title: Antioxidant action and photosensitizing effects of three different chlorpromazines.
abstract: Chlorpromazine inhibits by about 60% the lipid peroxidation stimulated by Fe2+/ascorbate in liposomes and the lipid peroxidation stimulated by cumene hydroperoxide in microsomes. Under the same conditions, two new synthetic derivatives of chlorpromazine, i.e., a N-benzoyloxymethylchlorpromazine and a N-pivaloyloxymethylchlorpromazine, induce no more than a 20% inhibition. On the other hand, when the different chlorpromazines are entrapped in liposomes and subsequently irradiated with near-UV light, they act as photosensitizing agents giving rise to lipid peroxidation. The latter is quite extensive in the presence of chlorpromazine or N-pivaloyloxymethylchlorpromazine, whereas it is drastically lower in the presence of N-benzoyloxymethylchlopromazine. The N-benzoyloxymethylchlorpromazine molecule, despite its low photodynamic effect, retains its neuroleptic properties. The possible mechanisms of the antioxidant and prooxidant actions of these compounds are discussed.
authors.affiliation: Centro Studio Fisiologia Mitocondriale, CNR, Padova, Italy.
authors.forename: A
authors.initials: A
authors.lastname: Bindoli
authors.forename: M P
authors.initials: MP
authors.lastname: Rigobello
authors.forename: A
authors.initials: A
authors.lastname: Favel
authors.forename: L
authors.initials: L
authors.lastname: Galzigna
mesh_terms: D000818:Animals; D000975:Antioxidants; D002417:Cattle; D002746:Chlorpromazine / Q000031:analogs & derivatives* / Q000494:pharmacology*; D004278:DNA, Superhelical / Q000187:drug effects / Q000528:radiation effects; D007700:Kinetics; D008027:Light; D008054:Lipid Peroxides / Q000378:metabolism*; D008081:Liposomes / Q000378:metabolism* / Q000528:radiation effects; D008297:Male; D008315:Malondialdehyde / Q000378:metabolism; D010101:Oxygen Consumption / Q000187:drug effects / Q000528:radiation effects; D010777:Photochemistry; D051381:Rats; D011919:Rats, Inbred Strains; D014466:Ultraviolet Rays
chemical_list: D000975:Antioxidants; D004278:DNA, Superhelical; D008054:Lipid Peroxides; D008081:Liposomes; C054382:N-pivaloyloxymethylchlorpromazine; D008315:Malondialdehyde; C054383:N-benzoyloxymethylchlorpromazine; D002746:Chlorpromazine