Abstract
A new type of turn-on fluorescent probe CF-AC for the detection of Cys was firstly reported. The probe exhibited an excellent response to Cys with high selectively and sensitivity. In the presence of Cys, two fluorescence emission peaks at 525 nm and 650 nm appeared accompanied by the fluorescence color change from blue to red. Morever, the probe had good biocompatibility and could be successfully used for fluorescence imaging of Cys in MCF-7 cells.
Similar content being viewed by others
References
Zhang S, Ong CN, Shen HM (2004) Critical roles of intracellular thiols and calcium in parthenolide-induced apoptosis in human colorectal cancer cells. Cancer Lett 208(2):143–153
Estrela JM, Ortega A, Obrador E (2006) Glutathione in cancer biology and therapy. Crit Rev Clin Lab Sci 43(2):143–181
Seshadri S, Beiser A, Selhub J, Jacques PF, Rosenberg IH, D'Agostino RB, Wilson PWF, Wolf PA (2002) Plasma homocysteine as a risk factor for dementia and alzheimer's disease. New Engl J Med 346(7):476–483
Basu A, Bhattacharjee A, Samanta A, Bhattacharya S (2015) Prevention of cyclophosphamide-induced hepatotoxicity and genotoxicity: effect of an L-cysteine based oxovanadium(IV) complex on oxidative stress and DNA damage. Environ Toxicol Pharmacol 40(3):747–757
Shahrokhian S (2001) Lead phthalocyanine as a selective carrier for preparation of a cysteine-selective electrode. Anal Chem 73(24):5972–5978
Nolin TD, McMenamin ME, Himmelfarb J (2007) Simultaneous determination of total homocysteine, cysteine, cysteinylglycine, and glutathione in human plasma by high-performance liquid chromatography: application to studies of oxidative stress. J Chromatogr B 852(1):554–561
Sato Y, Iwata T, Tokutomi S, Kandori H (2005) Reactive cysteine is protonated in the triplet excited state of the LOV2 domain in adiantum phytochrome3. J Am Chem Soc 127(4):1088–1089
Lima PR, Santos WJR, Luz RCS, Damos FS, Oliveira AB, Goulart MOF, Kubota LT (2008) 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. J Electroanal Chem 612(1):87–96
Yin CX, Xiong KM, Huo FJ, Salamanca JC, Strongin RM (2017) Fluorescent probes with multiple binding sites for the discrimination of Cys, Hcy, and GSH. Angew Chem Int Ed 56(43):13188–13198
Sun YC, Chen Z, Chen FZ, Liu H, He HP, Zhang XH, Wang SF (2017) An HBT-based near-infrared fluorescent probe for colorimetric and ratiometric detection of bisulfite and its application in living cells. J Fluoresc 27(4):1405–1411
Chen Z, Zhong XX, Qu WB, Shi T, Liu H, He HP, Zhang XH, Wang SF (2017) A highly selective HBT-based “turn-on” fluorescent probe for hydrazine detection and its application. Tetrahedron Lett 58(26):2596–2601
Chen W, Xu S, Day JJ, Wang D, Xian M (2017) A general strategy for development of near-infrared fluorescent probes for bioimaging. Angew Chem Int Ed 56(52):16611–16615
Chen W, Pacheco A, Takano Y, Day JJ, Hanaoka K, Xian M (2016) A single fluorescent probe to visualize hydrogen sulfide and hydrogen polysulfides with different fluorescence signals. Angew Chem Int Ed 55(34):9993–9996
Chen H, Tang Y, Lin W (2016) Recent progress in the fluorescent probes for the specific imaging of small molecular weight thiols in living cells. TrAC Trends Anal Chem 76:166–181
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(17):6143–6160
Chen W, Rosser EW, Matsunaga T, Pacheco A, Akaike T, Xian M (2015) The development of fluorescent probes for visualizing intracellular hydrogen polysulfides. Angew Chem Int Ed 127(47):14167–14171
Wang Y, Zhu M, Jiang E, Hua R, Na R, Li QX (2017) A simple and rapid turn on ESIPT fluorescent probe for colorimetric and ratiometric detection of biothiols in living cells. Sci Rep 7(1):4377
Zhang J, Lv Y, Zhang W, Ding H, Liu R, Zhao Y, Zhang G, Tian Z (2016) A flavone-based turn-on fluorescent probe for intracellular cysteine/homocysteine sensing with high selectivity. Talanta 146:41–48
Tang L, Shi J, Huang Z, Yan X, Zhang Q, Zhong K, Hou S, Bian Y (2016) An ESIPT-based fluorescent probe for selective detection of homocysteine and its application in live-cell imaging. Tetrahedron Lett 57(47):5227–5231
Diwan U, Kumar V, Mishra RK, Rana NK, Koch B, Upadhyay KK (2016) Harvesting red fluorescence through design specific tuning of ICT and ESIPT: an efficient optical detection of cysteine and live cell imaging. RSC Adv 6(98):95722–95728
Goswami S, Manna A, Paul S, Das AK, Nandi PK, Maity AK, Saha P (2014) A turn on ESIPT probe for rapid and ratiometric fluorogenic detection of homocysteine and cysteine in water with live cell-imaging. Tetrahedron Lett 55(2):490–494
Wang JY, Liu ZR, Ren M, Kong X, Lin W (2017) A fast-response two-photon fluorescent probe for the detection of Cys over GSH/Hcy with a large turn-on signal and its application in living tissues. J Mater Chem B 5:134–138
Mao Z, Wang M, Liu J, Liu LJ, Lee SMY, Leung CH, Ma DL (2016) A long lifetime switch-on iridium(iii) chemosensor for the visualization of cysteine in live zebrafish. Chem Commun 52(24):4450–4453
Garcia-Beltran O, Santos JG, Fuentealba S, De la Torre P, Pavez P, Mena N, Nunez MT, Aliaga ME (2015) Mechanism study of the thiol-addition reaction to benzothiazole derivative for sensing endogenous thiols. Tetrahedron Lett 56(19):2437–2440
Garcia-Beltran O, Mena N, Perez EG, Cassels BK, Nunez MT, Werlinger F, Zavala D, Aliaga ME, Pavez P (2011) The development of a fluorescence turn-on sensor for cysteine, glutathione and other biothiols. A kinetic study. Tetrahedron Lett 52(49):6606–6609
Chen CY, Zhou LQ, Huang X, Liu WS (2017) Rapid detection of intracellular Cys over Hcy and GSH using a novel two-photon coumarinocoumarin-based colorimetric and fluorescent probe. J Mater Chem B 5(29):5892–5897
Zhang LL, Li MM, Zhao CC, Gu XF (2016) A novel fluorescent probe for discrimination of Cys from GSH: inspiration from chemical ligation. Tetrahedron Lett 57(5):578–581
Lee D, Kim G, Yin J, Yoon J (2015) An aryl-thioether substituted nitrobenzothiadiazole probe for the selective detection of cysteine and homocysteine. Chem Commun 51(30):6518–6520
Chen YH, Tsai JC, Cheng TH, Yuan SS, Wang YM (2014) Sensitivity evaluation of NBD-SCN towards cysteine/homocysteine and its bioimaging applications. Biosens Bioelectron 56:117–123
Xiao YD, Guo YJ, Dang RL, Yan X, Xu PF, Jiang P (2017) A dansyl-based fluorescent probe for the highly selective detection of cysteine based on a d-PeT switching mechanism. RSC Adv 7(34):21050–21053
Wang Q, Wang H, Huang J, Li N, Gu Y, Wang P (2017) Novel NIR fluorescent probe with dual models for sensitively and selectively monitoring and imaging Cys in living cells and mice. Sensors Actuators B Chem 253:400–406
Wang F, Feng C, Lu L, Xu Z, Zhang W (2017) A ratiometric fluorescent probe for rapid and sensitive detection of biothiols in fetal bovine serum. Talanta 169:149–155
Shen Y, Zhang X, Zhang Y, Zhang C, Jin J, Li H (2017) A new simple phthalimide-based fluorescent probe for highly selective cysteine and bioimaging for living cells. Spectrochim Acta A Mol Biomol Spectrosc 185:371–375
Liu XJ, Tian HH, Yang L, Su YA, Guo M, Song XZ (2017) An ESIPT-based fluorescent probe for sensitive and selective detection of Cys/Hcy over GSH with a red emission and a large stokes shift. Tetrahedron Lett 58(33):3209–3213
Liu G, Liu D, Han X, Sheng X, Xu Z, Liu SH, Zeng L, Yin J (2017) A hemicyanine-based colorimetric and ratiometric fluorescent probe for selective detection of cysteine and bioimaging in living cell. Talanta 170:406–412
Chen FZ, Chen Z, Sun YC, Liu H, Han DM, He HP, Zhang XH, Wang SF (2017) HBT-based turn-on fluorescent probe for discrimination of homocysteine from glutathione/cysteine and its bioimaging applications. RSC Adv 7(27):16387–16391
Manibalan K, Chen SM, Mani V, Huang TT, Huang ST (2016) A sensitive ratiometric long-wavelength fluorescent probe for selective determination of cysteine/homocysteine. J Fluoresc 26(4):1489–1495
Chen Y, Wang X, Yang XF, Zhong Y, Li Z, Li H (2015) Development of a ratiometric fluorescent probe for sulfite based on a coumarin–benzopyrylium platform. Sensors Actuators B Chem 206:268–275
Chen Z, Chen FZ, Sun YC, Liu H, He HP, Zhang XH, Wang SF (2017) A novel ratiometric fluorescent probe for selective detection of bisulfite in living cells. RSC Adv 7(5):2573–2577
Acknowledgments
This work was supported by Major Project of the Civil Aviation Administration of China (MHRD20160103), National Natural Science Foundation of China (NSFC.21602051).
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Jia, X., Niu, C., He, Y. et al. A Hybrid Coumarin-Semifluorescein-Based Fluorescent Probe for the Detection of Cysteine. J Fluoresc 28, 1059–1064 (2018). https://doi.org/10.1007/s10895-018-2269-5
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10895-018-2269-5