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Synthesis and structural characterisation of selective non-carbohydrate-based inhibitors of bacterial sialidases.

Brear P, Telford J, Taylor GL, Westwood NJ
Chembiochem 13 2374-83 (2012)
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Cited: 8 times
EuropePMC logo PMID: 23070966

Abstract

The major human pathogen Streptococcus pneumoniae plays a key role in several disease states including septicaemia, meningitis and community-acquired pneumonia. Although vaccines against S. pneumoniae are available as prophylactics, there remains a need to identify and characterise novel chemical entities that can treat the diseases caused by this pathogen. S. pneumoniae expresses three sialidases, enzymes that cleave sialic acid from carbohydrate-based surface molecules. Two of these enzymes, NanA and NanB, have been implicated in the pathogenesis of S. pneumoniae and are considered to be validated drug targets. Here we report our studies on the synthesis and structural characterisation of novel NanB-selective inhibitors that are inspired by the β-amino-sulfonic acid family of buffers.

Reviews citing this publication (1)

  1. Exploitation of physiology and metabolomics to identify pneumococcal vaccine candidates. Schulz C, Hammerschmidt S. Expert Rev Vaccines 12 1061-1075 (2013)

Articles citing this publication (7)

  1. Homologous ligands accommodated by discrete conformations of a buried cavity. Merski M, Fischer M, Balius TE, Eidam O, Shoichet BK. Proc Natl Acad Sci U S A 112 5039-5044 (2015)
  2. DeepFrag: a deep convolutional neural network for fragment-based lead optimization. Green H, Koes DR, Durrant JD. Chem Sci 12 8036-8047 (2021)
  3. Streptococcus pneumoniae Sialidase SpNanB-Catalyzed One-Pot Multienzyme (OPME) Synthesis of 2,7-Anhydro-Sialic Acids as Selective Sialidase Inhibitors. Xiao A, Slack TJ, Li Y, Shi D, Yu H, Li W, Liu Y, Chen X. J Org Chem 83 10798-10804 (2018)
  4. Crystal structure of the catalytic domain of Clostridium perfringens neuraminidase in complex with a non-carbohydrate-based inhibitor, 2-(cyclohexylamino)ethanesulfonic acid. Lee Y, Youn HS, Lee JG, An JY, Park KR, Kang JY, Ryu YB, Jin MS, Park KH, Eom SH. Biochem Biophys Res Commun 486 470-475 (2017)
  5. Sequence diversity of NanA manifests in distinct enzyme kinetics and inhibitor susceptibility. Xu Z, von Grafenstein S, Walther E, Fuchs JE, Liedl KR, Sauerbrei A, Schmidtke M. Sci Rep 6 25169 (2016)
  6. Triazole-linked transition state analogs as selective inhibitors against V. cholerae sialidase. Slack TJ, Li W, Shi D, McArthur JB, Zhao G, Li Y, Xiao A, Khedri Z, Yu H, Liu Y, Chen X. Bioorg Med Chem 26 5751-5757 (2018)
  7. 9-Azido-9-deoxy-2,3-difluorosialic Acid as a Subnanomolar Inhibitor against Bacterial Sialidases. Li W, Santra A, Yu H, Slack TJ, Muthana MM, Shi D, Liu Y, Chen X. J Org Chem 84 6697-6708 (2019)


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