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Tetra(3,4-pyrido)porphyrazines Caught in the Cationic Cage: Toward Nanomolar Active Photosensitizers
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SYSNO ASEP 0467049 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Tetra(3,4-pyrido)porphyrazines Caught in the Cationic Cage: Toward Nanomolar Active Photosensitizers Author(s) Macháček, M. (CZ)
Demuth, J. (CZ)
Čermák, P. (CZ)
Vavrečková, M. (CZ)
Hrubá, L. (CZ)
Jedličková, A. (CZ)
Kubát, Pavel (UFCH-W) RID, ORCID, SAI
Šimůnek, T. (CZ)
Nováková, V. (CZ)
Zimčík, P. (CZ)Source Title Journal of Medicinal Chemistry. - : American Chemical Society - ISSN 0022-2623
Roč. 59, č. 20 (2016), s. 9443-9456Number of pages 14 s. Language eng - English Country US - United States Keywords TARGETED PHOTODYNAMIC THERAPY ; SINGLET OXYGEN ; PHOTOPHYSICAL PROPERTIES Subject RIV CF - Physical ; Theoretical Chemistry Institutional support UFCH-W - RVO:61388955 UT WOS 000386641300013 EID SCOPUS 84994056126 DOI https://doi.org/10.1021/acs.jmedchem.6b01140 Annotation Investigation of a series of tetra(3,4-pyrido)porphyrazines (TPyPzs) substituted with hydrophilic substituents revealed important structure activity relationships for their use in photodynamic therapy (PDT). Among them, a cationic TPyPz derivative with total of 12 cationic charges above, below and in the plane of the core featured a unique spatial arrangement that caught the hydrophobic core in a cage, thereby protecting it fully from aggregation in water. This derivative exhibited exceptionally effective photodynamic activity on a number of tumor cell lines (HeLa, SK-MEL-28, A549, MCF-7) with effective concentrations (EC50) typically below 5 nM, at least an order of magnitude better than the EC50 values obtained for the clinically approved photosensitizers verteporfin, temoporfin, protoporphyrin IX, and trisulfonated hydroxyaluminum phthalocyanine. Its very low dark toxicity (TC50 > 400 mu M) and high ability to induce photo damage to endothelial cells (EA.hy926) without preincubation suggest the high potential of this cationic TPyPz derivative in vascular-targeted PDT. Workplace J. Heyrovsky Institute of Physical Chemistry Contact Michaela Knapová, michaela.knapova@jh-inst.cas.cz, Tel.: 266 053 196 Year of Publishing 2017
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