Journal
TETRAHEDRON
Volume 65, Issue 34, Pages 7064-7078Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2009.06.037
Keywords
Porphyrins; Carbodiimide; O-Nitrobenzyl; Photodynamic therapy; Tetrapyrroles
Categories
Funding
- Science Foundation Ireland Research Professorship Award [SFI 04/RP1/B482]
- Health Research Board [HRB TRA2007/11]
- Universiti Teknologi Malaysia
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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 (C) 2009 Elsevier Ltd. All rights reserved.
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