β-Lactamase-Dependent Prodrugs—Recent Developments

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 c...

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Bibliographic Details
Published in:Tetrahedron 2000-07, Vol.56 (31), p.5699-5707
Main Authors: Smyth, Timothy P., O'Donnell, Michael E., O'Connor, Michael J., St Ledger, James O.
Format: Article
Language:English
Subjects:
antibody-directed enzyme prodrug therapy
NMR
β-lactam
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Summary: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.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(00)00419-1