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Structural, kinetic, and thermodynamic analysis of glucoimidazole-derived glycosidase inhibitors.

Gloster TM, Roberts S, Perugino G, Rossi M, Moracci M, Panday N, Terinek M, Vasella A, Davies GJ
Biochemistry 45 11879-84 (2006)
Related entries: 2ceq, 2cer, 2ces, 2j75, 2j77, 2j78, 2j79, 2j7b, 2j7c, 2j7d, 2j7e, 2j7f, 2j7g, 2j7h

Cited: 30 times
EuropePMC logo PMID: 17002288

Abstract

Inhibition of glycosidases has great potential in the quest for highly potent and specific drugs to treat diseases such as diabetes, cancer, and viral infections. One of the most effective ways of designing such compounds is by mimicking the transition state. Here we describe the structural, kinetic, and thermodynamic dissection of binding of two glucoimidazole-derived compounds, which are among the most potent glycosidase inhibitors reported to date, with two family 1 beta-glycosidases. Provocatively, while inclusion of the phenethyl moiety improves binding by a factor of 20-80-fold, this does not appear to result from better noncovalent interactions with the enzyme; instead, improved affinity may be derived from significantly better entropic contributions to binding displayed by the phenethyl-substituted imidazole compound.

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  1. β-Glucosidases. Ketudat Cairns JR, Esen A. Cell Mol Life Sci 67 3389-3405 (2010)
  2. Mechanistic insights into glycosidase chemistry. Vocadlo DJ, Davies GJ. Curr Opin Chem Biol 12 539-555 (2008)
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  5. Development of inhibitors as research tools for carbohydrate-processing enzymes. Gloster TM. Biochem Soc Trans 40 913-928 (2012)

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  3. Insight into a strategy for attenuating AmpC-mediated beta-lactam resistance: structural basis for selective inhibition of the glycoside hydrolase NagZ. Balcewich MD, Stubbs KA, He Y, James TW, Davies GJ, Vocadlo DJ, Mark BL. Protein Sci 18 1541-1551 (2009)
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  12. Gluco-1 H-imidazole: A New Class of Azole-Type β-Glucosidase Inhibitor. Schröder SP, Wu L, Artola M, Hansen T, Offen WA, Ferraz MJ, Li KY, Aerts JMFG, van der Marel GA, Codée JDC, Davies GJ, Overkleeft HS. J Am Chem Soc 140 5045-5048 (2018)
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  14. Study on binding modes between cellobiose and β-glucosidases from glycoside hydrolase family 1. Liu L, Zeng Z, Zeng G, Chen M, Zhang Y, Zhang J, Fang X, Jiang M, Lu L. Bioorg Med Chem Lett 22 837-843 (2012)
  15. Discovery of new β-D-glucosidase inhibitors via pharmacophore modeling and QSAR analysis followed by in silico screening. Abu Khalaf R, Abdula AM, Mubarak MS, Taha MO. J Mol Model 17 443-464 (2011)
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  17. Binding interactions of hydrophobically-modified flavonols with β-glucosidase: fluorescence spectroscopy and molecular modelling study. Chepeleva LV, Demidov OO, Snizhko AD, Tarasenko DO, Chumak AY, Kolomoitsev OO, Kotliar VM, Gladkov ES, Kyrychenko A, Roshal AD. RSC Adv 13 34107-34121 (2023)
  18. Probing the role of an invariant active site His in family GH1 β-glycosidases. Strazzulli A, Perugino G, Mazzone M, Rossi M, Withers SG, Moracci M. J Enzyme Inhib Med Chem 34 973-980 (2019)
  19. Reaction Mechanism of Glycoside Hydrolase Family 116 Utilizes Perpendicular Protonation. Pengthaisong S, Piniello B, Davies GJ, Rovira C, Ketudat Cairns JR. ACS Catal 13 5850-5863 (2023)


Related citations provided by authors (1)

  1. Glycosidase inhibition: an assessment of the binding of 18 putative transition-state mimics.. Gloster TM, Meloncelli P, Stick RV, Zechel D, Vasella A, Davies GJ J Am Chem Soc 129 2345-54 (2007)

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