Lead structures for applications in photodynamic therapy part 2: synthetic studies for photo-triggered release systems of bioconjugate porphyrin photosensitizers

Bakar, Mohd Bakri, Oelgemöller, Michael, and Senge, Mathias O. (2009) Lead structures for applications in photodynamic therapy part 2: synthetic studies for photo-triggered release systems of bioconjugate porphyrin photosensitizers. Tetrahedron, 65 (34). pp. 7064-7078.

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Abstract

Photodynamic therapy (PDT) selectivity and specificity can be improved by binding the photosensitizers to target receptors. One approach is to cross-link porphyrins to a biological target receptor via the photocleavable o-nitrobenzyl linker, where a controlled released of the porphyrin can be monitored upon irradiation. The synthetic pathways involved esterification of a porphyrin–carboxylic acid and a unit containing the o-nitrobenzyl alcohol moiety and the bioconjugate. Reactions of a model porphyrin and o-nitrobenzyl alcohol using the carbonyl activating carbodiimide reagent DCC gave a stable N-acyl urea porphyrin, whereas use of EDAC (1-ethyl-3-(3-dimethyl aminopropyl)carbodiimide hydrochloride) gave the desired compounds. Further studies were carried out on the attachment of carbohydrates (i.e., potentially receptor binding ligands) through such a linker to porphyrins. Preliminary irradiation experiments of such a compound show that upon UV irradiation (350 nm) for 80 min, approximately 50% of the porphyrin was cleaved to release the carboxylic acid porphyrin photosensitizer indicating the utility of such systems as photosensitizers delivery systems.

Item ID: 10214
Item Type: Article (Refereed Research - C1)
Keywords: porphyrins; carbodiimide; O-Nitrobenzyl; photodynamic therapy; tetrapyrroles
ISSN: 1464-5416
Date Deposited: 12 Apr 2010 03:31
FoR Codes: 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis @ 100%
SEO Codes: 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%
Citation Count from Web of Science Web of Science 19
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