Journal
CHEMMEDCHEM
Volume 5, Issue 10, Pages 1770-1780Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cmdc.201000223
Keywords
anticancer agents; biological activity; macrocycles; photophysics; UV/Vis spectroscopy
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Funding
- National Centre for Research and Development (PL) [60303]
- FCT (PT) [0002/2008]
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Chlorin and bacteriochlorin derivatives of 5,10,15,20-tetrakis(2-chloro-5-sulfophenyl) porphyrin have intense absorptions in the phototherapeutic window, high water solubility, high photostability, low fluorescence quantum yield, long triplet lifetimes, and high singlet oxygen quantum yields. Biological studies revealed their negligible dark cytotoxicity, yet significant photodynamic effect against A549 (human lung adenocarcinoma), MCF7 (human breast carcinoma) and SK-MEL-188 (human melanoma) cell lines upon red light irradiation (cutoff lambda < 600 nm) at low light doses. Time-dependent cellular accumulation of the chlorinated sulfonated chlorin reached a plateau at 2 h, as previously observed for the related porphyrin. However, the optimal incubation time for the bacteriochlorin derivative was significantly longer (12 h). The spectroscopic, photophysical, and biological properties of the compounds are discussed in relevance to their PDT activity, leading to the conclusion that the bacteriochlorin derivative is a promising candidate for future in vivo experiments.
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