Modification on Ciprofloxacin Moiety to Synthesize Some New Derivatives with Screening Antibacterial Activity
DOI:
https://doi.org/10.21123/bsj.2023.9096Keywords:
Anti-bacterial, Cell line, Ciprofloxacin, Quinolone, Well diffusion assayAbstract
A major global public health problem is the emergence of antimicrobial resistance to common commercial medications. Therefore, there is an urgent need for new antimicrobials with enhanced biological activity. In this regard , in this study 5 novel Quinolone derivative A, B, C, D, and E were synthesized and their structure was analyzed using UV light, FTIR, 1H NMR, and 13C NMR techniques. The structure of synthesized compounds was investigated. The well diffusion assay method was used to test the synthetic compounds' antibacterial properties in vitro against two Gram-positive (Staphylococcus aureus and Streptococcus pyogenes) and two Gram-negative (Escherichia coli and Klebsiella pneumoniae) bacteria. Ciprofloxacin drug was used as an antibiotic standard. Best activity was shown by compound C against E. coli with an inhibition zone of 30mm and 33 mm at 250and 500 μg/mL respectively. While compound B in Staphylococcus aureus has high inhibition zone of 42mm and 47mm at 250and 500μg/mL respectively. However compound D in Klebsiella pneumoniae has high inhibition zone of 32mm and 35mm at 250 and 500μg/mL respectively, while compound A for Streptococcus pyogenes has inhibition zone of 45mm and 47mm at 250 and 500μg/mL respectively.
Received 20/05/2023
Revised 8/09/2023
Accepted 10/09/2023
Published Online First 25/12/2023
References
Al Salman J, Al Dabal L, Bassetti M, Alfouzan WA, Al Maslamani M, Alraddadi B, et al . Management of infections caused by WHO critical priority Gram-negative pathogens in Arab countries of the Middle East: a consensus paper. Int. J Antimicrob Agents. 2020; 56(4):106104.https://doi.org/10.1016/j.ijantimicag.2020.106104.
Panda S, Swain SK, Sahu BP, Sarangi R. Gene expression and involvement of signaling pathways during host–pathogen interplay in Orientia tsutsugamushi infection. Biotechnol J. 2022; 12(9): 180. http://dx.doi.org/10.1007/s13205-022-03239-7
Saleh GM. Green synthesis concept of nanoparticles from environmental bacteria and their effects on pathogenic bacteria. Iraqi J. Sci. 2020; 61(6): 1289-1297. https://doi.org/10.24996/ijs.2020.61.6.6
Sadiq AS, Khudhair ZT, Yousif SA, Mahmood WA. Synthesis, Identification, Theoretical Study, and Effect of the New Heterocyclic System from Ciprofloxacin Derivatives on the Activity of Some Liver Enzymes. Baghdad Sci J. 2022; 19(6): 1454. http://dx.doi.org/10.21123/bsj.2022.19.4.ID0000
Tabassum R, Ashfaq M, Oku H. Current pharmaceutical aspects of synthetic quinoline derivatives. Mini-Rev Med Chem. 2021; 21(10): 1152-1172. https://doi.org/10.2174/1389557520999201214234735
Persoons L, Vanderlinden E, Vangeel L, Wang X, Do ND, Foo SY, et al. Broad spectrum anti-coronavirus activity of a series of anti-malaria quinoline analogues. Antiviral Res. 2021; 193(1): 105127. https://doi.org/10.1016/j.antiviral.2021.105127
Panda P, Chakroborty S. Navigating the synthesis of quinoline hybrid molecules as promising anticancer agents. ChemistrySelect. 2020; 5(33): 10187-10199. https://doi.org/10.1002/slct.202002790.
Man RJ, Jeelani N, Zhou C, Yang YS. Recent progress in the development of quinoline derivatives for the exploitation of anti-cancer agents. Med Chem. 2021; 21(7): 825-838. https://doi.org/10.2174/1871520620666200516150345
Patel KB, Kumari P. A review: Structure-activity relationship and antibacterial activities of Quinoline based hybrids. J Mol Struct. 2022; 1268(1): 133634. https://doi.org/10.1016/j.molstruc.2022.133634
Zeleke D, Eswaramoorthy R, Belay Z, Melaku Y. Synthesis and antibacterial, antioxidant, and molecular docking analysis of some novel quinoline derivatives. J Chem. 2020; 2020(1): 1-16. https://doi.org/10.1155/2020/1324096
Ben Yaakov D, Shadkchan Y, Albert N, Kontoyiannis DP, Osherov N. The quinoline bromoquinol exhibits broad-spectrum antifungal activity and induces oxidative stress and apoptosis in Aspergillus fumigatus. J Antimicrob. Chemother. 2017; 72 (8): 2263–2272. https://doi.org/10.1093/jac/dkx117
Senerovic L, Opsenica D, Moric I, Aleksic I, Spasić M, Vasiljevic B. Quinolines and quinolones as antibacterial, antifungal, anti-virulence, antiviral and anti-parasitic agents. J Adv microbiol. 2020; 14(1): 37-69. https://doi.org/10.1007/5584_2019_428
Ajani OO, Iyaye KT, Ademosun OT. Recent advances in chemistry and therapeutic potential of functionalized quinoline motifs–a review. RSC Adv. 2022; 12(29): 18594-18614. https://doi.org/10.1039/D2RA02896D
Matada BS, Pattanashettar R, Yernale NG. A comprehensive review on the biological interest of quinoline and its derivatives. Bioorg Med Chem. 2021; 32(1): 115973. https://doi.org/10.1016/j.bmc.2020.115973
Savegnago L, Vieira AI, Seus N, Goldani BS, Castro MR, Lenardão EJ, et al. Synthesis and antioxidant properties of novel quinoline–chalcogenium compounds. Tetrahedron Lett. 2013; 54(1): 40–44. https://doi.org/10.1016/j.tetlet.2012.10.067
Ghanim AM, Girgis AS, Kariuki BM, Samir N, Said MF, Abdelnaser A, et al. Design and synthesis of ibuprofen-quinoline conjugates as potential anti-inflammatory and analgesic drug candidates. Bioorg Chem. 2022; 119(1): 105557. https://doi.org/10.1016/j.bioorg.2021.105557
George RF, Samir EM, Abdelhamed MN, Abdel-Aziz HA, Abbas SE. Synthesis and anti-proliferative activity of some new quinoline based 4, 5-dihydropyrazoles and their thiazole hybrids as EGFR inhibitors. Bioorg Chem. 2019; 83(1): 186-197. https://doi.org/10.1016/j.bioorg.2018.10.038
Borsoi AF, Alice LM, Sperotto N, Ramos AS, Abbadi BL, Macchi Hopf FS, et al. Antitubercular activity of novel 2-(quinoline-4-yloxy) acetamides with improved drug-like properties. ACS Med Chem Lett. 2022; 13(8): 1337-44. https://doi.org/10.1021/acsmedchemlett.2c00254
Al-Hussein IR, Al-Shuhaib ZA. Synthesis and Characterization of Some New Pyridine and Pyrimidine Derivatives and Studying Their Biological Activities. Baghdad Sci J; 2022. https://doi.org/10.21123/bsj.2022.7012
Godoy-Vitorino F. Human microbial ecology and the rising new medicine. Ann Transl Med. 2019; 7(14): 342–342. https://doi.org/10.21037%2Fatm.2019.06.56.
Ibraheem DR, Hussein NN, Sulaiman GM. Antibacterial Activity of Silver nanoparticles Against Pathogenic Bacterial Isolates from Diabetic Foot Patients. Iraqi J Sci. 2023; 64(5): 2223-2239. https://doi.org/10.24996/ijs.2023.64.5.11
Hussein NN, Marzoog TR, Al-Niaame AE .The antibacterial, antiheamolytic, and antioxidant activities of Laurus nobilis and Alhagi maurorum native to Iraq. Baghdad Sci J. 2019 ; 16(3): 707-712. http://dx.doi.org/10.21123/bsj.2019.16.3(Suppl.).0707
Toma JJ, Aziz FH. Antibacterial Activity of Three Algal Genera against some Pathogenic Bacteria. Baghdad Sci J. 2023; 20(1): 0032-0032. https://doi.org/10.21123/bsj.2022.6818
Abd-El-Raouf R, Ouf SA, Haggag MG, El-Yasergy KF, Zakaria MM. Mesenchymal and stemness transdifferentiation via in-vitro infection of T24 cell line with Klebsiella pneumoniae. Baghdad Sci J. 2023; 20(3): 797-804. https://dx.doi.org/10.21123/bsj.2022.6826
Ahmed BJ, Saleem MH, Matty FS .Synthesis and Study of the Antimicrobial Activity of Modified Polyvinyl Alcohol Films Incorporated with Silver Nanoparticles. Baghdad Sci J. 2023; Online-First (2). https://doi.org/10.21123/bsj.2023.7471
Al-Hasnawy HH, Judi MR, Hamza HJ.The dissemination of multidrug resistance MDR and extensively drug resistant XDR among uropathogenic E. coli UPEC isolates from urinary tract infection patients in Babylon Province, Iraq. Baghdad Sci J. 2019; 16(4 ): 986-922. http://dx.doi.org/10.21123/bsj.2019.16.4(Suppl.).0986
Behera S, Mohanty P, Behura R, Nath B, Barick AK, Jali BR. Antibacterial properties of quinoline derivatives:Amini. Biointerface Res Appl Chem. 2022; 12(5): 6078-6092. https://doi.org/10.33263/BRIAC125.60786092
Arshad AS, Chear NJ, Ezzat MO, Hanapi NA, Meesala R, Arshad S, et al . Synthesis, characterization and crystal structure of new tetrahydro-β-carboline as acetylcholinesterase inhibitor. J Mol Struct. 2020; 1200 (1):127070. https://doi.org/10.1016/j.molstruc.2019.127070
Khalid M, Ullah MA, Adeel M, Khan MU, Tahir MN, Braga AA. Synthesis, crystal structure analysis, spectral IR, UV–Vis, NMR assessments, electronic and nonlinear optical properties of potent quinoline based derivatives: Interplay of experimental and DFT study. J Saudi Chem. Soc. 2019 ; 23(5): 546-60. https://doi.org/10.1016/j.jscs.2018.09.006
Hussein EA, Kareem SH, Kadhim MM, Hadei MS. Effect of Ciprofloxacin and Metronidazole drugs on thermodynamic and surface properties of sodium Di-2-ethylhexylsulfosuccinate surfactant. AIP Conf Proc. 2022; 2547(1). https://doi.org/10.1063/5.0116063
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