Acetophenone substituted phthalocyanines and their graphene quantum dots conjugates as photosensitizers for photodynamic antimicrobial chemotherapy against Staphylococcus aureus
- Openda, Yolande I, Sen, Pinar, Managa, Muthumuni, Nyokong, Tebello
- Authors: Openda, Yolande I , Sen, Pinar , Managa, Muthumuni , Nyokong, Tebello
- Date: 2020
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/186507 , vital:44506 , xlink:href="https://doi.org/10.1016/j.pdpdt.2019.101607"
- Description: This work reports on the synthesis and characterization of novel acetophenone substituted phthalocyanines along with the self-assembled nanoconjugates formed via π-π stacking interaction between the synthesized unmetalated (2), zinc (3) and indium (4) phthalocyanines and graphene quantum dots (GQDs) to form 2@GQDs, 3@GQDs and 4@GQDs. The complexes and conjugates exhibited high singlet oxygen ranging from 0.20 to 0.79 in DMSO for Pcs and nanoconjugates where in all cases, the indium complexes showed the highest singlet oxygen quantum yields. The photodynamic antimicrobial chemotherapy activity of both phthalocyanines and nanoconjugates were tested against Staphylococcus aureus. 4@GQDs was found to be highly effective causing a 9.68 log reduction of the bacteria at 10 μM (based on Pc) when compared to 3.77 log reduction of 3@GQDs.
- Full Text:
- Date Issued: 2020
- Authors: Openda, Yolande I , Sen, Pinar , Managa, Muthumuni , Nyokong, Tebello
- Date: 2020
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/186507 , vital:44506 , xlink:href="https://doi.org/10.1016/j.pdpdt.2019.101607"
- Description: This work reports on the synthesis and characterization of novel acetophenone substituted phthalocyanines along with the self-assembled nanoconjugates formed via π-π stacking interaction between the synthesized unmetalated (2), zinc (3) and indium (4) phthalocyanines and graphene quantum dots (GQDs) to form 2@GQDs, 3@GQDs and 4@GQDs. The complexes and conjugates exhibited high singlet oxygen ranging from 0.20 to 0.79 in DMSO for Pcs and nanoconjugates where in all cases, the indium complexes showed the highest singlet oxygen quantum yields. The photodynamic antimicrobial chemotherapy activity of both phthalocyanines and nanoconjugates were tested against Staphylococcus aureus. 4@GQDs was found to be highly effective causing a 9.68 log reduction of the bacteria at 10 μM (based on Pc) when compared to 3.77 log reduction of 3@GQDs.
- Full Text:
- Date Issued: 2020
Photo-physicochemical properties and in vitro photodynamic therapy activity of morpholine-substituted Zinc (II)-Phthalocyanines π-π stacked on biotinylated graphene quantum dots
- Nene, Lindokuhle, Managa, Muthumuni, Nyokong, Tebello
- Authors: Nene, Lindokuhle , Managa, Muthumuni , Nyokong, Tebello
- Date: 2019
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/186993 , vital:44554 , xlink:href="https://doi.org/10.1016/j.dyepig.2019.03.002"
- Description: Two morpholine-substituted Zn(II) phthalocyanines, complex 4 and the cationic 5, were synthesized and conjugated to graphene quantum dots (GQDs) and biotinylated GQDs (GQDs-biotin) by non-covalent π-π interactions. The GQDs-biotin are prepared as potential nanoparticle-based Pc delivery vector combined with a receptor-mediated transport system using biotin. The photo-physicochemical properties of the Pc complexes and their corresponding conjugates were studied. Upon conjugation, the fluorescence quantum yields decrease for 4 and 5, however, the triplet quantum yields were increased for the conjugates. All samples demonstrated singlet oxygen generation. For conjugated complexes, the singlet quantum yields decreased due to the screening effect in some cases. An increase in the photodynamic therapy activities upon quaternization was observed for the conjugates, with the cell viability decreasing from 66.2% to 51.2% after treatment for 4-GQDs and 5-GQDs, respectively. A relatively better performance was also observed for the cationic complex in combination with the biotin functionalized GQDs, 5-GQDs-biotin, where the cell viability was 34.9% after treatment. Moreover, the cellular uptake of 5-GQDs-biotin over 24 h was relatively higher compared to Pc complex alone and other PcsGQDs conjugates.
- Full Text:
- Date Issued: 2019
- Authors: Nene, Lindokuhle , Managa, Muthumuni , Nyokong, Tebello
- Date: 2019
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/186993 , vital:44554 , xlink:href="https://doi.org/10.1016/j.dyepig.2019.03.002"
- Description: Two morpholine-substituted Zn(II) phthalocyanines, complex 4 and the cationic 5, were synthesized and conjugated to graphene quantum dots (GQDs) and biotinylated GQDs (GQDs-biotin) by non-covalent π-π interactions. The GQDs-biotin are prepared as potential nanoparticle-based Pc delivery vector combined with a receptor-mediated transport system using biotin. The photo-physicochemical properties of the Pc complexes and their corresponding conjugates were studied. Upon conjugation, the fluorescence quantum yields decrease for 4 and 5, however, the triplet quantum yields were increased for the conjugates. All samples demonstrated singlet oxygen generation. For conjugated complexes, the singlet quantum yields decreased due to the screening effect in some cases. An increase in the photodynamic therapy activities upon quaternization was observed for the conjugates, with the cell viability decreasing from 66.2% to 51.2% after treatment for 4-GQDs and 5-GQDs, respectively. A relatively better performance was also observed for the cationic complex in combination with the biotin functionalized GQDs, 5-GQDs-biotin, where the cell viability was 34.9% after treatment. Moreover, the cellular uptake of 5-GQDs-biotin over 24 h was relatively higher compared to Pc complex alone and other PcsGQDs conjugates.
- Full Text:
- Date Issued: 2019
Photodynamic activity of novel cationic porphyrins conjugated to graphene quantum dots against Staphylococcus aureus
- Magaela, Bridged N, Makola, Lekgowa C, Managa, Muthumuni, Nyokong, Tebello
- Authors: Magaela, Bridged N , Makola, Lekgowa C , Managa, Muthumuni , Nyokong, Tebello
- Date: 2022
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/295797 , vital:57379 , xlink:href="https://doi.org/10.1142/S1088424622500316"
- Description: Novel 5-(pyridyl)-10-15-20-tris(4-bromophenyl) porphyrin (complex 1), indium metal derivative (complex 2), and quaternized derivative (complex 3) were synthesized and conjugated to graphene quantum dots (GQDs). The conjugation of the porphyrins to GQDs was through ππ-ππ stacking. Herein, the ππ-ππ stacking approach was used to avoid covalent conjugation which might compromise the intrinsic chemical and physical properties. The photodynamic activities of the proposed nanomaterials were assessed towards Staphylococcus aureus cell obliteration. The photophysical properties of the prepared complexes were also studied prior to the application. Moreover, a decrease in fluorescence lifetimes was observed upon metalation of complex 1. As anticipated, singlet oxygen quantum yield (ΦΔ)ΦΔ) increased notably upon heavy metal (indium) insertion and upon composite formation. Antimicrobial photodynamic therapy comparative studies were done on quaternized and unquaternized indium porphyrins conjugated to GQDs. Complex 3-GQDs exhibited the highest antibacterial activities compared to other complexes, and this was attributed to the high ΦΔΦΔ which plays an imperative role in photodynamic therapy applications.
- Full Text:
- Date Issued: 2022
- Authors: Magaela, Bridged N , Makola, Lekgowa C , Managa, Muthumuni , Nyokong, Tebello
- Date: 2022
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/295797 , vital:57379 , xlink:href="https://doi.org/10.1142/S1088424622500316"
- Description: Novel 5-(pyridyl)-10-15-20-tris(4-bromophenyl) porphyrin (complex 1), indium metal derivative (complex 2), and quaternized derivative (complex 3) were synthesized and conjugated to graphene quantum dots (GQDs). The conjugation of the porphyrins to GQDs was through ππ-ππ stacking. Herein, the ππ-ππ stacking approach was used to avoid covalent conjugation which might compromise the intrinsic chemical and physical properties. The photodynamic activities of the proposed nanomaterials were assessed towards Staphylococcus aureus cell obliteration. The photophysical properties of the prepared complexes were also studied prior to the application. Moreover, a decrease in fluorescence lifetimes was observed upon metalation of complex 1. As anticipated, singlet oxygen quantum yield (ΦΔ)ΦΔ) increased notably upon heavy metal (indium) insertion and upon composite formation. Antimicrobial photodynamic therapy comparative studies were done on quaternized and unquaternized indium porphyrins conjugated to GQDs. Complex 3-GQDs exhibited the highest antibacterial activities compared to other complexes, and this was attributed to the high ΦΔΦΔ which plays an imperative role in photodynamic therapy applications.
- Full Text:
- Date Issued: 2022
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