Synthesis, Characterization and Antibacterial Mechanism of Action of (Fluoro) Quinolones: An Overview

Authors

  • Dominique Patomo Arama Chemistry Laboratory, faculty of pharmacy (FAPH), university of sciences, technics and technologies of Bamako (USTTB), P. O. Box: 1805, Bamako, Mali
  • Anou Moїse Somboro Chemistry Laboratory, faculty of pharmacy (FAPH), university of sciences, technics and technologies of Bamako (USTTB), P. O. Box: 1805, Bamako, Mali
  • Blaise Dackouo Chemistry Laboratory, faculty of pharmacy (FAPH), university of sciences, technics and technologies of Bamako (USTTB), P. O. Box: 1805, Bamako, Mali

DOI:

https://doi.org/10.14738/aivp.111.13177

Abstract

Quinolones are used to treat bacterial infections. Given their good tolerance and demonstrated activity, fluoroquinolones are widely prescribed. This wide use has unfortunately led to bacterial resistance increase. Many efforts have been made to develop new fluoroquinolone antibiotics. However, new and more effective derivatives need to be investigated. This is an overview of studies done these last decades, on fluoroquinolone synthesis, their characterization and their mechanism of actions.

References

Abdou M. M. Chemistry of 4-Hydroxy-2-(1H)-quinolone. Part 1: Synthesis and reactions. Arabian Journal of Chemistry. 2017, 10 (2): S3324-37. DOI : https://doi.org/10.1016/j.arabjc.2014.01.012.

George Y. L., Ernest J. F., Monte D. G., John Hays. B. and R. Pauline. B. 1,8-Naphtyridine derivatives. A new class of chemotherapeutic agents. Journal of Medicinal and Pharmaceutical Chemistry. 1962, 5 (5) : 1063-5 ; https://doi.org/10.1021/jm01240a021

Hooper D. C and Jocoby G. A. Mechanisms of drug resistance: quinolone resistance. Ann. N. Y. Sci. 2015; 1354:12-31; DOI: 10.1111/nyas.12830

Hooper D. C and Jacoby G. A. Topoisomerase Inhibitors: Fluoroquinolones Mechanisms of Action and Resistance. Cold Spring Harb Perspect Med 2016 ; 6 : a025320 ; DOI : 10.1101/cshperspect.a025320 215

Rama K., Vishal S., Gopal N., Satish K. A., Alka Al. Design, synthesis and biological evaluation of ciprofloxacin tethered bis-1,2,3-triazole conjugates as potent antibacterial agents. European Journal of Medicinal Chemistry. 2016, Volume 124 (29) : 218-28 ; https://doi.org/10.1016/j.ejmech.2016.08.031

Abdou M. M. Chemistry of 4-Hydroxy-2(1H)-quinolone. Part 2. As synthons in heterocyclic synthesis. Arabian Journal of Chemistry (2014), http://dx.doi.org/10.1016/j.arabajc.2014.11.021

Heeb S., Fletcher M. P., Chhabra S. R., Diggle S. P., William P and Camara M. Quinolones: from antibiotics to autoinducers (Review article). FEMS Microbiol. Rev. 2011;35:247-74; DOI: 10.1111/j.1574-6976.2010.00247.x

Gledraitiené A., Vitkausklené A., Naginiené R., Pavilonis A. Antibiotic Resistance Mechanisms of Clinically Important Bacteria. Medicina (Kaunas) 2011 ; 47(3) :137-46 ; https://doi.org/10.3390/medicina47030019

Namboodri S. S., Opintan J. A., Lijek R. S., Newman M. J., Okeke I. N. Quinolone resistance in Escherichia coli from Accra, Ghana. B. M. C. Microbio. 2011; 11(44):1-9; http://www.biomedcentral.com/1471-2180/11/44

Blondeau J. M. Fluoroquinolones: Mechanism of Action, Classification, and Development of Resistance. Survey of Ophthalmology 2004 ; 49(2) :S73-8 ; DOI : 10.1016/j.survophthal.2004.01.005

Fabrega A., Madurga S., Giralt E and Vila J. Mechanism of action of and resistance to quinolones. Microb. Biotech. 2009 ; 2(1) :40-61 ; DOI : 10.1111/j.1751-7915.2008.00063.x

Zhang G., Liu X., Zhang S., Pan B., Liu M. Ciprofloxacin derivatives and their antibacterial activities. Eur. J. Med. Chem. 2018;146:599-612; https://doi.org/10.1016/j.ejmech.2018.01.078

Hernandez. A., Sanchez M. B and Martinez J. Quinolone resistance: much more than predicted. Front. Microbiol. 2011; 2(22):1-6; DOI: 10.3389/fmicb.2011.00022

Schwanz H. A. Structural features of fluoroquinolone-class antibiotics that affect lethal and DNA binding. Thesis and Dissertation 2012 Iowa Research Online University of Iowa pp 206

Dirlica K., Malik M., Kerns R. J. and Zhao X. Quinolone-Mediated Bacterial Death (Minireview). Anticrob. Ag. Chemth. 2008 ; 52(2) :385-92 ; DOI : 10.1128/AAC.01617.06

Morales-Cid G., Feketen A., Simonet B. M., Lehmann R., Cẚrdenas S., Zhang X., Valcẚrcel M and Schimitt-Kopplin P. In Situ Synthesis of Magnetic Multiwalled Carbon Nanotube Composites for the Clean-up of (Fluoro) Quinolones from Human Plasma Prior to Ultrahigh Pressure Liquid Chromatography Analysis. Anal. Chem. 2010;82(7):2743-52; DOI:10.102/ac902631h

Junza A., Amatya R., Barron D., Barbosa. Comparative study of the LC-MS/MS and UPLC-MS/MS for the multiresidue analysis of quinolones, penicillin and cephalosporins in cow milk, and validation according to the regulation 2002/657/EC. J. Chrom. B. 2011; 879:2601-10; DOI: 10.1016/jchromb2011.07018

Aldred K. J., Kerns R. J., Osheroff N. Mechanism of Quinolone Action and Resistance. Biochemistry 2014, 53(10) :1565-74. DOI : 10. 1021/bi5000564

Flavia S., James T. H., Laura C., Stephen M. G., Warren R. J. D. G., Martin W., and David R. S. The Synthesis of Quinolone Natural Products from Pseudonocardia sp. European Journal of Organic Chemistry. 2016, 2016 (3) : 434–7 ; DOI: 10.1002/ejoc.201501400

Kumar N., Dhamija I., Raj P. V., Jayashree B. S., Parihar V., Manjula S. N., Thomas S., Kutty N. G., Rao C. M. Preliminary investigatigation of cytotoxic potential of 2-quinolone derivatives using in vitro and in vivo (solid tumor and liquid tumor) models of cancer. Arab. J. Chem. 2014;7:409-17 ; http://dx.doi.org/10.1016/j.arabjc.2012.12.029 216

Sharma P. C., Jain A., Yar M. S., Pahwa R., Singh J and Chanadstitia P. Novel fluoroquinolone derivatives bearing N-thiomide with 6-substituted-2-aminobenzothiazoles: Synthesis and antibacterial evaluation. Ara. J. Chem. 2017;10:S568-75; http://dx.doi.org/10.1016/j.arabjc.2012.11.002

Lucia P. Quinolones: Synthesis and Antibacterial Activity. In Antimicrobial Agents. IntechOpen. 2012; 12:255-72.

Winter R. W., Kelly J. X., Smilkstein M. J., Dodean R., Hinrichs D. and Riscoe M. K. Antimalarial Quinolones: Synthesis, potency, and mechanistic studies. Exp. Parasitol. 2008; 118(4):487-97

Wube A. A., Hufner A., Thomaschitz C., Blunder M., Kollroser M., Bauer R., Bucar F. Design, synthesis and antimycobacterial activities of 1-methyl-2-alkenyl-4(1H)-quinolones. Bioorg. Med. Chem. 2011; 19:567-79; DOI:10.1016/bmc.2010.10.060

Wube A. A., Bacar F., Hochfellner C., Blunder M., Bauer R. Hufner A. Synthesis of N-substituted 2-[(1E)-alkenyl]-4-(1H)-quinolone derivatives as antimycobacterial agents against non-tubercular mycobacteria. Eur. J. Med. Chem. 2011;46:2091-101; DOI:10.1016/j.ejmech.2011.02.062

Jacoby G. A., Strahilevitz J. Hooper D. C. Plasmid-Mediated Quinolone Resistance. Micobio. Spectr. 2013; 2(5):1-24; DOI: 10.1128/mcrobiolspec.PLAS-0006-2013

Jardosh H. H., Patel M. P. Antimicrobial and antioxidant evaluation of new quinolone based aurone analogs. Arab. J. Chem. 2017; 10:S3781-9; http://dx.doi.org/10.1016/j.arabjc.2014.05.014

Chen J., Lu N., Shen X., Tang Q., Zhag C., Xu J., Sun Y., Huang X., Xu Z and Lei H. Investigation of an Immunoassay with Broad Specificity to Quinolone Drugs by Genetic Algorithm with Linear Assignment of Hypermolecular Alignment of Data Sets and Advanced Quantitative Structure-Activity Relationship Analysis. J. Agric. Food. Chem. 2016 ; 64 :2772-9 ; DOI : 10.1021/acs.jafc.6b0039

Berning M., Krasz S and Miehlke S. Should quinolones come first in Helicobacter pylori therapy ? Ther. Adv. Gastroenterol. 2011,4(2) :103-14. DOI : 10.1177/1756283X10384171

Boteva A. A. and Krasnykh O. P. THE METHODS OF SYNTHESIS, MODIFICATION, AND BIOLOGICAL ACTIVITY OF 4-QUINOLONES (REVIEW). Chemistry of Heterocyclic Compounds, 2009 ; 45(7) :757-89 ; https://doi.org/10.1007/s10593-009-0360-1

Leekha S., Terrell C. L and Edson R. S. General Principles of Antimicrobial Therapy. Mayo. Clin. Proc. 2011; 86(2):156-67; DOI: 10.4065/mcp.2010.0639

Barlow A. M. Nalidixic Acid In Infections Of Urinary Tract. Br. Med. J. 1963, 23 ; 2 (5368) : 1308-10 ; doi:10.1136/bmj.2.5368.1308

Downloads

Published

2023-01-20

How to Cite

Arama, D. P., Somboro, A. M., & Dackouo, B. (2023). Synthesis, Characterization and Antibacterial Mechanism of Action of (Fluoro) Quinolones: An Overview. European Journal of Applied Sciences, 11(1), 209–217. https://doi.org/10.14738/aivp.111.13177

Most read articles by the same author(s)