New thioderivatives of gossypol and gossypolone, as prodrugs of cytotoxic agents.
Bioorg Med Chem
; 11(9): 2001-6, 2003 May 01.
Article
en En
| MEDLINE
| ID: mdl-12670651
ABSTRACT
New dithiane or dithiolane derivatives of gossypol and gossypolone were synthesized with dithiolethane or dithiolpropane in the presence of BF(3)/Et(2)O. These thioderivatives exhibited low toxicity on KB cells (human epidermoid carcinoma cells of the mouth). They react easily with electrophiles in aprotic solvents to regenerate gossypolone or to form dehydrogossypoldithianes and dehydrogossypoldithiolanes, which display higher toxicity on KB cells. In addition, the low toxicity of gossypol thioderivatives was reversed by nitric oxide donors in physiological media. These experiments suggest that gossypol and gossypolone dithianes and dithiolanes can be used as prodrugs that target tumor cells surrounded by high concentrations of nitric oxide.
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Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Compuestos de Sulfhidrilo
/
Gosipol
/
Profármacos
Límite:
Humans
Idioma:
En
Revista:
Bioorg Med Chem
Asunto de la revista:
BIOQUIMICA
/
QUIMICA
Año:
2003
Tipo del documento:
Article
País de afiliación:
Francia