Literature DB >> 27994767

Discovery and Optimization of Two Eis Inhibitor Families as Kanamycin Adjuvants against Drug-Resistant M. tuberculosis.

Atefeh Garzan1, Melisa J Willby2, Keith D Green1, Oleg V Tsodikov1, James E Posey2, Sylvie Garneau-Tsodikova1.   

Abstract

Drug-resistant tuberculosis (TB) is a global threat and innovative approaches such as using adjuvants of anti-TB therapeutics are required to combat it. High-throughput screening yielded two lead scaffolds of inhibitors of Mycobacterium tuberculosis (Mtb) acetyltransferase Eis, whose upregulation causes resistance to the anti-TB drug kanamycin (KAN). Chemical optimization on these scaffolds resulted in potent Eis inhibitors. One compound restored the activity of KAN in a KAN-resistant Mtb strain. Model structures of Eis-inhibitor complexes explain the structure-activity relationship.

Entities:  

Keywords:  Aminoglycoside acetyltransferase; drug combination; enzyme inactivation; resistance; structure−activity relationship

Year:  2016        PMID： 27994767      PMCID： PMC5150678          DOI： 10.1021/acsmedchemlett.6b00261

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


  9 in total

1.  Aminoglycoside multiacetylating activity of the enhanced intracellular survival protein from Mycobacterium smegmatis and its inhibition.

Authors:  Wenjing Chen; Keith D Green; Oleg V Tsodikov; Sylvie Garneau-Tsodikova
Journal:  Biochemistry       Date:  2012-06-05       Impact factor: 3.162

2.  Overexpression of the chromosomally encoded aminoglycoside acetyltransferase eis confers kanamycin resistance in Mycobacterium tuberculosis.

Authors:  M Analise Zaunbrecher; R David Sikes; Beverly Metchock; Thomas M Shinnick; James E Posey
Journal:  Proc Natl Acad Sci U S A       Date:  2009-11-11       Impact factor: 11.205

3.  Unexpected N-acetylation of capreomycin by mycobacterial Eis enzymes.

Authors:  Jacob L Houghton; Keith D Green; Rachel E Pricer; Abdelrahman S Mayhoub; Sylvie Garneau-Tsodikova
Journal:  J Antimicrob Chemother       Date:  2012-12-11       Impact factor: 5.790

4.  Potent Inhibitors of Acetyltransferase Eis Overcome Kanamycin Resistance in Mycobacterium tuberculosis.

Authors:  Melisa J Willby; Keith D Green; Chathurada S Gajadeera; Caixia Hou; Oleg V Tsodikov; James E Posey; Sylvie Garneau-Tsodikova
Journal:  ACS Chem Biol       Date:  2016-04-07       Impact factor: 5.100

5.  Biochemical and structural analysis of an Eis family aminoglycoside acetyltransferase from bacillus anthracis.

Authors:  Keith D Green; Tapan Biswas; Changsoo Chang; Ruiying Wu; Wenjing Chen; Brian K Janes; Dominika Chalupska; Piotr Gornicki; Philip C Hanna; Oleg V Tsodikov; Andrzej Joachimiak; Sylvie Garneau-Tsodikova
Journal:  Biochemistry       Date:  2015-05-12       Impact factor: 3.162

6.  Unusual regioversatility of acetyltransferase Eis, a cause of drug resistance in XDR-TB.

Authors:  Wenjing Chen; Tapan Biswas; Vanessa R Porter; Oleg V Tsodikov; Sylvie Garneau-Tsodikova
Journal:  Proc Natl Acad Sci U S A       Date:  2011-05-31       Impact factor: 11.205

7.  Identification and characterization of inhibitors of the aminoglycoside resistance acetyltransferase Eis from Mycobacterium tuberculosis.

Authors:  Keith D Green; Wenjing Chen; Sylvie Garneau-Tsodikova
Journal:  ChemMedChem       Date:  2011-09-05       Impact factor: 3.466

8.  Comparative Study of Eis-like Enzymes from Pathogenic and Nonpathogenic Bacteria.

Authors:  Keith D Green; Rachel E Pricer; Megan N Stewart; Sylvie Garneau-Tsodikova
Journal:  ACS Infect Dis       Date:  2015-05-04       Impact factor: 5.084

9.  Exploring the substrate promiscuity of drug-modifying enzymes for the chemoenzymatic generation of N-acylated aminoglycosides.

Authors:  Keith D Green; Wenjing Chen; Jacob L Houghton; Micha Fridman; Sylvie Garneau-Tsodikova
Journal:  Chembiochem       Date:  2010-01-04       Impact factor: 3.164
  9 in total
  12 in total

1.  Combating Enhanced Intracellular Survival (Eis)-Mediated Kanamycin Resistance of Mycobacterium tuberculosis by Novel Pyrrolo[1,5-a]pyrazine-Based Eis Inhibitors.

Authors:  Atefeh Garzan; Melisa J Willby; Huy X Ngo; Chathurada S Gajadeera; Keith D Green; Selina Y L Holbrook; Caixia Hou; James E Posey; Oleg V Tsodikov; Sylvie Garneau-Tsodikova
Journal:  ACS Infect Dis       Date:  2017-02-17       Impact factor: 5.084

2.  Structure-Guided Optimization of Inhibitors of Acetyltransferase Eis from Mycobacterium tuberculosis.

Authors:  Ankita Punetha; Huy X Ngo; Selina Y L Holbrook; Keith D Green; Melisa J Willby; Shilah A Bonnett; Kyle Krieger; Emily K Dennis; James E Posey; Tanya Parish; Oleg V Tsodikov; Sylvie Garneau-Tsodikova
Journal:  ACS Chem Biol       Date:  2020-05-18       Impact factor: 5.100

Review 3.  Comprehensive review of chemical strategies for the preparation of new aminoglycosides and their biological activities.

Authors:  Nishad Thamban Chandrika; Sylvie Garneau-Tsodikova
Journal:  Chem Soc Rev       Date:  2018-02-19       Impact factor: 54.564

4.  Probing the Robustness of Inhibitors of Tuberculosis Aminoglycoside Resistance Enzyme Eis by Mutagenesis.

Authors:  Keith D Green; Ankita Punetha; Caixia Hou; Sylvie Garneau-Tsodikova; Oleg V Tsodikov
Journal:  ACS Infect Dis       Date:  2019-08-21       Impact factor: 5.084

5.  Discovery of substituted benzyloxy-benzylamine inhibitors of acetyltransferase Eis and their anti-mycobacterial activity.

Authors:  Allan H Pang; Keith D Green; Nishad Thamban Chandrika; Atefeh Garzan; Ankita Punetha; Selina Y L Holbrook; Melisa J Willby; James E Posey; Oleg V Tsodikov; Sylvie Garneau-Tsodikova
Journal:  Eur J Med Chem       Date:  2022-08-18       Impact factor: 7.088

6.  Structure-based design of haloperidol analogues as inhibitors of acetyltransferase Eis from Mycobacterium tuberculosis to overcome kanamycin resistance.

Authors:  Ankita Punetha; Keith D Green; Atefeh Garzan; Nishad Thamban Chandrika; Melisa J Willby; Allan H Pang; Caixia Hou; Selina Y L Holbrook; Kyle Krieger; James E Posey; Tanya Parish; Oleg V Tsodikov; Sylvie Garneau-Tsodikova
Journal:  RSC Med Chem       Date:  2021-10-05

7.  Potent 1,2,4-Triazino[5,6 b]indole-3-thioether Inhibitors of the Kanamycin Resistance Enzyme Eis from Mycobacterium tuberculosis.

Authors:  Huy X Ngo; Keith D Green; Chathurada S Gajadeera; Melisa J Willby; Selina Y L Holbrook; Caixia Hou; Atefeh Garzan; Abdelrahman S Mayhoub; James E Posey; Oleg V Tsodikov; Sylvie Garneau-Tsodikova
Journal:  ACS Infect Dis       Date:  2018-03-30       Impact factor: 5.084

8.  Acetylation by Eis and Deacetylation by Rv1151c of Mycobacterium tuberculosis HupB: Biochemical and Structural Insight.

Authors:  Keith D Green; Tapan Biswas; Allan H Pang; Melisa J Willby; Matthew S Reed; Olga Stuchlik; Jan Pohl; James E Posey; Oleg V Tsodikov; Sylvie Garneau-Tsodikova
Journal:  Biochemistry       Date:  2018-01-18       Impact factor: 3.162

Review 9.  Amikacin: Uses, Resistance, and Prospects for Inhibition.

Authors:  Maria S Ramirez; Marcelo E Tolmasky
Journal:  Molecules       Date:  2017-12-19       Impact factor: 4.411

10.  Interfering With DNA Decondensation as a Strategy Against Mycobacteria.

Authors:  Enzo M Scutigliani; Edwin R Scholl; Anita E Grootemaat; Sadhana Khanal; Jakub A Kochan; Przemek M Krawczyk; Eric A Reits; Atefeh Garzan; Huy X Ngo; Keith D Green; Sylvie Garneau-Tsodikova; Jan M Ruijter; Henk A van Veen; Nicole N van der Wel
Journal:  Front Microbiol       Date:  2018-09-05       Impact factor: 5.640
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