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Research Article

Norfloxacin Derivatives as DNA Gyrase and Urease Inhibitors: Synthesis, Biological Evaluation and Molecular Docking

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Pages 2181-2194 | Received 31 Jul 2023, Accepted 16 Oct 2023, Published online: 24 Nov 2023

References

  • Abdel-Aziz SA , CirnskiK , HerrmannJ , Abdel-AalMA , YoussifBG , SalemOIA. Novel fluoroquinolone hybrids as dual DNA gyrase and urease inhibitors with potential antibacterial activity: design, synthesis, and biological evaluation. J. Mol. Struc.1271, 134049 (2023).
  • Kim OK , OhemengK , BarrettJF. Advances in DNA gyrase inhibitors. Expert. Opin. Investig. Drugs10(2), 199–212 (2001).
  • Tsakou F , Jersie-ChristensenR , JenssenH , MojsoskaB. The role of proteomics in bacterial response to antibiotics. Pharmaceuticals (Basel)13(9), 214 (2020).
  • Alagumuthu M , MuralidharanVP , AndrewM , AhmedMH , IyerSK , ArumugamS. Computational approaches to develop isoquinoline based antibiotics through DNA gyrase inhibition mechanisms unveiled through antibacterial evaluation and molecular docking. Mol. Inform.37(12), 1800048 (2018).
  • Belzer C , KustersJ , KuipersE , Van VlietAHM. Urease induced calcium precipitation by Helicobacter species may initiate gallstone formation. Gut55(11), 1678–1679 (2006).
  • Hanif M , SaleemM , HussainMTet al. Synthesis, urease inhibition, antioxidant and antibacterial studies of some 4-amino-5-aryl-3H-1, 2, 4-triazole-3-thiones and their 3, 6-disubstituted 1, 2, 4-triazolo [3, 4-b] 1, 3, 4-thiadiazole derivatives. J. Braz. Chem. Soc.23, 854–860 (2012).
  • Hanif M , ShoaibK , SaleemM , HasanRama N , ZaibS , IqbalJ. Synthesis, urease inhibition, antioxidant, antibacterial, and molecular docking studies of 1, 3, 4-oxadiazole derivatives. ISRN Pharmacol. doi: 10.5402/2012/928901 (2012) ( Epub ahead of print).
  • Khan M , KhanKM , ParveenS , ShaikhM , FatimaN , ChoudharyMI. Syntheses, in vitro urease inhibitory activities of urea and thiourea derivatives of tryptamine, their molecular docking and cytotoxic studies. Bioorg. Chem.83, 595–610 (2019).
  • Lin W , MathysV , AngELYet al. Urease activity represents an alternative pathway for Mycobacterium tuberculosis nitrogen metabolism. Infect. Immun.80(8), 2771–2779 (2012).
  • Ajjah NT , NaserNH , AlardAaA , DiwanMF. Design, synthesis, docking study and preliminary pharmacological assessment of new norfloxacin analogues having thiazole nucleus. J. Biochem. Technol.11(3), 58–67 (2020).
  • Upadhyay DB , ValaRM , PatelSG , PatelPJ , ChiC , PatelHM. Water mediated TBAB catalyzed synthesis of spiro-indoline-pyrano [3, 2-c] quinolines as α-amylase inhibitor and in silico studies. J. Mol. Struc.1273, 134305 (2023).
  • Avula SK , UllahS , HalimSAet al. Synthesis of novel substituted quinoline derivatives as diabetics II inhibitors and along with their in-silico studies. J. Mol. Struc.1274, 134560 (2023).
  • Patel SG , González-BakkerA , ValaRMet al. Microwave-assisted multicomponent synthesis of antiproliferative 2, 4-dimethoxy-tetrahydropyrimido [4, 5-b] quinolin-6 (7 H)-ones. RSC Adv.12(47), 30404–30415 (2022).
  • Sharma S , SinghS. Molecular docking study for binding affinity of 2H-thiopyrano [2, 3-b] quinoline derivatives against CB1a. Interdiscip. Perspect. Infect. Dis.2023, 1618082 (2023).
  • Su J-B , WuW-L , DongC-Eet al. Synthesis, characterization, crystal structure and biological evaluation of 1, 3, 5-triazine-quinoline derivatives as butyrylcholinesterase inhibitors. J. Mol. Struct.1274, 134391 (2023).
  • Carraher CE Jr , RonerMR , ThibodeauR , JohnsonAM. Synthesis, structural characterization, and preliminary cancer cell study results for poly (amine esters) derived from triphenyl-group VA organometallics and norfloxacin. Inorganica Chim. Acta423, 123–131 (2014).
  • Shih M-K , TainY-L , ChengC-Met al. Separation and Identification of resveratrol butyrate ester complexes and their bioactivity in HepG2 cell models. Int. J. Mol. Sci.22(24), 13539 (2021).
  • Zhu S , WuY , YuZet al. One-pot synthesis of norfloxacin ethyl ester from 3-chloro-4-fluoroaniline in ionic liquid. Lett. Org. Chem.5(1), 1–2 (2008).
  • Sharma PC , JainS. Synthesis and in vitro antibacterial activity of some novel N-nicotinoyl-1-ethyl-6-fluoro-1, 4-dihydro-7-piperazin-1-yl-4-oxoquinoline-3-carboxylates. Acta Pol. Pharm.65, 551–556 (2008).
  • Rivault F , LiébertC , BurgerAet al. Synthesis of pyochelin–norfloxacin conjugates. Bioorg. Medi. Chem. Lett.17(3), 640–644 (2007).
  • Ajjah NT , NaserNH , AlardAAA , DiwanMF. Design, synthesis, docking study and preliminary pharmacological assessment of new norfloxacin analogues having thiazole nucleus. J. Biochem. Tech.11, 58–67 (2020).
  • Jyothi N , GanjiN , DaravathS , Shivaraj. Mononuclear cobalt (II), nickel (II) and copper (II) complexes: synthesis, spectral characterization and interaction study with nucleotide by in vitro biochemical analysis. J. Mol. Struc.1207, 127799 ( 2020).
  • Khaliq S , KhanMA , AhmadI , AhmadI , AhmedJ , UllahF. Synthesis, antimicrobial and molecular docking study of structural analogues of 3-((5-(dimethylcarbamoyl) pyrrolidin-3-yl) thio)-6-(1-hydroxyethyl)-4-methyl-7-oxo-1-azabicyclo [3.2.0] heptane-2-carboxylic acid. PLOS ONE17(12), e0278684 (2022).
  • Ejaz SA , HassanR , KhalidNJPJPS. Synthesis, spectral characterization and enzyme inhibition studies of different chlorinated sulfonamides. Pak. J. Pharm. Sci.27(6), 1739–1745 (2014).
  • Blanche F , CameronB , BernardF-Xet al. Differential behaviors of Staphylococcus aureus and Escherichia coli type II DNA topoisomerases. Antimicrob. Agents Chemother.40(12), 2714–2720 (1996).
  • Pedrood K , AzizianH , MontazerMNet al. Design and synthesis of new N-thioacylated ciprofloxacin derivatives as urease inhibitors with potential antibacterial activity. Sci. Rep.12(1), 1–17 (2022).
  • Sohrabi M , NazariMontazer M , FaridSMet al. Design and synthesis of novel nitrothiazolacetamide conjugated to different thioquinazolinone derivatives as anti-urease agents. Sci. Rep.12(1), 1–14 (2022).
  • Deepali G , SayaliL. Antioxidant and anti-inflammatory activity of synthesized 3-substituted Schiff bases of quinazoline 2, 4-diones. J. Chem. Pharm. Res.8(8), 1132–1138 (2016).
  • Bashford D , CaseDA. Generalized born models of macromolecular solvation effects. Annu. Rev. Phys. Chem.51(1), 129–152 (2000).
  • Harder E , DammW , MapleJet al. OPLS3: a force field providing broad coverage of drug-like small molecules and proteins. J. Chem. Theory. Comput.12(1), 281–296 (2016).
  • Friesner RA , BanksJL , MurphyRBet al. Glide: a new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy. J. Med. Chem.47(7), 1739–1749 (2004).
  • Halgren TA , MurphyRB , FriesnerRAet al. Glide: a new approach for rapid, accurate docking and scoring. 2. Enrichment factors in database screening. J. Med. Chem.47(7), 1750–1759 (2004).
  • De Fátima  , DePaula Pereira C , OlímpioCRSDG , DeFreitas Oliveira BG , FrancoLL , DaSilva PHC. Schiff bases and their metal complexes as urease inhibitors–a brief review. J. Adv. Res.13, 113–126 (2018).
  • Maroney MJ , CiurliS. Nonredox nickel enzymes. Chem. Rev.114(8), 4206–4228 (2014).
  • Boer JL , MulrooneySB , HausingerRP. Nickel-dependent metalloenzymes. Arch. Biochem. Biophys.544, 142–152 (2014).
  • Van Vliet AH , KuipersEJ , WaidnerBet al. Nickel-responsive induction of urease expression in Helicobacter pylori is mediated at the transcriptional level. Infect. Immun.69(8), 4891–4897 (2001).
  • Mentese MY , BayrakH , UygunYet al. Microwave assisted synthesis of some hybrid molecules derived from norfloxacin and investigation of their biological activities. Eur. J. Med. Chem.67, 230–242 (2013).
  • Hamilton AL , KammMA , NgSC , MorrisonM. Proteus spp. as putative gastrointestinal pathogens. Clin. Microbiol. Rev.31(3), e00085–e00017 (2018).
  • Marc G , AraniciuC , OnigaSDet al. Design, synthesis and biological evaluation of new piperazin-4-yl-(acetyl-thiazolidine-2, 4-dione) norfloxacin analogues as antimicrobial agents. Molecules24(21), 3959 (2019).
  • Traub WH . Intraphagocytic bactericidal activity of bacterial DNA gyrase inhibitors against Serratia marcescens. Chemotherapy30(6), 379–386 (1984).
  • Pakamwong B , ThongdeeP , KamsriBet al. Identification of potent DNA gyrase inhibitors active against Mycobacterium tuberculosis. J. Chem. Inf. Model.62(7), 1680–1690 (2022).
  • Almeida ST , PauloAC , BaboJet al. Absence of methicillin-resistant Staphylococcus aureus colonization among immunocompetent healthy adults: insights from a longitudinal study. PLOS ONE16(6), e0253739 (2021).
  • Kamal El-Sagheir AM , AbdelmessehNekhala I , AbdEl-Gaber MKet al. N4-substituted piperazinyl norfloxacin derivatives with broad-spectrum activity and multiple mechanisms on gyrase, topoisomerase IV, and bacterial cell wall synthesis. ACS Bio. Med. Chem. Au. (2023). https://doi.org/10.1021/acsbiomedchemau.3c00038
  • Mishra N , KumarK , PandeyHet al. Synthesis, characterization, optical and anti-bacterial properties of benzothiazole Schiff bases and their lanthanide (III) complexes. J. Saudi Chemical Society24(12), 925–933 (2020).
  • Zhang H , LuQ , ZhangJet al. Discovery of novel nitrogenous heterocyclic-containing quinoxaline-1, 4-di-N-oxides as potent activator of autophagy in M. tb-infected macrophages. Eur. J. Med. Chem.223, 113657 (2021).

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