Literature DB >> 25699152

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

William Tieu1, Steven W Polyak2, Ashleigh S Paparella3, Min Y Yap4, Tatiana P Soares da Costa3, Belinda Ng3, Geqing Wang3, Richard Lumb5, Jan M Bell5, John D Turnidge6, Matthew C J Wilce4, Grant W Booker2, Andrew D Abell1.   

Abstract

An improved synthesis of biotinol-5'-AMP, an acyl-AMP mimic of the natural reaction intermediate of biotin protein ligase (BPL), is reported. This compound was shown to be a pan inhibitor of BPLs from a series of clinically important bacteria, particularly Staphylococcus aureus and Mycobacterium tuberculosis, and kinetic analysis revealed it to be competitive against the substrate biotin. Biotinol-5'-AMP also exhibits antibacterial activity against a panel of clinical isolates of S. aureus and M. tuberculosis with MIC values of 1-8 and 0.5-2.5 μg/mL, respectively, while being devoid of cytotoxicity to human HepG2 cells.

Entities:  

Keywords:  Antibiotics; biotin protein ligase; chemical synthesis; drug design; enzyme inhibitors

Year:  2014        PMID： 25699152      PMCID： PMC4329585          DOI： 10.1021/ml500475n

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  29 in total

1.  Use of binding enthalpy to drive an allosteric transition.

Authors:  Patrick H Brown; Dorothy Beckett
Journal:  Biochemistry       Date:  2005-03-01       Impact factor: 3.162

2.  Rationally designed nucleoside antibiotics that inhibit siderophore biosynthesis of Mycobacterium tuberculosis.

Authors:  Ravindranadh V Somu; Helena Boshoff; Chunhua Qiao; Eric M Bennett; Clifton E Barry; Courtney C Aldrich
Journal:  J Med Chem       Date:  2006-01-12       Impact factor: 7.446

3.  Structural characterization of Staphylococcus aureus biotin protein ligase and interaction partners: an antibiotic target.

Authors:  Nicole R Pendini; Min Y Yap; D A K Traore; Steven W Polyak; Nathan P Cowieson; Andrew Abell; Grant W Booker; John C Wallace; Jacqueline A Wilce; Matthew C J Wilce
Journal:  Protein Sci       Date:  2013-06       Impact factor: 6.725

4.  Reaction intermediate analogues as bisubstrate inhibitors of pantothenate synthetase.

Authors:  Zhixiang Xu; Wei Yin; Leonardo K Martinelli; Joanna Evans; Jinglei Chen; Yang Yu; Daniel J Wilson; Valerie Mizrahi; Chunhua Qiao; Courtney C Aldrich
Journal:  Bioorg Med Chem       Date:  2014-01-23       Impact factor: 3.641

5.  Bisubstrate adenylation inhibitors of biotin protein ligase from Mycobacterium tuberculosis.

Authors:  Benjamin P Duckworth; Todd W Geders; Divya Tiwari; Helena I Boshoff; Paul A Sibbald; Clifton E Barry; Dirk Schnappinger; Barry C Finzel; Courtney C Aldrich
Journal:  Chem Biol       Date:  2011-11-23

6.  The design and synthesis of inhibitors of pantothenate synthetase.

Authors:  Kellie L Tuck; S Adrian Saldanha; Louise M Birch; Alison G Smith; Chris Abell
Journal:  Org Biomol Chem       Date:  2006-08-30       Impact factor: 3.876

7.  Molecular basis for the high-affinity binding and stabilization of firefly luciferase by PTC124.

Authors:  Douglas S Auld; Scott Lovell; Natasha Thorne; Wendy A Lea; David J Maloney; Min Shen; Ganesha Rai; Kevin P Battaile; Craig J Thomas; Anton Simeonov; Robert P Hanzlik; James Inglese
Journal:  Proc Natl Acad Sci U S A       Date:  2010-03-01       Impact factor: 11.205

8.  Selective inhibitors of bacterial phosphopantothenoylcysteine synthetase.

Authors:  James D Patrone; Jiangwei Yao; Nicole E Scott; Garry D Dotson
Journal:  J Am Chem Soc       Date:  2009-11-18       Impact factor: 15.419

9.  The biotin repressor: modulation of allostery by corepressor analogs.

Authors:  Patrick H Brown; John E Cronan; Morten Grøtli; Dorothy Beckett
Journal:  J Mol Biol       Date:  2004-04-02       Impact factor: 5.469

10.  A novel tool for studying auxin-metabolism: the inhibition of grapevine indole-3-acetic acid-amido synthetases by a reaction intermediate analogue.

Authors:  Christine Böttcher; Eric G Dennis; Grant W Booker; Steven W Polyak; Paul K Boss; Christopher Davies
Journal:  PLoS One       Date:  2012-05-23       Impact factor: 3.240
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  5 in total

1.  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

2.  An environment-friendly methodology for the construction of diversified bicycloacenaphtho[1,2-d]imidazole-8-thione scaffolds using spinel NiFe2O4 nanoparticles as a sustainable catalyst.

Authors:  Soumitra Rana; Soumyadip Basu; Chhanda Mukhopadhyay
Journal:  Mol Divers       Date:  2022-01-03       Impact factor: 3.364

3.  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

Review 4.  Biotin Protein Ligase Is a Target for New Antibacterials.

Authors:  Jiage Feng; Ashleigh S Paparella; Grant W Booker; Steven W Polyak; Andrew D Abell
Journal:  Antibiotics (Basel)       Date:  2016-07-25

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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