Literature DB >> 26699277

Discovery of bicyclic inhibitors against menaquinone biosynthesis.

Seoung-ryoung Choi1, Marilynn A Larson1, Steven H Hinrichs1, Amanda M Bartling1, Joel Frandsen1, Prabagaran Narayanasamy1.   

Abstract

INTRODUCTION: Menaquinone is used for transporting electrons and is essential for the aerobic and anaerobic respiratory systems of all pathogens and prokaryotes. Many Gram-positive bacteria use only menaquinone in the electron transport system. Thus, menaquinone biosynthesis is a potential target for the development of inhibitors against bacteria including drug-resistant pathogens.
RESULTS: After modeling, synthesis and in vitro testing, we determined that 7-methoxy-2-naphthol-based inhibitors targeted the MenA enzyme of the menaquinone biosynthesis pathway. The developmental compounds 1 and 2 were active against Mycobacterium tuberculosis and methicillin-resistant Staphylococcus aureus with a minimal inhibitory concentration of 3-5 μg/ml.
CONCLUSION: Nontraditional bicyclic inhibitors, compounds 1 and 2 could serve as lead compounds for the development of an antimicrobial agent, with activities against M. tuberculosis and methicillin-resistant S. aureus.

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Year:  2016        PMID: 26699277      PMCID: PMC5558544          DOI: 10.4155/fmc.15.168

Source DB:  PubMed          Journal:  Future Med Chem        ISSN: 1756-8919            Impact factor:   3.808


  14 in total

1.  Discovery of 1,4-dihydroxy-2-naphthoate [corrected] prenyltransferase inhibitors: new drug leads for multidrug-resistant gram-positive pathogens.

Authors:  Michio Kurosu; Prabagaran Narayanasamy; Kallolmay Biswas; Rakesh Dhiman; Dean C Crick
Journal:  J Med Chem       Date:  2007-07-21       Impact factor: 7.446

2.  An alternative menaquinone biosynthetic pathway operating in microorganisms.

Authors:  Tomoshige Hiratsuka; Kazuo Furihata; Jun Ishikawa; Haruyuki Yamashita; Nobuya Itoh; Haruo Seto; Tohru Dairi
Journal:  Science       Date:  2008-09-19       Impact factor: 47.728

Review 3.  Biosynthesis of menaquinone (vitamin K2) and ubiquinone (coenzyme Q): a perspective on enzymatic mechanisms.

Authors:  R Meganathan
Journal:  Vitam Horm       Date:  2001       Impact factor: 3.421

4.  Discovery of selective menaquinone biosynthesis inhibitors against Mycobacterium tuberculosis.

Authors:  Joy Debnath; Shajila Siricilla; Bajoie Wan; Dean C Crick; Anne J Lenaerts; Scott G Franzblau; Michio Kurosu
Journal:  J Med Chem       Date:  2012-04-06       Impact factor: 7.446

5.  CoA Adducts of 4-Oxo-4-Phenylbut-2-enoates: Inhibitors of MenB from the M. tuberculosis Menaquinone Biosynthesis Pathway.

Authors:  Xiaokai Li; Nina Liu; Huaning Zhang; Susan E Knudson; Huei-Jiun Li; Cheng-Tsung Lai; Carlos Simmerling; Richard A Slayden; Peter J Tonge
Journal:  ACS Med Chem Lett       Date:  2011-11-10       Impact factor: 4.345

Review 6.  Biosynthesis of vitamin K (menaquinone) in bacteria.

Authors:  R Bentley; R Meganathan
Journal:  Microbiol Rev       Date:  1982-09

7.  Stable analogues of OSB-AMP: potent inhibitors of MenE, the o-succinylbenzoate-CoA synthetase from bacterial menaquinone biosynthesis.

Authors:  Xuequan Lu; Rong Zhou; Indrajeet Sharma; Xiaokai Li; Gyanendra Kumar; Subramanyam Swaminathan; Peter J Tonge; Derek S Tan
Journal:  Chembiochem       Date:  2011-11-23       Impact factor: 3.164

Review 8.  Alternative respiratory pathways of Escherichia coli: energetics and transcriptional regulation in response to electron acceptors.

Authors:  G Unden; J Bongaerts
Journal:  Biochim Biophys Acta       Date:  1997-07-04

9.  Identification of a hotdog fold thioesterase involved in the biosynthesis of menaquinone in Escherichia coli.

Authors:  Minjiao Chen; Xinyu Ma; Xiaolei Chen; Ming Jiang; Haigang Song; Zhihong Guo
Journal:  J Bacteriol       Date:  2013-04-05       Impact factor: 3.490

10.  Structure of a membrane-embedded prenyltransferase homologous to UBIAD1.

Authors:  Hua Huang; Elena J Levin; Shian Liu; Yonghong Bai; Steve W Lockless; Ming Zhou
Journal:  PLoS Biol       Date:  2014-07-22       Impact factor: 8.029

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  10 in total

Review 1.  Menaquinone biosynthesis inhibition: a review of advancements toward a new antibiotic mechanism.

Authors:  M Boersch; S Rudrawar; G Grant; M Zunk
Journal:  RSC Adv       Date:  2018-01-29       Impact factor: 4.036

2.  A Synthetic Isoprenoid Lipoquinone, Menaquinone-2, Adopts a Folded Conformation in Solution and at a Model Membrane Interface.

Authors:  Jordan T Koehn; Estela S Magallanes; Benjamin J Peters; Cheryle N Beuning; Allison A Haase; Michelle J Zhu; Christopher D Rithner; Dean C Crick; Debbie C Crans
Journal:  J Org Chem       Date:  2017-12-12       Impact factor: 4.354

3.  Novel long-chain compounds with both immunomodulatory and MenA inhibitory activities against Staphylococcus aureus and its biofilm.

Authors:  Seoung-Ryoung Choi; Joel Frandsen; Prabagaran Narayanasamy
Journal:  Sci Rep       Date:  2017-01-10       Impact factor: 4.379

4.  Gallium nanoparticles facilitate phagosome maturation and inhibit growth of virulent Mycobacterium tuberculosis in macrophages.

Authors:  Seoung-Ryoung Choi; Bradley E Britigan; David M Moran; Prabagaran Narayanasamy
Journal:  PLoS One       Date:  2017-05-18       Impact factor: 3.240

5.  Ga(III) Nanoparticles Inhibit Growth of both Mycobacterium tuberculosis and HIV and Release of Interleukin-6 (IL-6) and IL-8 in Coinfected Macrophages.

Authors:  Seoung-Ryoung Choi; Bradley E Britigan; Prabagaran Narayanasamy
Journal:  Antimicrob Agents Chemother       Date:  2017-03-24       Impact factor: 5.191

Review 6.  Neuroprotection through flavonoid: Enhancement of the glyoxalase pathway.

Authors:  Joel R Frandsen; Prabagaran Narayanasamy
Journal:  Redox Biol       Date:  2017-10-18       Impact factor: 11.799

7.  Characterization of MenA (isoprenyl diphosphate:1,4-dihydroxy-2-naphthoate isoprenyltransferase) from Mycobacterium tuberculosis.

Authors:  Rakesh K Dhiman; Venugopal Pujari; James M Kincaid; Melanie A Ikeh; Tanya Parish; Dean C Crick
Journal:  PLoS One       Date:  2019-04-12       Impact factor: 3.240

8.  Novel MenA Inhibitors Are Bactericidal against Mycobacterium tuberculosis and Synergize with Electron Transport Chain Inhibitors.

Authors:  Bryan J Berube; Dara Russell; Lina Castro; Seoung-Ryoung Choi; Prabagaran Narayanasamy; Tanya Parish
Journal:  Antimicrob Agents Chemother       Date:  2019-05-24       Impact factor: 5.191

9.  New Insights Into the Antibacterial Mechanism of Cryptotanshinone, a Representative Diterpenoid Quinone From Salvia miltiorrhiza Bunge.

Authors:  Bo-Chen Chen; Zhi-Shan Ding; Jian-Sheng Dai; Ni-Pi Chen; Xing-Wen Gong; Lie-Feng Ma; Chao-Dong Qian
Journal:  Front Microbiol       Date:  2021-02-25       Impact factor: 5.640

Review 10.  Bioenergetics of Mycobacterium: An Emerging Landscape for Drug Discovery.

Authors:  Iram Khan Iqbal; Sapna Bajeli; Ajit Kumar Akela; Ashwani Kumar
Journal:  Pathogens       Date:  2018-02-23
  10 in total

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