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Lead structures for applications in photodynamic therapy. Part 2: Synthetic studies for photo-triggered release systems of bioconjugate porphyrin photosensitizers

Bakar, Mohd Bakri and 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. ISSN 00404020

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Official URL: http://dx.doi.org/10.1016/j.tet.2009.06.037

Abstract

Photodynamic therapy (PDT) selectivity and specificity can be improved by binding the photorsensitizers 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 Type:Article
Uncontrolled Keywords:porphyrins, carbodiimide, o-nitrobenzyl, photodynamic therapy, tetrapyrroles
Subjects:Q Science > Q Science (General)
Divisions:Chemical Engineering
ID Code:13206
Deposited By: S.N.Shahira Dahari
Deposited On:22 Jul 2011 01:47
Last Modified:22 Jul 2011 01:47

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