B-降胆甾苯并咪唑化合物对金属离子识别性能研究
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摘要
苯并咪唑是优良的离子探针活性基团,以3种不同取代基结构的B-降胆甾苯并咪唑化合物作为金属离子受体,采用紫外光谱法和荧光光谱法对12种不同的金属离子(Co~(2+)、K~+、Na~+、Li~+、Pb~(2+)、Ca~(2+)、Zn~(2+)、Sr~(2+)、Ni~(2+)、Ag~+、Hg~(2+)、Cu~(2+))进行检测,结果表明这3种化合物对Cu~(2+)离子具有高度的选择性,抗干扰能力好,可作为选择性光学传感器,检出限分别为7. 31×10~(-8)、7. 99×10~(-8)、5. 85×10~(-8)mol/L,采用Job法测试,3种化合物与Cu~(2+)的配合比为1∶1。
Benzimidazole is an excellent active group of ionic probe.Using three kinds of different groups substituted B-norcholesteryl benzimidazole compounds as metal ion acceptors,the recognition abilities towards various metal ions( Co~(2+),K~+,Na~+,Li~+,Pb~(2+),Ca~(2+),Zn~(2+),Sr~(2+)Ni~(2+),Ag~+,Hg~(2+),Cu~(2+)) have been investigated via ultraviolet spectroscopy and fluorescence.The compounds showed high selectivity and good anti-interference ability to Cu~(2+),so may be used as selective optical sensor.The detection limit was down to 7. 31×10~(-8) mol/L,7. 99×10~(-8) mol/L and 5. 85×10~(-8) mol/L,respectively.The stoichiometric ratio of the complex between Cu~(2+)and compound were determined as 1 ∶1 by Job method.
Benzimidazole is an excellent active group of ionic probe.Using three kinds of different groups substituted B-norcholesteryl benzimidazole compounds as metal ion acceptors,the recognition abilities towards various metal ions( Co~(2+),K~+,Na~+,Li~+,Pb~(2+),Ca~(2+),Zn~(2+),Sr~(2+)Ni~(2+),Ag~+,Hg~(2+),Cu~(2+)) have been investigated via ultraviolet spectroscopy and fluorescence.The compounds showed high selectivity and good anti-interference ability to Cu~(2+),so may be used as selective optical sensor.The detection limit was down to 7. 31×10~(-8) mol/L,7. 99×10~(-8) mol/L and 5. 85×10~(-8) mol/L,respectively.The stoichiometric ratio of the complex between Cu~(2+)and compound were determined as 1 ∶1 by Job method.
引文
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[29]KIM H J,HONG J,HONG A,et al.Cu2+-Induced intermolecular static excimer formation of pyrenealkylamine[J].Org.Lett.,2008,10(10):1 963-1 966.
[2]KANG D E,LIM C S,KIM J Y,et al.Two-photon probe for Cu2+with an internal reference:quantitative estimation of Cu2+in human tissues by two-photon microscopy[J].Anal.Chem.,2014,86(11):5 353-5 359.
[3]BINOLFI A,RODRIGUEZ E E,VALENSIN D,et al.Bioinorganic chemistry of parkinson's disease:structural determinants for the copper-mediated amyloid formation of alpha-synuclein[J].Inorg. Chem.,2010,49(22):10 668-10 679.
[4]CASTIGLIONI E T,HONG S,QIAN Y C.Copper handling by astrocytes:insights into neurodegenerative diseases[J].Int.J.Dev.Neurosci.,2011,29(8):811-818.
[5]HUNG Y,BUSH A,CHEMY R.Copper in the brain and Alzheimer's disease[J]. J. Biol. Inorg. Chem.,2010,15(1):61-76.
[6]GEORGOPOULOS P G,ROY A,LIOY M J Y,et al.Environmental copper:its dynamics and human exposure issues[J].J.Toxicol.Env.Heal.A,2001,4(4):341-394.
[7]ZAKSAS N P,GERASIMOVA V A,NEVINSKY G A.Simultaneous determination of Fe,P,Ca,Mg,Zn,and Cu in whole blood by two-jet plasma atomic emission spectrometry[J].Talanta,2010,80(5):2 187-2 190.
[8]POURREZA N,HOVEIZAVI R.Simultaneous preconcentration of Cu,Fe and Pb as methylthymol blue complexes on naphthalene adsorbent and flame atomic absorption determination[J]. Anal. Chim. Acta,2005,549(1/2):124-128.
[9]POURMAND N,SANAGI M M,NAIM A A,et al.Dispersive micro-solid phase extraction method using newly prepared poly(methyl methacrylate)grafted agarose combined with ICP-MS for simultaneous determination of Cd,Ni,Cu and Zn in vegetable and natural water samples[J].Anal.Methods,2015,7(7):3 215-3 223.
[10]LIN M,CHO M S,CHOE W S,et al.Electrochemical detection of copper ion using a modified copolythiophene electrode[J]. Electrochim. Acta,2009,54(27):7 012-7 017.
[11]崔爱军,黄伟,何明阳,等.基于Schiff碱结构的Cu2+荧光探针的合成及性能研究[J].化学试剂,2010,32(11):1 019-1 023.
[12]CHEN X Q,PRADHAN T,WANG F,et al.Fluorescent chemosensors based on spiroring-opening of xanthenes and related derivatives[J]. Chem. Rev.,2012,112(3):1 910-1 956.
[13]DU J J,HU M M,FAN J L,et al.Fluorescent chemodosimeters using"mild"chemical events for the detection of small anions and cations in biological and environmental media[J].Chem.Soc.Rev.,2012,41(12):4 511-4 535.
[14]曹丰璞,丁呈华,王宏伟.苯并咪唑类衍生物的合成、晶体结构及金属离子识别[J].分析测试学报,2013,32(3):381-384.
[15]冯少波,张业,周琪,等.新型脱氢松香基苯并咪唑类衍生物的合成及其氯离子识别性能[J].化学学报,2008,66(12):1 490-1 496.
[16]甘春芳,盛海兵,崔建国,等.具有特殊甾核结构甾体化合物的合成及生理活性研究进展[J].有机化学,2014,34(9):1 730-1 742.
[17]GAN C F,LIN Q F,CUI J G,et al.Synthesis and in vitro antiproliferative evaluation of some novel B-norcholesterols[J].Steroids,2014,79:37-43.
[18]GAN C F,FAN L H,CUI J G,et al. Synthesis and in vitro antiproliferative evaluation of some ring B abeo-sterols[J].Steroids,2012,77:1 061-1 068.
[19]CHHATRA R K,KUMAR A,PANDEY P S.Synthesis of a bile acid-based click-macrocycle and its application in selective recognition of chloride ion[J]. J. Org. Chem.,2011,76(21):9 086-9 089.
[20]MAITRA U.Unlocking the potential of bile acids in synthesis,supramolecular/materials chemistry and nanoscience[J].Org.Biomol.Chem.,2008,6(4):657-669.
[21]LI Y,LI G T,WANG X Y,et al.Unique twisted ribbons generated by self-assembly of oligo(p-phenylene ethylene)bearing dimeric bile acid pendant groups[J].Chemistry,2010,15(26):6 399-6 407.
[22]NATH S,MAITRA U.A simple and general strategy for the design of fluorescent cation sensor beads[J]. Org.Lett.,2006,8(15):3 239-3 242.
[23]KHATRI V K,CHAHAR M,PAVANI K,et al.Bile acidbased cyclic bisbenzimidazolium receptors for anion recognition:highly improved receptors for fluoride and chloride ions[J]. J. Org. Chem.,2007,72(26):10 224-10 226.
[24]CUI J G,QI B B,GAN C F,et al.Synthesis and in vitro antiproliferative evaluation of some B-norcholesteryl benzimidazole and benzothiazole derivatives[J].Mar.Drugs,2015,13(4):2 488-2 504.
[25]CHHATRA R K. KUMAR A. Synthesis of a bile acidbased click-macrocycle and its application in selective recognition of chloride ion[J]. J. Org. Chem.,2011,76(21):9 086-9 089.
[26]潘文龙,许炎妹,李超,等.1,1-二(2-苯并咪唑基)-2-苯基乙烯衍生物荧光受体的合成与阳离子识别[J].分析测试学报,2007,26(2):160-164.
[27]赵媛,陈涛,孙绍发.铜离子比率荧光探针的研究进展[J].化学与生物工程,2017,34(6):12-17.
[28]刘海兴,刘清,郇延富.基于罗丹明类荧光探针的研究进展[J].现代化工,2017,37(4):197-204.
[29]KIM H J,HONG J,HONG A,et al.Cu2+-Induced intermolecular static excimer formation of pyrenealkylamine[J].Org.Lett.,2008,10(10):1 963-1 966.
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