Literature DB >> 24550336

Mechanism of action of 5-nitrothiophenes against Mycobacterium tuberculosis.

Ruben C Hartkoorn1, Olga B Ryabova, Laurent R Chiarelli, Giovanna Riccardi, Vadim Makarov, Stewart T Cole.   

Abstract

On using the streptomycin-starved 18b strain as a model for nonreplicating Mycobacterium tuberculosis, we identified a 5-nitrothiophene compound as highly active but not cytotoxic. Mutants resistant to 5-nitrothiophenes were found be cross-resistant to the nitroimidazole PA-824 and unable to produce the F420 cofactor. Furthermore, 5-nitrothiophenes were shown to be activated by the F420-dependent nitroreductase Ddn and to release nitric oxide, a mechanism of action identical to that described for nitroimidazoles.

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Year:  2014        PMID： 24550336      PMCID： PMC3993272          DOI： 10.1128/AAC.02693-13

Source DB:  PubMed          Journal:  Antimicrob Agents Chemother        ISSN： 0066-4804            Impact factor:   5.191


  16 in total

1.  A diarylquinoline drug active on the ATP synthase of Mycobacterium tuberculosis.

Authors:  Koen Andries; Peter Verhasselt; Jerome Guillemont; Hinrich W H Göhlmann; Jean-Marc Neefs; Hans Winkler; Jef Van Gestel; Philip Timmerman; Min Zhu; Ennis Lee; Peter Williams; Didier de Chaffoy; Emma Huitric; Sven Hoffner; Emmanuelle Cambau; Chantal Truffot-Pernot; Nacer Lounis; Vincent Jarlier
Journal:  Science       Date:  2004-12-09       Impact factor: 47.728

2.  Use of transposon Tn5367 mutagenesis and a nitroimidazopyran-based selection system to demonstrate a requirement for fbiA and fbiB in coenzyme F(420) biosynthesis by Mycobacterium bovis BCG.

Authors:  K P Choi; T B Bair; Y M Bae; L Daniels
Journal:  J Bacteriol       Date:  2001-12       Impact factor: 3.490

3.  A small-molecule nitroimidazopyran drug candidate for the treatment of tuberculosis.

Authors:  C K Stover; P Warrener; D R VanDevanter; D R Sherman; T M Arain; M H Langhorne; S W Anderson; J A Towell; Y Yuan; D N McMurray; B N Kreiswirth; C E Barry; W R Baker
Journal:  Nature       Date:  2000-06-22       Impact factor: 49.962

4.  SOS chromotest, a direct assay of induction of an SOS function in Escherichia coli K-12 to measure genotoxicity.

Authors:  P Quillardet; O Huisman; R D'Ari; M Hofnung
Journal:  Proc Natl Acad Sci U S A       Date:  1982-10       Impact factor: 11.205

5.  Identification of a nitroimidazo-oxazine-specific protein involved in PA-824 resistance in Mycobacterium tuberculosis.

Authors:  Ujjini H Manjunatha; Helena Boshoff; Cynthia S Dowd; Liang Zhang; Thomas J Albert; Jason E Norton; Lacy Daniels; Thomas Dick; Siew Siew Pang; Clifton E Barry
Journal:  Proc Natl Acad Sci U S A       Date:  2005-12-30       Impact factor: 11.205

6.  Demonstration that fbiC is required by Mycobacterium bovis BCG for coenzyme F(420) and FO biosynthesis.

Authors:  Kwang-Pil Choi; Nathan Kendrick; Lacy Daniels
Journal:  J Bacteriol       Date:  2002-05       Impact factor: 3.490

7.  Discovery of Q203, a potent clinical candidate for the treatment of tuberculosis.

Authors:  Kevin Pethe; Pablo Bifani; Jichan Jang; Sunhee Kang; Seijin Park; Sujin Ahn; Jan Jiricek; Juyoung Jung; Hee Kyoung Jeon; Jonathan Cechetto; Thierry Christophe; Honggun Lee; Marie Kempf; Mary Jackson; Anne J Lenaerts; Ha Pham; Victoria Jones; Min Jung Seo; Young Mi Kim; Mooyoung Seo; Jeong Jea Seo; Dongsik Park; Yoonae Ko; Inhee Choi; Ryangyeo Kim; Se Yeon Kim; SeungBin Lim; Seung-Ae Yim; Jiyoun Nam; Hwankyu Kang; Haejin Kwon; Chun-Taek Oh; Yoojin Cho; Yunhee Jang; Junghwan Kim; Adeline Chua; Bee Huat Tan; Mahesh B Nanjundappa; Srinivasa P S Rao; Whitney S Barnes; René Wintjens; John R Walker; Sylvie Alonso; Saeyeon Lee; Jungjun Kim; Soohyun Oh; Taegwon Oh; Ulf Nehrbass; Sung-Jun Han; Zaesung No; Jinhwa Lee; Priscille Brodin; Sang-Nae Cho; Kiyean Nam; Jaeseung Kim
Journal:  Nat Med       Date:  2013-08-04       Impact factor: 53.440

8.  Sample pretreatment with nitrate reductase and glucose-6-phosphate dehydrogenase quantitatively reduces nitrate while avoiding interference by NADP+ when the Griess reaction is used to assay for nitrite.

Authors:  C P Verdon; B A Burton; R L Prior
Journal:  Anal Biochem       Date:  1995-01-20       Impact factor: 3.365

9.  OPC-67683, a nitro-dihydro-imidazooxazole derivative with promising action against tuberculosis in vitro and in mice.

Authors:  Makoto Matsumoto; Hiroyuki Hashizume; Tatsuo Tomishige; Masanori Kawasaki; Hidetsugu Tsubouchi; Hirofumi Sasaki; Yoshihiko Shimokawa; Makoto Komatsu
Journal:  PLoS Med       Date:  2006-11       Impact factor: 11.069

10.  PA-824 kills nonreplicating Mycobacterium tuberculosis by intracellular NO release.

Authors:  Ramandeep Singh; Ujjini Manjunatha; Helena I M Boshoff; Young Hwan Ha; Pornwaratt Niyomrattanakit; Richard Ledwidge; Cynthia S Dowd; Ill Young Lee; Pilho Kim; Liang Zhang; Sunhee Kang; Thomas H Keller; Jan Jiricek; Clifton E Barry
Journal:  Science       Date:  2008-11-28       Impact factor: 63.714
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  11 in total

Review 1.  Targeting Phenotypically Tolerant Mycobacterium tuberculosis.

Authors:  Ben Gold; Carl Nathan
Journal:  Microbiol Spectr       Date:  2017-01

2.  Machine Learning Models for Mycobacterium tuberculosis In Vitro Activity: Prediction and Target Visualization.

Authors:  Thomas R Lane; Fabio Urbina; Laura Rank; Jacob Gerlach; Olga Riabova; Alexander Lepioshkin; Elena Kazakova; Anthony Vocat; Valery Tkachenko; Stewart Cole; Vadim Makarov; Sean Ekins
Journal:  Mol Pharm       Date:  2021-12-29       Impact factor: 5.364

3.  Dual Mechanism of Action of 5-Nitro-1,10-Phenanthroline against Mycobacterium tuberculosis.

Authors:  Saqib Kidwai; Chan-Yong Park; Shradha Mawatwal; Prabhakar Tiwari; Myung Geun Jung; Tannu Priya Gosain; Pradeep Kumar; David Alland; Sandeep Kumar; Avinash Bajaj; Yun-Kyung Hwang; Chang Sik Song; Rohan Dhiman; Ill Young Lee; Ramandeep Singh
Journal:  Antimicrob Agents Chemother       Date:  2017-10-24       Impact factor: 5.191

4.  Coenzyme F420-Dependent Glucose-6-Phosphate Dehydrogenase-Coupled Polyglutamylation of Coenzyme F420 in Mycobacteria.

Authors:  Endang Purwantini; Usha Loganathan; Biswarup Mukhopadhyay
Journal:  J Bacteriol       Date:  2018-11-06       Impact factor: 3.490

5.  Thiophenecarboxamide Derivatives Activated by EthA Kill Mycobacterium tuberculosis by Inhibiting the CTP Synthetase PyrG.

Authors:  Giorgia Mori; Laurent R Chiarelli; Marta Esposito; Vadim Makarov; Marco Bellinzoni; Ruben C Hartkoorn; Giulia Degiacomi; Francesca Boldrin; Sean Ekins; Ana Luisa de Jesus Lopes Ribeiro; Leonardo B Marino; Ivana Centárová; Zuzana Svetlíková; Jaroslav Blaško; Elena Kazakova; Alexander Lepioshkin; Nathalie Barilone; Giuseppe Zanoni; Alessio Porta; Marco Fondi; Renato Fani; Alain R Baulard; Katarína Mikušová; Pedro M Alzari; Riccardo Manganelli; Luiz Pedro S de Carvalho; Giovanna Riccardi; Stewart T Cole; Maria Rosalia Pasca
Journal:  Chem Biol       Date:  2015-06-18

Review 6.  Nitroaromatic Antibiotics as Nitrogen Oxide Sources.

Authors:  Allison M Rice; Yueming Long; S Bruce King
Journal:  Biomolecules       Date:  2021-02-12

7.  Rapid, Semiquantitative Assay To Discriminate among Compounds with Activity against Replicating or Nonreplicating Mycobacterium tuberculosis.

Authors:  Ben Gold; Julia Roberts; Yan Ling; Landys Lopez Quezada; Jou Glasheen; Elaine Ballinger; Selin Somersan-Karakaya; Thulasi Warrier; J David Warren; Carl Nathan
Journal:  Antimicrob Agents Chemother       Date:  2015-08-03       Impact factor: 5.191

8.  Novel Cephalosporins Selectively Active on Nonreplicating Mycobacterium tuberculosis.

Authors:  Ben Gold; Robert Smith; Quyen Nguyen; Julia Roberts; Yan Ling; Landys Lopez Quezada; Selin Somersan; Thulasi Warrier; David Little; Maneesh Pingle; David Zhang; Elaine Ballinger; Matthew Zimmerman; Véronique Dartois; Paul Hanson; Lester A Mitscher; Patrick Porubsky; Steven Rogers; Frank J Schoenen; Carl Nathan; Jeffrey Aubé
Journal:  J Med Chem       Date:  2016-06-17       Impact factor: 7.446

9.  An efficient synthesis of N-substituted 3-nitrothiophen-2-amines.

Authors:  Sundaravel Vivek Kumar; Shanmugam Muthusubramanian; J Carlos Menéndez; Subbu Perumal
Journal:  Beilstein J Org Chem       Date:  2015-09-22       Impact factor: 2.883

Review 10.  Profiling Pretomanid as a Therapeutic Option for TB Infection: Evidence to Date.

Authors:  Stephani L Stancil; Fuad Mirzayev; Susan M Abdel-Rahman
Journal:  Drug Des Devel Ther       Date:  2021-06-28       Impact factor: 4.162
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