β-Lactamase-Dependent Prodrugs—Recent Developments

Autor:	Michael E. O'Donnell, Michael J. O'Connor, Timothy P. Smyth, James O. St Ledger
Rok vydání:	2000
Předmět:	chemistry.chemical_classification medicine.drug_class Organic Chemistry Cephalosporin Antibiotics Adept Prodrug Cleavage (embryo) Biochemistry Combinatorial chemistry Enzyme chemistry Drug Discovery polycyclic compounds medicine Side chain Moiety
Zdroj:	Tetrahedron. 56:5699-5707
ISSN:	0040-4020
DOI:	10.1016/s0040-4020(00)00419-1
Popis:	Penicillins and cephalosporins bearing an S-aminosulfenimine side chain at the 6- and 7-positions, respectively, are prototypic examples of novel classes of β-lactamase-dependent prodrugs wherein enzyme-catalyzed cleavage of the β-lactam ring triggers the rapid expulsion of the S-amino moiety. The cephalosporin structure behaves as a dual-release prodrug as here release of both the S-amino moiety and of the 3′-substituent occurs sequentially following cleavage of the β-lactam ring. This reaction pattern constitutes an enabling technology at the molecular level and has potential application in antibody-directed enzyme prodrug therapy (ADEPT) and in the further development of β-lactamase-dependent prodrugs for use as antibiotics.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::c85fc8d8f6bd4c35b854245c9c2ebcb8 https://doi.org/10.1016/s0040-4020(00)00419-1 Zobrazit plný text záznamu Full Text from ScienceDirect