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Cationic Versus Anionic Phthalocyanines for Photodynamic Therapy: What a Difference the Charge Makes
J. Kollar, M. Machacek, M. Halaskova, J. Lenco, R. Kucera, J. Demuth, M. Rohlickova, K. Hasonova, M. Miletin, V. Novakova, P. Zimcik,
Journal of medicinal chemistry.
2020 ;
63 (14) :
7616-7632.
[pub] 20200714
Language English Country United States
Document type Journal Article, Research Support, Non-U.S. Gov't
Persistent link
https://www.medvik.cz/link/bmc20028004
- MeSH
- Phosphatidylcholines chemistry metabolism MeSH
- Photochemotherapy MeSH
- Photosensitizing Agents chemical synthesis metabolism pharmacology radiation effects MeSH
- Indoles chemical synthesis metabolism pharmacology radiation effects MeSH
- Humans MeSH
- Liposomes chemistry metabolism MeSH
- Molecular Structure MeSH
- Cell Line, Tumor MeSH
- Antineoplastic Agents chemical synthesis metabolism pharmacology radiation effects MeSH
- Drug Screening Assays, Antitumor MeSH
- Serum Albumin, Bovine metabolism MeSH
- Singlet Oxygen metabolism MeSH
- Light MeSH
- Zinc chemistry MeSH
- Check Tag
- Humans MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
The literature reports on cationic and anionic phthalocyanines (Pcs) for photodynamic therapy suggest systematically significant differences in activity. In this work, ten different zinc(II) Pcs with carboxylate functions or quaternary nitrogens (hydrophilic anionic, hydrophilic cationic, amphiphilic anionic, and amphiphilic cationic) were investigated, with the aim of revealing reasons for such differences. In vitro assays on HeLa, MCF-7, and HCT-116 cells confirmed higher photoactivity for cationic Pcs (EC50 ∼ 3-50 nM) than for anionic Pcs (EC50 ∼ 0.3-10 μM), the latter being additionally significantly more active in serum-free medium. The environmental pH, binding to serum proteins, interaction with biomembranes, differences in subcellular localization, and relocalization after irradiation were found to be the main factors contributing to the generally lower photoactivity of anionic Pcs than that of the cationic derivatives. This result is not limited only to the presented derivatives and should be considered in the design of novel photosensitizers.
References provided by Crossref.org
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- $a The literature reports on cationic and anionic phthalocyanines (Pcs) for photodynamic therapy suggest systematically significant differences in activity. In this work, ten different zinc(II) Pcs with carboxylate functions or quaternary nitrogens (hydrophilic anionic, hydrophilic cationic, amphiphilic anionic, and amphiphilic cationic) were investigated, with the aim of revealing reasons for such differences. In vitro assays on HeLa, MCF-7, and HCT-116 cells confirmed higher photoactivity for cationic Pcs (EC50 ∼ 3-50 nM) than for anionic Pcs (EC50 ∼ 0.3-10 μM), the latter being additionally significantly more active in serum-free medium. The environmental pH, binding to serum proteins, interaction with biomembranes, differences in subcellular localization, and relocalization after irradiation were found to be the main factors contributing to the generally lower photoactivity of anionic Pcs than that of the cationic derivatives. This result is not limited only to the presented derivatives and should be considered in the design of novel photosensitizers.
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