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Proceedings Paper

Syntheses of new porphyrin-type photosensitizers for photodynamic therapy
Author(s): Kevin M. Smith; Ravindra K. Pandey; Fuu-Yau Shiau; Norman W. Smith; Panos Iakovides; Thomas J. Dougherty
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Paper 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.

Paper Details

Date Published: 1 June 1992
PDF: 10 pages
Proc. SPIE 1645, Optical Methods for Tumor Treatment and Detection: Mechanisms and Techniques in Photodynamic Therapy, (1 June 1992); doi: 10.1117/12.60949
Show Author Affiliations
Kevin M. Smith, Univ. of California/Davis (United States)
Ravindra K. Pandey, Univ. of California/Davis and Roswell Park Cancer Institute (United States)
Fuu-Yau Shiau, Univ. of California/Davis (United States)
Norman W. Smith, Univ. of California/Davis (United States)
Panos Iakovides, Univ. of California/Davis (United States)
Thomas J. Dougherty, Roswell Park Cancer Institute (United States)


Published in SPIE Proceedings Vol. 1645:
Optical Methods for Tumor Treatment and Detection: Mechanisms and Techniques in Photodynamic Therapy
Thomas J. Dougherty, Editor(s)

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