| 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. | |
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MedLine Citation:
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PMID: 15109639 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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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Authors:
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Kiyoshi Nakayama; 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 |
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Publication Detail:
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Type: Journal Article |
Journal Detail:
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Title: Bioorganic & medicinal chemistry letters Volume: 14 ISSN: 0960-894X ISO Abbreviation: Bioorg. Med. Chem. Lett. Publication Date: 2004 May |
Date Detail:
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Created Date: 2004-04-27 Completed Date: 2004-12-22 Revised Date: 2005-11-17 |
Medline Journal Info:
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Nlm Unique ID: 9107377 Medline TA: Bioorg Med Chem Lett Country: England |
Other Details:
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Languages: eng Pagination: 2493-7 Citation Subset: IM |
Affiliation:
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Daiichi Pharmaceutical Co., Ltd, 1-16-13, Kitakasai, Edogawa, Tokyo 134-8630, Japan. nakaygoi@daiichipharm.co.jp |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Acrylates
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pharmacology Bacterial Outer Membrane Proteins / antagonists & inhibitors* Drug Resistance, Bacterial / drug effects* Drug Stability Isomerism Membrane Transport Modulators* Membrane Transport Proteins / antagonists & inhibitors* Microbial Sensitivity Tests Photochemistry Pseudomonas aeruginosa / drug effects* Pyrimidines / chemical synthesis, pharmacology Structure-Activity Relationship |
| Chemical | |
Reg. No./Substance:
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0/Acrylates; 0/Bacterial Outer Membrane Proteins; 0/Membrane Transport Modulators; 0/Membrane Transport Proteins; 0/MexA protein, Pseudomonas aeruginosa; 0/MexB protein, Pseudomonas aeruginosa; 0/Pyrimidines; 79-10-7/acrylic acid |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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