Recent Advances in Quinolone Hybrids With Potential Antibacterial Activity Against drug-resistant Bacteria

References

• Fernández L , Cima-CabalMD, DuarteACet al. Developing diagnostic and therapeutic approaches to bacterial infections for a new era: implications of globalization. Antibiotics9(12), 1–12 (2020).
   Google Scholar
• Parreira P , MartinsMCL. The biophysics of bacterial infections: adhesion events in the light of force spectroscopy. Cell Surf.7, e100048 (2021).
   PubMedGoogle Scholar
• Vila J , Moreno-MoralesJ, Ballesté-DelpierreC. Current landscape in the discovery of novel antibacterial agents. Clin. Microbiol. Infect.26(5), 596–603 (2020).
   PubMed Web of Science ®Google Scholar
• Al-Tawfiq JA , MomattinH, Al-AliAYet al. Antibiotics in the pipeline: a literature review (2017–2020). Infection50(3), 553–564 (2022).
   PubMed Web of Science ®Google Scholar
• Baker SJ , PayneDJ, RappuoliRet al. Technologies to address antimicrobial resistance. PNAS115(51), 12887–12895 (2018).
   PubMed Web of Science ®Google Scholar
• Urban-Chmiel R , MarekA, Stępień-PyśniakDet al. Antibiotic resistance in bacteria–a review. Antibiotics11(8), e1079 (2022).
   Google Scholar
• Murray CJL , IkutaKS, ShararaFet al. Global burden of bacterial antimicrobial resistance in 2019: a systematic analysis. Lancet399(10325), 629–655 (2022).
   PubMed Web of Science ®Google Scholar
• Laxminarayan R . The overlooked pandemic of antimicrobial resistance. Lancet399(10325), 606–607 (2022).
   PubMed Web of Science ®Google Scholar
• O'Neill J . Review on antimicrobial resistance antimicrobial resistance: tackling a crisis for the health and wealth of nations. (2014) (Accessed March 2023). https:// amr-review.org/sites/default/files/AMR%20Review%20Paper%20-%20Tackling%20a%20crisis% 20for%20the%20health%20and%20wealth%20of%20nations_1.pdf
   Google Scholar
• WHO . Global action plan on antimicrobial resistance. Genève. Accessed (March 2023). https://ahpsr.who.int/publications/i/item/global-action-plan-on-antimicrobial-resistance
   Google Scholar
• Pham TDM , ZioraZM, BlaskovichMAT. Quinolone antibiotics. Med. Chem. Comm.10, 1719–1739 (2019).
   Google Scholar
• Bush NG , Diez-SantosI, AbbottLRet al. Quinolones: mechanism, lethality and their contributions to antibiotic resistance. Molecules25(23), e5662 (2020).
   PubMed Web of Science ®Google Scholar
• Jia YS , ZhaoLY. The antibacterial activity of fluoroquinolone derivatives: an update (2018–2021). Eur. J. Med. Chem.224, e113741 (2021).
   PubMed Web of Science ®Google Scholar
• Gao J , HouH, GaoF. Current scenario of quinolone hybrids with potential antibacterial activity against ESKAPE pathogens. Eur. J. Med. Chem.247, e115026 (2023).
   PubMed Web of Science ®Google Scholar
• Redgrave LS , SuttonSB, WebberMAet al. Fluoroquinolone resistance: mechanisms, impact on bacteria, and role in evolutionary success. Trends Microbiol.22(8), 438–445 (2014).
   PubMed Web of Science ®Google Scholar
• Lungu IA , MoldovanOL, BirişVet al. Fluoroquinolones hybrid molecules as promising antibacterial agents in the fight against antibacterial resistance. Pharmaceutics14(8), e1749 (2022).
   PubMed Web of Science ®Google Scholar
• Dhiman P , AroraN, ThanikachalamPVet al. Recent advances in the synthetic and medicinal perspective of quinolones: a review. Bioorg. Chem.92, e103291 (2019).
   PubMed Web of Science ®Google Scholar
• Gao F , WangP, YangHet al. Recent developments of quinolone-based derivatives and their activities against Escherichia coli. Eur. J. Med. Chem.157, 1223–1248 (2018).
   PubMed Web of Science ®Google Scholar
• Alkhzem AH , WoodmanTJ, BlagbroughIS. Design and synthesis of hybrid compounds as novel drugs and medicines. RSC Adv.12(30), 19470–19484 (2022).
   PubMed Web of Science ®Google Scholar
• Fedorowicz J , SączewskiJ. Modifications of quinolones and fluoroquinolones: hybrid compounds and dual-action molecules. Monatsh. Chem.149(7), 1199–1245 (2018).
   PubMed Web of Science ®Google Scholar
• Dorababu A . Pharmacology profile of recently developed multi-functional azoles; SAR-based predictive structural modification. ChemistrySelect5(22), 6730–6758 (2020).
   Web of Science ®Google Scholar
• Li J , ZhangJ. The antibacterial activity of 1,2,3-triazole-and 1,2,4-triazole-containing hybrids against Staphylococcus aureus: an updated review (2020-present). Curr. Top. Med. Chem.22(1), 41–63 (2022).
   PubMed Web of Science ®Google Scholar
• Zhang HZ , GanLL, WangHet al. New progress in azole compounds as antimicrobial agents. Mini-Rev. Med. Chem.17(2), 122–166 (2017).
   PubMed Web of Science ®Google Scholar
• Deng C , YanH, WangJet al. 1,2,3-Triazole-containing hybrids with potential antibacterial activity against ESKAPE pathogens. Eur. J. Med. Chem.244, e114888 (2022).
   PubMed Web of Science ®Google Scholar
• Huddar S , JangS, KimHJet al. Discovery of 4-hydroxy-2-oxo-1,2-dihydroquinolines as potential inhibitors of Streptococcus pneumoniae, including drug-resistant strains. Bioorg. Med. Chem. Lett.30, e127071 (2020).
   PubMed Web of Science ®Google Scholar
• Litim B , DjahoudiA, MelianiSet al. Synthesis and potential antimicrobial activity of novel α-aminophosphonates derivatives bearing substituted quinoline or quinolone and thiazole moieties. Med. Chem. Res.31(1), 60–74 (2022).
   PubMed Web of Science ®Google Scholar
• Xue W , LiX, MaGet al. N-Thiadiazole-4-hydroxy-2-quinolone-3-carboxamides bearing heteroaromatic rings as novel antibacterial agents: design, synthesis, biological evaluation and target identification. Eur. J. Med. Chem.188, e112022 (2020).
   PubMed Web of Science ®Google Scholar
• Wang LL , BattiniN, BheemanaboinaRRYet al. Design and synthesis of aminothiazolyl norfloxacin analogues as potential antimicrobial agents and their biological evaluation. Eur. J. Med. Chem.167, 105–123 (2019).
   PubMed Web of Science ®Google Scholar
• Wang LL , BattiniN, BheemanaboinaRRYet al. A new exploration towards aminothiazolquinolone oximes as potentially multi-targeting antibacterial agents: design, synthesis and evaluation acting on microbes, DNA, HSA and topoisomerase IV. Eur. J. Med. Chem.179, 166–181 (2019).
   PubMed Web of Science ®Google Scholar
• Cui SF , AddlaD, ZhouCH. Novel 3-aminothiazolquinolones: design, synthesis, bioactive evaluation, SARs, and preliminary antibacterial mechanism. J. Med. Chem.59(10), 4488–4510 (2016).
   PubMed Web of Science ®Google Scholar
• Cheng Y , AvulaSR, GaoWWet 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).
   PubMed Web of Science ®Google Scholar
• Chen JP , BattiniN, AnsariMFet al. Membrane active 7-thiazoxime quinolones as novel DNA binding agents to decrease the genes expression and exert potent anti-methicillin-resistant Staphylococcus aureus activity. Eur. J. Med. Chem.217, e113340 (2021).
   PubMed Web of Science ®Google Scholar
• Aziz HA , El-SaghierAMM, BadrMet al. Thiazolidine-2,4-dione-linked ciprofloxacin derivatives with broad-spectrum antibacterial, MRSA and topoisomerase inhibitory activities. Mol. Divers.26(3), 1743–1759 (2022).
   PubMed Web of Science ®Google Scholar
• Balasubramaniyan S , IrfanN, SenthilkumarCet al. The synthesis and biological evaluation of virtually designed fluoroquinolone analogs against fluoroquinolone-resistant: escherichia coli intended for UTI treatment. New J. Chem.44(31), 13308–13318 (2020).
   Web of Science ®Google Scholar
• Garza I , WallaceMJ, FernandoDet al. Synthesis and evaluation of thiazolidine amide and N-thiazolyl amide fluoroquinolone derivatives. Arch. Pharm.350(6), E201700029 (2017).
   Web of Science ®Google Scholar
• Guo Y , XuT, BaoCet al. Design and synthesis of new norfloxacin-1,3,4-oxadiazole hybrids as antibacterial agents against methicillin-resistant Staphylococcus aureus (MRSA). Eur. J. Pharm. Sci.136, e104966 (2019).
   PubMed Web of Science ®Google Scholar
• Yang P , LuoJB, ZhangLLet al. Design, synthesis and antibacterial studies of 1,3,4-oxadiazole-fluoroquinolone hybrids and their molecular docking studies. ChemistrySelect6(46), 13209–13214 (2021).
   Web of Science ®Google Scholar
• Gu XL , LiuHB, JiaQHet al. Design and synthesis of novel miconazole-based ciprofloxacin hybrids as potential antimicrobial agents. Monatsh. Chem.146(4), 713–720 (2015).
   Web of Science ®Google Scholar
• Li Q , XingJ, ChengHet al. Design, synthesis, antibacterial evaluation and docking study of novel 2-hydroxy-3-(nitroimidazolyl)-propyl-derived quinolone. Chem. Biol. Drug Des.85(1), 79–90 (2015).
   PubMed Web of Science ®Google Scholar
• Zhang L , KumarKV, RasheedSet al. Design, synthesis, and antimicrobial evaluation of novel quinolone imidazoles and interactions with MRSA DNA. Chem. Biol. Drug Des.86(4), 648–655 (2015).
   PubMed Web of Science ®Google Scholar
• Cui SF , PengLP, ZhangHZet 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).
   PubMed Web of Science ®Google Scholar
• Zhang L , KumarKV, RasheedS, ZhangSLet al. Design, synthesis, and antibacterial evaluation of novel azolylthioether quinolones as MRSA DNA intercalators. Med. Chem. Comm.6(7), 1303–1310 (2015).
   Google Scholar
• Wang YN , BheemanaboinaRRY, GaoWWet al. Discovery of benzimidazole-quinolone hybrids as new cleaving agents toward drug-resistant Pseudomonas aeruginosa DNA. Chem. Med. Chem.13(10), 1004–1017 (2018).
   Google Scholar
• Scaiola A , LeibundgutM, BoehringerDet al. Structural basis of translation inhibition by cadazolid, a novel quinoxolidinone antibiotic. Sci. Rep.9(1), e5634 (2019).
   PubMedGoogle Scholar
• Liu LL , ShaoLP, LiJet al. Synthesis, antibacterial activities, mode of action and acute toxicity studies of new oxazolidinone-fluoroquinolone hybrids. Molecules24(8), e1641 (2019).
   PubMed Web of Science ®Google Scholar
• Gao LZ , XieYS, LiTet al. Synthesis and antibacterial activity of novel [1,2,4]triazolo[3,4-h][1,8]naphthyridine-7-carboxylic acid derivatives. Chin. Chem. Lett.26(1), 149–151 (2015).
   Web of Science ®Google Scholar
• Plech T , WujecM, KosikowskaUet al. Synthesis and in vitro activity of 1,2,4-triazole-ciprofloxacin hybrids against drug-susceptible and drug-resistant bacteria. Eur. J. Med. Chem.60, 128–134 (2013).
   PubMed Web of Science ®Google Scholar
• Gao Y , NaLX, XuZet al. Design, synthesis and antibacterial evaluation of 1-[(1R,2S)-2-fluorocyclopropyl]ciprofloxacin-1,2,4-triazole-5(4H)-thione hybrids. Chem. Biodivers.15(10), E1800261 (2018).
   PubMed Web of Science ®Google Scholar
• Geng YH , WeiZQ, XuZet al. Design, synthesis and antibacterial evaluation of 1-[(1R,2S)-2-fluorocyclopropyl] ciprofloxacin-(4-methyl-3-aryl)-1,2,4-triazole-5(4H)-thione hybrids. Rev. Roum. Chim.64(1), 101–107 (2019).
   Web of Science ®Google Scholar
• Cui SF , RenY, ZhangSLet 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).
   PubMed Web of Science ®Google Scholar
• Rajulu GG , NaikHSB, ViswanathanAet al. Design and synthesis of new N-substituted amino methyl-[1,2,3]triazolyl moieties of fluoroquinolones as antibacterial agents. Med. Chem. Res.22(8), 3843–3856 (2013).
   Web of Science ®Google Scholar
• Rajulu GG , NaikHSB, ViswanathanAet al. New hydroxamic acid derivatives of fluoroquinolones: synthesis and evaluation of antibacterial and anticancer properties. Chem. Pharm. Bull.62(2), 168–175 (2014).
   PubMed Web of Science ®Google Scholar
• Abu-Sini M , MayyasA, Al-KarabliehNet al. Synthesis of 1,2,3-triazolo[4,5-h]quinolone derivatives with novel anti-microbial properties against metronidazole resistant Helicobacter pylori. Molecules22(5), e841 (2017).
   PubMed Web of Science ®Google Scholar
• Qin Y , MaS. Recent advances in the development of macrolide antibiotics as antimicrobial agents. Mini-Rev. Med. Chem.20(7), 601–625 (2020).
   PubMed Web of Science ®Google Scholar
• Jednačak T , MikulandraI, NovakP. Advanced methods for studying structure and interactions of macrolide antibiotics. Int. J. Mol. Sci.21(20), e7799 (2020).
   PubMed Web of Science ®Google Scholar
• Liu XP , LvW, ZhaoFet al. Design and synthesis of novel macrolones bridged with linkers from 11,12-positions of macrolides. Bioorg. Med. Chem. Lett.68, e128761 (2022).
   PubMed Web of Science ®Google Scholar
• Ma CX , LvW, LiYXet al. Design, synthesis and structure-activity relationships of novel macrolones: hybrids of 2-fluoro 9-oxime ketolides and carbamoyl quinolones with highly improved activity against resistant pathogens. Eur. J. Med. Chem.169, 1–20 (2019).
   PubMed Web of Science ®Google Scholar
• Li XM , LvW, GuoSYet al. Synthesis and structure-bactericidal activity relationships of non-ketolides: 9-oxime clarithromycin 11,12-cyclic carbonate featured with three-to eight-atom-length spacers at 3-OH. Eur. J. Med. Chem.171, 235–254 (2019).
   PubMed Web of Science ®Google Scholar
• Pavlović D , KimminsS, MutakS. Synthesis of novel 15-membered 8a-azahomoerythromycin A acylides: consequences of structural modification at the C-3 and C-6 position on antibacterial activity. Eur. J. Med. Chem.125, 210–224 (2017).
   PubMed Web of Science ®Google Scholar
• Pavlović D , MutakS. Synthesis and antibacterial evaluation of novel 4′-glycyl linked quinolyl-azithromycins with potent activity against macrolide-resistant pathogens. Bioorg. Med. Chem.24(6), 1255–1267 (2016).
   PubMed Web of Science ®Google Scholar
• Paljetak HČ , VerbanacD, PadovanJet al. Macrolones are a novel class of macrolide antibiotics active against key resistant respiratory pathogens in vitro and in vivo. Antimicrob. Agents Chemother.60(9), 5337–5348 (2016).
   PubMed Web of Science ®Google Scholar
• Fan BZ , HiasaH, LvWet al. Design, synthesis and structure-activity relationships of novel 15-membered macrolides: quinolone/quinoline-containing sidechains tethered to the C-6 position of azithromycin acylides. Eur. J. Med. Chem.193, e112222 (2020).
   PubMed Web of Science ®Google Scholar
• Nadar S , KhanT. Pyrimidine: an elite heterocyclic leitmotif in drug discovery-synthesis and biological activity. Chem. Biol. Drug Des.100(6), 818–842 (2022).
   PubMed Web of Science ®Google Scholar
• Abu-Taweel GM , IbrahimMM, KhanSet al. Medicinal importance and chemosensing applications of pyridine derivatives: a review. Crit. Rev. Anal. Chem.10.1080/10408347.2022.2089839 (2023).
   Web of Science ®Google Scholar
• Patel KB , KumariP. A review: structure-activity relationship and antibacterial activities of quinoline based hybrids. J. Mol. Struct.1268, e133634 (2022).
   Web of Science ®Google Scholar
• Wahan SK , SharmaB, ChawlaPA. Medicinal perspective of quinazolinone derivatives: recent developments and structure-activity relationship studies. J. Heterocyclic Chem.59(2), 239–257 (2022).
   Web of Science ®Google Scholar
• Schultz JR , CostaSK, JachakGRet al. Identification of 5-(aryl/heteroaryl)amino-4-quinolones as potent membrane-disrupting agents to combat antibiotic-resistant Gram-positive bacteria. J. Med. Chem.65(20), 13910–13934 (2022).
   PubMed Web of Science ®Google Scholar
• Mahdavi M , MostafaviH, ShahbaziAet al. Novel N-4-piperazinyl ciprofloxacin-ester hybrids: synthesis, biological evaluation, and molecular docking studies. Russ. J. Gen. Chem.90(8), 1558–1565 (2020).
   Web of Science ®Google Scholar
• Hong G , LiWT, MaoLet al. Synthesis and antibacterial activity evaluation of N (7) position-modified balofloxacins. Front. Chem.10, e963442 (2022).
   PubMed Web of Science ®Google Scholar
• Chen PT , LinWP, LeeARet al. New 7-[4-(4-(un)substituted)piperazine-1-carbonyl]-piperazin-1-yl] derivatives of fluoroquinolone: synthesis and antimicrobial evaluation. Molecules18(7), 7557–7569 (2013).
   PubMed Web of Science ®Google Scholar
• Song R , WangY, WangMet al. Design and synthesis of novel desfluoroquinolone-aminopyrimidine hybrids as potent anti-MRSA agents with low hERG activity. Bioorg. Chem.103, e104176 (2020).
   PubMed Web of Science ®Google Scholar
• Tan YM , LiD, LiFFet al. Pyrimidine-conjugated fluoroquinolones as new potential broad-spectrum antibacterial agents. Bioorg. Med. Chem. Lett.73, e128885 (2022).
   PubMed Web of Science ®Google Scholar
• Abdel-Aziz SA , CirnskiK, HerrmannJet al. Novel fluoroquinolone hybrids as dual DNA gyrase and urease inhibitors with potential antibacterial activity: design, synthesis, and biological evaluation. J. Mol. Struct.1271, e134049 (2023).
   Web of Science ®Google Scholar
• Samir M , RamadanM, AbdelrahmanMHet al. New potent ciprofloxacin-uracil conjugates as DNA gyrase and topoisomerase IV inhibitors against methicillin-resistant Staphylococcus aureus. Bioorg. Med. Chem.73, e117004 (2022).
   PubMed Web of Science ®Google Scholar
• Fu HG , LiZW, HuXXet al. Synthesis and biological evaluation of quinoline derivatives as a novel class of broad-spectrum antibacterial agents. Molecules24(3), e548 (2019).
   PubMed Web of Science ®Google Scholar
• Adhel E , AnquetinG, DuongNTHet al. Modified fluoroquinolones as antimicrobial compounds targeting Chlamydia trachomatis. Int. J. Mol. Sci.23(12), e6741 (2022).
   PubMed Web of Science ®Google Scholar
• Ciura K , FallareroA, FedorowiczJet al. Synthesis and biological evaluation of hybrid quinolone-based quaternary ammonium antibacterial agents. Eur. J. Med. Chem.179, 576–590 (2019).
   PubMed Web of Science ®Google Scholar
• Ross AG , BentonBM, ChinDet al. Synthesis of ciprofloxacin dimers for evaluation of bacterial permeability in atypical chemical space. Bioorg. Med. Chem. Lett.25(17), e22899 (2015).
   Web of Science ®Google Scholar
• Han Z , KirchmairJ, LiXet al. Discovery of N-quinazolinone-4-hydroxy-2-quinolone-3-carboxamides as DNA gyrase B-targeted antibacterial agents. J. Enzym. Inhib. Med. Chem.37(1), 1620–1631 (2022).
   PubMed Web of Science ®Google Scholar
• Norouzbahari M , SalarinejadS, GüranMet al. Design, synthesis, molecular docking study, and antibacterial evaluation of some new fluoroquinolone analogues bearing a quinazolinone moiety. DARU J. Pharm. Sci.28(2), 661–672 (2020).
   Web of Science ®Google Scholar
• Dhuguru J , ZviaginE, SkoutaR. FDA-approved oximes and their significance in medicinal chemistry. Pharmaceuticals15(1), e66 (2022).
   Web of Science ®Google Scholar
• Walton JC . Functionalised oximes: emergent precursors for carbon-, nitrogen- and oxygen-centered radicals. Molecules21(1), e63 (2016).
   PubMed Web of Science ®Google Scholar
• Sharma V , DasR, MehtaDKet al. Recent insight into the biological activities and SAR of quinolone derivatives as multifunctional scaffold. Bioorg. Med. Chem.59, e116674 (2022).
   PubMed Web of Science ®Google Scholar
• Hu YQ , ZhangS, XuZet al. 4-Quinolone hybrids and their antibacterial activities. Eur. J. Med. Chem.141, 335–345 (2017).
   PubMed Web of Science ®Google Scholar
• Lv K , WuJ, WangJet al. Synthesis and in vitro antibacterial activity of quinolone/naphthyridone derivatives containing 3-alkoxyimino-4-(methyl)aminopiperidine scaffolds. Bioorg. Med. Chem. Lett.23(6), 1754–1759 (2013).
   PubMed Web of Science ®Google Scholar
• Wei Z , WangJ, LiuMet al. Synthesis, in vitro antimycobacterial and antibacterial evaluation of IMB-070593 derivatives containing a substituted benzyloxime moiety. Molecules18(4), 3872–3893 (2013).
   PubMed Web of Science ®Google Scholar
• Zhang T , ShenW, LiuMet al. Synthesis, antimycobacterial and antibacterial activity of fluoroquinolone derivatives containing an 3-alkoxyimino-4-(cyclopropylanimo)methylpyrrolidine moiety. Eur. J. Med. Chem.104, 73–85 (2015).
   PubMed Web of Science ®Google Scholar
• Huang J , WangM, WangBet al. Synthesis, antimycobacterial and antibacterial activity of 1-(6-amino-3,5-difluoropyridin-2-yl)fluoroquinolone derivatives containing an oxime functional moiety. Bioorg. Med. Chem. Lett.26(9), 2262–2267 (2016).
   PubMed Web of Science ®Google Scholar
• Huang J , LiuH, LiuMet al. Synthesis, antimycobacterial and antibacterial activity of l-[(1R,2S)-2-fluorocyclopropyl]naphthyridone derivatives containing an oxime-functionalized pyrrolidine moiety. Bioorg. Med. Chem. Lett.25(22), 5058–5063 (2015).
   PubMed Web of Science ®Google Scholar
• Liu H , HuangJ, WangJet al. Synthesis, antimycobacterial and antibacterial evaluation of l-[(1R,2S)-2-fluorocyclopropyl]fluoroquinolone derivatives containing an oxime functional moiety. Eur. J. Med. Chem.86, 628–638 (2014).
   PubMed Web of Science ®Google Scholar
• Peek J , KoiralaB, BradySF. Synthesis and evaluation of dual-action kanglemycin-fluoroquinolone hybrid antibiotics. Bioorg. Med. Chem. Lett.57, e128484 (2022).
   PubMed Web of Science ®Google Scholar
• Govender H , MocktarC, KumaloHMet al. Synthesis, antibacterial activity and docking studies of substituted quinolone thiosemicarbazones. Phosphorus Sulfur Silicon Relat. Elem.194(11), 1074–1081 (2019).
   Web of Science ®Google Scholar
• Luo JB , ShiQS, WangZZet al. Synthesis and in vitro antibacterial activity of N-acylarylhydrazone-ciprofloxacin hybrids as novel fluoroquinolone derivatives. J. Mol. Struct.1262, e133007 (2022).
   Web of Science ®Google Scholar
• Rajulu GG , NaikHSB, KumarGCet al. New azetidine-3-carbonyl-N-methyl-hydrazino derivatives of fluoroquinolones: synthesis and evaluation of antibacterial and anticancer properties. Med. Chem. Res.23(6), 2856–2868 (2014).
   Web of Science ®Google Scholar
• Taghavi Z , HassanshahianM, HassanshahiG. Study of antimicrobial effect of a new fluoroquinolone derivative against pathogenic bacteria in planktonic form and biofilm. Proc. Natl Acad. Sci., India, Sect. B Biol. Sci.10.1007/s40011-022-01408-5 (2023).
   Google Scholar
• Sedghizadeh PP , SunS, JunkaAFet al. Design, synthesis, and antimicrobial evaluation of a novel bone-targeting bisphosphonate-ciprofloxacin conjugate for the treatment of osteomyelitis biofilms. J. Med. Chem.60(6), 2326–2343 (2017).
   PubMed Web of Science ®Google Scholar
• Yang JQ , CheWL, WangWet al. Synthesis and antibacterial activity of novel 7-phosphoryl quinolone derivatives. Chin. Pharm. J.54(2), 86–90 (2019).
   Google Scholar
• Bukharov SV , BulatovaES, BurilovARet al. Synthesis and antibacterial activity of fluoroquinolones with sterically hindered phenolic moieties. Russ. Chem. Bull.71(3), 508–516 (2022).
   Web of Science ®Google Scholar
• Komarnicka UK , StarostaR, Guz-RegnerKet al. Phosphine derivatives of sparfloxacin–synthesis, structures and in vitro activity. J. Mol. Struct.1096, 55–63 (2015).
   Web of Science ®Google Scholar
• Hur JK , JungY, KangSet al. Membrane-targeting triphenylphosphonium functionalized ciprofloxacin for methicillin-resistant Staphylococcus aureus (MRSA). Antibiotics9(11), e758 (2020).
   Google Scholar
• Purkayastha N , CaponeS, BeckAKet al. Antibacterial activity of enrofloxacin and ciprofloxacin derivatives of β-octaarginine. Chem. Biodivers.12, 179–193 (2015).
   PubMed Web of Science ®Google Scholar
• Berry L , DomalaonR, BrizuelaMet al. Polybasic peptide-levofloxacin conjugates potentiate fluoroquinolones and other classes of antibiotics against multidrug-resistant Gram-negative bacteria. MedChemComm10(4), 517–527 (2019).
   PubMed Web of Science ®Google Scholar
• Durcik M , SkokŽ, IlašJet al. Hybrid inhibitors of DNA gyrase A and B: design, synthesis and evaluation. Pharmaceutics13(1), e6 (2021).
   Web of Science ®Google Scholar
• Fois B , SkokŽ, TomašičTet al. Dual Escherichia coli DNA gyrase A and B inhibitors with antibacterial activity. Chem. Med. Chem.15(3), 265–269 (2020).
   Google Scholar
• Xiao ZP , WangXD, WangPFet al. Design, synthesis, and evaluation of novel fluoroquinolone-flavonoid hybrids as potent antibiotics against drug-resistant microorganisms. Eur. J. Med. Chem.80, 92–100 (2014).
   PubMed Web of Science ®Google Scholar
• Esfahani EN , Mohammadi-KhanaposhtaniM, RezaeiZet al. Biology-oriented drug synthesis (BIODS) approach towards synthesis of ciprofloxacin-dithiocarbamate hybrids and their antibacterial potential both in vitro and in silico. Chem. Biodivers.15(10), E1800273 (2018).
   PubMed Web of Science ®Google Scholar
• Wang XD , WeiW, WangPFet al. Novel 3-arylfuran-2(5H)-one-fluoroquinolone hybrid: design, synthesis and evaluation as antibacterial agent. Bioorg. Med. Chem.22(14), 3620–3628 (2014).
   PubMed Web of Science ®Google Scholar
• Wang R , YinX, ZhangYet al. Design, synthesis and antimicrobial evaluation of propylene-tethered ciprofloxacin-isatin hybrids. Eur. J. Med. Chem.156, 580–586 (2018).
   PubMed Web of Science ®Google Scholar
• Gao F , YeL, KongFet al. Design, synthesis and antibacterial activity evaluation of moxifloxacin-amide-1,2,3-triazole-isatin hybrids. Bioorg. Chem.91, e103162 (2019).
   PubMed Web of Science ®Google Scholar
• Guo H . Design, synthesis, and antibacterial evaluation of propylene-tethered 8-methoxyl ciprofloxacin-isatin hybrids. J. Heterocyclic Chem.55(10), 2434–2440 (2018).
   Web of Science ®Google Scholar
• Guo H . Design, synthesis, and in vitro antibacterial activities of propylene-tethered gatifloxacin-isatin hybrids. J. Heterocyclic Chem.55(8), 1899–1905 (2018).
   Web of Science ®Google Scholar
• Domalaon R , AmmeterD, BrizuelaMet al. Repurposed antimicrobial combination therapy: tobramycin-ciprofloxacin hybrid augments activity of the anticancer drug mitomycin C against multidrug-resistant Gram-negative bacteria. Front. Microbiol.10, e1556 (2019).
   PubMed Web of Science ®Google Scholar
• Shavit M , PokrovskayaV, BelakhovVet al. Covalently linked kanamycin-ciprofloxacin hybrid antibiotics as a tool to fight bacterial resistance. Bioorg. Med. Chem.25(11), 2917–2925 (2017).
   PubMed Web of Science ®Google Scholar
• Mohammed AAM , SuaifanGARY, ShehadehMBet al. Design, synthesis and antimicrobial evaluation of novel glycosylated-fluoroquinolones derivative. Eur. J. Med. Chem.202, e112513 (2020).
   PubMed Web of Science ®Google Scholar
• Mohammed AAM , SuaifanGARY, ShehadehMBet al. Design, synthesis, and biological evaluation of 1,8-naphthyridine glucosamine conjugates as antimicrobial agents. Drug Dev. Res.80(1), 179–186 (2019).
   PubMed Web of Science ®Google Scholar
• Tahir S , MahmoodT, DastgirFet al. Design, synthesis and anti-bacterial studies of piperazine derivatives against drug resistant bacteria. Eur. J. Med. Chem.166, 224–231 (2019).
   PubMed Web of Science ®Google Scholar
• Kulabaş N , TüreA, BozdeveciAet al. Novel fluoroquinolones containing 2-arylamino-2-oxoethyl fragment: design, synthesis, evaluation of antibacterial and antituberculosis activities and molecular modeling studies. J. Heterocyclic Chem.59(5), 909–926 (2022).
   Web of Science ®Google Scholar
• Li WT , HongG, MaoLet al. Synthesis, antibacterial evaluation and in silico study of DOTA-fluoroquinolone derivatives. Med. Chem. Res.31(5), 705–719 (2022).
   Web of Science ®Google Scholar
• Allaka TR , AnireddyJS. Novel 7-substituted fluoroquinolone citrate conjugates as powerful antibacterial and anticancer agents: synthesis and molecular docking studies. Curr. Org. Chem.23, 1992–2003 (2019).
   Web of Science ®Google Scholar
• Milner MJ , SnellingAM, KerrKGet al. Probing linker design in citric acid-ciprofloxacin conjugates. Bioorg. Med. Chem.22(16), 4499–4505 (2014).
   PubMed Web of Science ®Google Scholar
• Evans LE , KrishnaA, MaYet al. Exploitation of antibiotic resistance as a novel drug target: development of a β-lactamase-activated antibacterial prodrug. J. Med. Chem.62(9), 4411–4425 (2019).
   PubMed Web of Science ®Google Scholar
• Balasubramaniyan S , IrfanN, SenthilkumarCet al. The synthesis and biological evaluation of virtually designed fluoroquinolone analogs against fluoroquinolone-resistant: escherichia coli intended for UTI treatment. New J. Chem.44(31), 13308–13318 (2020).
   Web of Science ®Google Scholar
• Moynihan E , MackeyK, BlaskovichMATet al. N-alkyl-2-quinolonopyrones demonstrate antimicrobial activity against ESKAPE pathogens including Staphylococcus aureus. ACS Med. Chem. Lett.13(8), 1358–1362 (2022).
   PubMed Web of Science ®Google Scholar