O羧甲基化壳聚糖季铵盐的制备及抑菌活性

792011,Vol.32,No.09O-(741001)3--2-(CTA)O-O-(E.coli)(S.aureus)(A.niger)O-E.coliS.aureusA.nigerO-PreparationandAntibacterialActivityofWater-solubleO-CarboxymethylChitosanQuaternaryAmmoniumSaltLIXiao-fangFENGXiao-qiangYANGShengMAZhi-junXUBen-jin(CollegeofLifeScienceandChemistry,TianshuiNormalUniversity,Tianshui741001,China)AbstractObjective:Toprepareandstructurallycharacterizewater-solubleO-carboxymethylchitosanquaternaryammoniumsalt(CMCQAS),andtoevaluateitsantibacterialactivity.Method:Thepreparationofwater-solubleCMCQASwasconductedbyusing3-chloro-2-hydroxypropyltrimethylammoniumchloride(CTA)andchloroaceticacidasgraftingagents.ItsstructurewascharacterizedbyIRandultravioletspectroscopyanditsantibacterialactivitiyagainstS.aureus,E.coliandA.nigerwereevaluated.Results:Thepreparedwater-solubleCMCQAShadadistinctantibacterialactivityagainstS.aureus,E.coliandA.niger,whichwashigherthanthatofchitosan(CS).KeywordschitosancarboxymethylquaternaryammoniumsaltantibacterialactivityO627.181A1002-6630(2011)09-0079-032010-09-03(ZD0840)(1983)[e-mail](chitosanCS),[1-2][3-4][5-7][8-9]6-OHO-(CMC)CMCO-(CMCQAS)(S.aureus)(E.coli)(A.niger)11.1(5104D95%)O-(CMC)[4]SpectrumOnePerkinElmereUV-2450-1.2(E.coliATCC35218)(S.aureusATCC26113)(A.niger)2011,Vol.32,No.0980(PDA)[10]200g30min20g1520g1000mLpH12120min()[10]1000mL10g3g5gNaCl20gpH7.47.612120min1.3O-(CMCQAS)O-1.0g20mL15mL40%NaOH457.5mL2,3-809089h0.62[4]0.54KBrCSCMCCMCQAS1.0%CSCMCCMCQAS1.0mg/mL190450nm1.41.4.11.0%CSCMCCMCQAS10mg/mL3724h1mLCSCMCCMCQAS29mL37610nm(OD610nm)CMCQAS(MIC)E.coliS.aureus0.9%OD610nm0.001CMCQASCMCQAS0.0250.050.10.150.20.25mg/mL12120min0.1mL30min37E.coliS.aureus24h48hMIC51.4.2A.nigerPDA2772h0.8cm3.0mLCSCMCCMCQASPDACSCMCCMCQAS1.0mg/mL1.0%12120min27A.niger22.1O-2.1.11CS1152.841083.041664.51cm-1OCOCONH1599.46cm-11325.13cm-1CNCMC1742.55cm-1CO1217.72cm-1CH2COOHCOOH(CH2COOH)1138.4cm-11068.51cm-1OCOCS6OHCMCQASCSNH1380cm-11CMCQAS2.1.21CSCMCCMCQASFig.1IRspectraofCS,CMCandCMCQASCS/cm136002800200016001200800400CMCCMCQAS2CS(a)CMC(b)CMCQAS(c)Fig.2UVspectraofCS(a)CMC(b)andCMCQAS(c)a/nm2.01.51.00.50.0A190300400450bc812011,Vol.32,No.092CS220.5nmn*CMC210nm198250nmCMCCOOHCO*CMCQAS288nmCSCMC2.2CMCQAS3CSCMCCMCQASE.coliS.aureusCSCMCCMCQASCMCQASOD610nmCMCQASE.coliS.aureusCMCQAS0.1mg/mLE.coliS.aureusCMCQASE.coliS.aureusMIC0.1mg/mLCSE.coliS.aureusMIC0.5mg/mL[11]CMCQASE.coliS.aureusMICCS5CMCQASE.coliS.aureusCSCSCMCCMCQAS44dCSCMCCMCQASCSCMCCMCQASCMCQAS3CMCQASE.coliS.aureusA.nigerCMCQASE.coliS.aureusMICCS5CMCQASE.coliS.aureusCS[1]CHUNGYC,CHENCY.Antibacterialcharacteristicsandactivityofacid-solublechitosan[J].BioresourceTechnol,2008,99:2806-2814.[2]JEONYJ,KIMSK.Chitosanderivativeskilledbacteriabydisruptingtheouterandinnermembrane[J].JournalofAgriculturalandFoodChemistry,2006,54(18):6629-6633.[3]LIUXiaofei,GUANYunlin,YANGDongzhi,etal.Antibacterialactionofchitosanandcarboxymethylatedchitosan[J].JournalofAppliedPoly-merScience,2001,79:1324-1335.[4],,.O-[J].,2010,31(11):77-80.[5]RUNARSSONOV,HOLAPPAJ,MALAINERC,etal.AntibacterialactivityofN-quaternarychitosanderivatives:synthesis,characterizationandstructureactivityrelationship(SAR)investigations[J].EuropeanPolymerJournal,2010,46(6):1251-1267.[6]SAJOMSANGW,GONILP,TANTAYANONS.Antibacterialactivityofquaternaryammoniumchitosancontainingmonoordisaccharidemoieties:preparationandcharacterization[J].InternationalJournalofBiologicalMacromolecules,2009,44:419-427.[7]SAJOMSANGW,TANTAYANONS,TANGPASUTHADOLV,etal.QuaternizationofN-arylchitosanderivatives:synthesis,characterization,andantibacterialactivity[J].CarbohydrateResearch,2009,344:2502-2511.[8],,.HeLa[J].,2008,25(6):734-737.[9],,.[J].,2006,23(11):22-24.[10],,.[M].:,1999:214-215.[11],,,.[J].,2009,30(7):63-67.3CSCMCCMCQASE.coli(A)S.aureus(B)OD610nmFig.3OD610nmofE.coli(A)andS.aureus(B)cellsversusexposuretimetoCS,CMCorCMCQASCMCCMCQAS/h0.400.350.300.250.200.150.100.050.00OD610nm14710131619222528CSACMCCMCQAS/h0.450.400.350.300.250.200.150.100.050.00OD610nm14710131619222528CSBa.b.CSc.CMCd.CMCQAS4CSCMCCMCQASFig.4EffectofCS,CMCandCMCQASonthegrowthofA.nigerabcd..