Abstract
Thiol-containing biomolecules (biothiols), including cysteine (Cys), homocysteine (Hcy), glutathione (GSH) and hydrogen sulphide (H2S), have crucial implications in human physiology and pathophysiology. They can be qualitatively and quantitatively analysed in the tissues of interest using sensitive and specific fluorescent probes, which may in turn reflect alternations in cellular activities and disease manifestations. In this regard, probes with aggregation-induced emission (AIE) properties are preferential owing to their enhanced emission in the aqueous environment present in biological systems. In this chapter, we review the recent progress in biothiol-specific probes that are derived from the well-documented tetraphenylethene (TPE) scaffold. In particular, we highlight their underlying reaction mechanisms with the target biothiol(s) and their applications in cell imaging where available.
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References
Ueland PM et al (1993) Total homocysteine in plasma or serum: methods and clinical applications. Clin Chem 39:1764–1779
Brigham MP, Stein WH, Moore S (1960) The concentrations of cysteine and cystine in human blood plasma. J Clin Invest 39:1633–1638
Tsogas GZ, Kappi FA, Vlessidis AG, Giokas DL (2018) Recent advances in nanomaterial probes for optical biothiol sensing: a review. Anal Lett 51:443–468
Mansoor MA, Svardal AM, Ueland PM (1992) Determination of the in vivo redox status of cysteine, cysteinylglycine, homocysteine, and glutathione in human plasma. Anal Biochem 200:218–229
Suzuki K, Sagara M, Aoki C, Tanaka S, Aso Y (2017) Clinical implication of plasma hydrogen sulfide levels in Japanese patients with Type 2 diabetes. Intern Med 56:17–21
Jiang J et al (2016) Hydrogen sulfide - mechanisms of toxicity and development of an antidote. Sci Rep 6:20831
Maulik VT, Jennifer SL, Teruna JS (2009) The role of thiols and disulfides on protein stability. Curr Protein Pept Sci 10:614–625
Jensen KP, Ryde U (2003) Conversion of homocysteine to methionine by methionine synthase: a density functional study. J Am Chem Soc 125:13970–13971
Medina MÁ, Urdiales JL, Amores-Sánchez MI (2001) Roles of homocysteine in cell metabolism. Eur J Biochem 268:3871–3882
Townsend DM, Tew KD, Tapiero H (2003) The importance of glutathione in human disease. Biomed Pharmacother 57:145–155
Nakagawa I, Suzuki M, Yanagiya T, Imura N, Naganuma A (1995) Effect of glutathione depletion on metallothionein synthesis induced by paraquat in mice. Tohoku J Exp Med 177:249–262
Moskaug JØ, Carlsen H, Myhrstad MC, Blomhoff R (2005) Polyphenols and glutathione synthesis regulation. Am J Clin Nutr 81:277S–283S
Li L, Moore PK (2007) An overview of the biological significance of endogenous gases: new roles for old molecules. Biochem Soc Trans 35:1138–1141
Bhatia M (2015) In: Moore PK, Whiteman M (eds) Chemistry, biochemistry and pharmacology of hydrogen sulfide. Springer, Berlin, pp 165–180
Papapetropoulos A et al (2009) Hydrogen sulfide is an endogenous stimulator of angiogenesis. Proc Natl Acad Sci 106:21972–21977
Bhatia M (2005) Hydrogen sulfide as a vasodilator. IUBMB Life 57:603–606
Kimura Y, Goto Y-I, Kimura Y-I (2009) Hydrogen sulfide increases glutathione production and suppresses oxidative stress in mitochondria Antioxid. Redox Signal 12:1–13
Whiteman M et al (2004) The novel neuromodulator hydrogen sulfide: an endogenous peroxynitrite ‘scavenger’? J Neurochem 90:765–768
Lieberman MW et al (1996) Growth retardation and cysteine deficiency in gamma-glutamyl transpeptidase-deficient mice. Proc Natl Acad Sci U S A 93:7923–7926
Alena F, Dixon W, Thomas P, Jimbow K (1995) Glutathione plays a key role in the depigmenting and melanocytotoxic action of N-acetyl-4-S-cysteaminylphenol in black and yellow hair follicles. J Invest Dermatol 104:792–797
Khoshbaten M et al (2010) N-Acetylcysteine improves liver function in patients with non-alcoholic fatty liver disease. Hepat Mon 10:12–16
Nakai K et al (2015) Effects of topical N-acetylcysteine on skin hydration/transepidermal water loss in healthy volunteers and atopic dermatitis patients. Ann Dermatol 27:450–451
Zhang SM et al (2003) A prospective study of plasma total cysteine and risk of breast cancer. Cancer Epidemiol Biomarkers Prev 12:1188–1193
Bostom AG, Culleton BF (1999) Hyperhomocysteinemia in chronic renal disease. J Am Soc Nephrol 10:891–900
Ganguly P, Alam SF (2015) Role of homocysteine in the development of cardiovascular disease. Nutr J 14:6
Sachdev P (2004) Homocisteína e transtornos psiquiátricos. Rev Bras Psiquiatr 26:50–56
Uys JD, Mulholland PJ, Townsend DM (2014) Glutathione and redox signaling in substance abuse. Biomed Pharmacother 68:799–807
Prussick R, Prussick L, Gutman J (2013) Psoriasis improvement in patients using glutathione-enhancing, nondenatured whey protein isolate: a pilot study. J Clin Aesthet Dermatol 6:23–26
Yuan L, Kaplowitz N (2009) Glutathione in liver diseases and hepatotoxicity. Mol Aspects Med 30:29–41
Balendiran GK, Dabur R, Fraser D (2004) The role of glutathione in cancer. Cell Biochem Funct 22:343–352
Conklin KA (2004) Chemotherapy-associated oxidative stress: impact on chemotherapeutic effectiveness. Integr Cancer Ther 3:294–300
Eto K, Kimura H (2002) The production of hydrogen sulfide is regulated by testosterone and S-adenosyl-l-methionine in mouse brain. J Neurochem 83:80–86
Cao X, Cao L, Ding L, Bian J-S (2018) A new hope for a devastating disease: hydrogen sulfide in Parkinson’s disease. Mol Neurobiol 55:3789–3799
Zhang L-M, Jiang C-X, Liu D-W (2009) Hydrogen sulfide attenuates neuronal injury induced by vascular dementia via inhibiting apoptosis in rats. Neurochem Res 34:1984–1992
Yin C-X, Xiong K-M, Huo F-J, Salamanca JC, Strongin RM (2017) Fluorescent probes with multiple binding sites for the discrimination of Cys, Hcy, and GSH. Angew Chem Int Ed 56:13188–13198
Chen X, Zhou Y, Peng X, Yoon J (2010) Fluorescent and colorimetric probes for detection of thiols. Chem Soc Rev 39:2120–2135. https://doi.org/10.1039/B925092A
de Silva AP et al (1997) Signaling recognition events with fluorescent sensors and switches. Chem Rev 97:1515–1566
Martínez-Máñez R, Sancenón F (2003) Fluorogenic and chromogenic chemosensors and reagents for anions. Chem Rev 103:4419–4476
Kim SA, Schwille P (2003) Intracellular applications of fluorescence correlation spectroscopy: prospects for neuroscience. Curr Opin Neurobiol 13:583–590
Zhang H, Zhang C, Liu R, Yi L, Sun H (2015) A highly selective and sensitive fluorescent thiol probe through dual-reactive and dual-quenching groups. Chem Commun 51:2029–2032
Rusin O et al (2004) Visual detection of cysteine and homocysteine. J Am Chem Soc 126:438–439
Matsumoto T, Urano Y, Shoda T, Kojima H, Nagano T (2007) A thiol-reactive fluorescence probe based on donor-excited photoinduced electron transfer: key role of ortho substitution. Org Lett 9:3375–3377
Wang S-P et al (2009) A colorimetric and fluorescent merocyanine-based probe for biological thiols. Org Biomol Chem 7:4017–4020
Luo J et al (2001) Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole. Chem Commun 0:1740–1741. https://pubs.rsc.org/en/content/articlelanding/2001/cc/b105159h#!divAbstract
Tang BZ et al (2001) Efficient blue emission from siloles. J Mater Chem 11:2974–2978
Liu M et al (2017) 9-Vinylanthracene based fluorogens: synthesis, structure-property relationships and applications. Molecules 22:2148
Dong Y et al (2012) Supramolecular interactions induced fluorescent organic nanowires with high quantum yield based on 9,10-distyrylanthracene. CrstEngComm 14:6593–6598
Peng L et al (2014) A fluorescent probe for thiols based on aggregation-induced emission and its application in live-cell imaging. Dyes Pigm 108:24–31
Chen S et al (2013) Full-range intracellular pH sensing by an aggregation-induced emission-active two-channel ratiometric fluorogen. J Am Chem Soc 135:4926–4929
Chen M et al (2015) Tetraphenylpyrazine-based AIEgens: facile preparation and tunable light emission. Chem Sci 6:1932–1937
Mei J, Leung NLC, Kwok RTK, Lam JWY, Tang BZ (2015) Aggregation-induced emission: together we shine, united we soar! Chem Rev 115:11718–11940
Leung CWT et al (2014) Superior fluorescent probe for detection of cardiolipin. Anal Chem 86:1263–1268
Huang Y et al (2014) Tetraphenylethylene conjugated with a specific peptide as a fluorescence turn-on bioprobe for the highly specific detection and tracing of tumor markers in live cancer cells. Chem A Eur J 20:158–164
Hong Y, Chen S, Leung CWT, Lam JWY, Tang BZ (2013) Water-soluble tetraphenylethene derivatives as fluorescent “light-up” probes for nucleic acid detection and their applications in cell imaging. Chem Asian J 8:1806–1812
Michael A (1887) On the addition of sodium acetacetic ether and analogous sodium compounds to unsaturated organic ethers. Am Chem J 9:115
Vernon B, Tirelli N, Bächi T, Haldimann D, Hubbell JA (2003) Water-borne, in situ crosslinked biomaterials from phase-segregated precursors. J Biomed Mater Res A 64A:447–456
Mather BD, Viswanathan K, Miller KM, Long TE (2006) Michael addition reactions in macromolecular design for emerging technologies. Prog Polym Sci 31:487–531
Li X et al (2012) Simple fluorescent probe derived from tetraphenylethylene and benzoquinone for instantaneous biothiol detection. Anal Methods 4:3338–3443
Zhang R et al (2014) Fluorogen-peptide conjugates with tunable aggregation-induced emission characteristics for bioprobe design. ACS Appl Mater Interfaces 6:14302–14310
Yuan Y et al (2014) Rational design of fluorescent light-up probes based on an AIE luminogen for targeted intracellular thiol imaging. Chem Commun 50:295–297
Yu Y et al (2013) Thiol-reactive molecule with dual-emission-enhancement property for specific prestaining of cysteine containing proteins in SDS-PAGE. ACS Appl Mater Interfaces 5:4613–4616
Liu Y et al (2010) Simple biosensor with high selectivity and sensitivity: thiol-specific biomolecular probing and intracellular imaging by AIE fluorogen on a TLC plate through a thiol–ene click mechanism. Chem A Eur J 16:8433–8438
Chen MZ et al (2017) A thiol probe for measuring unfolded protein load and proteostasis in cells. Nat Commun 8:474
Lou X et al (2014) A selective glutathione probe based on AIE fluorogen and its application in enzymatic activity assay. Sci Rep 4:4272
Zhao N et al (2015) A fluorescent probe with aggregation-induced emission characteristics for distinguishing homocysteine over cysteine and glutathione. J Mater Chem C 3:8397–8402
Chen S et al (2014) Discrimination of homocysteine, cysteine and glutathione using an aggregation-induced-emission-active hemicyanine dye. J Mater Chem B 2:3919–3923
Lou X et al (2014) A new turn-on chemosensor for bio-thiols based on the nanoaggregates of a tetraphenylethene-coumarin fluorophore. Nanoscale 6:14691–14696
Cai Y et al (2014) A sensitivity tuneable tetraphenylethene-based fluorescent probe for directly indicating the concentration of hydrogen sulfide. Chem Commun 50:8892–8895
Zhang W, Kang J, Li P, Wang H, Tang B (2015) Dual signaling molecule sensor for rapid detection of hydrogen sulfide based on modified tetraphenylethylene. Anal Chem 87:8964–8969
Zhang Y et al (2016) Organic nanoparticles formed by aggregation-induced fluorescent molecules for detection of hydrogen sulfide in living cells. Sci China Chem 59:106–113
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Liu, M., Hong, Y. (2019). Utilisation of Tetraphenylethene-Derived Probes with Aggregation-Induced Emission Properties in Fluorescence Detection of Biothiols. In: Tang, Y., Tang, B. (eds) Principles and Applications of Aggregation-Induced Emission. Springer, Cham. https://doi.org/10.1007/978-3-319-99037-8_16
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DOI: https://doi.org/10.1007/978-3-319-99037-8_16
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