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Bioorg Med Chem Lett. 2013 Mar 15;23(6):1676-9. doi: 10.1016/j.bmcl.2013.01.071. Epub 2013 Jan 26.

A novel fluorogenic substrate for dinuclear Zn(II)-containing metallo-β-lactamases.

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Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of Ministry of Education, College of Chemistry and Materials Science, Northwest University, Xi'an 710069, PR China.

Erratum in

  • Bioorg Med Chem Lett. 2013 May 1;23(9):2813. Zhang, Yin-Lin [corrected to Zhang, Yi-Lin].


In an effort to prepare a fluorogenic substrate to be used in activity assays with metallo-β-lactamases, (6R,7R)-8-oxo-7-(2-oxo-2H-chromene-3-carboxamido)-3-((4-(2-oxo-2H-chromene-3-carboxamido)-phenylthio)methyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (CA) was synthesized and characterized. CA exhibited a fluorescence quantum yield (φ) of 0.0059, two fluorescence lifetimes of 3.63×10(-10) and 5.38×10(-9)s, and fluorescence intensity that is concentration-dependent. Steady-state kinetic assays revealed that CA is a substrate for metallo-β-lactamases (MβLs) L1 and CcrA, exhibiting Km and kcat values of 18μM and 5s(-1) and 11μM and 17s(-1), respectively.

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