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Abstract
In this paper, we report the synthesis, characterization and investigation of the optical properties of a new fluorescent probe, 4ʹ-nitroolefinylflavone (4ʹ-NOF) 1, based on a flavone skeleton and bearing a nitroolefin moiety. Upon the addition of cysteine, a remarkable fluorescence enhancement (200 fold) was observed for probe 1 accompanied with a slight blue shift from 457 nm to 459 nm. The prepared probe displays high selectivity and sensitivity towards cysteine over other amino acids. The Michael addition of cysteine to probe 1 was confirmed by 1H-NMR spectroscopy. The detection limit of probe 1 towards cysteine was found to be 1.63 μΜ, a lower concentration than the normal human cysteine level, 30-200 μΜ.
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References
- Stamler, J.S. and Adam, S. Biological chemistry of thiols in the vasculature and in vascular-related disease. Nutrition Reviews, 1996, 54, 1-30.
- Wood, Z.A., Schroder, E., Harris, J.R. and Poole, L.B. Structure, mechanism and regulation of peroxiredoxins. Trends in Biochemical Sciences, 2003, 28, 32-40.
- Townsend, D.M., Tew, K.D. and Tapiero, H. The important of glutathione in human disease, Biomedicine & Pharmacotherapy, 2003, 57, 145-155.
- Poole, L.B. and Nelson, K.J. Discovering mechanism of signaling-mediated cysteine oxidation. Current Opinion in Chemical Biology, 2008, 12, 18-24.
- Wachtershauser, G. From volcanic origins of chemoautotrophic life to bacteria, archaea and eukarya. Philosophical Transactions of the Royal Society B: Biological Sciences, 2006, 361, 1787-1806.
- Paulsen, C.E. and Carroll, K.S. Cysteine-mediated redox signaling: Chemistry, biology, and tools for discovery. Chemical Reviews, 2013, 113, 4633-4679.
- Reddie, K.G. and Carroll, K.S. Expanding the functional diversity of proteins through cysteine oxidation. Current Opinion in Chemical Biology, 2008, 12, 746-754.
- Shahrokhian, S. Lead phthalocyanine as a selective carrier for preparation of a cysteine selective electrode. Analytical Chemistry, 2001, 73, 5972-5978.
- Wang, X.F. and Cynader, M.S. Astrocytes provide cysteine to neurons by releasing glutathione. Journal of Neuroscience, 2001, 21, 3322-3331.
- Refsum, H., Ueland, P.M., Nygard, O. and Vollset, S.E. Homocysteine and cardiovascular disease. Annual Review of Medicine, 1998, 49, 31-62.
- Seshadri, S., Beiser, A., Selhub, J., Jacques, P.F., Rosenberg, I.H., D’Agostino, R.B., Wilson, P.W.F. and Wolf, P.A. Plasma homocysteine as a risk factor for dementia and Alzeheimer’s disease. The New England Journal of Medicine, 2002, 346, 476-483.
- Sigit, J.I., Hages, M., Brensing, K.A., Frotscher, U., Pietrzik, K., von Bergmann, K. and Lutjohann, D. Total plasma homocysteine and related amino acids in end-stage renal disease (ESRD) patients measured by gas chromatography-mass spectrometry: Comparison with AbbottJMx homocysteine assay and HPLC method. Clinical Chemistry and Laboratory Medicine, 2001, 39, 681-690.
- Tcherkas, Y.V. and Denisenko, A.D. Simultaneous determination of several amino acids, including homocysteine, cysteine and glutamic acid in human plasma by isocratic reversed-phase high performance liquid chromatography with fluorimetric detection. Journal of Chromatography A, 2001, 913, 309-313.
- Wang, W., Escobedo, J.O., Lawrence, C.M. and Strongin, R.M. Direct detection of homocysteine. The Journal of American Chemical Society, 2004, 126, 3400-3401.
- Lima, P.R., Santos, W.J.R., Luz, R.D.C.S., Damos, F.S., Oliveira, A.B., Goulart, M.O.F. and Kubota, L.T. An amperometric sensor based on electrochemically triggered reaction: Redox-active Ar-NO/Ar-NHOH from 4-nitrophthalonitrile-modified electrode for the low voltage cysteine detection. Journal of Electroanalytical Chemistry, 2008, 612, 87-96.
- Zhou, Y. and Yoon, J. Recent progress in fluorescent and colorimetric chemosensors for detection of amino acids. Chemical Society Reviews, 2012, 41, 52-67.
- Chen, X., Pradhan, T., Wang, F., Kim, J.S. and Yoon, J. Fluorescent chemosensors based on spiroring-opening of xanthenes and related derivatives. Chemical reviews, 2012, 112, 1910-1956.
- Lou, X., Zhang, L., Qin, J. and Li, Z. Coumarin-melonitrile as a fluorescence turn-on for biothiols and its cellular expression. Langmuir, 2010, 26, 1566-1569.
- Zhou, X., Jin, X., Sun, G., Li, D. and Wu, X. A cysteine probe with high selectivity and sensitivity promoted by response-assisted electrostatic attraction. Chemical Communications, 2012, 48, 8793-8795.
- Yue, Y., Guo, Y., Xu, J. and Shao, S. Abodipy-based derivative for selective fluorescence sensing of homocysteine and cysteine. New Journal of Chemistry, 2011, 35, 61-64.
- Lu, J., Sun, C., Chen, W., Ma, H., Shi, W. and Li, X. Determination of non-protein cysteine in human serum by a designed BODIPY-based fluorescent probe. Talanta, 2011, 83, 1050-1056.
- Feuster, E.K. and Glass, T.E. Detection of amines and unprotected amino acids in aqueous condition by formation of highly fluorescent iminium ions. The Journal of the American Chemical Society, 2003, 125, 16174-16175.
- Lv, H.-M., Yuan, D.-H., Liu, W., Chen, Y. and Au, C.-T. A highly selective ESIPT-based fluorescent probe for cysteine sensing and its bioimaging application in living cells. Sensors and Actuators B: Chemical, 2016, 233, 173-179.
- Wang, H., Zhou, G., Mao, C. and Chen, X. A fluorescent sensor bearing nitroolefin moiety for the detection of thiols and its biological imaging. Dyes and Pigments, 2013, 96, 232-236.
- Huo, F.-J., Sun, Y.-Q., Su, J., Yang, Y.-T., Yin, C.-X. and Chao, J.-B. Chromene ʻʻlockˮ, thiol ʻʻkeyˮ and mercury (II) ion ʻʻhandˮ; A single molecular machine recognition system. Organic Letters, 2010, 12, 4756- 4759.
- Kwon, H., Lee, K. and Kim, H.-J. Coumarin-melonitrile as a fluorescence turn-on for biothiols and its cellular expression. Chemical Communications, 2011, 47, 1773-1775.
- Jung, H.S., Ko, K.C., Kim, G.-H., Lee, A.-R. Na, Y.-C., Kang, C., Lee, J. Y. and Kim, J.S. Coumarin-based thiol chemosensor: synthesis, turn-on mechanism, and its biological application. Organic Letters, 2011, 13, 1498-1501.
- Anila, H.A., Upendar, R.G., Firoj, A., Nandaraj, T. and Samit, C. A reagent for specific recognition of cysteine in aqueous buffer and in natural milk: imaging studies, enzymetic reaction and analysis of whey protein. Chemical Communications, 2015, 51, 5592-95.
- Babur, B., Seferoglu, N., Ocal, M., Songur, G., Akbulut, H. and Seferoglu, Z. A novel fluorescence turn-on coumarin-pyrazolone based monomethine probe for bithiol detection. Tetrahedron, 2016, 72, 4498-4502.
- Smirnov, A.N., Aksenov, N.A., Malikova, I.V., and Aksenov, A.V. Arenes and Hetarenes in Reactions with unsaturated Nitro Compounds, Chemistry of Heterocyclic Compounds, Springer Science and Business Media, New York, 2014.
- Liu, X., Yang, D., Chen, W., Yang, L., Qi, F. and Song, X. A red-emitting fluorescent probe for specific cysteine over homocysteine and glutathione with a large Strokes shift. Sensors and Actuators B: Chemical, 2016, 234, 27-33.
- Liu, T., Huo, F., Li, J., Chao, J., Zhang, Y. and Yin, C. An off-on fluorescent probe for specifically detecting cysteine and its application in bioimaging, Sensors and Actuators B: Chemical, 2016, 237, 127-132.
- Rani, B.K. and John, S.A. A novel pyrene based fluorescent probe for selective detection of cysteine in presence of bio-thiol in living cells. Biosensors and Bioelectronics, 2016, 83, 237-242.
- Chen, X., Ko, S.-K., Kim, M.J., Shin, I. and Yoon, J. A thiol-specific fluorescent probe and its application for bioimaging. Chemical Communications, 2010, 46, 2751-2753.
- Dai, X., Zhang, T., Liu, Y.-Z., Yan, T., Li, Y., Miao, J.-Y. and Zhao, B.-X. A ratiometric fluorescent probe for cysteine and its application in living cells. Sensors and Actuators B: Chemical, 2015, 207, 872-877.
- Guo, Z., Nam, S., Park, S. and Yoon, J. A highly selective ratiometer near-infrared fluorescent cyanine sensor for cysteine with remarkable shift and its application in bioimaging. Chemical Science, 2012, 3, 2760-2765.
- Lin, L.-Z., He, X.-G., Lindenmaier, M., Nolan, G., Yang, J., Cleary, M., Qiu, S.-X. and Cordell, G.A. Liquid chromatography-electrospray ionization mass spectrometry study of the flavonoids of the roots of Astragalus mongholicus and A. membranaceus. Journal of Chromatography A, 2000, 876, 87-95.
- de Rijke, E., Joshi, H.C., Sanderse, H.R., Ariese, F., Brinkman, U.A.T. and Gooijer, C. Natively fluorescent isoflavones exhibiting anomalous Stokesʼ shifts. Analytica Chimica Acta, 2002, 468, 3-11.
- Chen, W., Sun, S., Cao, W., Liang, Y. and Song, J. Antioxidant property of quercetin–Cr(III)
- complex: The role of Cr(III) ion. Journal of Molecular Structure, 2009, 918, 194-197.
- Patwardhan, J. and Bhatt, P. Flavonoids derived from Abelmoschus esculentus attenuates UV-B induced cell damage in human dermal fibroblasts through Nrf2-ARE pathway. Pharmacognosy Magazine, 2016, 12, 129-138.
- Havsteen, B.H. The biochemistry and medical significance of the flavonoids. Pharmacology and Therapeutics, 2002, 96, 67-202.
- Sanzmedel, A., Alonso, J.I.G. and Gonzalez, E.B. Metal chelate fluorescence enhancement in micellar media and its applications to niobium and tantalum ultratrace determinations. Analytical Chemistry, 1985, 57, 1681-1687.
- Lan, M., Wu, J., Liu, W., Zhang, H., Zhang, W., Zhang, X. and Wang, P. Highly sensitive fluorescent probe for thiols based on combination of PET and ESIPT mechanisms. Sensors and Actuators B: Chemical, 2011, 156, 332-337.
References
Stamler, J.S. and Adam, S. Biological chemistry of thiols in the vasculature and in vascular-related disease. Nutrition Reviews, 1996, 54, 1-30.
Wood, Z.A., Schroder, E., Harris, J.R. and Poole, L.B. Structure, mechanism and regulation of peroxiredoxins. Trends in Biochemical Sciences, 2003, 28, 32-40.
Townsend, D.M., Tew, K.D. and Tapiero, H. The important of glutathione in human disease, Biomedicine & Pharmacotherapy, 2003, 57, 145-155.
Poole, L.B. and Nelson, K.J. Discovering mechanism of signaling-mediated cysteine oxidation. Current Opinion in Chemical Biology, 2008, 12, 18-24.
Wachtershauser, G. From volcanic origins of chemoautotrophic life to bacteria, archaea and eukarya. Philosophical Transactions of the Royal Society B: Biological Sciences, 2006, 361, 1787-1806.
Paulsen, C.E. and Carroll, K.S. Cysteine-mediated redox signaling: Chemistry, biology, and tools for discovery. Chemical Reviews, 2013, 113, 4633-4679.
Reddie, K.G. and Carroll, K.S. Expanding the functional diversity of proteins through cysteine oxidation. Current Opinion in Chemical Biology, 2008, 12, 746-754.
Shahrokhian, S. Lead phthalocyanine as a selective carrier for preparation of a cysteine selective electrode. Analytical Chemistry, 2001, 73, 5972-5978.
Wang, X.F. and Cynader, M.S. Astrocytes provide cysteine to neurons by releasing glutathione. Journal of Neuroscience, 2001, 21, 3322-3331.
Refsum, H., Ueland, P.M., Nygard, O. and Vollset, S.E. Homocysteine and cardiovascular disease. Annual Review of Medicine, 1998, 49, 31-62.
Seshadri, S., Beiser, A., Selhub, J., Jacques, P.F., Rosenberg, I.H., D’Agostino, R.B., Wilson, P.W.F. and Wolf, P.A. Plasma homocysteine as a risk factor for dementia and Alzeheimer’s disease. The New England Journal of Medicine, 2002, 346, 476-483.
Sigit, J.I., Hages, M., Brensing, K.A., Frotscher, U., Pietrzik, K., von Bergmann, K. and Lutjohann, D. Total plasma homocysteine and related amino acids in end-stage renal disease (ESRD) patients measured by gas chromatography-mass spectrometry: Comparison with AbbottJMx homocysteine assay and HPLC method. Clinical Chemistry and Laboratory Medicine, 2001, 39, 681-690.
Tcherkas, Y.V. and Denisenko, A.D. Simultaneous determination of several amino acids, including homocysteine, cysteine and glutamic acid in human plasma by isocratic reversed-phase high performance liquid chromatography with fluorimetric detection. Journal of Chromatography A, 2001, 913, 309-313.
Wang, W., Escobedo, J.O., Lawrence, C.M. and Strongin, R.M. Direct detection of homocysteine. The Journal of American Chemical Society, 2004, 126, 3400-3401.
Lima, P.R., Santos, W.J.R., Luz, R.D.C.S., Damos, F.S., Oliveira, A.B., Goulart, M.O.F. and Kubota, L.T. An amperometric sensor based on electrochemically triggered reaction: Redox-active Ar-NO/Ar-NHOH from 4-nitrophthalonitrile-modified electrode for the low voltage cysteine detection. Journal of Electroanalytical Chemistry, 2008, 612, 87-96.
Zhou, Y. and Yoon, J. Recent progress in fluorescent and colorimetric chemosensors for detection of amino acids. Chemical Society Reviews, 2012, 41, 52-67.
Chen, X., Pradhan, T., Wang, F., Kim, J.S. and Yoon, J. Fluorescent chemosensors based on spiroring-opening of xanthenes and related derivatives. Chemical reviews, 2012, 112, 1910-1956.
Lou, X., Zhang, L., Qin, J. and Li, Z. Coumarin-melonitrile as a fluorescence turn-on for biothiols and its cellular expression. Langmuir, 2010, 26, 1566-1569.
Zhou, X., Jin, X., Sun, G., Li, D. and Wu, X. A cysteine probe with high selectivity and sensitivity promoted by response-assisted electrostatic attraction. Chemical Communications, 2012, 48, 8793-8795.
Yue, Y., Guo, Y., Xu, J. and Shao, S. Abodipy-based derivative for selective fluorescence sensing of homocysteine and cysteine. New Journal of Chemistry, 2011, 35, 61-64.
Lu, J., Sun, C., Chen, W., Ma, H., Shi, W. and Li, X. Determination of non-protein cysteine in human serum by a designed BODIPY-based fluorescent probe. Talanta, 2011, 83, 1050-1056.
Feuster, E.K. and Glass, T.E. Detection of amines and unprotected amino acids in aqueous condition by formation of highly fluorescent iminium ions. The Journal of the American Chemical Society, 2003, 125, 16174-16175.
Lv, H.-M., Yuan, D.-H., Liu, W., Chen, Y. and Au, C.-T. A highly selective ESIPT-based fluorescent probe for cysteine sensing and its bioimaging application in living cells. Sensors and Actuators B: Chemical, 2016, 233, 173-179.
Wang, H., Zhou, G., Mao, C. and Chen, X. A fluorescent sensor bearing nitroolefin moiety for the detection of thiols and its biological imaging. Dyes and Pigments, 2013, 96, 232-236.
Huo, F.-J., Sun, Y.-Q., Su, J., Yang, Y.-T., Yin, C.-X. and Chao, J.-B. Chromene ʻʻlockˮ, thiol ʻʻkeyˮ and mercury (II) ion ʻʻhandˮ; A single molecular machine recognition system. Organic Letters, 2010, 12, 4756- 4759.
Kwon, H., Lee, K. and Kim, H.-J. Coumarin-melonitrile as a fluorescence turn-on for biothiols and its cellular expression. Chemical Communications, 2011, 47, 1773-1775.
Jung, H.S., Ko, K.C., Kim, G.-H., Lee, A.-R. Na, Y.-C., Kang, C., Lee, J. Y. and Kim, J.S. Coumarin-based thiol chemosensor: synthesis, turn-on mechanism, and its biological application. Organic Letters, 2011, 13, 1498-1501.
Anila, H.A., Upendar, R.G., Firoj, A., Nandaraj, T. and Samit, C. A reagent for specific recognition of cysteine in aqueous buffer and in natural milk: imaging studies, enzymetic reaction and analysis of whey protein. Chemical Communications, 2015, 51, 5592-95.
Babur, B., Seferoglu, N., Ocal, M., Songur, G., Akbulut, H. and Seferoglu, Z. A novel fluorescence turn-on coumarin-pyrazolone based monomethine probe for bithiol detection. Tetrahedron, 2016, 72, 4498-4502.
Smirnov, A.N., Aksenov, N.A., Malikova, I.V., and Aksenov, A.V. Arenes and Hetarenes in Reactions with unsaturated Nitro Compounds, Chemistry of Heterocyclic Compounds, Springer Science and Business Media, New York, 2014.
Liu, X., Yang, D., Chen, W., Yang, L., Qi, F. and Song, X. A red-emitting fluorescent probe for specific cysteine over homocysteine and glutathione with a large Strokes shift. Sensors and Actuators B: Chemical, 2016, 234, 27-33.
Liu, T., Huo, F., Li, J., Chao, J., Zhang, Y. and Yin, C. An off-on fluorescent probe for specifically detecting cysteine and its application in bioimaging, Sensors and Actuators B: Chemical, 2016, 237, 127-132.
Rani, B.K. and John, S.A. A novel pyrene based fluorescent probe for selective detection of cysteine in presence of bio-thiol in living cells. Biosensors and Bioelectronics, 2016, 83, 237-242.
Chen, X., Ko, S.-K., Kim, M.J., Shin, I. and Yoon, J. A thiol-specific fluorescent probe and its application for bioimaging. Chemical Communications, 2010, 46, 2751-2753.
Dai, X., Zhang, T., Liu, Y.-Z., Yan, T., Li, Y., Miao, J.-Y. and Zhao, B.-X. A ratiometric fluorescent probe for cysteine and its application in living cells. Sensors and Actuators B: Chemical, 2015, 207, 872-877.
Guo, Z., Nam, S., Park, S. and Yoon, J. A highly selective ratiometer near-infrared fluorescent cyanine sensor for cysteine with remarkable shift and its application in bioimaging. Chemical Science, 2012, 3, 2760-2765.
Lin, L.-Z., He, X.-G., Lindenmaier, M., Nolan, G., Yang, J., Cleary, M., Qiu, S.-X. and Cordell, G.A. Liquid chromatography-electrospray ionization mass spectrometry study of the flavonoids of the roots of Astragalus mongholicus and A. membranaceus. Journal of Chromatography A, 2000, 876, 87-95.
de Rijke, E., Joshi, H.C., Sanderse, H.R., Ariese, F., Brinkman, U.A.T. and Gooijer, C. Natively fluorescent isoflavones exhibiting anomalous Stokesʼ shifts. Analytica Chimica Acta, 2002, 468, 3-11.
Chen, W., Sun, S., Cao, W., Liang, Y. and Song, J. Antioxidant property of quercetin–Cr(III)
complex: The role of Cr(III) ion. Journal of Molecular Structure, 2009, 918, 194-197.
Patwardhan, J. and Bhatt, P. Flavonoids derived from Abelmoschus esculentus attenuates UV-B induced cell damage in human dermal fibroblasts through Nrf2-ARE pathway. Pharmacognosy Magazine, 2016, 12, 129-138.
Havsteen, B.H. The biochemistry and medical significance of the flavonoids. Pharmacology and Therapeutics, 2002, 96, 67-202.
Sanzmedel, A., Alonso, J.I.G. and Gonzalez, E.B. Metal chelate fluorescence enhancement in micellar media and its applications to niobium and tantalum ultratrace determinations. Analytical Chemistry, 1985, 57, 1681-1687.
Lan, M., Wu, J., Liu, W., Zhang, H., Zhang, W., Zhang, X. and Wang, P. Highly sensitive fluorescent probe for thiols based on combination of PET and ESIPT mechanisms. Sensors and Actuators B: Chemical, 2011, 156, 332-337.