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OBSERVATIONS ON THE SYNTHESIS AND in vivo PHOTODYNAMIC ACTIVITY OF SOME BENZOCHLORINS
Author(s) -
Morgan Alan R.,
Skalkos Dimitris,
Maguire George,
Rampersaud Ashraf,
Garbo Greta,
Keck Rick,
Selman Steven H.
Publication year - 1992
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1992.tb04219.x
Subject(s) - photodynamic therapy , in vivo , derivative (finance) , formamide , chemistry , yield (engineering) , nitro , nitration , sulfuric acid , combinatorial chemistry , pharmacology , medicine , organic chemistry , biology , materials science , alkyl , microbiology and biotechnology , financial economics , metallurgy , economics
— An improved synthesis of benzochlorins is reported. Demetallation of the meso ‐hydroxymethylvinyl derivative of octaethylporphyrin, followed by treatment with sulfuric acid results in cyclization to generate the corresponding octaethylbenzochlorin in high yield. Prolonged treatment with acid generates the sulfonated derivative. These sensitizers were shown to be efficient photodynamic agents in vivo. Animals bearing a transplanted N ‐{4‐(5‐nitro‐2‐furyl)‐2‐thiazolyl}formamide induced urothelial tumor were treated with either the benzochlorin or its sulfonated derivative. Irradiation of tumors 24 h later resulted in a significant tumoricidal effect in a short term assay. We conclude that benzochlorins warrant further examination as potential agents for use in photodynamic therapy.