N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate (TCFH), a powerful coupling reagent for bioconjugation.
Prodrugs are increasingly used as delivery vehicles for pharmaceutical agents that present solubility and/or pharmacokinetic/metabolic issues. In the course of the development of prodrugs for the antitumoral agent thiocoraline, standard coupling reagents and procedures failed to provide the desired target derivatives because of the lack of reactivity of its quinolinic alcohol. In contrast, the use of N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate (TCFH) resulted in good yields of ester prodrugs of thiocoraline and could be applicable to other drugs with similar limitations.
Tulla-Puche
Judit
J
Institute for Research in Biomedicine, Combinatorial Chemistry Unit, CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, 08028 Barcelona, Spain.
Torres
Angela
A
Calvo
Pilar
P
Royo
Miriam
M
Albericio
Fernando
F
D000578:Amidines / Q000737:chemistry*; D045744:Cell Line, Tumor; D047630:Depsipeptides / Q000737:chemistry / Q000494:pharmacology; D003959:Diamines / Q000737:chemistry*; D004952:Esters / Q000737:chemistry; D006801:Humans; D011355:Prodrugs / Q000737:chemistry / Q000494:pharmacology
D000578:Amidines; D047630:Depsipeptides; D003959:Diamines; D004952:Esters; C533686:N,N,N',N'-tetramethylchloroformamidinium; D011355:Prodrugs; C109005:thiocoraline