1 June 1992 Syntheses of new porphyrin-type photosensitizers for photodynamic therapy
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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.
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Kevin M. Smith, Kevin M. Smith, Ravindra K. Pandey, Ravindra K. Pandey, Fuu-Yau Shiau, Fuu-Yau Shiau, Norman W. Smith, Norman W. Smith, Panos Iakovides, Panos Iakovides, Thomas J. Dougherty, 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); doi: 10.1117/12.60949; https://doi.org/10.1117/12.60949

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