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X-ray snapshot of the mechanism of inactivation of human neutrophil elastase by 1,2,5-thiadiazolidin-3-one 1,1-dioxide derivatives.

Huang W, Yamamoto Y, Li Y, Dou D, Alliston KR, Hanzlik RP, Williams TD, Groutas WC
J Med Chem 51 2003-8 (2008)
Cited: 19 times
EuropePMC logo PMID: 18318470

Abstract

The mechanism of action of a general class of mechanism-based inhibitors of serine proteases, including human neutrophil elastase (HNE), has been elucidated by determining the X-ray crystal structure of an enzyme-inhibitor complex. The captured intermediate indicates that processing of inhibitor by the enzyme generates an N-sulfonyl imine functionality that is tethered to Ser195, in accordance with the postulated mechanism of action of this class of inhibitors. The identity of the HNE-N-sulfonyl imine species was further corroborated using electrospray ionization mass spectrometry.

Articles - 2rg3 mentioned but not cited (1)

  1. X-ray snapshot of the mechanism of inactivation of human neutrophil elastase by 1,2,5-thiadiazolidin-3-one 1,1-dioxide derivatives. Huang W, Yamamoto Y, Li Y, Dou D, Alliston KR, Hanzlik RP, Williams TD, Groutas WC. J. Med. Chem. 51 2003-2008 (2008)


Reviews citing this publication (3)

  1. Structures of human proteinase 3 and neutrophil elastase--so similar yet so different. Hajjar E, Broemstrup T, Kantari C, Witko-Sarsat V, Reuter N. FEBS J. 277 2238-2254 (2010)
  2. Targeting COPD: advances on low-molecular-weight inhibitors of human neutrophil elastase. Lucas SD, Costa E, Guedes RC, Moreira R. Med Res Rev 33 Suppl 1 E73-101 (2013)
  3. Inhibitors and Antibody Fragments as Potential Anti-Inflammatory Therapeutics Targeting Neutrophil Proteinase 3 in Human Disease. Korkmaz B, Lesner A, Guarino C, Wysocka M, Kellenberger C, Watier H, Specks U, Gauthier F, Jenne DE. Pharmacol. Rev. 68 603-630 (2016)

Articles citing this publication (15)

  1. Unexpected active-site flexibility in the structure of human neutrophil elastase in complex with a new dihydropyrimidone inhibitor. Hansen G, Gielen-Haertwig H, Reinemer P, Schomburg D, Harrenga A, Niefind K. J. Mol. Biol. 409 681-691 (2011)
  2. Design, synthesis, and in vitro evaluation of potential West Nile virus protease inhibitors based on the 1-oxo-1,2,3,4-tetrahydroisoquinoline and 1-oxo-1,2-dihydroisoquinoline scaffolds. Dou D, Viwanathan P, Li Y, He G, Alliston KR, Lushington GH, Brown-Clay JD, Padmanabhan R, Groutas WC. J Comb Chem 12 836-843 (2010)
  3. Mechanism-based inhibitors of serine proteases with high selectivity through optimization of S' subsite binding. Li Y, Dou D, He G, Lushington GH, Groutas WC. Bioorg. Med. Chem. 17 3536-3542 (2009)
  4. Oxidized von Willebrand factor is efficiently cleaved by serine proteases from primary granules of leukocytes: divergence from ADAMTS-13. Lancellotti S, De Filippis V, Pozzi N, Oggianu L, Rutella S, Scaglione GL, Maset F, Peyvandi F, Mannucci PM, De Cristofaro R. J. Thromb. Haemost. 9 1620-1627 (2011)
  5. Inhibition of human neutrophil elastase by pentacyclic triterpenes. Feng L, Liu X, Zhu W, Guo F, Wu Y, Wang R, Chen K, Huang C, Li Y. PLoS ONE 8 e82794 (2013)
  6. Paucimannose-Rich N-glycosylation of Spatiotemporally Regulated Human Neutrophil Elastase Modulates Its Immune Functions. Loke I, Østergaard O, Heegaard NHH, Packer NH, Thaysen-Andersen M. Mol. Cell Proteomics 16 1507-1527 (2017)
  7. Dual function inhibitors of relevance to chronic obstructive pulmonary disease. Dou D, He G, Alliston KR, Groutas WC. Bioorg. Med. Chem. Lett. 21 3177-3180 (2011)
  8. Inhibitors of human neutrophil elastase based on a highly functionalized N-amino-4-imidazolidinone scaffold. He G, Dou D, Wei L, Alliston KR, Groutas WC. Eur J Med Chem 45 4280-4287 (2010)
  9. Effects of structure on inhibitory activity in a series of mechanism-based inhibitors of human neutrophil elastase. Dou D, He G, Kuang R, Fu Q, Venkataraman R, Groutas WC. Bioorg. Med. Chem. 18 6646-6650 (2010)
  10. Crystal structure of highly glycosylated human leukocyte elastase in complex with an S2' site binding inhibitor. Hochscherf J, Pietsch M, Tieu W, Kuan K, Abell AD, Gütschow M, Niefind K. Acta Crystallogr F Struct Biol Commun 74 480-489 (2018)
  11. N-Acyl and N-sulfonyloxazolidine-2,4-diones are pseudo-irreversible inhibitors of serine proteases. Santana AB, Lucas SD, Gonçalves LM, Correia HF, Cardote TA, Guedes RC, Iley J, Moreira R. Bioorg. Med. Chem. Lett. 22 3993-3997 (2012)
  12. Neutrophil elastase inhibitory effects of pentacyclic triterpenoids from Eriobotrya japonica (loquat leaves). Zhang J, Xu HY, Wu YJ, Zhang X, Zhang LQ, Li YM. J Ethnopharmacol 242 111713 (2019)
  13. Sequence preference and scaffolding requirement for the inhibition of human neutrophil elastase by ecotin peptide. Bagga T, Loh SN, Sivaraman J, Shankar S. Protein Sci 31 933-941 (2022)
  14. Synthesis and biological evaluation of nigranoic acid esters as novel human neutrophil elastase inhibitors. Huang G, Feng L, Liu B, He Y, Li Y, Chen Y. Nat. Prod. Res. 29 1650-1656 (2015)
  15. The role of neutrophil elastase in aortic valve calcification. Liu Y, Jiang P, An L, Zhu M, Li J, Wang Y, Huang Q, Xiang Y, Li X, Shi Q, Weng Y. J Transl Med 20 167 (2022)


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