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Photobinding of Flutamide to Phospholipid Vesicles: Additional Evidence for Photoprocesses Unexpectedly Triggered by Conformational Changes in the Bilayer
Author(s) -
Sortino Salvatore,
Marconi Giancarlo,
Petralia Salvatore,
Condorelli Giuseppe
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200205)85:5<1407::aid-hlca1407>3.0.co;2-e
Subject(s) - chemistry , vesicle , bilayer , biophysics , lipid bilayer , phospholipid , liposome , drug , membrane , biochemistry , pharmacology , medicine , biology
It is demonstrated that irradiation of the anticancer drug flutamide (FM) in the presence of unilamellar phospholipid bilayer vesicles, chosen as a model for cell membranes, leads to an efficient photobinding process. This pathway is triggered by an unexpected hydrogen‐abstraction reaction of the excited drug by the lipid chain and provides additional evidence that the overall photochemical scenario observed in the vesicles is unusually triggered by conformational change of the drug's molecular structure upon incarceration in the ‘close‐packed' bilayer. The present investigation, beyond contributing to the general picture concerning fundamental aspects of the light‐induced processes in self‐organized assemblies, may also provide important insights for a more satisfactory understanding of the recently reported adverse photoallergic and phototoxic phenomena displayed by this anticancer drug.