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PDBsum entry 4llz

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Oxidoreductase/oxidoreductase inhibitor PDB id
4llz
Jmol
Contents
Protein chains
552 a.a.
Ligands
BOG
NAG-NAG ×2
NAG ×4
LUR ×2
Waters ×256

References listed in PDB file
Key reference
Title Exploring the molecular determinants of substrate-Selective inhibition of cyclooxygenase-2 by lumiracoxib.
Authors M.A.Windsor, P.L.Valk, S.Xu, S.Banerjee, L.J.Marnett.
Ref. Bioorg Med Chem Lett, 2013, 23, 5860-5864. [DOI no: 10.1016/j.bmcl.2013.08.097]
PubMed id 24060487
Abstract
Lumiracoxib is a substrate-selective inhibitor of endocannabinoid oxygenation by cyclooxygenase-2 (COX-2). We assayed a series of lumiracoxib derivatives to identify the structural determinants of substrate-selective inhibition. The hydrogen-bonding potential of the substituents at the ortho positions of the aniline ring dictated the potency and substrate selectivity of the inhibitors. The presence of a 5'-methyl group on the phenylacetic acid ring increased the potency of molecules with a single ortho substituent. Des-fluorolumiracoxib (2) was the most potent and selective inhibitor of endocannabinoid oxygenation. The positioning of critical substituents in the binding site was identified from a 2.35Å crystal structure of lumiracoxib bound to COX-2.
PROCHECK
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 Headers