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
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
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 investigation of in vitro dark cytotoxicity and photodynamic therapy effect of a 2, 6-dibromo-3, 5-distyryl BODIPY dye encapsulated in Pluronic® F-127 micelles
- Molupe, Nthabeleng, Babu, Balaji, Oluwole, David O, Prinsloo, Earl, Mack, John, Nyokong, Tebello
- Authors: Molupe, Nthabeleng , Babu, Balaji , Oluwole, David O , Prinsloo, Earl , Mack, John , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187862 , vital:44704 , xlink:href="https://doi.org/10.1080/00958972.2018.1522536"
- Description: A 2,6-dibrominated 3,5-distyryl boron-dipyrromethene (BODIPY) dye with a moderately high singlet oxygen quantum yield was encapsulated in Pluronic® F-127 micelles, and its dark cytotoxicity and photodynamic activity were investigated on the human breast adenocarcinoma MCF-7 cell line. The BODIPY dye exhibited very low dark toxicity and a significant PDT effect when added in drug formulations consisting of 5.0% (v/v) DMSO in supplemented Dulbecco’s modified Eagle’s medium (DMEM) and as Pluronic® F-127 micelle encapsulation complexes in supplemented DMEM alone. An IC50 value of 4 ± 2 μM was obtained when the BODIPY dye was encapsulated in Pluronic® F-127 micelles during in vitro photodynamic activity studies in MCF-7 cancer cells with a 660 nm light emitting diode.
- Full Text:
- Date Issued: 2018
- Authors: Molupe, Nthabeleng , Babu, Balaji , Oluwole, David O , Prinsloo, Earl , Mack, John , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187862 , vital:44704 , xlink:href="https://doi.org/10.1080/00958972.2018.1522536"
- Description: A 2,6-dibrominated 3,5-distyryl boron-dipyrromethene (BODIPY) dye with a moderately high singlet oxygen quantum yield was encapsulated in Pluronic® F-127 micelles, and its dark cytotoxicity and photodynamic activity were investigated on the human breast adenocarcinoma MCF-7 cell line. The BODIPY dye exhibited very low dark toxicity and a significant PDT effect when added in drug formulations consisting of 5.0% (v/v) DMSO in supplemented Dulbecco’s modified Eagle’s medium (DMEM) and as Pluronic® F-127 micelle encapsulation complexes in supplemented DMEM alone. An IC50 value of 4 ± 2 μM was obtained when the BODIPY dye was encapsulated in Pluronic® F-127 micelles during in vitro photodynamic activity studies in MCF-7 cancer cells with a 660 nm light emitting diode.
- Full Text:
- Date Issued: 2018
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