Photoantimicrobial activity of Schiff-base morpholino phthalocyanines against drug resistant micro-organisms in their planktonic and biofilm forms
- Sindelo, Azole, Sen, Pinar, Nyokong, Tebello
- Authors: Sindelo, Azole , Sen, Pinar , Nyokong, Tebello
- Date: 2023
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/360437 , vital:65088 , xlink:href="https://doi.org/10.1016/j.pdpdt.2023.103519"
- Description: Antimicrobial photodynamic inactivation (aPDI) is a treatment for the eradication of drug-resistant micro-organisms. One of the advantages of this technique, is that there is minimal possibility of microbial resistance. Hence, herein, the preparation and characterization of novel neutral and cationic morpholine containing Schiff base phthalocyanines are reported. The cationic complexes gave moderate singlet oxygen quantum yields (ΦΔ) of ∼0.2 in aqueous media. Conversely, the neutral complexes generated very low ΦΔ values making them very poor candidates for antimicrobial studies. The cationic phthalocyanines showed excellent photodynamic activity against planktonic cells of all micro-organisms (Candida albicans, Escherichia coli, Klebsiella pneumoniae, Staphylococcus aureus, Salmonella enterica subspecies enterica serovar Choleraesuis, vancomycin-resistant Enterococcus faecium, and methicillin-resistant Staphylococcus aureus). The efficiency of aPDI was shown to be both concentration and light-dose-dependent. Mono biofilms were susceptible when treated with 200 µM of cationic Pcs at 108 J/cm2. However, ∼10% of the mixed biofilm survived after treatment.
- Full Text:
- Date Issued: 2023
- Authors: Sindelo, Azole , Sen, Pinar , Nyokong, Tebello
- Date: 2023
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/360437 , vital:65088 , xlink:href="https://doi.org/10.1016/j.pdpdt.2023.103519"
- Description: Antimicrobial photodynamic inactivation (aPDI) is a treatment for the eradication of drug-resistant micro-organisms. One of the advantages of this technique, is that there is minimal possibility of microbial resistance. Hence, herein, the preparation and characterization of novel neutral and cationic morpholine containing Schiff base phthalocyanines are reported. The cationic complexes gave moderate singlet oxygen quantum yields (ΦΔ) of ∼0.2 in aqueous media. Conversely, the neutral complexes generated very low ΦΔ values making them very poor candidates for antimicrobial studies. The cationic phthalocyanines showed excellent photodynamic activity against planktonic cells of all micro-organisms (Candida albicans, Escherichia coli, Klebsiella pneumoniae, Staphylococcus aureus, Salmonella enterica subspecies enterica serovar Choleraesuis, vancomycin-resistant Enterococcus faecium, and methicillin-resistant Staphylococcus aureus). The efficiency of aPDI was shown to be both concentration and light-dose-dependent. Mono biofilms were susceptible when treated with 200 µM of cationic Pcs at 108 J/cm2. However, ∼10% of the mixed biofilm survived after treatment.
- Full Text:
- Date Issued: 2023
Photodynamic inactivation of methicillin-resistant Staphylococcus aureus using pyrrolidinium containing Schiff base phthalocyanines
- Sindelo, Azole, Sen, Pinar, Nyokong, Tebello
- Authors: Sindelo, Azole , Sen, Pinar , Nyokong, Tebello
- Date: 2023
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/360449 , vital:65089 , xlink:href="https://doi.org/10.1016/j.jphotochem.2022.114535"
- Description: New tetra-substituted zinc and indium Schiff base phthalocyanines (ZnPc and InPc, respectively) are synthesized and characterized herein. The ethyl pyrrolidine (ZnPc-2, InPc-2) and propyl pyrrolidine (ZnPc-3, InPc-3) substituted Schiff base Pcs were reacted with methyl iodide to form their cationic derivatives (ZnPc-2Q, InPc-2Q, ZnPc-3Q, and InPc-3Q, respectively). The photophysical and photochemical properties of the Pcs were studied. The cationic Pcs generated higher singlet oxygen quantum yield in aqueous media than the neutral Pcs. The photoinactivation of Methicillin-resistant Staphylococcus aureus (MRSA) and Methicillin-sensitive Staphylococcus aureus (MSSA) strains was evaluated. 5 µM ZnPc-3Q and InPc-3Q inactivated 100 % of the MSSA and MRSA while 5 µM ZnPc-2Q and InPc-2Q eradicated 100 % for MSSA and 97.2 % and 98.7 % (respectively) of the MRSA. The photodynamic antimicrobial chemotherapy studies depended on singlet oxygen ability, the charges, and the extension of the alkyl groups.
- Full Text:
- Date Issued: 2023
- Authors: Sindelo, Azole , Sen, Pinar , Nyokong, Tebello
- Date: 2023
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/360449 , vital:65089 , xlink:href="https://doi.org/10.1016/j.jphotochem.2022.114535"
- Description: New tetra-substituted zinc and indium Schiff base phthalocyanines (ZnPc and InPc, respectively) are synthesized and characterized herein. The ethyl pyrrolidine (ZnPc-2, InPc-2) and propyl pyrrolidine (ZnPc-3, InPc-3) substituted Schiff base Pcs were reacted with methyl iodide to form their cationic derivatives (ZnPc-2Q, InPc-2Q, ZnPc-3Q, and InPc-3Q, respectively). The photophysical and photochemical properties of the Pcs were studied. The cationic Pcs generated higher singlet oxygen quantum yield in aqueous media than the neutral Pcs. The photoinactivation of Methicillin-resistant Staphylococcus aureus (MRSA) and Methicillin-sensitive Staphylococcus aureus (MSSA) strains was evaluated. 5 µM ZnPc-3Q and InPc-3Q inactivated 100 % of the MSSA and MRSA while 5 µM ZnPc-2Q and InPc-2Q eradicated 100 % for MSSA and 97.2 % and 98.7 % (respectively) of the MRSA. The photodynamic antimicrobial chemotherapy studies depended on singlet oxygen ability, the charges, and the extension of the alkyl groups.
- Full Text:
- Date Issued: 2023
Decoration of glass wool with zinc (II) phthalocyanine for the photocatalytic transformation of methyl orange
- Sindelo, Azole, Britton, Jonathan, Lanterna, Anabel E, Scaiano, Juan C, Nyokong, Tebello
- Authors: Sindelo, Azole , Britton, Jonathan , Lanterna, Anabel E , Scaiano, Juan C , Nyokong, Tebello
- Date: 2022
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/295742 , vital:57374 , xlink:href="https://doi.org/10.1016/j.jphotochem.2022.114127"
- Description: Zinc phthalocyanines containing one (mono carboxy phenoxy, ZnMCPPc), four (tetra carboxy phenoxy, ZnTCPPc), and eight (tetra isophthalic acid, ZnTIPAPc) carboxyl groups were covalently conjugated to amine-functionalized glass wool (GW). The GW-Pcs were characterized and evaluated for singlet oxygen generation. The photocatalytic efficiencies of the GW-Pcs were assessed using methyl orange. Glass wool alone and the modified conjugates exhibited low to no degradation of methyl orange in the dark. The improved catalytic rate was observed for GW-ZnMCPPc and GW-ZnTCPPc compared to GW-ZnTIPAPc due to the latter's lower singlet oxygen quantum yield generation. In addition, the modified glass wool was recyclable, making it suitable candidates for future environmental applications.
- Full Text:
- Date Issued: 2022
- Authors: Sindelo, Azole , Britton, Jonathan , Lanterna, Anabel E , Scaiano, Juan C , Nyokong, Tebello
- Date: 2022
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/295742 , vital:57374 , xlink:href="https://doi.org/10.1016/j.jphotochem.2022.114127"
- Description: Zinc phthalocyanines containing one (mono carboxy phenoxy, ZnMCPPc), four (tetra carboxy phenoxy, ZnTCPPc), and eight (tetra isophthalic acid, ZnTIPAPc) carboxyl groups were covalently conjugated to amine-functionalized glass wool (GW). The GW-Pcs were characterized and evaluated for singlet oxygen generation. The photocatalytic efficiencies of the GW-Pcs were assessed using methyl orange. Glass wool alone and the modified conjugates exhibited low to no degradation of methyl orange in the dark. The improved catalytic rate was observed for GW-ZnMCPPc and GW-ZnTCPPc compared to GW-ZnTIPAPc due to the latter's lower singlet oxygen quantum yield generation. In addition, the modified glass wool was recyclable, making it suitable candidates for future environmental applications.
- Full Text:
- Date Issued: 2022
Fabrication of asymmetrical morpholine phthalocyanines conjugated chitosan-polyacrylonitrile nanofibers for improved photodynamic antimicrobial chemotherapy activity
- Sindelo, Azole, Mafukidze, Donovan M, Nyokong, Tebello
- Authors: Sindelo, Azole , Mafukidze, Donovan M , Nyokong, Tebello
- Date: 2022
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/229873 , vital:49719 , xlink:href="https://doi.org/10.1016/j.pdpdt.2022.102760"
- Description: The work is based on the synthesis and photodynamic antimicrobial chemotherapy (PACT) activities of neutral (1 and 2) and cationic (1Q and 2Q) morpholine substituted phthalocyanines. For applicability, these complexes were covalently linked to modified polyacrylonitrile (PAN) to form 1-PAN, 2-PAN, 1Q-PAN, and 2Q-PAN, respectively. Chitosan was conjugated to PAN (to form PAN-CS) which was then linked to the Pcs to form PAN-CS-1, PAN-CS-2, PAN-CS-1Q, and PAN-CS-2Q, respectively. Singlet oxygen quantum yields improved following the inclusion of chitosan. The PACT activities of the complexes alone and when anchored to both PAN and PAN-CS was evaluated against bacteria: S. aureus, E. coli and fungi C. albicans. Cationic phthalocyanine showed high efficacy values of >7 log reduction value for all microorganisms. These results translated into excellent bacterial colony reduction of >90% against both S. aureus and C. albicans after 1 h of photoirradiation on PAN-CS support.
- Full Text:
- Date Issued: 2022
- Authors: Sindelo, Azole , Mafukidze, Donovan M , Nyokong, Tebello
- Date: 2022
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/229873 , vital:49719 , xlink:href="https://doi.org/10.1016/j.pdpdt.2022.102760"
- Description: The work is based on the synthesis and photodynamic antimicrobial chemotherapy (PACT) activities of neutral (1 and 2) and cationic (1Q and 2Q) morpholine substituted phthalocyanines. For applicability, these complexes were covalently linked to modified polyacrylonitrile (PAN) to form 1-PAN, 2-PAN, 1Q-PAN, and 2Q-PAN, respectively. Chitosan was conjugated to PAN (to form PAN-CS) which was then linked to the Pcs to form PAN-CS-1, PAN-CS-2, PAN-CS-1Q, and PAN-CS-2Q, respectively. Singlet oxygen quantum yields improved following the inclusion of chitosan. The PACT activities of the complexes alone and when anchored to both PAN and PAN-CS was evaluated against bacteria: S. aureus, E. coli and fungi C. albicans. Cationic phthalocyanine showed high efficacy values of >7 log reduction value for all microorganisms. These results translated into excellent bacterial colony reduction of >90% against both S. aureus and C. albicans after 1 h of photoirradiation on PAN-CS support.
- Full Text:
- Date Issued: 2022
Effect of ultrasonic frequency and power on the sonodynamic therapy activity of cationic Zn (II) phthalocyanines
- Nene, Lindokuhle C, Sindelo, Azole, Britton, Jonathan, Nyokong, Tebello
- Authors: Nene, Lindokuhle C , Sindelo, Azole , Britton, Jonathan , Nyokong, Tebello
- Date: 2021
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/185737 , vital:44419 , xlink:href="https://doi.org/10.1016/j.jinorgbio.2021.111397"
- Description: We report on the sonodynamic activity of cationic phthalocyanines (Pcs) and the effect of the variation of two parameters: ultrasound frequency and power (Par I (1 MHz, 1 W cm−2), Par II (1 MHz, 2 W cm−2), Par III (3 MHz, 1 W cm−2) and Par IV (3 MHz, 2 W cm−2)) on the efficiency of their reactive oxygen species generation and cancer eradication in vitro thereof. Where Par stands for the various combinations of these parameters. Four Pcs were investigated with substituents bearing diethylamine, ortho- and para-pyridine and morpholine groups. Overall, the para-pyridine and morpholine Pcs showed substantial sono-activity in the various ultrasound parameters with Par I and IV generally showing better singlet oxygen and hydroxyl radicals generation confirmed by electron paramagnetic resonance spectroscopy. In some cases, very high hydroxyl radicals' generation was observed at Par II. Furthermore, the fragmentation of the Pcs after Par II treatments was confirmed using UV–vis and magnetic circular dichroism spectroscopy. The reactive species generation efficacy decreased at Par III for all samples. Ultrasound assisted cytotoxicity of the Pcs was confirmed in vitro using the human (Michigan Cancer Foundation-7) breast cancer cell line.
- Full Text:
- Date Issued: 2021
- Authors: Nene, Lindokuhle C , Sindelo, Azole , Britton, Jonathan , Nyokong, Tebello
- Date: 2021
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/185737 , vital:44419 , xlink:href="https://doi.org/10.1016/j.jinorgbio.2021.111397"
- Description: We report on the sonodynamic activity of cationic phthalocyanines (Pcs) and the effect of the variation of two parameters: ultrasound frequency and power (Par I (1 MHz, 1 W cm−2), Par II (1 MHz, 2 W cm−2), Par III (3 MHz, 1 W cm−2) and Par IV (3 MHz, 2 W cm−2)) on the efficiency of their reactive oxygen species generation and cancer eradication in vitro thereof. Where Par stands for the various combinations of these parameters. Four Pcs were investigated with substituents bearing diethylamine, ortho- and para-pyridine and morpholine groups. Overall, the para-pyridine and morpholine Pcs showed substantial sono-activity in the various ultrasound parameters with Par I and IV generally showing better singlet oxygen and hydroxyl radicals generation confirmed by electron paramagnetic resonance spectroscopy. In some cases, very high hydroxyl radicals' generation was observed at Par II. Furthermore, the fragmentation of the Pcs after Par II treatments was confirmed using UV–vis and magnetic circular dichroism spectroscopy. The reactive species generation efficacy decreased at Par III for all samples. Ultrasound assisted cytotoxicity of the Pcs was confirmed in vitro using the human (Michigan Cancer Foundation-7) breast cancer cell line.
- Full Text:
- Date Issued: 2021
Thien-2-yl substituted chlorins as photosensitizers for photodynamic therapy and photodynamic antimicrobial chemotherapy
- Babu, Balaji, Sindelo, Azole, Mack, John, Nyokong, Tebello
- Authors: Babu, Balaji , Sindelo, Azole , Mack, John , Nyokong, Tebello
- Date: 2021
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/190578 , vital:45007 , xlink:href="https://doi.org/10.1016/j.dyepig.2020.108886"
- Description: The synthesis and characterization of meso-tetra(thien-2-yl)chlorin (1) and meso-tetra(5-bromothien-2-yl)chlorin (2) is reported. These dyes have red-shifted absorption maxima compared to those of the analogous meso-tetraphenylchlorin (3). 1 and 2 have Q bands at 660 and 664 nm, respectively, singlet oxygen quantum yields of 0.60 and 0.64 and exhibit good photostability. The triplet states were found to have lifetimes of 8.6 μs in N2 purged DMF. Time-dependent cellular uptake of chlorins reached a maximum in MCF-7 cancer cells after 12 h. Upon irradiation with a Thorlabs M660L3 LED (280 mW cm−2), 2 exhibited better photocytotoxicity with an IC50 value of 2.7 μM against MCF-7 cells. The 2ʹ,7ʹ-dichlorodihydrofluorescein diacetate (DCFDA) assay provided evidence for intracellular generation of reactive oxygen species. Photodynamic inactivation of bacteria by the chlorins was also studied. 2 exhibits better activity with log reduction values of 7.42 and 8.34 towards Staphylococcus aureus and Escherichia coli, respectively, under illumination for 60 min at 660 nm with a Thorlabs M660L3 LED (280 mW cm−2). These results demonstrate that 2 is a promising candidate for future in vivo experiments and merits further in-depth investigation.
- Full Text:
- Date Issued: 2021
- Authors: Babu, Balaji , Sindelo, Azole , Mack, John , Nyokong, Tebello
- Date: 2021
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/190578 , vital:45007 , xlink:href="https://doi.org/10.1016/j.dyepig.2020.108886"
- Description: The synthesis and characterization of meso-tetra(thien-2-yl)chlorin (1) and meso-tetra(5-bromothien-2-yl)chlorin (2) is reported. These dyes have red-shifted absorption maxima compared to those of the analogous meso-tetraphenylchlorin (3). 1 and 2 have Q bands at 660 and 664 nm, respectively, singlet oxygen quantum yields of 0.60 and 0.64 and exhibit good photostability. The triplet states were found to have lifetimes of 8.6 μs in N2 purged DMF. Time-dependent cellular uptake of chlorins reached a maximum in MCF-7 cancer cells after 12 h. Upon irradiation with a Thorlabs M660L3 LED (280 mW cm−2), 2 exhibited better photocytotoxicity with an IC50 value of 2.7 μM against MCF-7 cells. The 2ʹ,7ʹ-dichlorodihydrofluorescein diacetate (DCFDA) assay provided evidence for intracellular generation of reactive oxygen species. Photodynamic inactivation of bacteria by the chlorins was also studied. 2 exhibits better activity with log reduction values of 7.42 and 8.34 towards Staphylococcus aureus and Escherichia coli, respectively, under illumination for 60 min at 660 nm with a Thorlabs M660L3 LED (280 mW cm−2). These results demonstrate that 2 is a promising candidate for future in vivo experiments and merits further in-depth investigation.
- Full Text:
- Date Issued: 2021
Magnetic nanoparticle-indium phthalocyanine conjugate embedded in electrospun fiber for photodynamic antimicrobial chemotherapy and photodegradation of methyl red
- Sindelo, Azole, Nyokong, Tebello
- Authors: Sindelo, Azole , Nyokong, Tebello
- Date: 2019
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/186857 , vital:44540 , xlink:href="https://doi.org/10.1016/j.heliyon.2019.e02352"
- Description: ClIn(III) octacarboxy phthalocyanine (ClInOCPc) when alone or conjugated to magnetic nanoparticles (MNPClInOCPc) was employed for both photodynamic antimicrobial chemotherapy of an unknown water sample and Staphylococcus aureus, and for photo-degradation of methyl red (MR). The singlet oxygen quantum yields (ΦΔ) in water using ClInOCPc and MNP-ClInOCPc embedded in polyacrylonitrile (PAN) electrospun fibers were 0.36 and 0.22, respectively. When in solution, MNP-ClInOCPc gave 90.6% photoinactivation of microbes in a water sample from the stream and of ClInOCPc resulted in 84.8 % photoinactivation. When embedded to the polymer, there was 48.0% clearance for ClInOCPc and 63.7% clearance for MNP-ClInOCPc for the microbes in the water sample from the stream. For the photo-degradation of MR, the rate of degradation increased with decrease of the MR concentration with the MNP-ClInOCPc having the fastest rate.
- Full Text:
- Date Issued: 2019
- Authors: Sindelo, Azole , Nyokong, Tebello
- Date: 2019
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/186857 , vital:44540 , xlink:href="https://doi.org/10.1016/j.heliyon.2019.e02352"
- Description: ClIn(III) octacarboxy phthalocyanine (ClInOCPc) when alone or conjugated to magnetic nanoparticles (MNPClInOCPc) was employed for both photodynamic antimicrobial chemotherapy of an unknown water sample and Staphylococcus aureus, and for photo-degradation of methyl red (MR). The singlet oxygen quantum yields (ΦΔ) in water using ClInOCPc and MNP-ClInOCPc embedded in polyacrylonitrile (PAN) electrospun fibers were 0.36 and 0.22, respectively. When in solution, MNP-ClInOCPc gave 90.6% photoinactivation of microbes in a water sample from the stream and of ClInOCPc resulted in 84.8 % photoinactivation. When embedded to the polymer, there was 48.0% clearance for ClInOCPc and 63.7% clearance for MNP-ClInOCPc for the microbes in the water sample from the stream. For the photo-degradation of MR, the rate of degradation increased with decrease of the MR concentration with the MNP-ClInOCPc having the fastest rate.
- Full Text:
- Date Issued: 2019
Physicochemical and photodynamic antimicrobial chemotherapy activity of morpholine-substituted phthalocyanines: Effect of point of substitution and central metal
- Sindelo, Azole, Kobayashi, Nagao, Kimura, Mutsumi, Nyokong, Tebello
- Authors: Sindelo, Azole , Kobayashi, Nagao , Kimura, Mutsumi , Nyokong, Tebello
- Date: 2019
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187438 , vital:44652 , xlink:href="https://doi.org/10.1016/j.jphotochem.2019.01.025"
- Description: In this study, novel metal-free, zinc and indium 1(4),8(11),15(18),22(25)-tetramorpholine (1a, 2a, 3a respectively) and 2(3), 9(10), 16(17),23(24)-tetramorpholine (1b, 2b, 3b respectively) phthalocyanines were synthesized and complexes 2 and 3 were quaternized. The photophysical and photochemical properties were investigated in dimethylsulfoxide. The non-peripherally substituted phthalocyanines generated higher singlet oxygen than the peripherally substituted phthalocyanines. Photodynamic antimicrobial chemotherapy activities towards inactivation of Escherichia coli, Staphylococcus aureus and Candida albican were evaluated, where all the quaternized Pcs showed total elimination of the micro-organism with log reductions greater than 9. Though the neutral Pcs had log reductions less than 2, for C. albican the percentage reduction was 68.5% for 2b showing the antifungal properties of the morpholine group.
- Full Text:
- Date Issued: 2019
- Authors: Sindelo, Azole , Kobayashi, Nagao , Kimura, Mutsumi , Nyokong, Tebello
- Date: 2019
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187438 , vital:44652 , xlink:href="https://doi.org/10.1016/j.jphotochem.2019.01.025"
- Description: In this study, novel metal-free, zinc and indium 1(4),8(11),15(18),22(25)-tetramorpholine (1a, 2a, 3a respectively) and 2(3), 9(10), 16(17),23(24)-tetramorpholine (1b, 2b, 3b respectively) phthalocyanines were synthesized and complexes 2 and 3 were quaternized. The photophysical and photochemical properties were investigated in dimethylsulfoxide. The non-peripherally substituted phthalocyanines generated higher singlet oxygen than the peripherally substituted phthalocyanines. Photodynamic antimicrobial chemotherapy activities towards inactivation of Escherichia coli, Staphylococcus aureus and Candida albican were evaluated, where all the quaternized Pcs showed total elimination of the micro-organism with log reductions greater than 9. Though the neutral Pcs had log reductions less than 2, for C. albican the percentage reduction was 68.5% for 2b showing the antifungal properties of the morpholine group.
- Full Text:
- Date Issued: 2019
Spectroscopic characterization and photodynamic antimicrobial chemotherapy of phthalocyanine-silver triangular nanoprism conjugates when supported on asymmetric polymer membranes
- Mafukidze, Donovan M, Sindelo, Azole, Nyokong, Tebello
- Authors: Mafukidze, Donovan M , Sindelo, Azole , Nyokong, Tebello
- Date: 2019
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/186927 , vital:44548 , xlink:href="https://doi.org/10.1016/j.saa.2019.04.054"
- Description: Silver triangular nanoprisms were synthesized and conjugated to zinc (ZnPc) and indium (InPc) phthalocyanines prior to embedding in asymmetric membranes. Conjugation of nanoparticles increased triplet state and singlet oxygen quantum yields of the phthalocyanines as well as enhancing photodynamic antimicrobial chemotherapy (PACT) activity against bacteria (S. aureus). The ZnPc derivative showed higher PACT activity when compared to the InPc, possibly due to degradation of the latter in aqueous media.
- Full Text:
- Date Issued: 2019
- Authors: Mafukidze, Donovan M , Sindelo, Azole , Nyokong, Tebello
- Date: 2019
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/186927 , vital:44548 , xlink:href="https://doi.org/10.1016/j.saa.2019.04.054"
- Description: Silver triangular nanoprisms were synthesized and conjugated to zinc (ZnPc) and indium (InPc) phthalocyanines prior to embedding in asymmetric membranes. Conjugation of nanoparticles increased triplet state and singlet oxygen quantum yields of the phthalocyanines as well as enhancing photodynamic antimicrobial chemotherapy (PACT) activity against bacteria (S. aureus). The ZnPc derivative showed higher PACT activity when compared to the InPc, possibly due to degradation of the latter in aqueous media.
- Full Text:
- Date Issued: 2019
Synthesis and photophysicochemical properties of novel axially di-substituted silicon (IV) phthalocyanines and their photodynamic antimicrobial chemotherapy (PACT) activity against Staphylococcus aureus
- Sen, Pinar, Sindelo, Azole, Mafukidze, Donovan M, Nyokong, Tebello
- Authors: Sen, Pinar , Sindelo, Azole , Mafukidze, Donovan M , Nyokong, Tebello
- Date: 2019
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/186757 , vital:44531 , xlink:href="https://doi.org/10.1016/j.synthmet.2019.116203"
- Description: In this study, novel silicon (IV) phthalocyanine axially di-substituted with benzimidazole moieties (3) and its quaternized derivative (4) have been synthesized and fully characterized. The photophysical and photochemical properties of both phthalocyanines such as absorption, fluorescence and, singlet oxygen quantum yields, triplet state quantum yields and exited state lifetimes were investigated in solutions. These new silicon phthalocyanines exhibited low fluorescence but produced high singlet oxygen yields in both DMSO (compound 3 and 4) and aqueous media (compound 4). The quaternization of Si(IV)Pc (3) improved the triplet state quantum yield (ΦT) 0.61 to 0.83, consequently singlet oxygen generation (ΦΔ) increased to 0.69 from 0.42. Photodynamic antimicrobial chemotherapy activities (PACT) of Si(IV)Pc photosensitizers were determined towards Staphylococcus aureus. The higher efficiency was obtained with cationic derivative (4) giving reduction percentage value of 99.75%.
- Full Text:
- Date Issued: 2019
- Authors: Sen, Pinar , Sindelo, Azole , Mafukidze, Donovan M , Nyokong, Tebello
- Date: 2019
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/186757 , vital:44531 , xlink:href="https://doi.org/10.1016/j.synthmet.2019.116203"
- Description: In this study, novel silicon (IV) phthalocyanine axially di-substituted with benzimidazole moieties (3) and its quaternized derivative (4) have been synthesized and fully characterized. The photophysical and photochemical properties of both phthalocyanines such as absorption, fluorescence and, singlet oxygen quantum yields, triplet state quantum yields and exited state lifetimes were investigated in solutions. These new silicon phthalocyanines exhibited low fluorescence but produced high singlet oxygen yields in both DMSO (compound 3 and 4) and aqueous media (compound 4). The quaternization of Si(IV)Pc (3) improved the triplet state quantum yield (ΦT) 0.61 to 0.83, consequently singlet oxygen generation (ΦΔ) increased to 0.69 from 0.42. Photodynamic antimicrobial chemotherapy activities (PACT) of Si(IV)Pc photosensitizers were determined towards Staphylococcus aureus. The higher efficiency was obtained with cationic derivative (4) giving reduction percentage value of 99.75%.
- Full Text:
- Date Issued: 2019
Synthesis of indium phthalocyanines for photodynamic antimicrobial chemotherapy and photo-oxidation of pollutants
- Authors: Sindelo, Azole
- Date: 2019
- Subjects: Phthalocyanines , Azo dyes , Indium compounds , Photochemotherapy , Nanoparticles , Photodegradation , Pollutants , Water -- Purification
- Language: English
- Type: text , Thesis , Masters , MSc
- Identifier: http://hdl.handle.net/10962/67581 , vital:29116
- Description: Indium (III) octacarboxyl phthalocyanine (ClInOCPc) alone and when conjugated to magnetic nanoparticles (MNP-ClInOCPc), 2(3),9(10),16(17),23(24)-octapyridylsulfanyl phthalocyaninato chloroindium (III) (ClInOPyPc) and its quaternized derivative 2(3),9(10),16(17),23(24)-octamethylpyridylsulfanyl phthalocyaninato chloroindium (III) (ClInOMePyPc) were synthesized. All Pcs were tested for both photodynamic antimicrobial chemotherapy (PACT) of an unknown water sample and photo-degradation of methyl red (MR). The singlet quantum yield (ΦΔ) for the ClInOCPc and MNP-ClInOCPc in PAN polymer fibers were 0.36 and 0.20 respectively using ADMA as a quencher in water. The photo-inactivation of bacteria in a water sample with unknown microbes was tested, with the MNP-ClInOCPc inactivating 90.6 % of the microbes and the ClInOCPc with 84.8 %. When embedded to the polymer, there was 48% bacterial clearance for ClInOCPc and 64% clearance for the MNP-ClInOCPc. The rate of degradation of MR increased with decrease of the MR concentration, with the MNP-ClInOCPc having the fastest rate. For ClInOPyPc and ClInOMePyPc, the singlet quantum yields were 0.46 and 0.33 in dimethylformamide (DMF), respectively. The PACT activity of ClInOMePyPc (containing 8 positive charges) was compared to those of 9(10),16(17),23(24)-tri-N-methyl-4-pyridylsulfanyl-2(3)-(4-aminophenoxy) phthalocyaninato chloro indium (III) triiodide (1) (containing 3 positive charges) and 2-[4-(N-methylpyridyloxy) phthalocyaninato] chloroindium (III) iodide (2) (containing 4 positive charges). When comparing ClInOMePyPc, 1 and 2, the largest log reduction for E. coli were obtained for complex 2 containing four positive charges hence showing it is not always the charge that determines the PACT activity, but the bridging atom in the phthalocyanine plays a role.
- Full Text:
- Date Issued: 2019
- Authors: Sindelo, Azole
- Date: 2019
- Subjects: Phthalocyanines , Azo dyes , Indium compounds , Photochemotherapy , Nanoparticles , Photodegradation , Pollutants , Water -- Purification
- Language: English
- Type: text , Thesis , Masters , MSc
- Identifier: http://hdl.handle.net/10962/67581 , vital:29116
- Description: Indium (III) octacarboxyl phthalocyanine (ClInOCPc) alone and when conjugated to magnetic nanoparticles (MNP-ClInOCPc), 2(3),9(10),16(17),23(24)-octapyridylsulfanyl phthalocyaninato chloroindium (III) (ClInOPyPc) and its quaternized derivative 2(3),9(10),16(17),23(24)-octamethylpyridylsulfanyl phthalocyaninato chloroindium (III) (ClInOMePyPc) were synthesized. All Pcs were tested for both photodynamic antimicrobial chemotherapy (PACT) of an unknown water sample and photo-degradation of methyl red (MR). The singlet quantum yield (ΦΔ) for the ClInOCPc and MNP-ClInOCPc in PAN polymer fibers were 0.36 and 0.20 respectively using ADMA as a quencher in water. The photo-inactivation of bacteria in a water sample with unknown microbes was tested, with the MNP-ClInOCPc inactivating 90.6 % of the microbes and the ClInOCPc with 84.8 %. When embedded to the polymer, there was 48% bacterial clearance for ClInOCPc and 64% clearance for the MNP-ClInOCPc. The rate of degradation of MR increased with decrease of the MR concentration, with the MNP-ClInOCPc having the fastest rate. For ClInOPyPc and ClInOMePyPc, the singlet quantum yields were 0.46 and 0.33 in dimethylformamide (DMF), respectively. The PACT activity of ClInOMePyPc (containing 8 positive charges) was compared to those of 9(10),16(17),23(24)-tri-N-methyl-4-pyridylsulfanyl-2(3)-(4-aminophenoxy) phthalocyaninato chloro indium (III) triiodide (1) (containing 3 positive charges) and 2-[4-(N-methylpyridyloxy) phthalocyaninato] chloroindium (III) iodide (2) (containing 4 positive charges). When comparing ClInOMePyPc, 1 and 2, the largest log reduction for E. coli were obtained for complex 2 containing four positive charges hence showing it is not always the charge that determines the PACT activity, but the bridging atom in the phthalocyanine plays a role.
- Full Text:
- Date Issued: 2019
The photo-physicochemical properties and in vitro photodynamic therapy activity of differently substituted-zinc (II)-phthalocyanines and graphene quantum dots conjugates on MCF7 breast cancer cell line
- Nene, Lindokuhle C, Managa, Muthumuni E, Oluwole, David O, Mafukidze, Donovan M, Sindelo, Azole, Nyokong, Tebello
- Authors: Nene, Lindokuhle C , Managa, Muthumuni E , Oluwole, David O , Mafukidze, Donovan M , Sindelo, Azole , Nyokong, Tebello
- Date: 2019
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187449 , vital:44653 , xlink:href="https://doi.org/10.1016/j.ica.2019.01.012"
- Description: Several differently substituted Zn(II) phthalocyanines (ZnPcs) were prepared and conjugated to GQDs. The photophysical properties were determined for both the Pcs and their respective conjugates including the fluorescence/triplet quantum yields and lifetimes as well as the singlet oxygen generating abilities. Upon conjugation to GQDs, the fluorescence of the Pcs decreased (insignificant decrease in some cases), with an increase in the triplet quantum yields. However, the singlet quantum yields of the Pcs in the conjugates did not show an increase with the increase in the triplet quantum yields, this is suspected to be due to the screening effect. The cytotoxicity of the complexes in vitro decreased upon conjugation, as a result of the reduced actual number of Pcs units provided in the conjugate for therapy. Upon introduction of cationic charges, the photodynamic therapy activity of the complexes increased.
- Full Text:
- Date Issued: 2019
- Authors: Nene, Lindokuhle C , Managa, Muthumuni E , Oluwole, David O , Mafukidze, Donovan M , Sindelo, Azole , Nyokong, Tebello
- Date: 2019
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187449 , vital:44653 , xlink:href="https://doi.org/10.1016/j.ica.2019.01.012"
- Description: Several differently substituted Zn(II) phthalocyanines (ZnPcs) were prepared and conjugated to GQDs. The photophysical properties were determined for both the Pcs and their respective conjugates including the fluorescence/triplet quantum yields and lifetimes as well as the singlet oxygen generating abilities. Upon conjugation to GQDs, the fluorescence of the Pcs decreased (insignificant decrease in some cases), with an increase in the triplet quantum yields. However, the singlet quantum yields of the Pcs in the conjugates did not show an increase with the increase in the triplet quantum yields, this is suspected to be due to the screening effect. The cytotoxicity of the complexes in vitro decreased upon conjugation, as a result of the reduced actual number of Pcs units provided in the conjugate for therapy. Upon introduction of cationic charges, the photodynamic therapy activity of the complexes increased.
- Full Text:
- Date Issued: 2019
Optimizing phthalocyanine based dye-sensitized solar cells: The role of reduced graphene oxide
- Chindeka, Francis, Mashazi, Philani N, Britton, Jonathan, Fomo, Gertrude, Oluwole, David O, Sindelo, Azole, Nyokong, Tebello
- Authors: Chindeka, Francis , Mashazi, Philani N , Britton, Jonathan , Fomo, Gertrude , Oluwole, David O , Sindelo, Azole , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187770 , vital:44695 , xlink:href="https://doi.org/10.1016/j.synthmet.2018.10.021"
- Description: Dye-sensitized solar cells (DSSC) were fabricated by incorporating graphene materials as catalysts at the counter electrode. Platinum was also used as a catalyst for comparison purposes. Different phthalocyanines: hydroxyl indium tetracarboxyphenoxy phthalocyanine (1), chloro indium octacarboxy phthalocyanine (2) and dibenzoic acid silicon phthalocyanine (3) were used as dyes. Complex 3 gave the highest power conversion efficiency (η) of 3.19% when using nitrogen doped reduced graphene oxide nanosheets (NrGONS) as a catalyst at the counter electrode, and TiO2 containing rGONS at the anode. The value is close to 3.8% obtained when using Pt catalyst instead of NrGONS at the cathode, thus confirming that NrGONS is a promising candidate to replace the more expensive Pt. The study also shows that placing rGONS on both the anode and cathode improves efficiency.
- Full Text:
- Date Issued: 2018
- Authors: Chindeka, Francis , Mashazi, Philani N , Britton, Jonathan , Fomo, Gertrude , Oluwole, David O , Sindelo, Azole , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187770 , vital:44695 , xlink:href="https://doi.org/10.1016/j.synthmet.2018.10.021"
- Description: Dye-sensitized solar cells (DSSC) were fabricated by incorporating graphene materials as catalysts at the counter electrode. Platinum was also used as a catalyst for comparison purposes. Different phthalocyanines: hydroxyl indium tetracarboxyphenoxy phthalocyanine (1), chloro indium octacarboxy phthalocyanine (2) and dibenzoic acid silicon phthalocyanine (3) were used as dyes. Complex 3 gave the highest power conversion efficiency (η) of 3.19% when using nitrogen doped reduced graphene oxide nanosheets (NrGONS) as a catalyst at the counter electrode, and TiO2 containing rGONS at the anode. The value is close to 3.8% obtained when using Pt catalyst instead of NrGONS at the cathode, thus confirming that NrGONS is a promising candidate to replace the more expensive Pt. The study also shows that placing rGONS on both the anode and cathode improves efficiency.
- Full Text:
- Date Issued: 2018
Synthesis, photophysicochemical and photodynamic antimicrobial chemotherapy studies of indium pyridyl phthalocyanines: Charge versus bridging atom
- Sindelo, Azole, Nyokong, Tebello
- Authors: Sindelo, Azole , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187650 , vital:44683 , xlink:href="https://doi.org/10.1016/j.ica.2018.02.020"
- Description: 2(3), 9(10), 16(17), 23(24)-Octapyridylsulfanyl phthalocyaninato chloroindium(III) (complex 1a) and its quaternized derivative 2(3), 9(10), 16(17), 23(24)-octamethylpyridylsulfanyl phthalocyaninato chloroindium (III) (complex 1b) were synthesised. The triplet quantum yields were 0.53 and 0.48 while the singlet oxygen quantum yields were 0.46 and 0.33 in DMF for 1a and 1b, respectively. The photodynamic antimicrobial chemotherapy (PACT) activity of 1b (containing 8 positive charges) was compared to those of 9(10),16(17),23(24)-tri-N-methyl-4-pyridylsulfanyl-2(3)-(4-aminophenoxy) phthalocyaninato chloro indium(III) triiodide (2) (containing 3 positive charges) and 2-[4-(N-Methylpyridyloxy) phthalocyaninato] chloroindium (III) iodide (3) (containing 4 positive charges). Complex 1b gave log reductions of 4.21, 8.30 and 3.21 for Gram(−) E. coli, Gram(+) S. aureus and C. albicans, respectively. When comparing 1b, 2 and 3, the largest log reductions for E. coli were obtained for complex 3 containing four positive charges hence showing it is not always the charge that determines the PACT activity, but the bridging atom in the phthalocyanine plays a role.
- Full Text:
- Date Issued: 2018
- Authors: Sindelo, Azole , Nyokong, Tebello
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187650 , vital:44683 , xlink:href="https://doi.org/10.1016/j.ica.2018.02.020"
- Description: 2(3), 9(10), 16(17), 23(24)-Octapyridylsulfanyl phthalocyaninato chloroindium(III) (complex 1a) and its quaternized derivative 2(3), 9(10), 16(17), 23(24)-octamethylpyridylsulfanyl phthalocyaninato chloroindium (III) (complex 1b) were synthesised. The triplet quantum yields were 0.53 and 0.48 while the singlet oxygen quantum yields were 0.46 and 0.33 in DMF for 1a and 1b, respectively. The photodynamic antimicrobial chemotherapy (PACT) activity of 1b (containing 8 positive charges) was compared to those of 9(10),16(17),23(24)-tri-N-methyl-4-pyridylsulfanyl-2(3)-(4-aminophenoxy) phthalocyaninato chloro indium(III) triiodide (2) (containing 3 positive charges) and 2-[4-(N-Methylpyridyloxy) phthalocyaninato] chloroindium (III) iodide (3) (containing 4 positive charges). Complex 1b gave log reductions of 4.21, 8.30 and 3.21 for Gram(−) E. coli, Gram(+) S. aureus and C. albicans, respectively. When comparing 1b, 2 and 3, the largest log reductions for E. coli were obtained for complex 3 containing four positive charges hence showing it is not always the charge that determines the PACT activity, but the bridging atom in the phthalocyanine plays a role.
- Full Text:
- Date Issued: 2018
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