Bioorganic and Medicinal Chemistry Letters p. 5855 - 5859 (2013)
Update date:2022-08-10
Topics:
Yang, Ke-Wu
Feng, Lei
Yang, Shao-Kang
Aitha, Mahesh
Lacuran, Alecander E.
Oelschlaeger, Peter
Crowder, Michael W.
In an effort to test whether a transition state analog is an inhibitor of the metallo-β-lactamases, a phospholactam analog of carbapenem has been synthesized and characterized. The phospholactam 1 proved to be a weak, time-dependent inhibitor of IMP-1 (70%), CcrA (70%), L1 (70%), NDM-1 (53%), and Bla2 (94%) at an inhibitor concentration of 100 μM. The phospholactam 1 activated ImiS and BcII at the same concentration. Docking studies were used to explain binding and to offer suggestions for modifications to the phospholactam scaffold to improve binding affinities.
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