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Cationic amphiphilic Zn-porphyrin with high antifungal photodynamic potency.

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Date
2017-11
Authors
Moghnie, Sara
Tovmasyan, Artak
Craik, James
Batinic-Haberle, Ines
Benov, Ludmil
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Abstract
Photodynamic therapy (PDT) is a promising alternative approach particularly attractive for treatment of localized fungal infections. It is based on compounds, photosensitizers (PSs), which when excited with visible light, generate reactive species that ultimately cause cell death. Such species have short lifespans; as a consequence, efficiency and selectivity of the PDT treatment depend mainly on the properties of the PSs. This study is the first to explore the effect of cationic porphyrin-based photosensitizers on Saccharomyces cerevisiae, a member of the fungus kingdom. The study investigates which properties of the PS are essential for efficient antifungal PDT. Cationic Zn(ii) meso-tetrakis(N-alkylpyridinium-2-yl)porphyrins (ZnP) with identical tetrapyrrole core and photo-physical properties, but with different substituents at the meso positions of the porphyrin ring were studied. Attaching six-carbon aliphatic chains to the four pyridyl nitrogens at all meso positions to the porphyrin ring produced a highly photo-efficient amphiphilic, water soluble PS, with minimal dark toxicity. It was taken up by the yeast cells and upon illumination suppressed metabolism by inactivating cytoplasmic and mitochondrial enzymes, and compromising plasma membrane barrier function. At low concentrations (up to 5 μM) the tetrahexyl derivative was a much more powerful antifungal agent than the commercially available chlorin e6. The more lipophilic tetraoctyl analog was also highly photo-efficient but displayed strong dark toxicity, presumably due to higher lipophilicity which might affect the lipid bilayer of membranes. Results presented here can assist the design of antifungal agents whose biological action depends on efficient and rapid uptake by the cells.
Type
Journal article
Subject
Saccharomyces cerevisiae
Cations
Zinc
Metalloporphyrins
Photosensitizing Agents
Antifungal Agents
Surface-Active Agents
Photochemotherapy
Microbial Sensitivity Tests
Permalink
https://hdl.handle.net/10161/24999
Published Version (Please cite this version)
10.1039/c7pp00143f
Publication Info
Moghnie, Sara; Tovmasyan, Artak; Craik, James; Batinic-Haberle, Ines; & Benov, Ludmil (2017). Cationic amphiphilic Zn-porphyrin with high antifungal photodynamic potency. Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology, 16(11). pp. 1709-1716. 10.1039/c7pp00143f. Retrieved from https://hdl.handle.net/10161/24999.
This is constructed from limited available data and may be imprecise. To cite this article, please review & use the official citation provided by the journal.
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Scholars@Duke

Batinic-Haberle

Ines Batinic-Haberle

Professor Emeritus of Radiation Oncology
            A major interest of mine has been in the design and synthesis of Mn porphyrin(MnP)-based powerful catalytic antioxidants which helped establish structure-activity relationship (SAR). It relates the redox property of metalloporphyrins to their ability to remove superoxide. SAR has facilitated the design of redox-active therapeutics and served as a tool for mechanistic considerations. Importantly SAR parallels the magnitu
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