Literature DB >> 15109639

MexAB-OprM specific efflux pump inhibitors in Pseudomonas aeruginosa. Part 4: Addressing the problem of poor stability due to photoisomerization of an acrylic acid moiety.

Kiyoshi Nakayama1, Noriko Kuru, Masami Ohtsuka, Yoshihiro Yokomizo, Atsunobu Sakamoto, Haruko Kawato, Ken-ichi Yoshida, Toshiharu Ohta, Kazuki Hoshino, Katsuya Akimoto, Junko Itoh, Hiroko Ishida, Aesop Cho, Monica H Palme, Jason Z Zhang, Ving J Lee, William J Watkins.   

Abstract

Exchange of the ethylene tether in a series of pyridopyrimidine-based MexAB-OprM specific efflux pump inhibitors to an amide bond stabilized the olefin of the acrylic acid moiety, preventing facile photoisomerization to the Z-isomer. Furthermore, the activity was drastically improved in the amide tether variants, providing extremely potent acrylic acid and vinyl tetrazole analogues.

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Year:  2004        PMID： 15109639     DOI： 10.1016/j.bmcl.2004.03.007

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


  10 in total

Review 1.  Efflux-mediated drug resistance in bacteria: an update.

Authors:  Xian-Zhi Li; Hiroshi Nikaido
Journal:  Drugs       Date:  2009-08-20       Impact factor: 9.546

2.  Structure-activity relationships of a novel pyranopyridine series of Gram-negative bacterial efflux pump inhibitors.

Authors:  Son T Nguyen; Steven M Kwasny; Xiaoyuan Ding; Steven C Cardinale; Courtney T McCarthy; Hong-Suk Kim; Hiroshi Nikaido; Norton P Peet; John D Williams; Terry L Bowlin; Timothy J Opperman
Journal:  Bioorg Med Chem       Date:  2015-03-13       Impact factor: 3.641

Review 3.  The hydrophobic trap-the Achilles heel of RND efflux pumps.

Authors:  Zachary Aron; Timothy J Opperman
Journal:  Res Microbiol       Date:  2017-11-13       Impact factor: 3.992

Review 4.  Optimization of a novel series of pyranopyridine RND efflux pump inhibitors.

Authors:  Zachary Aron; Timothy J Opperman
Journal:  Curr Opin Microbiol       Date:  2016-05-24       Impact factor: 7.934

Review 5.  Microbial efflux pump inhibition: tactics and strategies.

Authors:  George P Tegos; Mark Haynes; J Jacob Strouse; Mohiuddin Md T Khan; Cristian G Bologa; Tudor I Oprea; Larry A Sklar
Journal:  Curr Pharm Des       Date:  2011       Impact factor: 3.116

6.  Characterization of a novel pyranopyridine inhibitor of the AcrAB efflux pump of Escherichia coli.

Authors:  Timothy J Opperman; Steven M Kwasny; Hong-Suk Kim; Son T Nguyen; Chad Houseweart; Sanjay D'Souza; Graham C Walker; Norton P Peet; Hiroshi Nikaido; Terry L Bowlin
Journal:  Antimicrob Agents Chemother       Date:  2013-11-18       Impact factor: 5.191

Review 7.  Recent advances toward a molecular mechanism of efflux pump inhibition.

Authors:  Timothy J Opperman; Son T Nguyen
Journal:  Front Microbiol       Date:  2015-05-05       Impact factor: 5.640

8.  Metal free C-3 chalcogenation (sulfenylation and selenylation) of 4H-pyrido[1,2-a]pyrimidin-4-ones.

Authors:  Prasanjit Ghosh; Gautam Chhetri; Sajal Das
Journal:  RSC Adv       Date:  2021-03-09       Impact factor: 3.361

9.  The intrinsic resistome of bacterial pathogens.

Authors:  Jorge Olivares; Alejandra Bernardini; Guillermo Garcia-Leon; Fernando Corona; Maria B Sanchez; Jose L Martinez
Journal:  Front Microbiol       Date:  2013-04-30       Impact factor: 5.640

Review 10.  Current Advances in Developing Inhibitors of Bacterial Multidrug Efflux Pumps.

Authors:  Hannah Y Mahmood; Shirin Jamshidi; J Mark Sutton; Khondaker M Rahman
Journal:  Curr Med Chem       Date:  2016       Impact factor: 4.530
  10 in total

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