Antimicrobial 2-aminothiazolyl quinolones: what is their potential in the clinic?

Abstract

Future Medicinal ChemistryVol. 9, No. 13 EditorialAntimicrobial 2-aminothiazolyl quinolones: what is their potential in the clinic?Wei-Wei Gao & Cheng-He ZhouWei-Wei Gao Institute of Bioorganic & Medicinal Chemistry, Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry & Chemical Engineering, Southwest University, Chongqing 400715, ChinaSearch for more papers by this author & Cheng-He Zhou*Author for correspondence: Tel.: +86 023 68254967; Fax: +86 023 68254967; E-mail Address: zhouch@swu.edu.cn Institute of Bioorganic & Medicinal Chemistry, Key Laboratory of Applied Chemistry of Chongqing Municipality, School of Chemistry & Chemical Engineering, Southwest University, Chongqing 400715, ChinaSearch for more papers by this authorPublished Online:10 Aug 2017https://doi.org/10.4155/fmc-2017-0108AboutSectionsView ArticleView Full TextPDF/EPUB ToolsAdd to favoritesDownload CitationsTrack CitationsPermissionsReprints ShareShare onFacebookTwitterLinkedInReddit View articleKeywords: aminothiazole quinolonesantibacterial resistancebenzimidazolecoumarinDNA intercalatingimidazolemembrane activemulti-targeting abilitytetrazoletriazoleReferences1 World Health Organization. Antimicrobial Resistance: Global Surveillance Report. WHO, Geneva, Switzerland (2014).Google Scholar2 Zowawi HM, Harris PNA, Roberts MJ et al. The emerging threat of multidrug-resistant Gram-negative bacteria in urology. Nat. Rev. Urol. 12(10), 570–584 (2015).Crossref, Medline, CAS, Google Scholar3 Yan L, Liu D, Wang XH et al. Bacterial plasmid-mediated quinolone resistance genes in aquatic environments in China. Sci. Rep. 7, 40610 (2017).Crossref, Medline, CAS, Google Scholar4 Zhang HZ, Gan LL, Wang H et al. New progress in azole compounds as antimicrobial agents. Mini-Rev. Med. Chem. 17(2), 122–166 (2017).Crossref, Medline, CAS, Google Scholar5 Peng XM, Peng LP, Rao AS et al. Quinazolinone azolyl ethanols: potential lead antibacterial agents with dual action modes targeting MRSA DNA. Future Med. Chem. 8(15), 1927–1940 (2016).Link, CAS, Google Scholar6 Peng LP, Nagarajan S, Syed Rasheed S et al. Synthesis and biological evaluation of a new class of quinazolinone azoles as potential antimicrobial agents and their interaction with calf thymus DNA and human serum albumin. Med. Chem. Commun. 6(1), 222–229 (2015).Crossref, CAS, Google Scholar7 Peng XM, Damu GLV, Zhou CH. Current developments of coumarin compounds in medicinal chemistry. Curr. Pharm. Des. 19, 3884–3930 (2013).Crossref, Medline, CAS, Google Scholar8 Zhang L, Kumar KV, Geng RX et al. Design and biological evaluation of novel quinolone-based metronidazole derivatives as potent Cu2+ mediated DNA-targeting antibacterial agents. Bioorg. Med. Chem. Lett. 25(17), 3699–3705 (2015).Crossref, Medline, CAS, Google Scholar9 Cui SF, Peng LP, Zhang HZ et al. Novel hybrids of metronidazole and quinolones: synthesis, bioactive evaluation, cytotoxicity, preliminary antimicrobial mechanism and effect of metal ions on their transportation by human serum albumin. Eur. J. Med. Chem. 86, 318–334 (2014).Crossref, Medline, CAS, Google Scholar10 Zhang L, Kumar KV, Rasheed S et al. Design, synthesis, and antimicrobial evaluation of novel quinolone imidazoles and interactions with MRSA DNA. Chem. Biol. Drug Des. 86(4), 648–655 (2015).Crossref, Medline, CAS, Google Scholar11 Cui SF, Ren Y, Zhang SL et al. Synthesis and biological evaluation of a class of quinolone triazoles as potential antimicrobial agents and their interactions with calf thymus DNA. Bioorg. Med. Chem. Lett. 23(11), 3267–3272 (2013).Crossref, Medline, CAS, Google Scholar12 Zhang L, Kumar KV, Rasheed S et al. Design, synthesis, antibacterial evaluation of novel azolylthioether quinolones as MRSA DNA intercalators. Med. Chem. Commun. 6(7), 1303–1310 (2015).Crossref, CAS, Google Scholar13 Zhang L, Addla D, Ponmani J et al. Discovery of membrane active benzimidazole quinolones-based topoisomerase inhibitors as potential DNA-binding antimicrobial agents. Eur. J. Med. Chem. 111, 160–182 (2016).Crossref, Medline, CAS, Google Scholar14 Kao CY, Wu HM, Lin WH et al. Plasmid-mediated quinolone resistance determinants in quinolone-resistant Escherichia coli isolated from patients with bacteremia in a university hospital in Taiwan, 2001–2015. Sci. Rep. 6, 32281 (2016).Crossref, Medline, CAS, Google Scholar15 Poon IKH, Chiu YH, Armstrong AJ et al. Unexpected link between an antibiotic, pannexin channels and apoptosis. Nature 507(7492), 329–334 (2014).Crossref, Medline, CAS, Google Scholar16 Zhang L, Peng XM, Damu GLV et al. Comprehensive review in current developments of imidazole-based medicinal chemistry. Med. Res. Rev. 34(2), 340–437 (2014).Crossref, Medline, Google Scholar17 Zhou CH, Wang Y. Recent researches in triazole compounds as medicinal drugs. Curr. Med. Chem. 19(2), 239–280 (2012).Crossref, Medline, CAS, Google Scholar18 Peng XM, Cai GX, Zhou CH. Recent developments in azole compounds as antibacterial and antifungal agents. Curr. Top. Med. Chem. 13(16), 1963–2010 (2013).Crossref, Medline, CAS, Google Scholar19 Das D, Sikdar P, Bairagi M. Recent developments of 2-aminothiazoles in medicinal chemistry. Eur. J. Med. Chem. 109, 89–98 (2016).Crossref, Medline, CAS, Google Scholar20 Addla D, Wen SQ, Gao WW et al. Design, synthesis, and biological evaluation of novel carbazole aminothiazoles as potential DNA targeting antimicrobial agents. Med. Chem. Commun. 7(10), 1988–1994 (2016).Crossref, CAS, Google Scholar21 Cui SF, Addla D, Zhou CH. Novel 3-aminothiazolquinolones: Design, synthesis, bioactive evaluation, SARs, and preliminary antibacterial mechanism. J. Med. Chem. 59(10), 4488–4510 (2016).Crossref, Medline, CAS, Google Scholar22 Cheng Y, Avula SR, Gao WW et al. Multi-targeting exploration of new 2-aminothiazolyl quinolones: Synthesis, antimicrobial evaluation, interaction with DNA, combination with topoisomerase IV and penetrability into cells. Eur. J. Med. Chem. 124, 935–945 (2016).Crossref, Medline, CAS, Google ScholarFiguresReferencesRelatedDetailsCited ByQuantitative structure–activity relationship modeling and docking of some synthesized bioactive oxopyrolidines against Staphylococcus aureusJournal of Saudi Chemical Society, Vol. 26, No. 4Natural Berberine-derived Azolyl Ethanols as New Structural Antibacterial Agents against Drug-Resistant Escherichia coli29 December 2021 | Journal of Medicinal Chemistry, Vol. 65, No. 1Natural Berberine-Hybridized Benzimidazoles as Novel Unique Bactericides against Staphylococcus aureus6 July 2021 | Journal of Agricultural and Food Chemistry, Vol. 69, No. 28Identification of Unique Quinazolone Thiazoles as Novel Structural Scaffolds for Potential Gram-Negative Bacterial Conquerors19 May 2021 | Journal of Medicinal Chemistry, Vol. 64, No. 11Synthesis and Biological Evaluation of Quinazolonethiazoles as New Potential Conquerors towards Pseudomonas Aeruginosa22 April 2021 | Chinese Journal of Chemistry, Vol. 39, No. 5Membrane active 7-thiazoxime quinolones as novel DNA binding agents to decrease the genes expression and exert potent anti-methicillin-resistant Staphylococcus aureus activityEuropean Journal of Medicinal Chemistry, Vol. 217Aloe-emodin derived azoles as a new structural type of potential antibacterial agents: design, synthesis, and evaluation of the action on membrane, DNA, and MRSA DNA isomerase1 January 2021 | RSC Medicinal Chemistry, Vol. 12, No. 4An unexpected discovery toward novel membrane active sulfonyl thiazoles as potential MRSA DNA intercalatorsYuan-Yuan Hu, Juan Wang, Tie-Jun Li, Rammohan R Yadav Bheemanaboina, Mohammad Fawad Ansari, Yu Cheng & Cheng-He Zhou8 October 2020 | Future Medicinal Chemistry, Vol. 12, No. 19Design and biological evaluation of a novel type of potential multi-targeting antimicrobial sulfanilamide hybrids in combination of pyrimidine and azolesBioorganic & Medicinal Chemistry Letters, Vol. 30, No. 6A new exploration towards aminothiazolquinolone oximes as potentially multi-targeting antibacterial agents: Design, synthesis and evaluation acting on microbes, DNA, HSA and topoisomerase IVEuropean Journal of Medicinal Chemistry, Vol. 179Design and synthesis of aminothiazolyl norfloxacin analogues as potential antimicrobial agents and their biological evaluationEuropean Journal of Medicinal Chemistry, Vol. 167Quinolone derivatives and their activities against methicillin-resistant Staphylococcus aureus (MRSA)European Journal of Medicinal Chemistry, Vol. 157Azoalkyl ether imidazo[2,1-b]benzothiazoles as potentially antimicrobial agents with novel structural skeletonBioorganic & Medicinal Chemistry Letters, Vol. 28, No. 14Novel carbazole-triazole conjugates as DNA-targeting membrane active potentiators against clinical isolated fungiEuropean Journal of Medicinal Chemistry, Vol. 155Discovery of Benzimidazole-Quinolone Hybrids as New Cleaving Agents toward Drug-Resistant Pseudomonas aeruginosa DNA16 April 2018 | ChemMedChem, Vol. 13, No. 10Discovery of natural berberine-derived nitroimidazoles as potentially multi-targeting agents against drug-resistant Escherichia coli28 December 2017 | Science China Chemistry, Vol. 61, No. 5Novel purine benzimidazoles as antimicrobial agents by regulating ROS generation and targeting clinically resistant Staphylococcus aureus DNA grooveBioorganic & Medicinal Chemistry Letters, Vol. 28, No. 9Novel naphthalimide nitroimidazoles as multitargeting antibacterial agents against resistant Acinetobacter baumanniiJie Kang, Lavanya Gopala, Vijai Kumar Reddy Tangadanchu, Wei-Wei Gao & Cheng-He Zhou19 April 2018 | Future Medicinal Chemistry, Vol. 10, No. 7Potential Antimicrobial Isopropanol-Conjugated Carbazole Azoles as Dual Targeting Inhibitors of Enterococcus faecalis5 February 2018 | ACS Medicinal Chemistry Letters, Vol. 9, No. 3Discovery of 2-aminothiazolyl berberine derivatives as effectively antibacterial agents toward clinically drug-resistant Gram-negative Acinetobacter baumaniiEuropean Journal of Medicinal Chemistry, Vol. 146Novel aminopyrimidinyl benzimidazoles as potentially antimicrobial agents: Design, synthesis and biological evaluationEuropean Journal of Medicinal Chemistry, Vol. 143Novel organophosphorus aminopyrimidines as unique structural DNA-targeting membrane active inhibitors towards drug-resistant methicillin-resistant Staphylococcus aureus1 January 2018 | MedChemComm, Vol. 9, No. 9Novel Naphthalimide Aminothiazoles as Potential Multitargeting Antimicrobial Agents7 December 2017 | ACS Medicinal Chemistry Letters, Vol. 8, No. 12Discovery of novel nitroimidazole enols as Pseudomonas aeruginosa DNA cleavage agentsBioorganic & Medicinal Chemistry, Vol. 25, No. 24Novel potentially antifungal hybrids of 5-flucytosine and fluconazole: Design, synthesis and bioactive evaluationBioorganic & Medicinal Chemistry Letters, Vol. 27, No. 22 Vol. 9, No. 13 Follow us on social media for the latest updates Metrics Downloaded 134 times History Published online 10 August 2017 Published in print September 2017 Information© 2017 Future Science LtdKeywordsaminothiazole quinolonesantibacterial resistancebenzimidazolecoumarinDNA intercalatingimidazolemembrane activemulti-targeting abilitytetrazoletriazoleFinancial & competing interests disclosureThe project leading to this article has received funding from National Natural Science Foundation of China (no. 21672173, 21372186, 21172181), the Research Fund for International Young Scientists from International (Regional) Cooperation and Exchange Program NSFC (no. 81650110529, 81450110451, 81450110094), Chongqing Special Foundation for Postdoctoral Research Proposal (no. Xm2015031, Xm2016039), the Key Program of Natural Science Foundation of Chongqing (CSTC2012jjB10026) and the Specialized Research Fund for the Doctoral Program of Higher Education of China (SRFDP 20110182110007). The authors have no other relevant affiliations or financialinvolvement with any organization or entity with a financial interest in or financial conflict with the subject matter or materials discussed in the manuscript apart from those disclosed.No writing assistance was utilized in the production of this manuscript.PDF download