Kinetic characterization of 4,4'-biphenylsulfonamides as selective non-zinc binding MMP inhibitors

J Enzyme Inhib Med Chem. 2015 Dec;30(6):947-54. doi: 10.3109/14756366.2014.1000889. Epub 2015 Feb 19.

Abstract

We describe the characterisation of a series of 4,4'-biphenylsulfonamides as selective inhibitors of matrix metalloproteases MMP-2 and -13, two enzymes involved in cell invasion and angiogenesis. Double-inhibitor studies in the presence of acetohydroxamic acid show that these molecules do not bind the catalytic zinc. Moreover, two of the characterised inhibitors (11 and 19) act as non-competitive inhibitors, whereas the para-methyl ester derivative 13 behaves as a competitive inhibitor. This finding suggests that this class of molecules binds to a catalytic subsite, possibly the S1'-pocket. Moreover, since these compounds also act as inhibitors of carbonic anhydrases (CAs), another family of enzymes involved in cell invasion, they could be potentially useful as CA/MMP dual target inhibitors with increased efficacy as anticancer agents.

Keywords: Carbonic anhydrase; matrix metalloproteases; non-competitive inhibitors; non-zinc binding inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biphenyl Compounds / chemical synthesis
  • Biphenyl Compounds / chemistry
  • Biphenyl Compounds / pharmacology*
  • Dose-Response Relationship, Drug
  • Humans
  • Kinetics
  • Matrix Metalloproteinase 13 / metabolism*
  • Matrix Metalloproteinase 2 / metabolism*
  • Matrix Metalloproteinase Inhibitors / chemical synthesis
  • Matrix Metalloproteinase Inhibitors / chemistry
  • Matrix Metalloproteinase Inhibitors / pharmacology*
  • Molecular Structure
  • Structure-Activity Relationship
  • Sulfonamides / chemical synthesis
  • Sulfonamides / chemistry
  • Sulfonamides / pharmacology*

Substances

  • Biphenyl Compounds
  • Matrix Metalloproteinase Inhibitors
  • Sulfonamides
  • Matrix Metalloproteinase 13
  • Matrix Metalloproteinase 2