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Literature DB >> 25466176

β-Keto and β-hydroxyphosphonate analogs of biotin-5'-AMP are inhibitors of holocarboxylase synthetase.

Wantanee Sittiwong¹, Elizabeth L Cordonier², Janos Zempleni³, Patrick H Dussault⁴.

Abstract

Holocarboxylase synthetase (HLCS) catalyzes the covalent attachment of biotin to cytoplasmic and mitochondrial carboxylases, nuclear histones, and over a hundred human proteins. Nonhydrolyzable ketophosphonate (β-ketoP) and hydroxyphosphonate (β-hydroxyP) analogs of biotin-5'-AMP inhibit holocarboxylase synthetase (HLCS) with IC50 values of 39.7 μM and 203.7 μM. By comparison, an IC50 value of 7 μM was observed with the previously reported biotinol-5'-AMP. The Ki values, 3.4 μM and 17.3 μM, respectively, are consistent with the IC50 results, and close to the Ki obtained for biotinol-5'-AMP (7 μM). The β-ketoP and β-hydroxyP molecules are competitive inhibitors of HLCS while biotinol-5'-AMP inhibited HLCS by a mixed mechanism.

Entities: Chemical Disease Gene Species

Keywords: Biotin-5′-AMP; Biotinylation; Holocarboxylase synthetase; β-Hydroxyphosphonate; β-Ketophosphonate

Mesh：

Substances：

Year: 2014 PMID： 25466176 PMCID： PMC4255142 DOI： 10.1016/j.bmcl.2014.11.010

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

26 in total

1. Human holocarboxylase synthetase with a start site at methionine-58 is the predominant nuclear variant of this protein and has catalytic activity.

Authors: Baolong Bao; Subhashinee S K Wijeratne; Rocio Rodriguez-Melendez; Janos Zempleni
Journal: Biochem Biophys Res Commun Date: 2011-07-23 Impact factor: 3.575

2. Holocarboxylase synthetase interacts physically with nuclear receptor co-repressor, histone deacetylase 1 and a novel splicing variant of histone deacetylase 1 to repress repeats.

Authors: Dandan Liu; Janos Zempleni
Journal: Biochem J Date: 2014-08-01 Impact factor: 3.857

3. Selective inhibition of biotin protein ligase from Staphylococcus aureus.

Authors: Tatiana P Soares da Costa; William Tieu; Min Y Yap; Nicole R Pendini; Steven W Polyak; Daniel Sejer Pedersen; Renato Morona; John D Turnidge; John C Wallace; Matthew C J Wilce; Grant W Booker; Andrew D Abell
Journal: J Biol Chem Date: 2012-03-21 Impact factor: 5.157

4. 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

5. Holocarboxylase synthetase synergizes with methyl CpG binding protein 2 and DNA methyltransferase 1 in the transcriptional repression of long-terminal repeats.

Authors: Jing Xue; Subhashinee S K Wijeratne; Janos Zempleni
Journal: Epigenetics Date: 2013-04-27 Impact factor: 4.528

6. Effects of single-nucleotide polymorphisms in the human holocarboxylase synthetase gene on enzyme catalysis.

Authors: Shingo Esaki; Sridhar A Malkaram; Janos Zempleni
Journal: Eur J Hum Genet Date: 2011-10-26 Impact factor: 4.246

7. Lysine biotinylation and methionine oxidation in the heat shock protein HSP60 synergize in the elimination of reactive oxygen species in human cell cultures.

Authors: Yong Li; Sridhar A Malkaram; Jie Zhou; Janos Zempleni
Journal: J Nutr Biochem Date: 2014-01-28 Impact factor: 6.048

Review 8. Structure guided design of biotin protein ligase inhibitors for antibiotic discovery.

Authors: Ashleigh S Paparella; Tatiana P Soares da Costa; Min Y Yap; William Tieu; Matthew C J Wilce; Grant W Booker; Andrew D Abell; Steven W Polyak
Journal: Curr Top Med Chem Date: 2014 Impact factor: 3.295

9. Holocarboxylase synthetase interacts physically with euchromatic histone-lysine N-methyltransferase, linking histone biotinylation with methylation events.

Authors: Yong Li; Yousef I Hassan; Hideaki Moriyama; Janos Zempleni
Journal: J Nutr Biochem Date: 2013-01-20 Impact factor: 6.048

10. 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

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