Syntheses of new porphyrin-type photosensitizers for photodynamic therapy
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.
Publication Source (Journal or Book title)
Proceedings of SPIE - The International Society for Optical Engineering
Smith, K., Pandey, R., Shiau, F., Smith, N., Iakovides, P., & Dougherty, T. (1992). Syntheses of new porphyrin-type photosensitizers for photodynamic therapy. Proceedings of SPIE - The International Society for Optical Engineering, 1645, 274-283. Retrieved from https://digitalcommons.lsu.edu/chemistry_pubs/1864