The synthesis of N-acetyl-4-S-cysteaminyl [U-14C]phenol as a basis for the development of an antimelanoma and melanoma-radioimaging agent.
This study reports the synthesis of 14C-labelled N-acetyl-4-S-cysteaminylphenol ([14C]N-Ac-4-S-CAP), a potent melanocytotoxic and anti-melanoma agent. A reaction of [U-14C]phenol with NH2CH2CH2S+ cation in HBr solution was used for the synthesis of (4-S-cysteaminyl[14C]phenol[14C]4-S-CAP). The excess cystamine was removed, and [14C]4-S-CAP and 2-S-cysteaminyl[14C]phenol ([14C]2-S-CAP) were separated on preparative thin layer chromatography. [14C]4-S-CAP was acetylated with acetic anhydride in pyridine and subsequently O-deacetylated with NH3 in methanol, resulting [14C]N-Ac-4-S-CAP (3.8% radiochemical yield; a sp. act. of 450 kBq/mumol; radiochemical purity > 99%).
Faculty of Medicine, Division of Dermatology and Cutaneous Sciences, University of Alberta, Edmonton, Canada.
T
T
Iwashina
K
K
Jimbow
L I
LI
Wiebe
D000107:Acetylation; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002250:Carbon Radioisotopes; D003543:Cysteamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D007553:Isotope Labeling / Q000379:methods*; D008545:Melanoma / Q000000981:diagnostic imaging / Q000188:drug therapy; D008956:Models, Chemical; D010636:Phenols / Q000138:chemical synthesis* / Q000494:pharmacology; D011877:Radionuclide Imaging
D000970:Antineoplastic Agents; D002250:Carbon Radioisotopes; D010636:Phenols; D003543:Cysteamine; C066420:N-acetyl-4-S-cysteaminylphenol