Synthesis and antibacterial studies of ciprofloxacin-metal complexes
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摘要
Metal complexes of ciprofloxacin were synthesized to study the effect of the drug on the metals present in the body or metals co-administered as multivitamin therapy. These complexes were then characterized by IR, UV, 1 H NMR, CHN and AA analyses. It was found that the metals coordinated through the β-keto carboxylic group, forming four coordinated complexes having square planar geometry. The effect of the antibacterial activity of these complexes with respect to parent drug was also studied against 14 different Gram + ve and Gram – ve organisms by the disk susceptibility technique. Some complexes showed improve activity as compared with the stated drug.
Metal complexes of ciprofloxacin were synthesized to study the effect of the drug on the metals present in the body or metals co-administered as multivitamin therapy. These complexes were then characterized by IR, UV, ~1H NMR, CHN and AA analyses. It was found that the metals coordinated through the β-keto carboxylic group, forming four coordinated complexes having square planar geometry. The effect of the antibacterial activity of these complexes with respect to parent drug was also studied against 14 different Gram + ve and Gram – ve organisms by the disk susceptibility technique. Some complexes showed improve activity as compared with the stated drug.
Metal complexes of ciprofloxacin were synthesized to study the effect of the drug on the metals present in the body or metals co-administered as multivitamin therapy. These complexes were then characterized by IR, UV, ~1H NMR, CHN and AA analyses. It was found that the metals coordinated through the β-keto carboxylic group, forming four coordinated complexes having square planar geometry. The effect of the antibacterial activity of these complexes with respect to parent drug was also studied against 14 different Gram + ve and Gram – ve organisms by the disk susceptibility technique. Some complexes showed improve activity as compared with the stated drug.
引文
[1]Chapman&Hall/CRC Published on CD-ROM Hampden Data Services Ltd.1999.
[2]Siddiqui,F.A.;Arayne,M.S.;Sultana,N.;Mirza,A.Z.;Qureshi,F.;Zuberi,M.H.Facile and manifest spectrophotometric methods for the determination of six quinolone antibiotics in pharmaceutical formulations using iron salts.Med.Chem.Res.2010,19,1259-1272.
[3]Rakhshinda,S.;Najma,S.;Khalid,M.K.;Nosheen,A.;Muhammad,A.;Saeed,A.Effects of skeletal modifications of ciprofloxacin on antibacterial,antifungal and cytotoxic activities,J.Chin.Clin.Med.2007,2,188-195.
[4]Arayne,M.S.;Sultana,N.;Rizvi,S.B.S.;Haroon,U.In vitro drug interaction studies of atorvastatin with ciprofloxacin,gatifloxacin,and ofloxacin.Med.Chem.Res.2010,19,717-731.
[5]Barriere,S.L.;Catlin,D.H.;Orlando,P.L;Noe.A.;Frost,R.W.Alteration in the pharmacokinetic disposition of ciprofloxacin by simultaneous administration of azlocillin.Antimicrob.Agents Chemother.1990,34,823-826.
[6]Avent,C.K.;Krinsky,D.;Kirklin,J.K.;Bourge,R.C.;Figg,W.D.Synergistic nephrotoxicity due to ciprofloxacin and cyclosporine.Am.J.Med.1988,85,452-454.
[7]Shafi,N.;Siddiqui,F.A.;Arayne,M.S.;Sultana,N.In-vitro drug-drug interaction studies of diltiazem with floroquinolones.J.Liq.Chromatogr.Relat.Technol.2017,40,1003-1014.
[8]Arayne,M.S.;Sultana,N.;Hussain,F.Interactions between ciprofloxacin and antacids-dissolution and adsorption studies.Drug Metabol.Drug Interact.2005,21,117-129.
[9]Najma,S.M.;Saeed,A.;Fida,H.In vitro Monitoring of Ciprofloxacin Antacids Interactions by UV&HPLC.Pakistan J.Pharm.Sci.2005,18,23-31.
[10]Polk,R.E.;Healy,D.P.;Sahai,J.;Drawl,L.;Racht,E.Effect of ferrous sulfate and multivitamins with zinc on absorption of ciprofloxacin in normal volunteers.Antimicrob.Agent.Chemother.1989,33,1841-1844.
[11]Ndagi,U.;Mhlongo,N.;Soliman,M.E.Metal complexes in cancer therapy-an update from drug design perspective.Drug Des.Devel.Ther.2017,11,599-616.
[12]Bauer,A.W.;Kirby,W.M.M.;Sherris,J.C.;Turck,M.Antibiotic susceptibility testing by a standardized single disk method.Am.J.Clin.Pathol.1966,45,493-496.
[13]Victor,L.M.D.Antibiotics in Laboratory Medicine.Williams and Wilkins,1991,3,17,19 and 27.
[14]National Committee on Clinical Laboratory Standards,2012,Performance Standards for Antimicrobial Disk Susceptibility Tests;Approved Standard-11th Edition,M02-A11 Vol.32 No.1 Replaces M02-A10 Vol.29 No.1.
[15]Hartshorn,E.A.;Lomaestero,B.N.;Bailie,G.R.QuinoloneCation Interactions:A Review.Ann.Pharm.1991,25,1249-1258.
[16]Turel,I.;Leban,I.;Bukovec,N.Synthesis,characterization,and crystal structure of a copper(II)complex with quinolone family member(ciprofloxacin):bis(1)-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-piperazin-1ylquinoline-3-carboxylate)copper(II)chloride hexahydrate.J.Inorg.Biochem.1994,56,273-282.
[17]Guanggun,W.U.;Guoping,W.;Xuchun,F.;Longguan,Z.Synthesis,Crystal Structure,Stacking Effect and Antibacterial Studies of a Novel Quaternary Copper(II)Complex with Quinolone.Molecule.2003,8,287-296.
[18]Lecomte,S.;Baron,M.H.;Chenon,M.T.;Coupry,C.;Moreau,N.J.Effect of magnesium complexation by fluoroquinolones on their antibacterial properties.Antimicrob.Agent.Chemother.1994,38,2810-2816.
[19]Marija,Z.;Iztok,T.;Peter,B.;Andrew,J.P.W.;David,J.W.Synthesis and Characterization of Two Novel Zinc(II)Complexes with Ciprofloxacin.Crystal Structure of[C17H19N3O3F]2?[ZnCl4]?2H2O.Croat.Chem.Acta.2001,74,61-74.
[20]Heinz,G.W.;Marc,S.;Hans,V.T.;Axel,D.;Wolfgang,K.Degradation of Ciprofloxacin by Basidiomycetes and Identification of Metabolites Generated by the Brown Rot Fungus Gloeophyllum striatum.Appl.Environ.Microbiol.1999,65,1556-1563.
[21]Arayne,M.S.;Sultana,N.;Mirza,A.Z.,Preparation and spectroscopic characterization of metal complexes of gliquidone.J.Mol.Struct.2009,927,54-59.
[2]Siddiqui,F.A.;Arayne,M.S.;Sultana,N.;Mirza,A.Z.;Qureshi,F.;Zuberi,M.H.Facile and manifest spectrophotometric methods for the determination of six quinolone antibiotics in pharmaceutical formulations using iron salts.Med.Chem.Res.2010,19,1259-1272.
[3]Rakhshinda,S.;Najma,S.;Khalid,M.K.;Nosheen,A.;Muhammad,A.;Saeed,A.Effects of skeletal modifications of ciprofloxacin on antibacterial,antifungal and cytotoxic activities,J.Chin.Clin.Med.2007,2,188-195.
[4]Arayne,M.S.;Sultana,N.;Rizvi,S.B.S.;Haroon,U.In vitro drug interaction studies of atorvastatin with ciprofloxacin,gatifloxacin,and ofloxacin.Med.Chem.Res.2010,19,717-731.
[5]Barriere,S.L.;Catlin,D.H.;Orlando,P.L;Noe.A.;Frost,R.W.Alteration in the pharmacokinetic disposition of ciprofloxacin by simultaneous administration of azlocillin.Antimicrob.Agents Chemother.1990,34,823-826.
[6]Avent,C.K.;Krinsky,D.;Kirklin,J.K.;Bourge,R.C.;Figg,W.D.Synergistic nephrotoxicity due to ciprofloxacin and cyclosporine.Am.J.Med.1988,85,452-454.
[7]Shafi,N.;Siddiqui,F.A.;Arayne,M.S.;Sultana,N.In-vitro drug-drug interaction studies of diltiazem with floroquinolones.J.Liq.Chromatogr.Relat.Technol.2017,40,1003-1014.
[8]Arayne,M.S.;Sultana,N.;Hussain,F.Interactions between ciprofloxacin and antacids-dissolution and adsorption studies.Drug Metabol.Drug Interact.2005,21,117-129.
[9]Najma,S.M.;Saeed,A.;Fida,H.In vitro Monitoring of Ciprofloxacin Antacids Interactions by UV&HPLC.Pakistan J.Pharm.Sci.2005,18,23-31.
[10]Polk,R.E.;Healy,D.P.;Sahai,J.;Drawl,L.;Racht,E.Effect of ferrous sulfate and multivitamins with zinc on absorption of ciprofloxacin in normal volunteers.Antimicrob.Agent.Chemother.1989,33,1841-1844.
[11]Ndagi,U.;Mhlongo,N.;Soliman,M.E.Metal complexes in cancer therapy-an update from drug design perspective.Drug Des.Devel.Ther.2017,11,599-616.
[12]Bauer,A.W.;Kirby,W.M.M.;Sherris,J.C.;Turck,M.Antibiotic susceptibility testing by a standardized single disk method.Am.J.Clin.Pathol.1966,45,493-496.
[13]Victor,L.M.D.Antibiotics in Laboratory Medicine.Williams and Wilkins,1991,3,17,19 and 27.
[14]National Committee on Clinical Laboratory Standards,2012,Performance Standards for Antimicrobial Disk Susceptibility Tests;Approved Standard-11th Edition,M02-A11 Vol.32 No.1 Replaces M02-A10 Vol.29 No.1.
[15]Hartshorn,E.A.;Lomaestero,B.N.;Bailie,G.R.QuinoloneCation Interactions:A Review.Ann.Pharm.1991,25,1249-1258.
[16]Turel,I.;Leban,I.;Bukovec,N.Synthesis,characterization,and crystal structure of a copper(II)complex with quinolone family member(ciprofloxacin):bis(1)-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-piperazin-1ylquinoline-3-carboxylate)copper(II)chloride hexahydrate.J.Inorg.Biochem.1994,56,273-282.
[17]Guanggun,W.U.;Guoping,W.;Xuchun,F.;Longguan,Z.Synthesis,Crystal Structure,Stacking Effect and Antibacterial Studies of a Novel Quaternary Copper(II)Complex with Quinolone.Molecule.2003,8,287-296.
[18]Lecomte,S.;Baron,M.H.;Chenon,M.T.;Coupry,C.;Moreau,N.J.Effect of magnesium complexation by fluoroquinolones on their antibacterial properties.Antimicrob.Agent.Chemother.1994,38,2810-2816.
[19]Marija,Z.;Iztok,T.;Peter,B.;Andrew,J.P.W.;David,J.W.Synthesis and Characterization of Two Novel Zinc(II)Complexes with Ciprofloxacin.Crystal Structure of[C17H19N3O3F]2?[ZnCl4]?2H2O.Croat.Chem.Acta.2001,74,61-74.
[20]Heinz,G.W.;Marc,S.;Hans,V.T.;Axel,D.;Wolfgang,K.Degradation of Ciprofloxacin by Basidiomycetes and Identification of Metabolites Generated by the Brown Rot Fungus Gloeophyllum striatum.Appl.Environ.Microbiol.1999,65,1556-1563.
[21]Arayne,M.S.;Sultana,N.;Mirza,A.Z.,Preparation and spectroscopic characterization of metal complexes of gliquidone.J.Mol.Struct.2009,927,54-59.