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Direct Spectroscopic Evidence that the Photochemical Outcome of Flutamide in a Protein Environment is Tuned by Modification of the Molecular Geometry: A Comparison with the Photobehavior in Cyclodextrin and Vesicles
Author(s) -
Sortino Salvatore,
Petralia Salvatore,
Condorelli Giuseppe,
Marconi Giancarlo
Publication year - 2003
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/hlca.200390027
Subject(s) - chemistry , cyclodextrin , circular dichroism , vesicle , photochemistry , bovine serum albumin , aqueous solution , molecular dynamics , biophysics , phototoxicity , computational chemistry , stereochemistry , organic chemistry , biochemistry , membrane , biology , in vitro
The photoreactivity of the phototoxic anticancer drug flutamide (FM) in the presence of bovine serum albumin (BSA) has been investigated. The presence of BSA induces a remarkable modification of the photochemical outcome of the drug with respect to that observed in aqueous solution. Induced circular dichroism (ICD) measurements combined with theoretical calculations provide strong evidence that the new photochemical scenario is tuned by changes of the molecular geometry of FM when incorporated in the protein microenvironment. This behavior presents close analogies to that found in the presence of either cyclodextrin or phospholipid vesicles, chosen as models for biological systems, and delineates a quite general photochemical picture that can be useful for a more appropriate understanding of the adverse phototoxic effects induced by this drug.