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Tethering identifies fragment that yields potent inhibitors of human caspase-1.

Fahr BT, O'Brien T, Pham P, Waal ND, Baskaran S, Raimundo BC, Lam JW, Sopko MM, Purkey HE, Romanowski MJ
Bioorg Med Chem Lett 16 559-62 (2006)
Cited: 22 times
EuropePMC logo PMID: 16274992

Abstract

Disulfide Tethering was applied to the active site of human caspase-1, resulting in the discovery of a novel, tricyclic molecular fragment that selectively binds in S4. This fragment was developed into a class of potent inhibitors of human caspase-1. Several key analogues determined the optimal distance of the tricycle from the catalytic residues, the relative importance of various features of the tricycle, and the importance of the linker.

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  2. Recent Advances in Studying Toll-like Receptors with the Use of Computational Methods. Bzówka M, Bagrowska W, Góra A. J Chem Inf Model 63 3669-3687 (2023)

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  1. Fragment-based lead discovery: a chemical update. Erlanson DA. Curr Opin Biotechnol 17 643-652 (2006)
  2. Small Molecule Active Site Directed Tools for Studying Human Caspases. Poreba M, Szalek A, Kasperkiewicz P, Rut W, Salvesen GS, Drag M. Chem Rev 115 12546-12629 (2015)

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  1. Molecular docking and ligand specificity in fragment-based inhibitor discovery. Chen Y, Shoichet BK. Nat Chem Biol 5 358-364 (2009)
  2. Kinetic template-guided tethering of fragments. Nonoo RH, Armstrong A, Mann DJ. ChemMedChem 7 2082-2086 (2012)
  3. Naturally occurring genetic variants of human caspase-1 differ considerably in structure and the ability to activate interleukin-1β. Luksch H, Romanowski MJ, Chara O, Tüngler V, Caffarena ER, Heymann MC, Lohse P, Aksentijevich I, Remmers EF, Flecks S, Quoos N, Gramatté J, Petzold C, Hofmann SR, Winkler S, Pessler F, Kallinich T, Ganser G, Nimtz-Talaska A, Baumann U, Runde V, Grimbacher B, Birmelin J, Gahr M, Roesler J, Rösen-Wolff A. Hum Mutat 34 122-131 (2013)
  4. Protective effect of gedunin on TLR-mediated inflammation by modulation of inflammasome activation and cytokine production: Evidence of a multitarget compound. Borges PV, Moret KH, Raghavendra NM, Maramaldo Costa TE, Monteiro AP, Carneiro AB, Pacheco P, Temerozo JR, Bou-Habib DC, das Graças Henriques M, Penido C. Pharmacol Res 115 65-77 (2017)
  5. Letter Lazaroids U83836E and U74389G are potent, time-dependent inhibitors of caspase-1. Kawarski M, Hagerman TK, Karver CE. Chem Biol Drug Des 86 1049-1054 (2015)
  6. Synthesis of novel antibacterial and antifungal quinoxaline derivatives. Tang X, Zhou Q, Zhan W, Hu D, Zhou R, Sun N, Chen S, Wu W, Xue W. RSC Adv 12 2399-2407 (2022)
  7. Carboxylate isosteres for caspase inhibitors: the acylsulfonamide case revisited. Adriaenssens Y, Jiménez Fernández D, Vande Walle L, Elvas F, Joossens J, Lambeir A, Augustyns K, Lamkanfi M, Van der Veken P. Org Biomol Chem 15 7456-7473 (2017)


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