Morgan A R, Skalkos D, Maguire G, Rampersaud A, Garbo G, Keck R, Selman S H
Department of Chemistry, University of Toledo, OH 43606.
Photochem Photobiol. 1992 Jan;55(1):133-6. doi: 10.1111/j.1751-1097.1992.tb04219.x.
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-thiazoly]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.
