Syntheses of new porphyrin-type photosensitizers for photodynamic therapy

Kevin M. Smith; Ravindra K. Pandey; Fuu-Yau Shiau; Norman W. Smith; Panos Iakovides; Thomas J. Dougherty

doi:10.1117/12.60949

1 June 1992 Syntheses of new porphyrin-type photosensitizers for photodynamic therapy

Kevin M. Smith, Ravindra K. Pandey, Fuu-Yau Shiau, Norman W. Smith, Panos Iakovides, Thomas J. Dougherty

Proceedings Volume 1645, Optical Methods for Tumor Treatment and Detection: Mechanisms and Techniques in Photodynamic Therapy; (1992) https://doi.org/10.1117/12.60949
Event: OE/LASE '92, 1992, Los Angeles, CA, United States

Abstract

In the first part of this paper, syntheses of water-soluble photosensitizers for use in photodynamic therapy are described. Vinylporphyrins and vinylchlorins react with N.N- dimethylmethyleneammonium iodide (Eschenmoser's reagent) to give 2- (dimethylaminomethyl)vinyl derivatives which can be readily quaternized with methyl iodide to give highly water-soluble quaternary ammonium salts. Deuteroporphyrin-IX dimethyl ester undergoes direct substitution with dimethylaminomethyl at the nuclear 2- and 4-positions. The second part of this report describes the syntheses of bacteriochlorin analogues of natural chlorophyll derivatives; these are obtained by osmium tetraoxide oxidation of chlorins to give vic-dihydroxybacteriochlorins. Acid catalyzed pinacol-pinacolone rearrangements of a number of vic-dihydroxybacterochlorins to given ketobacteriochlorins are described, and the chemistry of the rearrangement is investigated. Biological studies of all sensitizers described will be reported elsewhere.

Citation Download Citation

Kevin M. Smith, Ravindra K. Pandey, Fuu-Yau Shiau, Norman W. Smith, Panos Iakovides, and Thomas J. Dougherty "Syntheses of new porphyrin-type photosensitizers for photodynamic therapy", Proc. SPIE 1645, Optical Methods for Tumor Treatment and Detection: Mechanisms and Techniques in Photodynamic Therapy, (1 June 1992); https://doi.org/10.1117/12.60949

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