Synergistic Activity of Nitroimidazole-Oxazolidinone Conjugates against Anaerobic Bacteria
The introductions of the bicyclic 4-nitroimidazole and the oxazolidinone classes of antimicrobial agents represented the most significant advancements in the infectious disease area during the past two decades. Pretomanid, a bicyclic 4-nitroimidazole, and linezolid, an oxazolidinone, are also part o...
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| Published in | Molecules (Basel, Switzerland) Vol. 25; no. 10; p. 2431 |
|---|---|
| Main Authors | , , , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
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| Abstract | The introductions of the bicyclic 4-nitroimidazole and the oxazolidinone classes of antimicrobial agents represented the most significant advancements in the infectious disease area during the past two decades. Pretomanid, a bicyclic 4-nitroimidazole, and linezolid, an oxazolidinone, are also part of a combination regimen approved recently by the US Food and Drug Administration for the treatment of pulmonary, extensively drug resistant (XDR), treatment-intolerant or nonresponsive multidrug-resistant (MDR)
(TB). To identify new antimicrobial agents with reduced propensity for the development of resistance, a series of dual-acting nitroimidazole-oxazolidinone conjugates were designed, synthesized and evaluated for their antimicrobial activity. Compounds in this conjugate series have shown synergistic activity against a panel of anaerobic bacteria, including those responsible for serious bacterial infections. |
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| AbstractList | The introductions of the bicyclic 4-nitroimidazole and the oxazolidinone classes of antimicrobial agents represented the most significant advancements in the infectious disease area during the past two decades. Pretomanid, a bicyclic 4-nitroimidazole, and linezolid, an oxazolidinone, are also part of a combination regimen approved recently by the US Food and Drug Administration for the treatment of pulmonary, extensively drug resistant (XDR), treatment-intolerant or nonresponsive multidrug-resistant (MDR)
(TB). To identify new antimicrobial agents with reduced propensity for the development of resistance, a series of dual-acting nitroimidazole-oxazolidinone conjugates were designed, synthesized and evaluated for their antimicrobial activity. Compounds in this conjugate series have shown synergistic activity against a panel of anaerobic bacteria, including those responsible for serious bacterial infections. The introductions of the bicyclic 4-nitroimidazole and the oxazolidinone classes of antimicrobial agents represented the most significant advancements in the infectious disease area during the past two decades. Pretomanid, a bicyclic 4-nitroimidazole, and linezolid, an oxazolidinone, are also part of a combination regimen approved recently by the US Food and Drug Administration for the treatment of pulmonary, extensively drug resistant (XDR), treatment-intolerant or nonresponsive multidrug-resistant (MDR) Mycobacterium tuberculosis (TB). To identify new antimicrobial agents with reduced propensity for the development of resistance, a series of dual-acting nitroimidazole-oxazolidinone conjugates were designed, synthesized and evaluated for their antimicrobial activity. Compounds in this conjugate series have shown synergistic activity against a panel of anaerobic bacteria, including those responsible for serious bacterial infections. The introductions of the bicyclic 4-nitroimidazole and the oxazolidinone classes of antimicrobial agents represented the most significant advancements in the infectious disease area during the past two decades. Pretomanid, a bicyclic 4-nitroimidazole, and linezolid, an oxazolidinone, are also part of a combination regimen approved recently by the US Food and Drug Administration for the treatment of pulmonary, extensively drug resistant (XDR), treatment-intolerant or nonresponsive multidrug-resistant (MDR) Mycobacterium tuberculosis (TB). To identify new antimicrobial agents with reduced propensity for the development of resistance, a series of dual-acting nitroimidazole-oxazolidinone conjugates were designed, synthesized and evaluated for their antimicrobial activity. Compounds in this conjugate series have shown synergistic activity against a panel of anaerobic bacteria, including those responsible for serious bacterial infections. |
| Author | Ding, Charles Z Ding, Jun Denny, William A Lynch, Anthony Simon Zhang, Qian He, Shijie Lu, Yu Zhuang, Zhijun Cooper, Christopher B Wang, Xiaomei Yuan, Ying Ma, Zhenkun Wan, Dawei Upton, Anna M |
| AuthorAffiliation | 2 Department of Pharmacology, Beijing Tuberculosis and Thoracic Tumor Research Institute, Beijing Chest Hospital, Capital Medical University, 97 Ma Chang Street, Beijing 101149, China; luyu4876@hotmail.com 3 WuXi AppTec. Co. Ltd., 288 Fute Zhong Road, Waigaoqiao Free Trade Zone, Shanghai 200131, China; charles_ding@wuxiapptec.com 6 Auckland Cancer Society Research Centre, School of Medical Sciences, University of Auckland, Private Bag 92019, Auckland 1142, New Zealand; b.denny@auckland.ac.nz 5 Global Alliance for TB Drug Development, 40 Wall Street, New York, NY 10005, USA; anna.upton@tballiance.org (A.M.U.); christopher.cooper@tballiance.org (C.B.C.) 1 TenNor Therapeutics Limited, 218 Xinghu Street, Building B2, Suite 711, Suzhou Industrial Park, Suzhou 215123, China; zhijun.zhuang@tennorx.com (Z.Z.); dawei.wan@tennorx.com (D.W.); jun.ding@tennorx.com (J.D.); shijie.he@tennorx.com (S.H.); qian.zhang@tennorx.com (Q.Z.); xiaomei.wang@tennorx.com (X.W.); ying.yuan@tennorx.com (Y.Y.) 4 Janssen |
| AuthorAffiliation_xml | – name: 4 Janssen Research & Development LLC., 1400 McKean Road, Spring House, PA 18940, USA; alynch2@its.jnj.com – name: 1 TenNor Therapeutics Limited, 218 Xinghu Street, Building B2, Suite 711, Suzhou Industrial Park, Suzhou 215123, China; zhijun.zhuang@tennorx.com (Z.Z.); dawei.wan@tennorx.com (D.W.); jun.ding@tennorx.com (J.D.); shijie.he@tennorx.com (S.H.); qian.zhang@tennorx.com (Q.Z.); xiaomei.wang@tennorx.com (X.W.); ying.yuan@tennorx.com (Y.Y.) – name: 3 WuXi AppTec. Co. Ltd., 288 Fute Zhong Road, Waigaoqiao Free Trade Zone, Shanghai 200131, China; charles_ding@wuxiapptec.com – name: 6 Auckland Cancer Society Research Centre, School of Medical Sciences, University of Auckland, Private Bag 92019, Auckland 1142, New Zealand; b.denny@auckland.ac.nz – name: 2 Department of Pharmacology, Beijing Tuberculosis and Thoracic Tumor Research Institute, Beijing Chest Hospital, Capital Medical University, 97 Ma Chang Street, Beijing 101149, China; luyu4876@hotmail.com – name: 5 Global Alliance for TB Drug Development, 40 Wall Street, New York, NY 10005, USA; anna.upton@tballiance.org (A.M.U.); christopher.cooper@tballiance.org (C.B.C.) |
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| Cites_doi | 10.1128/AAC.00699-11 10.1021/jm800379d 10.2147/DDDT.S164515 10.1016/j.str.2011.11.001 10.1021/acs.jmedchem.6b00485 10.1126/science.1164571 10.1056/NEJMoa1901814 10.1016/j.ejmech.2009.11.009 10.1007/s00044-015-1352-6 |
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| Keywords | nitroimidazole and oxazolidinone anaerobic bacterium synergy drug conjugates |
| Language | English |
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| References_xml | – ident: ref_9 – volume: 55 start-page: 5185 year: 2011 ident: ref_14 article-title: Clofazimine analogs with efficacy against experimental tuberculosis and reduced potential for accumulation publication-title: Antimicrob. Agents Chemother. doi: 10.1128/AAC.00699-11 contributor: fullname: Lu – volume: 51 start-page: 3353 year: 2008 ident: ref_6 article-title: Crystal structure of the oxazolidinone antibiotic linezolid bound to the 50S ribosomal subunit publication-title: J. Med. Chem. doi: 10.1021/jm800379d contributor: fullname: Ippolito – ident: ref_10 – ident: ref_11 – volume: 12 start-page: 1759 year: 2018 ident: ref_1 article-title: Linezolid: A review of its properties, function, and use in critical care publication-title: Drug Des. Dev. Ther. doi: 10.2147/DDDT.S164515 contributor: fullname: Hashemian – volume: 20 start-page: 101 year: 2012 ident: ref_2 article-title: Structure of Ddn, the deazaflavin-dependent nitroreductase from Mycobacterium tuberculosis involved in bioreductive activation of PA-824 publication-title: Structure doi: 10.1016/j.str.2011.11.001 contributor: fullname: Cellitti – volume: 59 start-page: 6645 year: 2016 ident: ref_5 article-title: Development of a dual-acting antibacterial agent (TNP-2092) for the treatment of persistent bacterial infections publication-title: J. Med. Chem. doi: 10.1021/acs.jmedchem.6b00485 contributor: fullname: Ma – volume: 39 start-page: 400 year: 2017 ident: ref_13 article-title: Induction in vitro and stability of Mycobacterium tuberculosis resistance to Linezolid publication-title: Chin. J. Antibio. contributor: fullname: Hu – volume: 322 start-page: 1392 year: 2008 ident: ref_3 article-title: PA-824 kills nonreplicating Mycobacterium tuberculosis by intracellular NO release publication-title: Science doi: 10.1126/science.1164571 contributor: fullname: Singh – ident: ref_16 – ident: ref_15 – ident: ref_17 – volume: 382 start-page: 893 year: 2020 ident: ref_4 article-title: Treatment of highly drug-resistant pulmonary tuberculosis publication-title: N. Engl. J. Med. doi: 10.1056/NEJMoa1901814 contributor: fullname: Conradie – volume: 42 start-page: 144 year: 2011 ident: ref_12 article-title: Induction and stability of Mycobacterium tuberculosis resistance to PA-824 in vitro publication-title: J. Chin. Ant. contributor: fullname: Hu – volume: 45 start-page: 661 year: 2010 ident: ref_7 article-title: Synthesis of nitroimidazole derived oxazolidinones as antibacterial agents publication-title: Eur. J. Med. Chem. doi: 10.1016/j.ejmech.2009.11.009 contributor: fullname: Varshney – volume: 24 start-page: 2986 year: 2015 ident: ref_8 article-title: Novel lead generation of an anti-tuberculosis agent active against non-replicating mycobacteria: Exploring hybridization of pyrazinamide with multiple fragments publication-title: Med. Chem. Res. doi: 10.1007/s00044-015-1352-6 contributor: fullname: Markad |
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| SubjectTerms | anaerobic bacterium Antitubercular Agents - chemistry Antitubercular Agents - pharmacology Bacteria, Anaerobic - drug effects drug conjugates Drug Resistance, Multiple, Bacterial - drug effects Drug Synergism Humans Linezolid - chemistry Mycobacterium tuberculosis - drug effects Mycobacterium tuberculosis - pathogenicity nitroimidazole and oxazolidinone Nitroimidazoles - chemistry Nitroimidazoles - pharmacology Oxazolidinones - chemistry Oxazolidinones - pharmacology synergy Tuberculosis, Multidrug-Resistant - drug therapy Tuberculosis, Multidrug-Resistant - microbiology |
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| Title | Synergistic Activity of Nitroimidazole-Oxazolidinone Conjugates against Anaerobic Bacteria |
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