- Date: 2020
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/186262 , vital:44479 , xlink:href="https://doi.org/10.1016/j.jlumin.2020.117158"
- Description: Photodynamic antimicrobial chemotherapy (PACT) is employed against multi drug resistant Staphylococcus aureus using porphyrins combined with silver nanoparticles to bring about a combined photodynamic effect. We employ Zn-meso-5,10,15,20-tetra(4-pyridyl) (1), Zn-meso-5,10,15,20-tetrathienyl (2), and Zn-meso-5-(4- hydroxyphenyl)- 10,15,20-tris(2-thienyl)(3) porphyrins and their self-assembled conjugates with silver nanoparticles for PACT against Staphylococcus aureus. Complex 3 with nanoparticles was found to perform better resulting in 0% bacterial viability at 60 min.
- Full Text:
- Date Issued: 2020
- Authors: Shabangu, Samuel M , Babu, Balaji , Soy, Rodah C , Ovim, James , Amuhaya, Edith K , Nyokong, Tebello
- Date: 2020
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/186262 , vital:44479 , xlink:href="https://doi.org/10.1016/j.jlumin.2020.117158"
- Description: Photodynamic antimicrobial chemotherapy (PACT) is employed against multi drug resistant Staphylococcus aureus using porphyrins combined with silver nanoparticles to bring about a combined photodynamic effect. We employ Zn-meso-5,10,15,20-tetra(4-pyridyl) (1), Zn-meso-5,10,15,20-tetrathienyl (2), and Zn-meso-5-(4- hydroxyphenyl)- 10,15,20-tris(2-thienyl)(3) porphyrins and their self-assembled conjugates with silver nanoparticles for PACT against Staphylococcus aureus. Complex 3 with nanoparticles was found to perform better resulting in 0% bacterial viability at 60 min.
- Full Text:
- Date Issued: 2020
The photophysicochemical properties and photodynamic therapy activity of In and Zn phthalocyanines when incorporated into individual or mixed Pluronic® micelles
- Motloung, Banele M, Babu, Balaji, Prinsloo, Earl, Nyokong, Tebello
- Authors: Motloung, Banele M , Babu, Balaji , Prinsloo, Earl , Nyokong, Tebello
- Date: 2020
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/186124 , vital:44465 , xlink:href="https://doi.org/10.1016/j.poly.2020.114683"
- Description: The synthesis, photophysicochemical properties and photodynamic activity (PDT) of tetra-pyridyloxy (1,2) and benzothiazole (3, 4) substituted indium (III) (1,3) and zinc (2, 4) phthalocyanines (Pcs) and their incorporation into Pluronic® F127 and Pluronic L121/F127 mixed micelles (the latter for 3 and 4 only) are presented in this study. The InPcs exhibited higher singlet oxygen (ΦΔ) at 0.76 and 0.68 compared to the ZnPc’s at 0.47 and 0.44 in dimethyl sulfoxide. The ΦΔ values in the presence of Pluronic® F127 and in water, were 0.39 and 0.42 for InPcs and 0.23 and 0.37 for ZnPc. The ΦΔ values in the presence of Pluronic F127/L121 mixed micelles for complex 3 and 4 were 0.51 and 0.29 in water. The Kp was determined using the water and octanol system. InPcs had larger Kp values suggesting that they are more likely to be taken up by the cancer cells hence they showed better PDT activity
- Full Text:
- Date Issued: 2020
- Authors: Motloung, Banele M , Babu, Balaji , Prinsloo, Earl , Nyokong, Tebello
- Date: 2020
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/186124 , vital:44465 , xlink:href="https://doi.org/10.1016/j.poly.2020.114683"
- Description: The synthesis, photophysicochemical properties and photodynamic activity (PDT) of tetra-pyridyloxy (1,2) and benzothiazole (3, 4) substituted indium (III) (1,3) and zinc (2, 4) phthalocyanines (Pcs) and their incorporation into Pluronic® F127 and Pluronic L121/F127 mixed micelles (the latter for 3 and 4 only) are presented in this study. The InPcs exhibited higher singlet oxygen (ΦΔ) at 0.76 and 0.68 compared to the ZnPc’s at 0.47 and 0.44 in dimethyl sulfoxide. The ΦΔ values in the presence of Pluronic® F127 and in water, were 0.39 and 0.42 for InPcs and 0.23 and 0.37 for ZnPc. The ΦΔ values in the presence of Pluronic F127/L121 mixed micelles for complex 3 and 4 were 0.51 and 0.29 in water. The Kp was determined using the water and octanol system. InPcs had larger Kp values suggesting that they are more likely to be taken up by the cancer cells hence they showed better PDT activity
- Full Text:
- Date Issued: 2020
‘There is nothing to hold onto here’:
- 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
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/156410 , vital:39987 , DOI: 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 self-assembly (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:
- Date Issued: 2020
- Authors: Shabangu, Samuel M , Babu, Balaji , Soy, Rodah C , Managa, Muthumuni , Sekhosana, Kutloano E , Nyokong, Tebello
- Date: 2020
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/156410 , vital:39987 , DOI: 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 self-assembly (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:
- Date Issued: 2020
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