title: N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate (TCFH), a powerful coupling reagent for bioconjugation.
abstract: 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.
authors.affiliation: Institute for Research in Biomedicine, Combinatorial Chemistry Unit, CIBER-BBN, Networking Centre on Bioengineering, Biomaterials and Nanomedicine, Barcelona Science Park, 08028 Barcelona, Spain.
authors.forename: Judit
authors.initials: J
authors.lastname: Tulla-Puche
authors.forename: Angela
authors.initials: A
authors.lastname: Torres
authors.forename: Pilar
authors.initials: P
authors.lastname: Calvo
authors.forename: Miriam
authors.initials: M
authors.lastname: Royo
authors.forename: Fernando
authors.initials: F
authors.lastname: Albericio
mesh_terms: 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
chemical_list: D000578:Amidines; D047630:Depsipeptides; D003959:Diamines; D004952:Esters; C533686:N,N,N',N'-tetramethylchloroformamidinium; D011355:Prodrugs; C109005:thiocoraline