A new role for old ligands: discerning chelators for zinc metalloproteinases

Journal of the American Chemical Society
Faith E JacobsenSeth M Cohen

Abstract

In an effort to identify promising non-hydroxamate inhibitors of matrix metalloproteinases (MMPs) several new zinc-binding groups (ZBGs) based on pyridine-derived or aza-macrocycle chelators have been examined. Fluorescence-based enzyme assays have been used to determine the IC50 values for these ZBGs against MMP-1, MMP-3, and anthrax lethal factor (LF). Many of these ligands were found to be remarkably potent, with IC50 values as much as 185-fold lower than that found for acetohydroxamic acid. These ligands are proposed to be more selective "warheads" for the inhibition of metalloenzymes that contain Zn2+ versus other metal ions at their active site.

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Citations

Sep 1, 2009·Chemical Reviews·Kathryn L Haas, Katherine J Franz
Dec 30, 2010·Journal of Medicinal Chemistry·Jennifer A JacobsenSeth M Cohen
Jan 28, 2009·Journal of Medicinal Chemistry·Arpita AgrawalSeth M Cohen
Jan 16, 2007·The Journal of Organic Chemistry·Maria Rosaria Rella, Paul G Williard
Nov 29, 2007·Proteins·Birte SeebeckMatthias Rarey
May 26, 2011·Chemical Biology & Drug Design·Jacob D DurrantJ Andrew McCammon
May 14, 2011·Chemical Biology & Drug Design·Sherida JohnsonMaurizio Pellecchia
Jan 27, 2011·Chemical Biology & Drug Design·Sarah L WilliamsJ Andrew McCammon
Nov 3, 2009·Journal of Molecular Recognition : JMR·Jacob D DurrantJ Andrew McCammon
Aug 29, 2009·Biochimica Et Biophysica Acta·Jennifer A JacobsenSeth M Cohen
Feb 27, 2007·Bioorganic Chemistry·Sherida L JohnsonMaurizio Pellecchia
Sep 16, 2008·Bioorganic & Medicinal Chemistry·Dimitris Georgiadis, Athanasios Yiotakis
Nov 22, 2007·Bioorganic & Medicinal Chemistry Letters·Ryuji HayashiGregory R Cook
Dec 14, 2006·ChemMedChem·Faith E JacobsenSeth M Cohen
Jan 9, 2008·ChemMedChem·Arpita AgrawalSeth M Cohen
Aug 27, 2009·Organic & Biomolecular Chemistry·Matthieu RouffetDominique Guillaume
Jan 9, 2010·ChemMedChem·Arpita AgrawalSeth M Cohen
Jul 31, 2008·Chembiochem : a European Journal of Chemical Biology·Faith E JacobsenSeth M Cohen
Jun 11, 2014·Dalton Transactions : an International Journal of Inorganic Chemistry·Britain BrunerPatrick J Farmer
Apr 20, 2021·Chemical Communications : Chem Comm·Kathleen E ProsserSeth M Cohen
Jul 10, 2008·Molecular Pharmaceutics·Rajeshwar P Verma, Corwin Hansch
May 29, 2015·Biochemistry·Hao YangDavid L Tierney
Jul 17, 2018·Inorganic Chemistry·Benjamin L Dick, Seth M Cohen
Jun 14, 2012·ACS Medicinal Chemistry Letters·Chris J VickersM Reza Ghadiri
Jul 18, 2017·Accounts of Chemical Research·Seth M Cohen
Oct 27, 2021·Inorganic Chemistry·Hyeonglim SeoSeth M Cohen

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