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Sugar-Based Arylsulfonamide Carboxylates as Selective and Water-Soluble Matrix Metalloproteinase-12 Inhibitors.

Nuti E, Cuffaro D, D'Andrea F, Rosalia L, Tepshi L, Fabbi M, Carbotti G, Ferrini S, Santamaria S, Camodeca C, Ciccone L, Orlandini E, Nencetti S, Stura EA, Dive V, Rossello A
ChemMedChem 11 1626-37 (2016)
Related entries: 5i12, 5i2z, 5i3m, 5i43, 5i4o

Cited: 17 times
EuropePMC logo PMID: 27356908

Abstract

Matrix metalloproteinase-12 (MMP-12) can be considered an attractive target to study selective inhibitors useful in the development of new therapies for lung and cardiovascular diseases. In this study, a new series of arylsulfonamide carboxylates, with increased hydrophilicity resulting from conjugation with a β-N-acetyl-d-glucosamine moiety, were designed and synthesized as MMP-12 selective inhibitors. Their inhibitory activity was evaluated on human MMPs by using the fluorimetric assay, and a crystallographic analysis was performed to characterize their binding mode. Among these glycoconjugates, a nanomolar MMP-12 inhibitor with improved water solubility, compound 3 [(R)-2-(N-(2-(3-(2-acetamido-2-deoxy-β-d-glucopyranosyl)thioureido)ethyl)biphenyl-4-ylsulfonamido)-3-methylbutanoic acid], was identified.

Reviews - 5i0l mentioned but not cited (1)

  1. Developments in Carbohydrate-Based Metzincin Inhibitors. Cuffaro D, Nuti E, D'Andrea F, Rossello A. Pharmaceuticals (Basel) 13 E376 (2020)


Reviews citing this publication (2)

  1. Digestive Inflammation: Role of Proteolytic Dysregulation. Mariaule V, Kriaa A, Soussou S, Rhimi S, Boudaya H, Hernandez J, Maguin E, Lesner A, Rhimi M. Int J Mol Sci 22 2817 (2021)
  2. Targeting Aggrecanases for Osteoarthritis Therapy: From Zinc Chelation to Exosite Inhibition. Cuffaro D, Ciccone L, Rossello A, Nuti E, Santamaria S. J Med Chem 65 13505-13532 (2022)

Articles citing this publication (14)

  1. An overview of carbohydrate-based carbonic anhydrase inhibitors. Cuffaro D, Nuti E, Rossello A. J Enzyme Inhib Med Chem 35 1906-1922 (2020)
  2. Exosite inhibition of ADAMTS-5 by a glycoconjugated arylsulfonamide. Santamaria S, Cuffaro D, Nuti E, Ciccone L, Tuccinardi T, Liva F, D'Andrea F, de Groot R, Rossello A, Ahnström J. Sci Rep 11 949 (2021)
  3. Solvent water interactions within the active site of the membrane type I matrix metalloproteinase. Decaneto E, Vasilevskaya T, Kutin Y, Ogata H, Grossman M, Sagi I, Havenith M, Lubitz W, Thiel W, Cox N. Phys Chem Chem Phys 19 30316-30331 (2017)
  4. Synthesis and Evaluation of New Oxadiazole, Thiadiazole, and Triazole Derivatives as Potential Anticancer Agents Targeting MMP-9. Özdemir A, Sever B, Altıntop MD, Temel HE, Atlı Ö, Baysal M, Demirci F. Molecules 22 E1109 (2017)
  5. Matrix metalloproteinase-12 deficiency attenuates experimental crescentic anti-glomerular basement membrane glomerulonephritis. Abraham AP, Ma FY, Mulley WR, Nikolic-Paterson DJ, Tesch GH. Nephrology (Carlton) 23 183-189 (2018)
  6. Bifunctional Inhibitors as a New Tool To Reduce Cancer Cell Invasion by Impairing MMP-9 Homodimerization. Nuti E, Rosalia L, Cuffaro D, Camodeca C, Giacomelli C, Da Pozzo E, Tuccinardi T, Costa B, Antoni C, Vera L, Ciccone L, Orlandini E, Nencetti S, Dive V, Martini C, Stura EA, Rossello A. ACS Med Chem Lett 8 293-298 (2017)
  7. Cinnamic acid derivatives as potential matrix metalloproteinase-9 inhibitors: molecular docking and dynamics simulations. Malekipour MH, Shirani F, Moradi S, Taherkhani A. Genomics Inform 21 e9 (2023)
  8. Efficient synthesis and enzymatic extension of an N-GlcNAz asparagine building block. Marqvorsen MHS, Paramasivam S, Doelman W, Fairbanks AJ, van Kasteren SI. Chem Commun (Camb) 55 5287-5290 (2019)
  9. Ligand-based pharmacophore modeling and molecular dynamic simulation approaches to identify putative MMP-9 inhibitors. Sanapalli BKR, Yele V, Jupudi S, Karri VVSR. RSC Adv 11 26820-26831 (2021)
  10. A Surface Acoustic Wave (SAW)-Based Lab-on-Chip for the Detection of Active α-Glycosidase. Gagliardi M, Agostini M, Lunardelli F, Miranda A, Luminare AG, Cervelli F, Gambineri F, Cecchini M. Biosensors (Basel) 12 1010 (2022)
  11. ATIQCTPC targeting MMP-9: a key step to slowing primary tumor growth and inhibiting metastasis of lewis lung carcinoma in vivo. Wang Y, Xu X, Song C, Wu J, Hu X, Zhu H, Zhang X, Wang Y, Gui L, Zhao M, Peng S. Oncotarget 8 63881-63889 (2017)
  12. Glycans Meet Sphingolipids: Structure-Based Design of Glycan Containing Analogues of a Sphingosine Kinase Inhibitor. Papakyriakou A, Cencetti F, Puliti E, Morelli L, Tricomi J, Bruni P, Compostella F, Richichi B. ACS Med Chem Lett 11 913-920 (2020)
  13. Molecular interactions of tannic acid and matrix metalloproteinases 2 and 9. Chiang YT, Xiao YB, Hsu SH, Chang SW, Chou CC. Comput Struct Biotechnol J 21 2792-2800 (2023)
  14. Synthesis of Some New 1,3,4-Oxadiazole Derivatives and Evaluation of Their Anticancer Activity. Yurttaş L, Evren AE, Kubilay A, Aksoy MO, Temel HE, Akalın Çiftçi G. ACS Omega 8 49311-49326 (2023)


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