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Design and synthesis of potent and selective macrocyclic thrombin inhibitors.

Nantermet PG, Barrow JC, Newton CL, Pellicore JM, Young M, Lewis SD, Lucas BJ, Krueger JA, McMasters DR, Yan Y, Kuo LC, Vacca JP, Selnick HG
Bioorg Med Chem Lett 13 2781-4 (2003)
Cited: 18 times
EuropePMC logo PMID: 12873514

Abstract

A series of potent and selective proline- and pyrazinone-based macrocyclic thrombin inhibitors is described. Detailed SAR studies led to the incorporation of specific functional groups in the tether that enhanced functional activity against thrombin and provided exquisite selectivity against trypsin and tPA. X-ray crystallography and molecular modeling studies revealed the inhibitor-enzyme interactions responsible for this selectivity.

Articles - 1nt1 mentioned but not cited (9)

  1. Two-component spike nanoparticle vaccine protects macaques from SARS-CoV-2 infection. Brouwer PJM, Brinkkemper M, Maisonnasse P, Dereuddre-Bosquet N, Grobben M, Claireaux M, de Gast M, Marlin R, Chesnais V, Diry S, Allen JD, Watanabe Y, Giezen JM, Kerster G, Turner HL, van der Straten K, van der Linden CA, Aldon Y, Naninck T, Bontjer I, Burger JA, Poniman M, Mykytyn AZ, Okba NMA, Schermer EE, van Breemen MJ, Ravichandran R, Caniels TG, van Schooten J, Kahlaoui N, Contreras V, Lemaître J, Chapon C, Fang RHT, Villaudy J, Sliepen K, van der Velden YU, Haagmans BL, de Bree GJ, Ginoux E, Ward AB, Crispin M, King NP, van der Werf S, van Gils MJ, Le Grand R, Sanders RW. Cell 184 1188-1200.e19 (2021)
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  3. Quantum and molecular dynamics study for binding of macrocyclic inhibitors to human alpha-thrombin. Wu EL, Mei Y, Han K, Zhang JZ. Biophys. J. 92 4244-4253 (2007)
  4. A Guided Tour of the Structural Biology of Gaucher Disease: Acid-β-Glucosidase and Saposin C. Lieberman RL. Enzyme Res 2011 973231 (2011)
  5. Structure-based predictions of activity cliffs. Husby J, Bottegoni G, Kufareva I, Abagyan R, Cavalli A. J Chem Inf Model 55 1062-1076 (2015)
  6. How Good is Jarzynski's Equality for Computer-Aided Drug Design? Ho K, Truong DT, Li MS. J Phys Chem B 124 5338-5349 (2020)
  7. Lassa virus glycoprotein nanoparticles elicit neutralizing antibody responses and protection. Brouwer PJM, Antanasijevic A, Ronk AJ, Müller-Kräuter H, Watanabe Y, Claireaux M, Perrett HR, Bijl TPL, Grobben M, Umotoy JC, Schriek AI, Burger JA, Tejjani K, Lloyd NM, Steijaert TH, van Haaren MM, Sliepen K, de Taeye SW, van Gils MJ, Crispin M, Strecker T, Bukreyev A, Ward AB, Sanders RW. Cell Host Microbe 30 1759-1772.e12 (2022)
  8. Enhancing and shaping the immunogenicity of native-like HIV-1 envelope trimers with a two-component protein nanoparticle. Brouwer PJM, Antanasijevic A, Berndsen Z, Yasmeen A, Fiala B, Bijl TPL, Bontjer I, Bale JB, Sheffler W, Allen JD, Schorcht A, Burger JA, Camacho M, Ellis D, Cottrell CA, Behrens AJ, Catalano M, Del Moral-Sánchez I, Ketas TJ, LaBranche C, van Gils MJ, Sliepen K, Stewart LJ, Crispin M, Montefiori DC, Baker D, Moore JP, Klasse PJ, Ward AB, King NP, Sanders RW. Nat Commun 10 4272 (2019)
  9. Structural conservation of Lassa virus glycoproteins and recognition by neutralizing antibodies. Perrett HR, Brouwer PJM, Hurtado J, Newby ML, Liu L, Müller-Kräuter H, Müller Aguirre S, Burger JA, Bouhuijs JH, Gibson G, Messmer T, Schieffelin JS, Antanasijevic A, Boons GJ, Strecker T, Crispin M, Sanders RW, Briney B, Ward AB. Cell Rep 42 112524 (2023)


Reviews citing this publication (3)

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  2. Recent advances in the discovery and development of factor XI/XIa inhibitors. Al-Horani RA, Afosah DK. Med Res Rev 38 1974-2023 (2018)
  3. N-, O- and S-Heterocycles Synthesis in Deep Eutectic Solvents. Perrone S, Messa F, Troisi L, Salomone A. Molecules 28 3459 (2023)

Articles citing this publication (6)

  1. Large-scale molecular dynamics simulation: Effect of polarization on thrombin-ligand binding energy. Duan LL, Feng GQ, Zhang QG. Sci Rep 6 31488 (2016)
  2. Efficient parallel synthesis of macrocyclic peptidomimetics. Marsault E, Hoveyda HR, Gagnon R, Peterson ML, Vézina M, Saint-Louis C, Landry A, Pinault JF, Ouellet L, Beauchemin S, Beaubien S, Mathieu A, Benakli K, Wang Z, Brassard M, Lonergan D, Bilodeau F, Ramaseshan M, Fortin N, Lan R, Li S, Galaud F, Plourde V, Champagne M, Doucet A, Bhérer P, Gauthier M, Olsen G, Villeneuve G, Bhat S, Foucher L, Fortin D, Peng X, Bernard S, Drouin A, Déziel R, Berthiaume G, Dory YL, Fraser GL, Deslongchamps P. Bioorg. Med. Chem. Lett. 18 4731-4735 (2008)
  3. Synthesis and bio-assay of RCM-derived Bowman-Birk inhibitor analogues. Miles SM, Leatherbarrow RJ, Marsden SP, Coates WJ. Org. Biomol. Chem. 2 281-283 (2004)
  4. Design, Synthesis, and Characterization of Macrocyclic Inhibitors of the Proprotein Convertase Furin. Van Lam van T, Ivanova T, Hardes K, Heindl MR, Morty RE, Böttcher-Friebertshäuser E, Lindberg I, Than ME, Dahms SO, Steinmetzer T. ChemMedChem 14 673-685 (2019)
  5. Quantum mechanical effect in protein-ligand interaction. Jing YQ, Han KL. Expert Opin Drug Discov 5 33-49 (2010)
  6. Structure of the complex of porcine pancreatic elastase with a trimacrocyclic peptide inhibitor FR901451. Kinoshita T, Kitatani T, Warizaya M, Tada T. Acta Crystallogr. Sect. F Struct. Biol. Cryst. Commun. 61 808-811 (2005)


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