Novel prodrug approach to photodynamic therapy: Fmoc solid-phase synthesis of a cell permeable peptide incorporating 5-aminolaevulinic acid

M J Dixon, L Bourre, A J MacRobert, I M Eggleston

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

The first example of the synthesis of a peptide incorporating 5-aminolaevulinic acid (5-ALA) using standard Fmoc solidphase chemistry is reported. The synthesised peptide contains residues 52-58 of the cell-permeable peptide Penetratin and represents a prototype for the enhanced topical delivery of 5-ALA using such oligopeptide vectors. Effective intracellular conversion of the peptide to the endogenous photosensitiser, protoporphyrin IX, is observed in PAM212 cells, thus demonstrating the potential of this approach for the development of novel peptide prodrugs for use in photodynamic therapy. (c) 2007 Elsevier Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)4518-4522
Number of pages5
JournalBioorganic & Medicinal Chemistry Letters
Volume17
Issue number16
DOIs
Publication statusPublished - 2007

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