Photochemistry and phototoxicity studies of flutamide, a phototoxic anti-cancer drug

Vargas, Franklin; Rivas, Carlos; Méndez, H; Fuentes, Alberto; Fraile, Germán; Velásquez, Mait

doi:10.1016/s1011-1344(00)00110-x

Cited by 11 publications

(9 citation statements)

References 20 publications

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“…) Our results presented in[20] are partially in contrast with those reported by Vargas et al[25], who found in addition to the formation of 1, that other photolysis products were also found. This apparent incongruity is probably due to the different experimental conditions used in the two works (i.e., light excitation wavelength, ground-state concentrations of FM).…”

contrasting

confidence: 99%

Photobinding of Flutamide to Phospholipid Vesicles: Additional Evidence for Photoprocesses Unexpectedly Triggered by Conformational Changes in the Bilayer

Sortino

Marconi

Petralia

et al. 2002

HCA

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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.

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contrasting

confidence: 99%

Photobinding of Flutamide to Phospholipid Vesicles: Additional Evidence for Photoprocesses Unexpectedly Triggered by Conformational Changes in the Bilayer

Sortino

Marconi

Petralia

et al. 2002

HCA

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“…Our patient had systemic symptoms similar to the patient with flutamide‐induced lupus described by Reid and Glode, in addition to photosensitivity 2 . The photosensitivity profile of flutamide includes phototoxicity, cytotoxicity, photohaemolysis and lipid peroxidation, and is not limited to photoallergic reactions alone 4 . The mouse model for systemic lupus erythematosus has also revealed an accelerated death in flutamide‐treated NZB × NZW F 1 mice 5 .…”

supporting

confidence: 71%

Flutamide-induced photosensitivity: is it a forme fruste of lupus?

Kaur

Thami

2003

Br J Dermatol

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“…1 In vitro , flutamide, the spectrum of action of which appears to be in the UVA-range, showed a photohaemolytic effect on human erythrocytes and induced lipid peroxidation. 2 Like us, other authors also found a decreased MED. 3,4 Photosensitivity to flutamide was also demonstrated by photopatch testing, although to date there seems to be no consensus regarding the nature of vehicle and the concentration of flutamide to be used.…”

supporting

confidence: 68%