Literature DB >> 14552758

Biphenyl-based analogues of thiolactomycin, active against Mycobacterium tuberculosis mtFabH fatty acid condensing enzyme.

Suzanne J Senior1, Petr A Illarionov, Sudagar S Gurcha, Ian B Campbell, Merrill L Schaeffer, David E Minnikin, Gurdyal S Besra.   

Abstract

Analogues of the antibiotic thiolactomycin, with biphenyl-based 5-substituents, were found to have excellent in vitro inhibitory activity against the recombinant Mycobacterium tuberculosis beta-ketoacyl-ACP synthase mtFabH condensing enzyme. In particular, 5-(4'-benzyloxy-biphen-4-ylmethyl)-4-hydroxy-3,5-dimethyl-5H-thiophen-2-one exhibited approximately a 4-fold increased potency against this key condensing enzyme involved in M. tuberculosis mycolic acid biosynthesis, compared to thiolactomycin.

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Year:  2003        PMID： 14552758     DOI： 10.1016/j.bmcl.2003.08.015

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


  11 in total

1.  Structure-activity relationships at the 5-position of thiolactomycin: an intact (5R)-isoprene unit is required for activity against the condensing enzymes from Mycobacterium tuberculosis and Escherichia coli.

Authors:  Pilho Kim; Yong-Mei Zhang; Gautham Shenoy; Quynh-Anh Nguyen; Helena I Boshoff; Ujjini H Manjunatha; Michael B Goodwin; John Lonsdale; Allen C Price; Darcie J Miller; Ken Duncan; Stephen W White; Charles O Rock; Clifton E Barry; Cynthia S Dowd
Journal:  J Med Chem       Date:  2006-01-12       Impact factor: 7.446

2.  Discovery of FabH/FabF inhibitors from natural products.

Authors:  Katherine Young; Hiranthi Jayasuriya; John G Ondeyka; Kithsiri Herath; Chaowei Zhang; Srinivas Kodali; Andrew Galgoci; Ronald Painter; Vickie Brown-Driver; Robert Yamamoto; Lynn L Silver; Yingcong Zheng; Judith I Ventura; Janet Sigmund; Sookhee Ha; Angela Basilio; Francisca Vicente; José Rubén Tormo; Fernando Pelaez; Phil Youngman; Doris Cully; John F Barrett; Dennis Schmatz; Sheo B Singh; Jun Wang
Journal:  Antimicrob Agents Chemother       Date:  2006-02       Impact factor: 5.191

Review 3.  Recent advances in the chemistry and biology of naturally occurring antibiotics.

Authors:  K C Nicolaou; Jason S Chen; David J Edmonds; Anthony A Estrada
Journal:  Angew Chem Int Ed Engl       Date:  2009       Impact factor: 15.336

4.  Molecular dynamics and docking simulations as a proof of high flexibility in E. coli FabH and its relevance for accurate inhibitor modeling.

Authors:  Yunierkis Pérez-Castillo; Matheus Froeyen; Miguel Angel Cabrera-Pérez; Ann Nowé
Journal:  J Comput Aided Mol Des       Date:  2011-04-23       Impact factor: 3.686

5.  Novel route to 5-position vinyl derivatives of thiolactomycin: Olefination vs. deformylation.

Authors:  Pilho Kim; Clifton E Barry; Cynthia S Dowd
Journal:  Tetrahedron Lett       Date:  2006-05-15       Impact factor: 2.415

Review 6.  Bacterial fatty acid metabolism in modern antibiotic discovery.

Authors:  Jiangwei Yao; Charles O Rock
Journal:  Biochim Biophys Acta Mol Cell Biol Lipids       Date:  2016-09-23       Impact factor: 4.698

7.  Thiolactomycin-Based Inhibitors of Bacterial β-Ketoacyl-ACP Synthases with in Vivo Activity.

Authors:  Gopal R Bommineni; Kanishk Kapilashrami; Jason E Cummings; Yang Lu; Susan E Knudson; Chendi Gu; Stephen G Walker; Richard A Slayden; Peter J Tonge
Journal:  J Med Chem       Date:  2016-05-24       Impact factor: 7.446

8.  X-ray crystal structure of Mycobacterium tuberculosis beta-ketoacyl acyl carrier protein synthase II (mtKasB).

Authors:  Sudharsan Sridharan; Lei Wang; Alistair K Brown; Lynn G Dover; Laurent Kremer; Gurdyal S Besra; James C Sacchettini
Journal:  J Mol Biol       Date:  2006-11-07       Impact factor: 5.469

Review 9.  Mycobacterial cell wall biosynthesis: a multifaceted antibiotic target.

Authors:  Katherine A Abrahams; Gurdyal S Besra
Journal:  Parasitology       Date:  2016-12-15       Impact factor: 3.234

10.  Identification of 2-aminothiazole-4-carboxylate derivatives active against Mycobacterium tuberculosis H37Rv and the beta-ketoacyl-ACP synthase mtFabH.

Authors:  Qosay Al-Balas; Nahoum G Anthony; Bilal Al-Jaidi; Amani Alnimr; Grainne Abbott; Alistair K Brown; Rebecca C Taylor; Gurdyal S Besra; Timothy D McHugh; Stephen H Gillespie; Blair F Johnston; Simon P Mackay; Geoffrey D Coxon
Journal:  PLoS One       Date:  2009-05-19       Impact factor: 3.240
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