比率型SO_2荧光探针的构建及细胞成像研究
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摘要
本文构建了一种基于苯并吲哚季铵盐结构的荧光探针用于检测SO_2衍生物。该荧光探针能够快速、灵敏、高选择性地检测HSO~-_3和SO~(2-)_3,并显示出颜色和荧光变化双重响应。其比率荧光强度(I_(462)/I_(588))与HSO~-_3的浓度(0~16μmol/L)之间具有良好的线性关系,检测限低至12nmol/L。~1 HNMR表明该探针的响应机制为1,4-亲核加成反应。激光共聚焦荧光成像结果表明,CZBI具有良好的细胞膜通透性,并且可以通过比率荧光成像实现对细胞内SO_2衍生物的监测。
In this study,we report a ratiometric fluorescent probe(CZBI)for sulfur dioxide(SO_2)derivatives based on the conjugate of carbazole and benzo[e]indolium, which displays colorimetric and ratiometric fluorescence dual response to HSO~-_3/SO~(2-)_3.The probe can quantitatively detect HSO~-_3with high specificity,fast response(within 40s)as well as low detection limit(12nmol/L).The fluorescence intensity ratios were linearly related to the concentrations of bisulfite ranging from 0to 16μmol/L.A 1,4-nucleophilic addition reaction was proposed for the sensing mechanism of this probe,which was confirmed by ~1 HNMR spectra.Fluorescence imaging of HeLa cells indicated that CZBI could be used for monitoring the intrinsically generated intracellular SO_2 derivatives in living cells by ratiometric fluorescence imaging.
In this study,we report a ratiometric fluorescent probe(CZBI)for sulfur dioxide(SO_2)derivatives based on the conjugate of carbazole and benzo[e]indolium, which displays colorimetric and ratiometric fluorescence dual response to HSO~-_3/SO~(2-)_3.The probe can quantitatively detect HSO~-_3with high specificity,fast response(within 40s)as well as low detection limit(12nmol/L).The fluorescence intensity ratios were linearly related to the concentrations of bisulfite ranging from 0to 16μmol/L.A 1,4-nucleophilic addition reaction was proposed for the sensing mechanism of this probe,which was confirmed by ~1 HNMR spectra.Fluorescence imaging of HeLa cells indicated that CZBI could be used for monitoring the intrinsically generated intracellular SO_2 derivatives in living cells by ratiometric fluorescence imaging.
引文
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[13]Gu X,Liu C,Zhu Y C,Zhu Y Z.A borondipyrromethene-based fluorescent probe for colorimetric and ratiometric detection of sulfite[J].Journal of Agricultural and Food Chemistry,2011,59(22):11935-11939.
[14]Ma X,Liu C,Shan Q,Guo W,Wei D,Du Y.A fluorescein-based probe with high selectivity and sensitivity for sulfite detection in aqueous solution[J].Sensors and Actuators B:Chemical,2013,188:1196-1200.
[15]Xu J,Liu K,Di D,Shao S,Guo Y.A selective colorimetric chemosensor for detecting in neutral aqueous solution[J].Inorganic Chemistry Communications,2007,10(6):681-684.
[16]Sun Y,Zhong C,Gong R,Mu H,Fu E.A ratiometric fluorescent chemodosimeter with selective recognition for sulfite in aqueous solution[J].The Journal of Organic Chemistry,2009,74(20):7943-7946.
[17]Choi M G,Hwang J,Eor S,Chang S K.Chromogenic and fluorogenic signaling of sulfite by selective deprotection of resorufinlevulinate[J].Organic Letters,2010,12(24):5624-5627.
[18]Yuan L,Lin W,Xie Y,Chen B,Song J.Fluorescent detectionof hypochlorous acid from turn-on to FRET-based ratiometry by a HOCl-mediated cyclization reaction[J].Chemistry-A European Journal,2012,18(9):2700-2706.
[19]Yuan L,Lin W,Song J,Yang Y.Development of an ICTbased ratiometric fluorescent hypochlorite probe suitable for living cell imaging[J].Chemical Communications,2011,47(47):12691-12693.
[20]Srikun D,Miller E W,Domaille D W,Chang C J.An ICTbased approach to ratiometric fluorescence imaging of hydrogen peroxide produced in living cells[J].Journal of the American Chemical Society,2008,130(14):4596-4609.
[21]Sun Y Q,Liu J,Zhang J,Yang T,Guo W.Fluorescent probe for biological gas SO2derivatives bisulfite and sulfite[J].Chemical Communications,2013,49(26):2637-2639.
[22]Wu M Y,Li K,Li C Y,Hou J T,Yu X Q.A watersoluble near-infrared probe for colorimetric and ratiometric sensing of SO2 derivatives in living cells[J].Chemical Communications,2014,50(2):183-185.
[23]Xu W,Teoh C L,Peng J,Su D,Yuan L,Chang Y T.A mitochondria-targeted ratiometric fluorescent probe to monitor endogenously generated sulfur dioxide derivatives in living cells[J].Biomaterials,2015,56:1-9.
[24]Liu Y,Li K,Wu M Y,Liu Y H,Xie Y M,Yu X Q.A mitochondria-targeted colorimetric and ratiometric fluorescent probe for biological SO2derivatives in living cells[J].Chemical Communications,2015,51(50):10236-10239.
[25]Ji A J,Savon S R,Jacobsen D W.Determination of total serum sulfite by HPLC with fluorescence detection[J].Clinical Chemistry,1995,41(6):897-903.
[26]Wang X B,Huang X M,Ochs T,Li X Y,Jin H F,Tang C S.Effect of sulfur dioxide preconditioning on rat myocardial ischemia/reperfusion injury by inducing endoplasmic reticulum stress[J].Basic Research in Cardiology,2011,106(5):865-878.
[2]Reist M,Jenner P,Halliwell B.Sulphite enhances peroxynitrite-dependentα1-antiproteinase inactivation:a mechanism of lung injury by sulphur dioxide[J].FEBS Letters,1998,423(2):231-234.
[3]Li G,Sang N.Delayed rectifier potassium channels are involved in SO2derivative-induced hippocampal neuronal injury[J].Ecotoxicology and Environmental Safety,2009,72(1):236-241.
[4]Li J,Li R,Meng Z.Sulfur dioxide upregulates the aortic nitric oxide pathway in rats[J].European Journal of Pharmacology,2010,645(1/3):143-150.
[5]Sang N,Yun Y,Li H,Hou L,Han M,Li G K.SO2inhalation contributes to the development and progression of ischemic stroke in the brain[J].Toxicological Sciences,2010,114(2):226-236.
[6]Du S X,Jin H F,Bu D F,Zhao X,Geng B,Tang C S.Endogenously generated sulfur dioxide and its vasorelaxant effect in rats[J].Acta Pharmacologica Sinica,2008,29(8):923-930.
[7]Luo L,Chen S,Jin H,Tang C,Du J.Endogenous generation of sulfur dioxide in rat tissues[J].Biochemical and Biophysical Research Communications,2011,415(1):61-67.
[8]Stipanuk M H,Ueki I.Dealing with methionine/homocysteine sulfur:cysteine metabolism to taurine and inorganic sulfur[J].Journal of Inherited Metabolic Disease,2011,34(1):17-32.
[9]Ubuka T,Yuasa S,Ohta J,Masuoka N,Yao K,Kinuta M.Formation of sulfate from L-cysteine in rat liver mitochondria[J].Acta Medica Okayama,1990,44(2):55-64.
[10]Meng Z Q,Yang Z H,Li J L,Zhang Q X.The vasorelaxant effect and its mechanisms of sodium bisulfite as a sulfur dioxide donor[J].Chemosphere,2012,89(5):579-584.
[11]Sun Y,Tian Y,Prabha M,Liu D,Chen S,Zhang R.Effects of sulfur dioxide on hypoxic pulmonary vascular structural remodeling[J].Laboratory Investigation,2010,90(1):68-82.
[12]Cheng X,Jia H,Feng J,Qin J,Li Z.“Reactive”probe for hydrogen sulfite:“turn-on”fluorescent sensing and bioimaging application[J].Journal of Materials Chemistry B,2013,1(33):4110-4114.
[13]Gu X,Liu C,Zhu Y C,Zhu Y Z.A borondipyrromethene-based fluorescent probe for colorimetric and ratiometric detection of sulfite[J].Journal of Agricultural and Food Chemistry,2011,59(22):11935-11939.
[14]Ma X,Liu C,Shan Q,Guo W,Wei D,Du Y.A fluorescein-based probe with high selectivity and sensitivity for sulfite detection in aqueous solution[J].Sensors and Actuators B:Chemical,2013,188:1196-1200.
[15]Xu J,Liu K,Di D,Shao S,Guo Y.A selective colorimetric chemosensor for detecting in neutral aqueous solution[J].Inorganic Chemistry Communications,2007,10(6):681-684.
[16]Sun Y,Zhong C,Gong R,Mu H,Fu E.A ratiometric fluorescent chemodosimeter with selective recognition for sulfite in aqueous solution[J].The Journal of Organic Chemistry,2009,74(20):7943-7946.
[17]Choi M G,Hwang J,Eor S,Chang S K.Chromogenic and fluorogenic signaling of sulfite by selective deprotection of resorufinlevulinate[J].Organic Letters,2010,12(24):5624-5627.
[18]Yuan L,Lin W,Xie Y,Chen B,Song J.Fluorescent detectionof hypochlorous acid from turn-on to FRET-based ratiometry by a HOCl-mediated cyclization reaction[J].Chemistry-A European Journal,2012,18(9):2700-2706.
[19]Yuan L,Lin W,Song J,Yang Y.Development of an ICTbased ratiometric fluorescent hypochlorite probe suitable for living cell imaging[J].Chemical Communications,2011,47(47):12691-12693.
[20]Srikun D,Miller E W,Domaille D W,Chang C J.An ICTbased approach to ratiometric fluorescence imaging of hydrogen peroxide produced in living cells[J].Journal of the American Chemical Society,2008,130(14):4596-4609.
[21]Sun Y Q,Liu J,Zhang J,Yang T,Guo W.Fluorescent probe for biological gas SO2derivatives bisulfite and sulfite[J].Chemical Communications,2013,49(26):2637-2639.
[22]Wu M Y,Li K,Li C Y,Hou J T,Yu X Q.A watersoluble near-infrared probe for colorimetric and ratiometric sensing of SO2 derivatives in living cells[J].Chemical Communications,2014,50(2):183-185.
[23]Xu W,Teoh C L,Peng J,Su D,Yuan L,Chang Y T.A mitochondria-targeted ratiometric fluorescent probe to monitor endogenously generated sulfur dioxide derivatives in living cells[J].Biomaterials,2015,56:1-9.
[24]Liu Y,Li K,Wu M Y,Liu Y H,Xie Y M,Yu X Q.A mitochondria-targeted colorimetric and ratiometric fluorescent probe for biological SO2derivatives in living cells[J].Chemical Communications,2015,51(50):10236-10239.
[25]Ji A J,Savon S R,Jacobsen D W.Determination of total serum sulfite by HPLC with fluorescence detection[J].Clinical Chemistry,1995,41(6):897-903.
[26]Wang X B,Huang X M,Ochs T,Li X Y,Jin H F,Tang C S.Effect of sulfur dioxide preconditioning on rat myocardial ischemia/reperfusion injury by inducing endoplasmic reticulum stress[J].Basic Research in Cardiology,2011,106(5):865-878.