Abstract
In this work, we designed and synthesized 3-cyano-2-oxo-2H-chromen-7-yl acrylate as a simple and effective probe 1, which is capable of detecting cysteine (Cys) over other biothiols, such as homocysteine and glutathione. Remarkably, with the addition of cysteine, the 125-fold increase in fluorescence intensity of probe 1 was observed at 450 nm with excitation at 413 nm and 5 min incubation time. Furthermore, it is more important that probe 1 possesses the detection limit of 80 nM, and there is good linear relationship between fluorescence intensity and concentration of Cys from 0 to 100 μM. Thus, these made a powerful safeguard for the detection of Cys in the biological system. Simultaneously, probe 1 showed low toxicity and could be used in living cell imaging.
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References
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
Dai X, Wu QH, Wang PC, Tian J, Xu Y, Wang SQ, Miao JY, Zhao BX (2014) A simple and effective coumarin-based fluorescent probe for cysteine. Biosens Bioelectron 59:35–39. https://doi.org/10.1016/j.bios.2014.03.018
Dai X, Kong X, Lin W (2017) A novel fluorescent probe with large Stokes shift for two-photon imaging of biothiols in living cells, liver tissues and tumor tissues. Dyes Pigments 142:306–314. https://doi.org/10.1016/j.dyepig.2017.03.045
Fan J, Wang ZY, Zhu HJ, Fu NY (2013) A fast response squaraine-based colorimetric probe for detection of thiols in physiological conditions. Sens Actuators B Chem 188:886–893. https://doi.org/10.1016/j.snb.2013.07.096
Fu YJ, Li Z, Li CY, Li YF, Wu P, Wen ZH (2017a) Borondipyrrolemethene-based fluorescent probe for distinguishing cysteine from biological thiols and its application in cell image. Dyes Pigment 139:381–387. https://doi.org/10.1016/j.dyepig.2016.12.033
Fu ZH, Han X, Shao Y, Fang J, Zhang ZH, Wang YW, Peng Y (2017b) A new fluorescein-based chromogenic and ratiometric fluorescence probe for highly selective detection of cysteine and its application in bioimaging. Anal Chem 89:1937–1944. https://doi.org/10.1021/acs.analchem.6b04431
Guan YS, Niu LY, Chen YZ, Wu LZ, Tung CH, Yang QZ (2014) A near-infrared fluorescent sensor for selective detection of cysteine and its application in live cell imaging. RSC Adv 4:8360–8364. https://doi.org/10.1039/C3RA47116K
Jo J, Lee D (2009) Turn-on fluorescence detection of cyanide in water: activation of latent fluorophores through remote hydrogen bonds that mimic peptide β-turn motif. J Am Chem Soc 131:16283–16291. https://doi.org/10.1021/ja907056m
Jung HS, Han JH, Pradhan T, Kim S, Lee SW, Sessler JL, Kim TW, Kang C, Kim JS (2012) A cysteine-selective fluorescent probe for the cellular detection of cysteine. Biomaterials 33:945–953. https://doi.org/10.1016/j.biomaterials.2011.10.040
Jung HS, Chen X, Kim JS, Yoon J (2013) Recent progress in luminescent and colorimetric chemosensors for detection of thiols. Chem Soc Rev 42:6019–6031. https://doi.org/10.1039/C3CS60024F
Kim Y, Choi M, Seo S, Manjare ST, Jon S, Churchill DG (2014) Selective fluorescent probe for cysteine and its imaging in live cells. RSC Adv 4:64183–64186. https://doi.org/10.1039/C4RA12981D
Kim Y, Mulay SV, Choi M, Yu SB, Jon S, Churchill DG (2015) Exceptional time response, stability and selectivity in doubly-activated phenyl selenium-based glutathione-selective platform. Chem Sci 6:5435–5439. https://doi.org/10.1039/C5SC02090E
Kobayashi H, Ogawa M, Alford R, Choyke PL, Urano Y (2010) New strategies for fluorescent probe design in medical diagnostic imaging. Chem Rev 110:2620–2640. https://doi.org/10.1021/cr900263j
Koopmans T, van Haren M, van Ufford LQ, Beekman JM, Martin NI (2013) A concise preparation of the fluorescent amino acid l-(7-hydroxycoumarin-4-yl) ethylglycine and extension of its utility in solid phase peptide synthesis. Bioorg Med Chem 21:553–559. https://doi.org/10.1016/j.bmc.2012.10.055
Leung KH, He HZ, Ma VPY, Chan DSH, Leung CH, Ma DL (2013) A luminescent G-quadruplex switch-on probe for the highly selective and tunable detection of cysteine and glutathione. Chem Commun 49:771–773. https://doi.org/10.1039/C2CC37710A
Li H, Fan J, Wang J, Tian M, Du J, Sun S, Sun P, Peng X (2009) A fluorescent chemodosimeter specific for cysteine: effective discrimination of cysteine from homocysteine. Chem Commun. https://doi.org/10.1039/B907511A
Liu X, Cole JM, Waddell PG, Lin TC, Radia J, Zeidler A (2012) Molecular origins of optoelectronic properties in coumarin dyes: toward designer solar cell and laser applications. J Phys Chem A 116:727–737. https://doi.org/10.1021/jp209925y
Liu X, Cole JM, Waddell PG, Lin TC, McKechnie SJ (2013) Molecular origins of optoelectronic properties in coumarins 343, 314T, 445, and 522B. Phys Chem C 117:14130–14141. https://doi.org/10.1021/jp400614e
MacDougall D, Crummett WB (1980) Guidelines for data acquisition and data quality evaluation in environmental chemistry. Anal Chem 52:2242–2249. https://doi.org/10.1021/ac50064a004
Murale DP, Kim H, Choi WS, Churchill DG (2013) Highly fluorescent and specific molecular probing of (homo)cysteine or superoxide: biothiol detection confirmed in living neuronal cells. Org Lett 15(14):3630–3633. https://doi.org/10.1021/ol401480w
Murale DP, Kim H, Choi WS, Kim Y, Churchill DG (2014a) Extremely selective and fluorescent detection of cysteine or superoxide: with aliphatic ester hydrolysis. RSC Adv 4:46513–46516. https://doi.org/10.1039/C4RA06891B
Murale DP, Kim H, Choi WS, Churchill DG (2014b) Rapid and selective detection of Cys in living neuronal cells utilizing a novel fluorescein with chloropropionate–ester functionalities. RSC Adv 4:5289–5292. https://doi.org/10.1039/c3ra47280a
Niu LY, Guan YS, Chen YZ, Wu LZ, Tung CH, Yang QZ (2013) A turn-on fluorescent sensor for the discrimination of cystein from homocystein and glutathione. Chem Commun 49:1294–1296. https://doi.org/10.1039/C2CC38429A
Niu LY, Chen YZ, Zheng HR, Wu LZ, Tung CH, Yang QZ (2015) Design strategies of fluorescent probes for selective detection among biothiols. Chem Soc Rev 44:6143–6160. https://doi.org/10.1039/C5CS00152H
Pang L, Zhou Y, Gao W, Zhang J, Song H, Wang X, Wang Y, Peng X (2017) Curcumin-based fluorescent and colorimetric probe for detecting cysteine in living cells and zebrafish. Ind Eng Chem Res 56:7650–7655. https://doi.org/10.1021/acs.iecr.7b02133
Paulsen CE, Carroll KS (2013) Cysteine-mediated redox signaling: chemistry, biology, and tools for discovery. Chem Rev 113:4633–4679. https://doi.org/10.1021/cr300163e
Rani BK, John SA (2016) A novel pyrene based fluorescent probe for selective detection of cysteine in presence of other bio-thiols in living cells. Biosens Bioelectron 83:237–242. https://doi.org/10.1016/j.bios.2016.04.013
Reddie KG, Carroll KS (2008) Expanding the functional diversity of proteins through cysteine oxidation. Curr Opin Chem Biol 12:746–754. https://doi.org/10.1016/j.cbpa.2008.07.028
Reddy GU, Agarwalla H, Taye N, Ghorai S, Chattopadhyay S, Das A (2014) A novel fluorescence probe for estimation of cysteine/histidine in human blood plasma and recognition of endogenous cysteine in live Hct116 cells. Chem Commun 50:9899–9902. https://doi.org/10.1039/C4CC04214J
Schaeferling M (2012) The art of fluorescence imaging with chemical sensors. Angew Chem Int Ed 51:3532–3554. https://doi.org/10.1002/anie.201105459
Schäferling S (2001) Lead phthalocyanine as a selective carrier for preparation of a cysteine-selective electrode. Anal Chem 73:5972–5978. https://doi.org/10.1021/ac010541m
Valizadeh H, Mamaghani M, Badrian A (2005) Effect of microwave irradiation on reaction of arylaldehyde derivatives with some active methylene compounds in aqueous media. Synth Commun 35:785–790. https://doi.org/10.1081/SCC-200050942
Weerapana E, Wang C, Simon GM, Richter F, Khare S, Dillon MB, Bachovchin DA, Mowen K, Baker D, Cravatt BF (2010) Quantitative reactivity profiling predicts functional cysteines in proteomes. Nature 468:790–795. https://doi.org/10.1038/nature09472
Wu J, Liu W, Ge J, Zhang H, Wang P (2011) New sensing mechanisms for design of fluorescent chemosensors emerging in recent years. Chem Soc Rev 40:3483–3495. https://doi.org/10.1039/C0CS00224K
Yang X, Guo Y, Strongin RM (2011) Conjugate addition/cyclization sequence enables selective and simultaneous fluorescence detection of cysteine and homocysteine. Angew Chem Int Ed 50:10690–10693. https://doi.org/10.1002/anie.201103759
Zhang N, Qu F, Luo HQ, Li NB (2013) Sensitive and selective detection of biothiols based on target-induced agglomeration of silver nanoclusters. Biosens Bioelectron 42:214–218. https://doi.org/10.1016/j.bios.2012.10.090
Zhou Y, Yoon J (2012) Recent progress in fluorescent and colorimetric chemosensors for detection of amino acids. Chem Soc Rev 41:52–67. https://doi.org/10.1039/C1CS15159B
Acknowledgements
This work was supported by the Natural Science Foundation of Hebei Province (No. B2016405026), Young Elitist Foundation of Hebei Province (No. BJ2016003), Guidance Projects of Science and Technology of Zhangjiakou City (No. 1621122H) and Guide Projects of Department of Education of Hebei Province (No. Z2017026).
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Qiao, H., Meng, Y., Zhang, Y. et al. A simple coumarin-based fluorescent probe for specific detection of cysteine over homocysteine and glutathione. Chem. Pap. 72, 1461–1466 (2018). https://doi.org/10.1007/s11696-018-0401-2
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DOI: https://doi.org/10.1007/s11696-018-0401-2