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Improving potency and selectivity of a new class of non-Zn-chelating MMP-13 inhibitors.

Heim-Riether A, Taylor SJ, Liang S, Gao DA, Xiong Z, Michael August E, Collins BK, Farmer BT, Haverty K, Hill-Drzewi M, Junker HD, Mariana Margarit S, Moss N, Neumann T, Proudfoot JR, Keenan LS, Sekul R, Zhang Q, Li J, Farrow NA
Bioorg Med Chem Lett 19 5321-4 (2009)
Cited: 32 times
EuropePMC logo PMID: 19692239

Abstract

Discovery and optimization of potency and selectivity of a non-Zn-chelating MMP-13 inhibitor with the aid of protein co-crystal structural information is reported. This inhibitor was observed to have a binding mode distinct from previously published MMP-13 inhibitors. Potency and selectivity were improved by extending the hit structure out from the active site into the S1' pocket.

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  2. PharmMapper server: a web server for potential drug target identification using pharmacophore mapping approach. Liu X, Ouyang S, Yu B, Liu Y, Huang K, Gong J, Zheng S, Li Z, Li H, Jiang H. Nucleic Acids Res. 38 W609-14 (2010)
  3. Network pharmacology-based prediction of the multi-target capabilities of the compounds in Taohong Siwu decoction, and their application in osteoarthritis. Zheng CS, Xu XJ, Ye HZ, Wu GW, Li XH, Xu HF, Liu XX. Exp Ther Med 6 125-132 (2013)
  4. iDrug: a web-accessible and interactive drug discovery and design platform. Wang X, Chen H, Yang F, Gong J, Li S, Pei J, Liu X, Jiang H, Lai L, Li H. J Cheminform 6 28 (2014)
  5. In Silico Prediction of Molecular Targets of Astragaloside IV for Alleviation of COVID-19 Hyperinflammation by Systems Network Pharmacology and Bioinformatic Gene Expression Analysis. Ge C, He Y. Front Pharmacol 11 556984 (2020)
  6. Structure-Based Design and Synthesis of Potent and Selective Matrix Metalloproteinase 13 Inhibitors. Choi JY, Fuerst R, Knapinska AM, Taylor AB, Smith L, Cao X, Hart PJ, Fields GB, Roush WR. J. Med. Chem. 60 5816-5825 (2017)
  7. An integrated computational approach to rationalize the activity of non-zinc-binding MMP-2 inhibitors. Di Pizio A, Agamennone M, Aschi M. PLoS ONE 7 e47774 (2012)
  8. Considering Rotatability of Hydroxyl Groups for the Active Site Residues of MMP-13 in Retrospective Virtual Screening Campaigns. Shamsara J. Open Med Chem J 10 1-6 (2016)
  9. Molecular Dynamics Simulations of Matrix Metalloproteinase 13 and the Analysis of the Specificity Loop and the S1'-Site. Choi JY, Chung E. Int J Mol Sci 24 10577 (2023)


Reviews citing this publication (7)

  1. Physiology and pathophysiology of matrix metalloproteases. Klein T, Bischoff R. Amino Acids 41 271-290 (2011)
  2. Regulation of matrix metalloproteinase activity in health and disease. Hadler-Olsen E, Fadnes B, Sylte I, Uhlin-Hansen L, Winberg JO. FEBS J. 278 28-45 (2011)
  3. The history of matrix metalloproteinases: milestones, myths, and misperceptions. Iyer RP, Patterson NL, Fields GB, Lindsey ML. Am. J. Physiol. Heart Circ. Physiol. 303 H919-30 (2012)
  4. New strategies for targeting matrix metalloproteinases. Fields GB. Matrix Biol. 44-46 239-246 (2015)
  5. Sulphonamides: Deserving class as MMP inhibitors? Jain P, Saravanan C, Singh SK. Eur J Med Chem 60 89-100 (2013)
  6. Regulation and involvement of matrix metalloproteinases in vascular diseases. Amin M, Pushpakumar S, Muradashvili N, Kundu S, Tyagi SC, Sen U. Front Biosci (Landmark Ed) 21 89-118 (2016)
  7. Clinical Implications of Compounds Designed to Inhibit ECM-Modifying Metalloproteinases. Amar S, Minond D, Fields GB. Proteomics 17 (2017)

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  2. A general solution for the 2-pyridyl problem. Dick GR, Woerly EM, Burke MD. Angew. Chem. Int. Ed. Engl. 51 2667-2672 (2012)
  3. General method for synthesis of 2-heterocyclic N-methyliminodiacetic acid boronates. Dick GR, Knapp DM, Gillis EP, Burke MD. Org. Lett. 12 2314-2317 (2010)
  4. Identification of novel, exosite-binding matrix metalloproteinase-13 inhibitor scaffolds. Roth J, Minond D, Darout E, Liu Q, Lauer J, Hodder P, Fields GB, Roush WR. Bioorg. Med. Chem. Lett. 21 7180-7184 (2011)
  5. Identification of Small Molecule Inhibitors of Tau Aggregation by Targeting Monomeric Tau As a Potential Therapeutic Approach for Tauopathies. Pickhardt M, Neumann T, Schwizer D, Callaway K, Vendruscolo M, Schenk D, St George-Hyslop P, Mandelkow EM, Dobson CM, McConlogue L, Mandelkow E, Tóth G. Curr Alzheimer Res 12 814-828 (2015)
  6. Simple pseudo-dipeptides with a P2' glutamate: a novel inhibitor family of matrix metalloproteases and other metzincins. Devel L, Beau F, Amoura M, Vera L, Cassar-Lajeunesse E, Garcia S, Czarny B, Stura EA, Dive V. J. Biol. Chem. 287 26647-26656 (2012)
  7. Characterization of selective exosite-binding inhibitors of matrix metalloproteinase 13 that prevent articular cartilage degradation in vitro. Spicer TP, Jiang J, Taylor AB, Choi JY, Hart PJ, Roush WR, Fields GB, Hodder PS, Minond D. J. Med. Chem. 57 9598-9611 (2014)
  8. Protective effects of biochanin A on articular cartilage: in vitro and in vivo studies. Wu DQ, Zhong HM, Ding QH, Ba L. BMC Complement Altern Med 14 444 (2014)
  9. Development of matrix metalloproteinase-13 inhibitors - A structure-activity/structure-property relationship study. Fuerst R, Yong Choi J, Knapinska AM, Smith L, Cameron MD, Ruiz C, Fields GB, Roush WR. Bioorg Med Chem 26 4984-4995 (2018)
  10. Strong nonadditivity as a key structure-activity relationship feature: distinguishing structural changes from assay artifacts. Kramer C, Fuchs JE, Liedl KR. J Chem Inf Model 55 483-494 (2015)
  11. Second Generation Triple-Helical Peptide Inhibitors of Matrix Metalloproteinases. Bhowmick M, Tokmina-Roszyk D, Onwuha-Ekpete L, Harmon K, Robichaud T, Fuerst R, Stawikowska R, Steffensen B, Roush W, Wong HR, Fields GB. J. Med. Chem. 60 3814-3827 (2017)
  12. Matrix metalloproteinase inhibitors based on the 3-mercaptopyrrolidine core. Jin Y, Roycik MD, Bosco DB, Cao Q, Constantino MH, Schwartz MA, Sang QX. J. Med. Chem. 56 4357-4373 (2013)
  13. Inhibition of human leukocyte elastase, plasmin and matrix metalloproteinases by oleic acid and oleoyl-galardin derivative(s). Moroy G, Bourguet E, Decarme M, Sapi J, Alix AJ, Hornebeck W, Lorimier S. Biochem. Pharmacol. 81 626-635 (2011)
  14. Indole Inhibitors of MMP-13 for Arthritic Disorders. Taylor SJ, Abeywardane A, Liang S, Xiong Z, Proudfoot JR, Farmer BS, Gao DA, Heim-Riether A, Smith-Keenan LL, Muegge I, Yu Y, Zhang Q, Souza D, Panzenbeck M, Goldberg D, Hill-Drzewi M, Margarit M, Collins B, Li JX, Zuvela-Jelaska L, Li J, Farrow NA. ACS Omega 6 18635-18650 (2021)
  15. Interleukin 36 receptor-inducible matrix metalloproteinase 13 mediates intestinal fibrosis. Koop K, Enderle K, Hillmann M, Ruspeckhofer L, Vieth M, Sturm G, Trajanoski Z, Kühl AA, Atreya R, Leppkes M, Baum P, Roy J, Martin A, Neurath MF, Neufert C. Front Immunol 14 1163198 (2023)
  16. Matrix Metalloproteinase 13 Inhibitors for Modulation of Osteoclastogenesis: Enhancement of Solubility and Stability. Knapinska AM, Singh C, Drotleff G, Blanco D, Chai C, Schwab J, Herd A, Fields GB. ChemMedChem 16 1133-1142 (2021)


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