Title

Use of the chlorophyll derivative, purpurin-18, for syntheses of sensitizers for use in photodynamic therapy

Document Type

Article

Publication Date

1-1-1993

Abstract

Reactions of purpurin-18 methyl ester 6 with various nucleophiles have been investigated as a means for synthesis of sensitizers for use in photodynamic therapy of tumours. Use of butylamine as the nucleophile resulted in ring-opening of the purpurin-18 anhydride ring to give a monoamide-γ- carboxylic acid 8. the purpurin-imide 11, and the di-amide-γ-carboxylic acid 12. When lysine or its esters were used as nucleophile, then lysylamide-γ-carboxylic acids 18, 20 and 23 were obtained, along with the purpurin lysyl-imides 21 and 22. Esterification and hydrolysis of the various carboxy functions were investigated as a means for obtaining stable water-soluble sensitizers. Similar reactions between ornithine and purpurin-18 methyl ester gave the corresponding ornithyl-chlorin-p6 derivatives (e.g. 31). The lysyl-chlorin-p6 18 was shown (in separate work) to be a highly effective tumour sensitizer.

Publication Source (Journal or Book title)

Journal of the Chemical Society, Perkin Transactions 1

First Page

2369

Last Page

2377

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