Observations on the synthesis and in vivo photodynamic activity of some benzochlorins.

Abstract

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.

• Authors: A R Morgan, D Skalkos, G Maguire, A Rampersaud, G Garbo, R Keck, S H Selman
• Journal: Photochemistry and photobiology (Photochem Photobiol) Vol. 55 Issue 1 Pg. 133-6 (Jan 1992) ISSN: 0031-8655 [Print] United States
• PMID: 1603843 (Publication Type: Comparative Study, Journal Article, Research Support, U.S. Gov't, P.H.S.)

Chemical References

• Antineoplastic Agents
• Porphyrins
• Radiation-Sensitizing Agents

Topics

• Animals
• Antineoplastic Agents (chemical synthesis, therapeutic use)
• Magnetic Resonance Spectroscopy
• Molecular Structure
• Photochemotherapy
• Porphyrins (chemical synthesis, therapeutic use)
• Radiation-Sensitizing Agents (chemical synthesis, therapeutic use)
• Rats
• Rats, Inbred F344
• Structure-Activity Relationship
• Urinary Bladder Neoplasms (drug therapy)