Two-Step Sensing, Colorimetric and Ratiometric Fluorescent Probe for Rapid Detection of Bisulfite in Aqueous Solutions and in Living Cells

Overview

Journal ACS Omega

Publisher American Chemical Society

Specialty Chemistry

Date 2018 Oct 16

PMID 30320277

Citations 10

Authors

Xue-Lin Zheng

Hao Li

Wei Feng

Hong-Cheng Xia

Qin-Hua Song

Affiliations

Soon will be listed here.

Abstract

Bisulfite and sulfite (HSO /SO ) are not only widely used toxic chemicals but also active anions with important biological functions. Hence, the development of new detection methods for HSO /SO is important for environmental security and human health. In this paper, we report a symmetrical hemicyanine for the detection of HSO /SO , , which is constructed with -diphthalaldehyde with trimethylbenzoindolium via condensation. The red fluorescent probe can fast respond to HSO /SO (<30 s) to give cyan fluorescence, and its sensing process is twice nucleophilic additions, which were observed from fluorescence response, initial ratiometric change, and subsequent turn-on increment; especially in a low-concentration level, the ratiometric fluorescence measurement can eliminate environmental interference. This probe can achieve a quantitative detection of HSO /SO in a wide concentration range. Furthermore, the probe is a mitochondria-specific probe for ratiometric fluorescent detection of HSO /SO in living cells.

Citing Articles

A Hemicyanin-Based Water-Soluble off-on Fluorescence and Colorimetric Probe for Detecting HSO/SO in Real Samples.

Kodiyawala A, Kiroriwal S, Sahoo S, Ghatak T, Dutta S J Fluoresc. 2024; .

PMID: 39656362 DOI: 10.1007/s10895-024-04040-w.

Organelle-targeting ratiometric fluorescent probes: design principles, detection mechanisms, bio-applications, and challenges.

Goshisht M, Tripathi N, Patra G, Chaskar M Chem Sci. 2023; 14(22):5842-5871.

PMID: 37293660 PMC: 10246671. DOI: 10.1039/d3sc01036h.

Small-Molecule Fluorescent Probe for Detection of Sulfite.

Li T, Chen X, Wang K, Hu Z Pharmaceuticals (Basel). 2022; 15(11).

PMID: 36355496 PMC: 9699022. DOI: 10.3390/ph15111326.

A chemosensor with a paddle structure based on a BODIPY chromophore for sequential recognition of Cu and HSO.

Li S, Cao D, Hu Z, Li Z, Meng X, Han X RSC Adv. 2022; 9(59):34652-34657.

PMID: 35530010 PMC: 9073911. DOI: 10.1039/c9ra08345f.

A real-time ratiometric fluorescent probe for imaging of SO derivatives in mitochondria of living cells.

Shi J, Shu W, Tian Y, Wu Y, Jing J, Zhang R RSC Adv. 2022; 9(39):22348-22354.

PMID: 35519500 PMC: 9066615. DOI: 10.1039/c9ra03207j.

References

Stipanuk M . Metabolism of sulfur-containing amino acids. Annu Rev Nutr. 1986; 6:179-209. DOI: 10.1146/annurev.nu.06.070186.001143. View

Li J, Li R, Meng Z . Sulfur dioxide upregulates the aortic nitric oxide pathway in rats. Eur J Pharmacol. 2010; 645(1-3):143-50. DOI: 10.1016/j.ejphar.2010.07.034. View

Wang X, Jin H, Tang C, Du J . The biological effect of endogenous sulfur dioxide in the cardiovascular system. Eur J Pharmacol. 2011; 670(1):1-6. DOI: 10.1016/j.ejphar.2011.08.031. View

Su X, Hu R, Li X, Zhu J, Luo F, Niu X . Hydrophilic Indolium Cycloruthenated Complex System for Visual Detection of Bisulfite with a Large Red Shift in Absorption. Inorg Chem. 2015; 55(2):745-54. DOI: 10.1021/acs.inorgchem.5b02210. View

Taylor S, Higley N, Bush R . Sulfites in foods: uses, analytical methods, residues, fate, exposure assessment, metabolism, toxicity, and hypersensitivity. Adv Food Res. 1986; 30:1-76. DOI: 10.1016/s0065-2628(08)60347-x. View

Yang X, Zhou Y, Zhang X, Yang S, Chen Y, Guo J . A TP-FRET-based two-photon fluorescent probe for ratiometric visualization of endogenous sulfur dioxide derivatives in mitochondria of living cells and tissues. Chem Commun (Camb). 2016; 52(67):10289-92. DOI: 10.1039/c6cc05254a. View

Ma Y, Tang Y, Zhao Y, Gao S, Lin W . Two-Photon and Deep-Red Emission Ratiometric Fluorescent Probe with a Large Emission Shift and Signal Ratios for Sulfur Dioxide: Ultrafast Response and Applications in Living Cells, Brain Tissues, and Zebrafishes. Anal Chem. 2017; 89(17):9388-9393. DOI: 10.1021/acs.analchem.7b02216. View

Lin V, Chen W, Xian M, Chang C . Chemical probes for molecular imaging and detection of hydrogen sulfide and reactive sulfur species in biological systems. Chem Soc Rev. 2014; 44(14):4596-4618. PMC: 4456340. DOI: 10.1039/c4cs00298a. View

Chan J, Dodani S, Chang C . Reaction-based small-molecule fluorescent probes for chemoselective bioimaging. Nat Chem. 2012; 4(12):973-84. PMC: 4096518. DOI: 10.1038/nchem.1500. View

10.

Li G, Chen Y, Wang J, Wu J, Gasser G, Ji L . Direct imaging of biological sulfur dioxide derivatives in vivo using a two-photon phosphorescent probe. Biomaterials. 2015; 63:128-36. DOI: 10.1016/j.biomaterials.2015.06.014. View

11.

Samanta S, Halder S, Dey P, Manna U, Ramesh A, Das G . A ratiometric fluorogenic probe for the real-time detection of SO in aqueous medium: application in a cellulose paper based device and potential to sense SO in mitochondria. Analyst. 2017; 143(1):250-257. DOI: 10.1039/c7an01368j. View

12.

Sang N, Yun Y, Li H, Hou L, Han M, Li G . SO2 inhalation contributes to the development and progression of ischemic stroke in the brain. Toxicol Sci. 2010; 114(2):226-36. DOI: 10.1093/toxsci/kfq010. View

13.

Liu Y, Li K, Xie K, Li L, Yu K, Wang X . A water-soluble and fast-response mitochondria-targeted fluorescent probe for colorimetric and ratiometric sensing of endogenously generated SO2 derivatives in living cells. Chem Commun (Camb). 2016; 52(16):3430-3. DOI: 10.1039/c5cc10505f. View

14.

Xu J, Pan J, Jiang X, Qin C, Zeng L, Zhang H . A mitochondria-targeted ratiometric fluorescent probe for rapid, sensitive and specific detection of biological SO2 derivatives in living cells. Biosens Bioelectron. 2015; 77:725-32. DOI: 10.1016/j.bios.2015.10.049. View

15.

Zhang H, Huang Z, Feng G . Colorimetric and ratiometric fluorescent detection of bisulfite by a new HBT-hemicyanine hybrid. Anal Chim Acta. 2016; 920:72-9. DOI: 10.1016/j.aca.2016.03.027. View

16.

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 Occup Health. 2008; 51(1):38-47. DOI: 10.1539/joh.l8075. View

17.

Liu X, Yang Q, Chen W, Mo L, Chen S, Kang J . A ratiometric fluorescent probe for rapid, sensitive and selective detection of sulfur dioxide with large Stokes shifts by single wavelength excitation. Org Biomol Chem. 2015; 13(32):8663-8. DOI: 10.1039/c5ob00765h. View

18.

Koch M, Koppen R, Siegel D, Witt A, Nehls I . Determination of total sulfite in wine by ion chromatography after in-sample oxidation. J Agric Food Chem. 2010; 58(17):9463-7. DOI: 10.1021/jf102086x. View

19.

Zhang W, Liu T, Huo F, Ning P, Meng X, Yin C . Reversible Ratiometric Fluorescent Probe for Sensing Bisulfate/HO and Its Application in Zebrafish. Anal Chem. 2017; 89(15):8079-8083. DOI: 10.1021/acs.analchem.7b01580. View

20.

Stipanuk M, Ueki I . Dealing with methionine/homocysteine sulfur: cysteine metabolism to taurine and inorganic sulfur. J Inherit Metab Dis. 2010; 34(1):17-32. PMC: 2901774. DOI: 10.1007/s10545-009-9006-9. View