Literature DB >> 20739223

The abyssomicin C family as in vitro inhibitors of Mycobacterium tuberculosis.

Joel S Freundlich1, Mallikarjun Lalgondar, Jun-Rong Wei, Stephanie Swanson, Erik J Sorensen, Eric J Rubin, James C Sacchettini.   

Abstract

The antimycobacterial efficacy of the abyssomicin C family of natural products, in addition to a key synthetic intermediate, has been investigated given their reported inhibition of Bacillus subtilis p-aminobenzoate biosynthesis. The naturally occurring (-)-abyssomicin C and its atropisomer were found to exhibit low micromolar growth inhibition against the relatively fast-growing and non-virulent Mycobacterium smegmatis and the vaccine strain Mycobacterium bovis BCG, while their antipodes were slightly less active. (-)-abyssomicin C and its atropisomer were particularly efficacious against Mycobacterium tuberculosis H37Rv, exhibiting MIC values of 3.6 and 7.2 μM, respectively. More specifically, (-)-abyssomicin C was bactericidal. This complex natural product and its analogs, thus, hold promise as chemical tools in the study of M. tuberculosis metabolism.
Copyright © 2010 Elsevier Ltd. All rights reserved.

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Year:  2010        PMID： 20739223      PMCID： PMC3213896          DOI： 10.1016/j.tube.2010.08.002

Source DB:  PubMed          Journal:  Tuberculosis (Edinb)        ISSN： 1472-9792            Impact factor:   3.131


  20 in total

1.  Abyssomicin C-A polycyclic antibiotic from a marine Verrucosispora strain as an inhibitor of the p-aminobenzoic acid/tetrahydrofolate biosynthesis pathway.

Authors:  Bojan Bister; Daniel Bischoff; Markus Ströbele; Julia Riedlinger; Andreas Reicke; Falko Wolter; Alan T Bull; Hans Zähner; Hans-Peter Fiedler; Roderich D Süssmuth
Journal:  Angew Chem Int Ed Engl       Date:  2004-05-03       Impact factor: 15.336

2.  A Diels-Alder macrocyclization enables an efficient asymmetric synthesis of the antibacterial natural product abyssomicin C.

Authors:  Christoph W Zapf; Bryce A Harrison; Carmen Drahl; Erik J Sorensen
Journal:  Angew Chem Int Ed Engl       Date:  2005-10-14       Impact factor: 15.336

3.  The Tuberculostatic Action of para-Aminosalicylic Acid.

Authors:  G P Youmans; G W Raleigh; A S Youmans
Journal:  J Bacteriol       Date:  1947-10       Impact factor: 3.490

Review 4.  Drugs versus bugs: in pursuit of the persistent predator Mycobacterium tuberculosis.

Authors:  James C Sacchettini; Eric J Rubin; Joel S Freundlich
Journal:  Nat Rev Microbiol       Date:  2008-01       Impact factor: 60.633

5.  Rapid, low-technology MIC determination with clinical Mycobacterium tuberculosis isolates by using the microplate Alamar Blue assay.

Authors:  S G Franzblau; R S Witzig; J C McLaughlin; P Torres; G Madico; A Hernandez; M T Degnan; M B Cook; V K Quenzer; R M Ferguson; R H Gilman
Journal:  J Clin Microbiol       Date:  1998-02       Impact factor: 5.948

6.  Transfer of a point mutation in Mycobacterium tuberculosis inhA resolves the target of isoniazid.

Authors:  Catherine Vilchèze; Feng Wang; Masayoshi Arai; Manzour Hernando Hazbón; Roberto Colangeli; Laurent Kremer; Torin R Weisbrod; David Alland; James C Sacchettini; William R Jacobs
Journal:  Nat Med       Date:  2006-08-13       Impact factor: 53.440

7.  Synthesis of the carbocyclic skeleton of abyssomicins C and D.

Authors:  Barry B Snider; Yefen Zou
Journal:  Org Lett       Date:  2005-10-27       Impact factor: 6.005

8.  The folate pathway is a target for resistance to the drug para-aminosalicylic acid (PAS) in mycobacteria.

Authors:  Jyothi Rengarajan; Christopher M Sassetti; Vera Naroditskaya; Alexander Sloutsky; Barry R Bloom; Eric J Rubin
Journal:  Mol Microbiol       Date:  2004-07       Impact factor: 3.501

9.  Deciphering the biology of Mycobacterium tuberculosis from the complete genome sequence.

Authors:  S T Cole; R Brosch; J Parkhill; T Garnier; C Churcher; D Harris; S V Gordon; K Eiglmeier; S Gas; C E Barry; F Tekaia; K Badcock; D Basham; D Brown; T Chillingworth; R Connor; R Davies; K Devlin; T Feltwell; S Gentles; N Hamlin; S Holroyd; T Hornsby; K Jagels; A Krogh; J McLean; S Moule; L Murphy; K Oliver; J Osborne; M A Quail; M A Rajandream; J Rogers; S Rutter; K Seeger; J Skelton; R Squares; S Squares; J E Sulston; K Taylor; S Whitehead; B G Barrell
Journal:  Nature       Date:  1998-06-11       Impact factor: 49.962

10.  Abyssomicins, inhibitors of the para-aminobenzoic acid pathway produced by the marine Verrucosispora strain AB-18-032.

Authors:  Julia Riedlinger; Andreas Reicke; Hans Zähner; Bernhard Krismer; Alan T Bull; Luis A Maldonado; Alan C Ward; Michael Goodfellow; Bojan Bister; Daniel Bischoff; Roderich D Süssmuth; Hans-Peter Fiedler
Journal:  J Antibiot (Tokyo)       Date:  2004-04       Impact factor: 2.649
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  12 in total

1.  Modular Synthesis of Novel Macrocycles Bearing α,β-Unsaturated Chemotypes through a Series of One-Pot, Sequential Protocols.

Authors:  Salim Javed; Mahipal Bodugam; Jessica Torres; Arghya Ganguly; Paul R Hanson
Journal:  Chemistry       Date:  2016-04-05       Impact factor: 5.236

2.  Genome sequence of the abyssomicin- and proximicin-producing marine actinomycete Verrucosispora maris AB-18-032.

Authors:  Hanseong Roh; Gabriel C Uguru; Hyeok-Jin Ko; Sujin Kim; Byung-Yong Kim; Michael Goodfellow; Alan T Bull; Kyoung Heon Kim; Mervyn J Bibb; In-Geol Choi; James E M Stach
Journal:  J Bacteriol       Date:  2011-05-06       Impact factor: 3.490

Review 3.  Revitalizing antifolates through understanding mechanisms that govern susceptibility and resistance.

Authors:  Shannon Lynn Kordus; Anthony David Baughn
Journal:  Medchemcomm       Date:  2019-05-08       Impact factor: 3.597

4.  Escaping mechanisms of ESKAPE pathogens from antibiotics and their targeting by natural compounds.

Authors:  Ragi Jadimurthy; Shilpa Borehalli Mayegowda; S Chandra Nayak; Chakrabhavi Dhananjaya Mohan; Kanchugarakoppal S Rangappa
Journal:  Biotechnol Rep (Amst)       Date:  2022-04-04

5.  Design and Synthesis of Molecular Scaffolds with Anti-infective Activity.

Authors:  Junjia Liu; T Aaron Bedell; Julian G West; Erik J Sorensen
Journal:  Tetrahedron       Date:  2016-01-28       Impact factor: 2.457

Review 6.  Spirotetronate polyketides as leads in drug discovery.

Authors:  Michelle H Lacoske; Emmanuel A Theodorakis
Journal:  J Nat Prod       Date:  2014-12-01       Impact factor: 4.050

7.  Characterization and heterologous expression of the neoabyssomicin/abyssomicin biosynthetic gene cluster from Streptomyces koyangensis SCSIO 5802.

Authors:  Jiajia Tu; Siting Li; Jiang Chen; Yongxiang Song; Shaobin Fu; Jianhua Ju; Qinglian Li
Journal:  Microb Cell Fact       Date:  2018-02-20       Impact factor: 5.328

Review 8.  Review on Abyssomicins: Inhibitors of the Chorismate Pathway and Folate Biosynthesis.

Authors:  Carmen Sadaka; Edmund Ellsworth; Paul Robert Hansen; Richard Ewin; Peter Damborg; Jeffrey L Watts
Journal:  Molecules       Date:  2018-06-06       Impact factor: 4.411

9.  Genome Mining for Antimicrobial Compounds in Wild Marine Animals-Associated Enterococci.

Authors:  Janira Prichula; Muriel Primon-Barros; Romeu C Z Luz; Ícaro M S Castro; Thiago G S Paim; Maurício Tavares; Rodrigo Ligabue-Braun; Pedro A d'Azevedo; Jeverson Frazzon; Ana P G Frazzon; Adriana Seixas; Michael S Gilmore
Journal:  Mar Drugs       Date:  2021-06-06       Impact factor: 5.118

10.  Abyssomicins from the South China Sea deep-sea sediment Verrucosispora sp.: natural thioether Michael addition adducts as antitubercular prodrugs.

Authors:  Qian Wang; Fuhang Song; Xue Xiao; Pei Huang; Li Li; Aaron Monte; Wael M Abdel-Mageed; Jian Wang; Hui Guo; Wenni He; Feng Xie; Huanqin Dai; Miaomiao Liu; Caixia Chen; Hao Xu; Mei Liu; Andrew M Piggott; Xueting Liu; Robert J Capon; Lixin Zhang
Journal:  Angew Chem Int Ed Engl       Date:  2012-12-06       Impact factor: 15.336
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