一种基于次氯酸根离子的比率型荧光探针及其应用
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摘要
以2-苯并噻唑-5-甲基苯酚为原料,合成了一种基于次氯酸根离子的比率型荧光探针ZN1,并对其进行了次氯酸根离子的检测性能测试。结果表明:该探针可以快速灵敏、选择性地识别次氯酸根离子,其检测下限为0.96μmol/L,并将该探针应用于实际水样中次氯酸根离子含量的检测,在自来水、雨水中的回收率均大于84%。此外,利用质谱和核磁谱图开展的检测机理研究表明,探针的识别机理与次氯酸的氧化脱氢作用和激发态分子内质子转移(ESIPT)过程破坏有关。
A novel ratiometric fluorescent probe ZN1 for the detection of hypochlorite ion was synthesized using 2-benzothiazole-5-methylphenol as raw material. The results showed that the synthesized probe exhibited rapid response and good selectivity to hypochlorite ion and its detection limit was 0.96 μmol/L.The probe was then applied for the detection of hypochlorite ion in real water samples. The recovery of hypochlorite ion in tap water and rainwater were more than 84%. In addition, the detection mechanism of the probe was investigated by mass spectrometry and nuclear magnetic spectroscopy. It was found that the recognition mechanism of the probe was related to the oxidative dehydrogenation of hypochlorous acid and the destruction of ESIPT process.
A novel ratiometric fluorescent probe ZN1 for the detection of hypochlorite ion was synthesized using 2-benzothiazole-5-methylphenol as raw material. The results showed that the synthesized probe exhibited rapid response and good selectivity to hypochlorite ion and its detection limit was 0.96 μmol/L.The probe was then applied for the detection of hypochlorite ion in real water samples. The recovery of hypochlorite ion in tap water and rainwater were more than 84%. In addition, the detection mechanism of the probe was investigated by mass spectrometry and nuclear magnetic spectroscopy. It was found that the recognition mechanism of the probe was related to the oxidative dehydrogenation of hypochlorous acid and the destruction of ESIPT process.
引文
[1]Fantel A G.Reactive oxygen species in developmental toxicity:Review and hypothesis[J].Teratology,1996,53(3):196-217.
[2]Wu W L,Ma H L,Xi L L et al.A novel lipid droplets-targeting ratiometric fluorescence probe for hypochlorous acid in living cells[J].Talanta,2018,194:308-313.
[3]Ou Z,Shi L,Huang W,et al.A ratiometric fluorescent probe for selective detection of hypochlorite anion[J].Bulletin of the Korean Chemical Society,2017,38(12):1443-1446.
[4]Hidalgo E,Bartolome R,Dominguez C.Cytotoxicity mechanisms of sodium hypochlorite in cultured human dermal fibroblasts and its bactericidal effectiveness[J].Chemico-Biological Interactions,2002,139(3):265-282.
[5]Pattison D I,Davies M J.Evidence for rapid inter-and intramolecular chlorine transfer reactions of histamine and carnosine chloramines:?Implications for the prevention of hypochlorous-acid-mediated damage[J].Biochemistry,2006,45(26):8152-8162.
[6]Yap Y W,Whiteman M,Cheung N S.Chlorinative stress:An under appreciated mediator of neurodegeneration?[J].Cellular Signalling,2007,19(2):219-228.
[7]Magalh?es L M,Segundo M A,Reis S,et al.Automatic in vitro determination of hypochlorous acid scavenging capacity exploiting multisyringe flow injection analysis and chemiluminescence[J].Analytical Chemistry,2007,79(10):3933-3939.
[8]Yue Y,Huo F,Yin C,et al.Recent progress in chromogenic and fluorogenic chemosensors for hypochlorous acid[J].Analyst,2016,141(6):1859-1873.
[9]Li J,Yang X,Zhang D,et al.A fluorescein-based“turn-on”fluorescence probe for hypochlorous acid detection and its application in cell imaging[J].Sensors and Actuators B:Chemical,2018,265:84-90.
[10]Chen X,Tian X,Shin I,et al.Fluorescent and luminescent probes for detection of reactive oxygen and nitrogen species[J].Chemical Society Reviews,2011,40(9):4783-4804.
[11]Wu D,Sedgwick A C,Gunnlaugsson T,et al.Fluorescent chemosensors:The past,present and future[J].Chemical Society Reviews,2017,46(23):7105-7123.
[12]Guo J,Yang S,Guo C,et al.Molecular engineering of alphasubstituted acrylate ester template for efficient fluorescence probe of hydrogen polysulfides[J].Analytical Chemistry,2018,90(1):881-887.
[13]Hong H,Shi L,Huang J,et al.A novel near-infrared fluorescent probe with a“donor-π-acceptor”type structure and its application in the selective detection of cysteine in living cells[J].New Journal of Chemistry,2018,43(1):72-76.
[14]Liu Y,Zhao Z M,Miao J Y,et al.A ratiometric fluorescent probe based on boron dipyrromethene and rhodamine f?rster resonance energy transfer platform for hypochlorous acid and its application in living cells[J].Analytica Chimica Acta,2016,921:77-83.
[15]Yuan Q,Zhao Z M,Zhang Y R,et al.A lysosome-targeted ratiometric fluorescent probe for detection of hypochlorous acid in living cells[J].Sensors and Actuators B:Chemical,2017,247:736-741.
[16]Lee H,Cho M,Chang S,et al.Ratiometric signaling of hypochlorite by the oxidative cleavage of sulfonhydrazide-based rhodaminedansyl dyad[J].Inorganic Chemistry,2015,54(17):8644-8649.
[17]Tang L,Dai X,Wen X,et al.A rhodamine-benzothiazole conjugated sensor for colorimetric,ratiometric and sequential recognition of copper(ii)and sulfide in aqueous media[J].Spectrochimica Acta Part A:Molecular and Biomolecular Spectroscopy,2015,139:329-334.
[18]Wang K,Lv Q,Chen Y,et al.Synthesis,structure and photophysical properties of a 2-(1′-hydroxypyrenyl)benzothiazole[J].Spectrochimica Acta,Part A:Molecular and Biomolecular Spectroscopy,2016,153:669-673.
[2]Wu W L,Ma H L,Xi L L et al.A novel lipid droplets-targeting ratiometric fluorescence probe for hypochlorous acid in living cells[J].Talanta,2018,194:308-313.
[3]Ou Z,Shi L,Huang W,et al.A ratiometric fluorescent probe for selective detection of hypochlorite anion[J].Bulletin of the Korean Chemical Society,2017,38(12):1443-1446.
[4]Hidalgo E,Bartolome R,Dominguez C.Cytotoxicity mechanisms of sodium hypochlorite in cultured human dermal fibroblasts and its bactericidal effectiveness[J].Chemico-Biological Interactions,2002,139(3):265-282.
[5]Pattison D I,Davies M J.Evidence for rapid inter-and intramolecular chlorine transfer reactions of histamine and carnosine chloramines:?Implications for the prevention of hypochlorous-acid-mediated damage[J].Biochemistry,2006,45(26):8152-8162.
[6]Yap Y W,Whiteman M,Cheung N S.Chlorinative stress:An under appreciated mediator of neurodegeneration?[J].Cellular Signalling,2007,19(2):219-228.
[7]Magalh?es L M,Segundo M A,Reis S,et al.Automatic in vitro determination of hypochlorous acid scavenging capacity exploiting multisyringe flow injection analysis and chemiluminescence[J].Analytical Chemistry,2007,79(10):3933-3939.
[8]Yue Y,Huo F,Yin C,et al.Recent progress in chromogenic and fluorogenic chemosensors for hypochlorous acid[J].Analyst,2016,141(6):1859-1873.
[9]Li J,Yang X,Zhang D,et al.A fluorescein-based“turn-on”fluorescence probe for hypochlorous acid detection and its application in cell imaging[J].Sensors and Actuators B:Chemical,2018,265:84-90.
[10]Chen X,Tian X,Shin I,et al.Fluorescent and luminescent probes for detection of reactive oxygen and nitrogen species[J].Chemical Society Reviews,2011,40(9):4783-4804.
[11]Wu D,Sedgwick A C,Gunnlaugsson T,et al.Fluorescent chemosensors:The past,present and future[J].Chemical Society Reviews,2017,46(23):7105-7123.
[12]Guo J,Yang S,Guo C,et al.Molecular engineering of alphasubstituted acrylate ester template for efficient fluorescence probe of hydrogen polysulfides[J].Analytical Chemistry,2018,90(1):881-887.
[13]Hong H,Shi L,Huang J,et al.A novel near-infrared fluorescent probe with a“donor-π-acceptor”type structure and its application in the selective detection of cysteine in living cells[J].New Journal of Chemistry,2018,43(1):72-76.
[14]Liu Y,Zhao Z M,Miao J Y,et al.A ratiometric fluorescent probe based on boron dipyrromethene and rhodamine f?rster resonance energy transfer platform for hypochlorous acid and its application in living cells[J].Analytica Chimica Acta,2016,921:77-83.
[15]Yuan Q,Zhao Z M,Zhang Y R,et al.A lysosome-targeted ratiometric fluorescent probe for detection of hypochlorous acid in living cells[J].Sensors and Actuators B:Chemical,2017,247:736-741.
[16]Lee H,Cho M,Chang S,et al.Ratiometric signaling of hypochlorite by the oxidative cleavage of sulfonhydrazide-based rhodaminedansyl dyad[J].Inorganic Chemistry,2015,54(17):8644-8649.
[17]Tang L,Dai X,Wen X,et al.A rhodamine-benzothiazole conjugated sensor for colorimetric,ratiometric and sequential recognition of copper(ii)and sulfide in aqueous media[J].Spectrochimica Acta Part A:Molecular and Biomolecular Spectroscopy,2015,139:329-334.
[18]Wang K,Lv Q,Chen Y,et al.Synthesis,structure and photophysical properties of a 2-(1′-hydroxypyrenyl)benzothiazole[J].Spectrochimica Acta,Part A:Molecular and Biomolecular Spectroscopy,2016,153:669-673.