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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
  • University of California at Davis

Research output: Chapter in Book/Report/Conference proceeding › Conference contribution › peer-review

11 Scopus citations

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.

Original languageEnglish
Title of host publicationProceedings of SPIE - The International Society for Optical Engineering
PublisherPubl by Int Soc for Optical Engineering
Pages274-283
Number of pages10
ISBN (Print)0819407917
StatePublished - 1992
EventOptical Methods for Tumor Treatment and Detection: Mechanisms and Techniques in Photodynamic Therapy - Los Angeles, CA, USA
Duration: Jan 20 1992 → Jan 21 1992

Publication series

NameProceedings of SPIE - The International Society for Optical Engineering
Volume1645
ISSN (Print)0277-786X

Conference

ConferenceOptical Methods for Tumor Treatment and Detection: Mechanisms and Techniques in Photodynamic Therapy
CityLos Angeles, CA, USA
Period01/20/92 → 01/21/92

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