Construction of a Ratiometric Fluorescent Probe for SO2 Derivative and Its Application for Cell Imaging

doi:10.7517/j.issn.1674-0475.2016.05.435

Abstract

Abstract:

In this study, we report a ratiometric fluorescent probe (CZBI) for sulfur dioxide (SO₂) derivatives based on the conjugate of carbazole and benzo[e]indolium, which displays colorimetric and ratiometric fluorescence dual response to HSO₃^-/SO₃^2-. The probe can quantitatively detect HSO₃^- with high specificity, fast response (within 40 s) as well as low detection limit (12 nmol/L). The fluorescence intensity ratios were linearly related to the concentrations of bisulfite ranging from 0 to 16 μmol/L. A 1, 4-nucleophilic addition reaction was proposed for the sensing mechanism of this probe, which was confirmed by ¹HNMR spectra. Fluorescence imaging of HeLa cells indicated that CZBI could be used for monitoring the intrinsically generated intracellular SO₂ derivatives in living cells by ratiometric fluorescence imaging.

Key words: fluorescent probe, SO₂, benzoindole, ratiometric, cell imaging

XIONG Chao, DUAN Chong, XU Junchao, HE Yuanyuan, ZHANG Yue, ZENG Lintao. Construction of a Ratiometric Fluorescent Probe for SO₂ Derivative and Its Application for Cell Imaging[J]. Imaging Science and Photochemistry, 2016, 34(5): 435-443.

References

[1] Iwasawa S, Kikuchi Y, Nishiwaki Y, Nakano M, Michikawa T, Tsuboi T.Effects of SO₂ on respiratory system of adult Miyakejima resident 2 years after returning to the island[J].Journal of Occupational Health, 2009, 51(1): 38-47.
[2] Reist M, Jenner P, Halliwell B. Sulphite enhances peroxynitrite-dependent α1-antiproteinase inactivation: a mecha-nism 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 SO₂ derivative-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. SO₂ inhalation 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 boron-dipyrromethene-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 detection of 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 ICT-based 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 ICT-based 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 SO₂ derivatives 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 water-soluble 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 SO₂ derivatives 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.

Construction of a Ratiometric Fluorescent Probe for SO₂ Derivative and Its Application for Cell Imaging

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	HUANG Haiqing, XIAO Saijin, YANG Guangzhaoyao, ZHAO Jiahui. Label-free and Rapid Detection of ATP Based on Molybdenum Oxide Quantum Dots [J]. Imaging Science and Photochemistry, 2020, 38(6): 950-955.
[2]	WANG Kaixia, XU Wei, HE Qingguo, CHENG Jiangong. Design, Synthesis and Properties of Highly Selective Fluorescent Probe for Methylamphetamine Vapor Detection [J]. Imaging Science and Photochemistry, 2018, 36(6): 478-488.
[3]	CHANG Shunzhou, XIANG Kaiqiang, MING Wei, ZHANG Zhizhong, TIAN Baozhu, ZHANG Jinlong. Synthesis and Properties of a pH Fluorescent Probe Based on PET Mechanism [J]. Imaging Science and Photochemistry, 2018, 36(5): 425-433.
[4]	WANG Qi, XIAO Yan, XIAO Bo, XIAO Song. Preparation of TCMePyP and Research on the Killing Effect of Photodynamic Therapy on SH-SY5Y Neuroblastoma Cell [J]. Imaging Science and Photochemistry, 2018, 36(5): 453-463.
[5]	MA Yaguang, ZHANG Yutao, MA Yiyu, GUO Zhiqian, ZHU Weihong. Near-infrared Cyanine-based Fluorescent Probe for Cysteine with High Selectivity [J]. Imaging Science and Photochemistry, 2018, 36(3): 236-244.
[6]	FENG Jia, YU Fang, WANG Yu. A Turn-on Fluorometric Sensor for Al³⁺ in Aqueous Medium with Cell Imaging Application [J]. Imaging Science and Photochemistry, 2018, 36(2): 178-186.
[7]	HUANG Zhentao, WANG Nannan, ZHANG Jian, ZHAO Weili. A Novel Turn-on Fluorescent Probe for Triphenylphosphine [J]. Imaging Science and Photochemistry, 2017, 35(6): 771-779.
[8]	ZHANG Jian, LÜ Minghuan, ZHANG Weijuan, ZHAO Weili. Flavone-based ESIPT Fluorescent Probe for Determination of Triphenylphosphine [J]. Imaging Science and Photochemistry, 2017, 35(4): 526-535.
[9]	WANG Yuan, CHEN Xiaoxiao, LIU Xueliang, CHEN Yuzhe, NIU Liya, WU Lizhu, YANG Qingzheng. A Fluorescent Probe for Selective Detection of GSH [J]. Imaging Science and Photochemistry, 2017, 35(4): 536-545.
[10]	FEI Qiang, AN Jiancai, ZHAO Chunchang. A BODIPY-based Fluorescent Probe for Selective Detection of GSH [J]. Imaging Science and Photochemistry, 2017, 35(4): 546-551.
[11]	LIU Chuantao, XIAO Ting, WANG Fang, CHEN Xiaoqiang. Synthesis and Application of a Highly Sensitive and High Selective Aluminum Ion Ratio Probe [J]. Imaging Science and Photochemistry, 2017, 35(3): 281-289.
[12]	HU Linli, ZHANG Yufeng, ZHANG Xin, YIN Jun. A Highly Selective Mercury Ion (Ⅱ) Fluorescent Probe Based on Dansyl Dye [J]. Imaging Science and Photochemistry, 2017, 35(3): 297-306.
[13]	ZHANG Peng, HAN Xiaoyue, YU Fabiao, CHEN Lingxin. Small-molecular Fluorescent Probes for the Detection of Hydrogen Polysulfides and Nitroxyl [J]. Imaging Science and Photochemistry, 2016, 34(5): 402-425.
[14]	WANG Manli, LI Xin, ZHANG Xiaohui, MING Huami, YIN Hongzong, XU Kun. Construction of Dysprosium Fluorescent Probe and Application of Determination on Tetracrycline Hydrochlorid Residues in Milk [J]. Imaging Science and Photochemistry, 2014, 32(6): 565-571.
[15]	ZHU Dongjian, JIANG Hua. Cyanine-based Near-infrared Ratiometric Fluorescent Probe for Thiols [J]. Imaging Science and Photochemistry, 2014, 32(1): 106-112.