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.
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- 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.
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Electrospun 3, 5-dithienylvinyleneBODIPY embedded polystyrene nanofibers for the photocatalytic degradation of azo dyes in industrial wastewaters
- Lebechi, Augustus K, Gai, Lizhi, Shen, Zhen, Nyokong, Tebello, Mack, John
- Authors: Lebechi, Augustus K , Gai, Lizhi , Shen, Zhen , Nyokong, Tebello , Mack, John
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187679 , vital:44686 , xlink:href="https://doi.org/10.1142/S1088424618500360"
- Description: The potential utility of electrospun polystyrene (PS) nanofibers embedded with 2,6-diiodo-8-phenyl-1,7-dimethyl-3,5-di-2-thienylvinyleneBODIPY for the photocatalytic degradation of azo dyes is investigated. A comparison of the singlet oxygen quantum yield of the ππ-extended BODIPY dye in solution and in the PS nanofibers demonstrates that its photosensitizer properties are retained when it is embedded in the solid phase. The photocatalytic degradation properties of the PS nanofibers for Methyl Orange and Orange G were determined by using a Thorlabs 625 nm light emitting diode. The rate of photodegradation increases with the Orange G and Methyl Orange concentration and follows pseudo-first order kinetics at pH 6.7.
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- Authors: Lebechi, Augustus K , Gai, Lizhi , Shen, Zhen , Nyokong, Tebello , Mack, John
- Date: 2018
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/187679 , vital:44686 , xlink:href="https://doi.org/10.1142/S1088424618500360"
- Description: The potential utility of electrospun polystyrene (PS) nanofibers embedded with 2,6-diiodo-8-phenyl-1,7-dimethyl-3,5-di-2-thienylvinyleneBODIPY for the photocatalytic degradation of azo dyes is investigated. A comparison of the singlet oxygen quantum yield of the ππ-extended BODIPY dye in solution and in the PS nanofibers demonstrates that its photosensitizer properties are retained when it is embedded in the solid phase. The photocatalytic degradation properties of the PS nanofibers for Methyl Orange and Orange G were determined by using a Thorlabs 625 nm light emitting diode. The rate of photodegradation increases with the Orange G and Methyl Orange concentration and follows pseudo-first order kinetics at pH 6.7.
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Optical Limiting Properties of 3, 5-Dithienylenevinylene BODIPY Dyes at 532 nm
- Harris, Jessica, Gai, Lizhi, Kubheka, Gugu, Mack, John, Nyokong, Tebello, Shen, Zhen
- Authors: Harris, Jessica , Gai, Lizhi , Kubheka, Gugu , Mack, John , Nyokong, Tebello , Shen, Zhen
- Date: 2017
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/189274 , vital:44833 , xlink:href="https://doi.org/10.1002/chem.201702503"
- Description: The optical limiting properties of a series of near infrared absorbing 3,5-dithienylenevinylene BODIPY (borondipyrromethene) dyes (1–3) that contain donor and acceptor moieties in their p-conjugation systems were studied by using the z-scan technique at 532 nm in the nanosecond pulse range. A strong reverse saturable absorption response was observed when the compounds are embedded into poly(bisphenol carbonate A) polymer thin films, which demonstrates that BODIPY dyes with this type of structure are suitable for use in optical limiting applications.
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- Authors: Harris, Jessica , Gai, Lizhi , Kubheka, Gugu , Mack, John , Nyokong, Tebello , Shen, Zhen
- Date: 2017
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/189274 , vital:44833 , xlink:href="https://doi.org/10.1002/chem.201702503"
- Description: The optical limiting properties of a series of near infrared absorbing 3,5-dithienylenevinylene BODIPY (borondipyrromethene) dyes (1–3) that contain donor and acceptor moieties in their p-conjugation systems were studied by using the z-scan technique at 532 nm in the nanosecond pulse range. A strong reverse saturable absorption response was observed when the compounds are embedded into poly(bisphenol carbonate A) polymer thin films, which demonstrates that BODIPY dyes with this type of structure are suitable for use in optical limiting applications.
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A chiral hemiporphyrazine derivative
- Wu, Yanping, Gai, Lizhi, Xiao, Xuqiong, Lu, Hua, Li, Zhifang, Mack, John, Harris, Jessica, Nyokong, Tebello, Shen, Zhen
- Authors: Wu, Yanping , Gai, Lizhi , Xiao, Xuqiong , Lu, Hua , Li, Zhifang , Mack, John , Harris, Jessica , Nyokong, Tebello , Shen, Zhen
- Date: 2016
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/240404 , vital:50831 , xlink:href="https://doi.org/10.1002/asia.201600754"
- Description: The synthesis of an optically active hemiporphyrazine with chiral binaphthyl substituents (1) is reported, providing the first example of the incorporation of an intrinsically chiral moiety into the macrocyclic core of a hemiporphyrazine analogue. A negative circular dichroism (CD) signal is observed in the 325–450 nm region of the CD spectrum of (S,S)-1, while mainly positive bands are observed in the 220–325 nm region. Mirror symmetry is observed across the entire wavelength range of the CD spectra of (R,R)-1 and (S,S)-1. An irreversible one-electron oxidation wave with an onset potential at 1.07 V is observed by cyclic voltammetry, along with a reversible one-electron reduction wave at −0.85 V. Density functional calculations reproduce the experimentally observed data and trends, and provide further insight into the nature of the electronic transitions.
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- Authors: Wu, Yanping , Gai, Lizhi , Xiao, Xuqiong , Lu, Hua , Li, Zhifang , Mack, John , Harris, Jessica , Nyokong, Tebello , Shen, Zhen
- Date: 2016
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/240404 , vital:50831 , xlink:href="https://doi.org/10.1002/asia.201600754"
- Description: The synthesis of an optically active hemiporphyrazine with chiral binaphthyl substituents (1) is reported, providing the first example of the incorporation of an intrinsically chiral moiety into the macrocyclic core of a hemiporphyrazine analogue. A negative circular dichroism (CD) signal is observed in the 325–450 nm region of the CD spectrum of (S,S)-1, while mainly positive bands are observed in the 220–325 nm region. Mirror symmetry is observed across the entire wavelength range of the CD spectra of (R,R)-1 and (S,S)-1. An irreversible one-electron oxidation wave with an onset potential at 1.07 V is observed by cyclic voltammetry, along with a reversible one-electron reduction wave at −0.85 V. Density functional calculations reproduce the experimentally observed data and trends, and provide further insight into the nature of the electronic transitions.
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Efficient energy transfer in ethynyl bridged corrole–BODIPY dyads
- Yan, Yu, Wu, Fan, Qin, Jiawei, Xu, Haijun, Shi, Maohu, Zhou, Jingfeng, Mack, John, Fomo, Gertrude, Nyokong, Tebello, Shen, Zhen
- Authors: Yan, Yu , Wu, Fan , Qin, Jiawei , Xu, Haijun , Shi, Maohu , Zhou, Jingfeng , Mack, John , Fomo, Gertrude , Nyokong, Tebello , Shen, Zhen
- Date: 2016
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/240899 , vital:50883 , xlink:href="https://doi.org/10.1039/C6RA12271J"
- Description: A series of new corrole–BODIPY dyads bridged by ethynyl linker moieties have been synthesized in high yields and fully characterized. The direction of energy transfer upon electronic excitation has been explored, and was found to be dependent on the number of corrole rings and their connection position on the BODIPY core. Intense bands in the absorption spectrum cover most of the visible region, which is potentially advantageous for capturing solar energy. Studies on the excitation spectra and lifetimes suggest that the energy transfer efficiency between the BODIPY and corrole moieties reaches almost 85%, which appears to be efficient in the context of energy transfer within the singlet manifold.
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- Authors: Yan, Yu , Wu, Fan , Qin, Jiawei , Xu, Haijun , Shi, Maohu , Zhou, Jingfeng , Mack, John , Fomo, Gertrude , Nyokong, Tebello , Shen, Zhen
- Date: 2016
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/240899 , vital:50883 , xlink:href="https://doi.org/10.1039/C6RA12271J"
- Description: A series of new corrole–BODIPY dyads bridged by ethynyl linker moieties have been synthesized in high yields and fully characterized. The direction of energy transfer upon electronic excitation has been explored, and was found to be dependent on the number of corrole rings and their connection position on the BODIPY core. Intense bands in the absorption spectrum cover most of the visible region, which is potentially advantageous for capturing solar energy. Studies on the excitation spectra and lifetimes suggest that the energy transfer efficiency between the BODIPY and corrole moieties reaches almost 85%, which appears to be efficient in the context of energy transfer within the singlet manifold.
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Optically active BODIPYs
- Lu, Hua, Mack, John, Nyokong, Tebello, Kobayashi, Nagao, Shen, Zhen
- Authors: Lu, Hua , Mack, John , Nyokong, Tebello , Kobayashi, Nagao , Shen, Zhen
- Date: 2016
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/240421 , vital:50833 , xlink:href="https://doi.org/10.1016/j.ccr.2016.03.015"
- Description: This review highlights and summarizes various optically active BODIPY molecules and describes the analysis of their circular dichroism (CD) and circularly polarized luminescence (CPL) spectroscopy, to provide a platform for the rational design of novel optically active BODIPY structures and the development of new chiroptical applications. Possible future research directions are also discussed.
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- Authors: Lu, Hua , Mack, John , Nyokong, Tebello , Kobayashi, Nagao , Shen, Zhen
- Date: 2016
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/240421 , vital:50833 , xlink:href="https://doi.org/10.1016/j.ccr.2016.03.015"
- Description: This review highlights and summarizes various optically active BODIPY molecules and describes the analysis of their circular dichroism (CD) and circularly polarized luminescence (CPL) spectroscopy, to provide a platform for the rational design of novel optically active BODIPY structures and the development of new chiroptical applications. Possible future research directions are also discussed.
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Corrole–BODIPY conjugates: enhancing the fluorescence and phosphorescence of the corrole complex via efficient through bond energy transfer
- Chen, Wei, Zhang, Jianfeng, Mack, John, Kubheka, Gugu Patience, Nyokong, Tebello, Shen, Zhen, Wei Chen
- Authors: Chen, Wei , Zhang, Jianfeng , Mack, John , Kubheka, Gugu Patience , Nyokong, Tebello , Shen, Zhen , Wei Chen
- Date: 2015-06-08
- Subjects: RSC Advances (2015), 5, 50962-50967, doi:10.1039/C5RA07250F
- Language: English
- Type: Article
- Identifier: vital:7268 , http://hdl.handle.net/10962/d1020277
- Description: New corrole–BODIPY conjugates have been synthesized in high yield under mild conditions. Upon excitation at the absorption maximum of the BODIPY antenna chromophore, the fluorescence intensity of the free base corrole–BODIPY conjugate increases by ca. 300%, and significant phosphorescence intensity is observed for the iridium(III) complex of the conjugate, while almost no phosphorescence is observed for the parent iridium(III) corrole, due to through-bond energy transfer from the BODIPY antenna-chromophore to the corrole core. , Original publication is available at http://dx.doi.org/10.1039/c5ra07250f , Arbortext Advanced Print Publisher 9.1.510/W Unicode , Acrobat Distiller 8.1.0 (Windows); modified using iText� 5.3.3 �2000-2012 1T3XT BVBA (AGPL-version)
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- Authors: Chen, Wei , Zhang, Jianfeng , Mack, John , Kubheka, Gugu Patience , Nyokong, Tebello , Shen, Zhen , Wei Chen
- Date: 2015-06-08
- Subjects: RSC Advances (2015), 5, 50962-50967, doi:10.1039/C5RA07250F
- Language: English
- Type: Article
- Identifier: vital:7268 , http://hdl.handle.net/10962/d1020277
- Description: New corrole–BODIPY conjugates have been synthesized in high yield under mild conditions. Upon excitation at the absorption maximum of the BODIPY antenna chromophore, the fluorescence intensity of the free base corrole–BODIPY conjugate increases by ca. 300%, and significant phosphorescence intensity is observed for the iridium(III) complex of the conjugate, while almost no phosphorescence is observed for the parent iridium(III) corrole, due to through-bond energy transfer from the BODIPY antenna-chromophore to the corrole core. , Original publication is available at http://dx.doi.org/10.1039/c5ra07250f , Arbortext Advanced Print Publisher 9.1.510/W Unicode , Acrobat Distiller 8.1.0 (Windows); modified using iText� 5.3.3 �2000-2012 1T3XT BVBA (AGPL-version)
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Organosilicon compounds as fluorescent chemosensors for fluoride anion recognition
- Gai, Lizhi, Mack, John, Lu, Hua, Nyokong, Tebello, Li, Zhifang, Kobayashi, Nagao, Shen, Zhen
- Authors: Gai, Lizhi , Mack, John , Lu, Hua , Nyokong, Tebello , Li, Zhifang , Kobayashi, Nagao , Shen, Zhen
- Date: 2015
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/241424 , vital:50938 , xlink:href="https://doi.org/10.1016/j.ccr.2014.10.009"
- Description: Recent developments in organosilicon-based chemosensors for F− recognition are reviewed. The design strategies for improving the photophysical properties of organosilicon-based chemosensors are elaborated, with an emphasis placed on their utility for biological applications. The photophysical properties and electronic structures are analyzed in depth with reference made to the results of molecular modeling calculation and possible future research directions are assessed.
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- Authors: Gai, Lizhi , Mack, John , Lu, Hua , Nyokong, Tebello , Li, Zhifang , Kobayashi, Nagao , Shen, Zhen
- Date: 2015
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/241424 , vital:50938 , xlink:href="https://doi.org/10.1016/j.ccr.2014.10.009"
- Description: Recent developments in organosilicon-based chemosensors for F− recognition are reviewed. The design strategies for improving the photophysical properties of organosilicon-based chemosensors are elaborated, with an emphasis placed on their utility for biological applications. The photophysical properties and electronic structures are analyzed in depth with reference made to the results of molecular modeling calculation and possible future research directions are assessed.
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Synthesis, characterization and photodynamic therapy properties of an octa-4-tert-butylphenoxy-substituted phosphorus (V) triazatetrabenzcorrole
- Shi, Maohu, Tian, Jiangwei, Mkhize, Colin, Kubheka, Gugu, Zhou, Jinfeng, Mack, John, Nyokong, Tebello, Shen, Zhen
- Authors: Shi, Maohu , Tian, Jiangwei , Mkhize, Colin , Kubheka, Gugu , Zhou, Jinfeng , Mack, John , Nyokong, Tebello , Shen, Zhen
- Date: 2014
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/241494 , vital:50944 , xlink:href="https://doi.org/10.1142/S1088424614500436"
- Description: A novel octa-4-tert-butylphenoxy-substituted phosphorus(V) triazatetrabenzcorrole (PVTBC), has been synthesized and characterized by MALDI-TOF MS and NMR, FT-IR and MCD spectroscopy. The fluorescence emission spectrum was used to determine the fluorescence quantum yield and the quantum yield for singlet oxygen generation was calculated by using 1,3-diphenylisobenzofuran as a scavenger. The photocytoxicity against U87MG cells was measured. The results indicated that PVTBC is potentially useful as an NIR region photosensitizer for photodynamic therapy (PDT).
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- Authors: Shi, Maohu , Tian, Jiangwei , Mkhize, Colin , Kubheka, Gugu , Zhou, Jinfeng , Mack, John , Nyokong, Tebello , Shen, Zhen
- Date: 2014
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/241494 , vital:50944 , xlink:href="https://doi.org/10.1142/S1088424614500436"
- Description: A novel octa-4-tert-butylphenoxy-substituted phosphorus(V) triazatetrabenzcorrole (PVTBC), has been synthesized and characterized by MALDI-TOF MS and NMR, FT-IR and MCD spectroscopy. The fluorescence emission spectrum was used to determine the fluorescence quantum yield and the quantum yield for singlet oxygen generation was calculated by using 1,3-diphenylisobenzofuran as a scavenger. The photocytoxicity against U87MG cells was measured. The results indicated that PVTBC is potentially useful as an NIR region photosensitizer for photodynamic therapy (PDT).
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Trends in the optical and redox properties of tetraphenyltetraphenanthroporphyrins
- Mack, John, Lobb, Kevin A, Nyokong, Tebello, Shen, Zhen, Kobayashi, Nagao
- Authors: Mack, John , Lobb, Kevin A , Nyokong, Tebello , Shen, Zhen , Kobayashi, Nagao
- Date: 2012
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/245809 , vital:51407 , xlink:href="https://doi.org/10.1142/S1088424612500885"
- Description: The results of TD-DFT calculations for a series of tetraaryltetraphenanthroporphyrins containing para-substituents with differing electron donating and accepting properties are compared to the observed optical and redox properties and Michl's perimeter model is used as a conceptual framework for analyzing the results.
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- Authors: Mack, John , Lobb, Kevin A , Nyokong, Tebello , Shen, Zhen , Kobayashi, Nagao
- Date: 2012
- Subjects: To be catalogued
- Language: English
- Type: text , article
- Identifier: http://hdl.handle.net/10962/245809 , vital:51407 , xlink:href="https://doi.org/10.1142/S1088424612500885"
- Description: The results of TD-DFT calculations for a series of tetraaryltetraphenanthroporphyrins containing para-substituents with differing electron donating and accepting properties are compared to the observed optical and redox properties and Michl's perimeter model is used as a conceptual framework for analyzing the results.
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