Literature DB >> 25193234

Heterocyclic acyl-phosphate bioisostere-based inhibitors of Staphylococcus aureus biotin protein ligase.

William Tieu1, Angie M Jarrad2, Ashleigh S Paparella2, Kelly A Keeling3, Tatiana P Soares da Costa2, John C Wallace2, Grant W Booker2, Steven W Polyak2, Andrew D Abell4.   

Abstract

Inhibitors of Staphylococcus aureus biotin protein ligase (SaBPL) are generated by replacing the acyl phosphate group of biotinyl-5'-AMP with either a 1,2,3-triazole (see 5/10a/10b) or a 1,2,4-oxadiazole (see 7) bioisostere. Importantly, the inhibitors are inactive against the human BPL. The nature of the 5-substituent in the component benzoxazolone of the optimum 1,2,3-triazole series is critical to activity, where this group binds in the ATP binding pocket of the enzyme.
Copyright © 2014 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  Antibiotics; Bioisosteres; Drug design; Inhibitors; Ligases

Mesh：

Substances：

Year:  2014        PMID： 25193234     DOI： 10.1016/j.bmcl.2014.08.030

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN： 0960-894X            Impact factor:   2.823


  5 in total

1.  Targeting Mycobacterium tuberculosis Biotin Protein Ligase (MtBPL) with Nucleoside-Based Bisubstrate Adenylation Inhibitors.

Authors:  Matthew R Bockman; Alvin S Kalinda; Riccardo Petrelli; Teresa De la Mora-Rey; Divya Tiwari; Feng Liu; Surrendra Dawadi; Madhumitha Nandakumar; Kyu Y Rhee; Dirk Schnappinger; Barry C Finzel; Courtney C Aldrich
Journal:  J Med Chem       Date:  2015-09-03       Impact factor: 7.446

2.  Improved Synthesis of Biotinol-5'-AMP: Implications for Antibacterial Discovery.

Authors:  William Tieu; Steven W Polyak; Ashleigh S Paparella; Min Y Yap; Tatiana P Soares da Costa; Belinda Ng; Geqing Wang; Richard Lumb; Jan M Bell; John D Turnidge; Matthew C J Wilce; Grant W Booker; Andrew D Abell
Journal:  ACS Med Chem Lett       Date:  2014-12-11       Impact factor: 4.345

3.  New Series of BPL Inhibitors To Probe the Ribose-Binding Pocket of Staphylococcus aureus Biotin Protein Ligase.

Authors:  Jiage Feng; Ashleigh S Paparella; William Tieu; David Heim; Sarah Clark; Andrew Hayes; Grant W Booker; Steven W Polyak; Andrew D Abell
Journal:  ACS Med Chem Lett       Date:  2016-10-10       Impact factor: 4.345

4.  Native mass spectrometry identifies an alternative DNA-binding pathway for BirA from Staphylococcus aureus.

Authors:  Jiulia Satiaputra; Louise M Sternicki; Andrew J Hayes; Tara L Pukala; Grant W Booker; Keith E Shearwin; Steven W Polyak
Journal:  Sci Rep       Date:  2019-02-26       Impact factor: 4.379

5.  Advanced Resistance Studies Identify Two Discrete Mechanisms in Staphylococcus aureus to Overcome Antibacterial Compounds that Target Biotin Protein Ligase.

Authors:  Andrew J Hayes; Jiulia Satiaputra; Louise M Sternicki; Ashleigh S Paparella; Zikai Feng; Kwang J Lee; Beatriz Blanco- Rodriguez; William Tieu; Bart A Eijkelkamp; Keith E Shearwin; Tara L Pukala; Andrew D Abell; Grant W Booker; Steven W Polyak
Journal:  Antibiotics (Basel)       Date:  2020-04-06
  5 in total

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