Abstract
A facile and dual fluorescent chemosensor (named 7-IDF) based on a phenylalanine derivative with an indole group was designed and synthesized. 7-IDF can selectively and sensitively detect Zn2+ via obvious fluorescence enhancement in an aqueous solution. Remarkably, the 7-IDF-Zn complex with blue luminescence has higher selectivity toward cysteine (Cys) and histidine (His) than for other amino acids. Intriguingly, 7-IDF can also be used as an excellent probe to detect Zn2+ in real water samples. Moreover, 7-IDF and 7-IDF-Zn possess excellent biocompatibility and cell permeability, and 7-IDF can consecutively detect Zn2+ and Cys/His in Hela cells through fluorescence imaging experiments. This study suggests that the phenylalanine-based chemosensor possesses great potential applications for the sequential detection of Zn2+ and Cys/His in biosystems.
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References
Jang HJ, Kim A, Jung JM, Lee M, Lim MH, Kim C (2018) Bull Korean Chem Soc 39:1373–1379
Wen X, Wang Q, Fan Z (2018) J Lumin 194:366–373
Zhang T-T, Wang F-W, Li M-M, Liu J-T, Miao J-Y, Zhao B-X (2013) Sens Actuators B-Chem 186:755–760
Du K, Niu S, Qiao L, Dou Y, Zhu Q, Chen X, Zhang P (2017) RSC Adv 7:40615–40620
Budri M, Naik G, Patil S, Kadolkar P, Gudasi K, Inamdar S (2020) J Photochem Photobiol A Chem 390:112298
Cuajungco MP, Lees GJ (1997) Brain Res Rev 23:219–236
Takeda A (2001) Biometals 14:343–351
Frederickson CJ, Koh J-Y, Bush AI (2005) Nat Rev Neurosci 6:449–462
Berg JM, Shi Y (1996) Science 271:1081
Tang YT, Cloquet C, Deng TH, Sterckeman T, Echevarria G, Yang WJ, Morel JL, Qiu RL (2016) Environ Sci Technol 50:8020–8027
Yue Y, Dong Q, Zhang Y, Sun Y, Gong Y (2015) Anal Methods 7:5661–5666
Voegelin A, Pfister S, Scheinost AC, Marcus MA, Kretzschmar R (2005) Environ Sci Technol 39:6616–6623
Ouyang R, Zhu Z, Tatum CE, Chambers JQ, Xue ZL (2011) J Electroanal Chem (Lausanne) 656:78–84
Antunes GA, dos Santos HS, da Silva YP, Silva MM, Piatnicki CMS, Samios D (2017) Energ Fuel 31:2944–2950
Talmard C, Bouzan A, Faller P (2007) Biochemistry 46:13658–13666
Wan Q, Ahmad MF, Fairman J, Gorzelle B, de la Fuente M, Dealwis C, Maguire ME (2011) Structure 19:700–710
Yan XJ, Gao YY, Liu HB, Qiao X, Xie CZ, Li QZ, Gao WZ, Sun HB, Xu JY (2021) Spectrochim Acta A Mol Biomol Spectrosc 261:120067
Yao H, Wang J, Zhou Q, Guan XW, Fan YQ, Zhang YM, Wei TB, Lin Q (2018) Soft Matter 14:8390–8394
Wang KP, Jin ZH, Shang HS, Lv CD, Zhang Q, Chen S, Hu ZQ (2017) J Fluoresc 27:629–633
Liu LZ, Wang L, Yu M, Zhao Q, Zhang Y, Sun YX, Dong WK (2019) Spectrochim Acta A Mol Biomol Spectrosc 222:117209
Tan N-D, Yin J-H, Pu G, Yuan Y, Meng L, Xu N (2016) Chem Phys Lett 666:68–72
Xu T, Duan H, Wang X, Meng X, Bu J (2015) Spectrochim Acta A Mol Biomol Spectrosc 138:603–608
Li CR, Li SL, Yang ZY (2017) Spectrochim Acta A Mol Biomol Spectrosc 174:214–222
Kim H, Kang J, Kim KB, Song EJ, Kim C (2014) Spectrochim Acta A Mol Biomol Spectrosc 118:883–887
Ma Y, Wang F, Kambam S, Chen X (2013) Sensor Actuators B-Chem 188:1116–1122
Huerta-Aguilar CA, Pandiyan T, Singh N, Jayanthi N (2015) Spectrochim Acta A Mol Biomol Spectrosc 146:142–150
Han Z-X, Zhang X-B, Li Z, Gong Y-J, Wu X-Y, Jin Z, He C-M, Jian L-X, Zhang J, Shen G-L, Yu R-Q (2010) Anal Chem 82:3108–3113
Williams NJ, Gan W, Reibenspies JH, Hancock RD (2009) Inorg Chem 48:1407–1415
Cui M, Xia L, Gu Y, Wang P (2020) New J Chem 44:973–980
Yang S, Jiang W, Ren L, Yuan Y, Zhang B, Luo Q, Guo Q, Bouchard LS, Liu M, Zhou X (2016) Anal Chem 88:5835–5840
Sasmal M, Maiti TK, Bhattacharyya TK (2015) IEEE T Nanobiosci 14:634–640
Xie Y, Yan L, Li J (2019) Appl Spectrosc 73:794–800
Yang X, He L, Xu K, Lin W (2017) Anal Chim Acta 981:86–93
Zhang Y, Shao X, Wang Y, Pan F, Kang R, Peng F, Huang Z, Zhang W, Zhao W (2015) Chem Commun (Camb) 51:4245–4248
Zheng X, Yao T, Zhu Y, Shi S (2015) Biosens Bioelectron 66:103–108
Jia X, Niu C, He Y, Sun Y, Liu H (2018) J Fluoresc 28:1059–1064
He Y, Wang X, Zhu J, Zhong S, Song G (2012) Analyst 137:4005–4009
Zhang S, Yang C, Zhu W, Zeng B, Yang Y, Xu Y, Qian X (2012) Org Biomol Chem 10:1653–1658
Hu L, Zheng T, Song Y, Fan J, Li H, Zhang R, Sun Y (2021) Anal Biochem 620:114138
Xu L, Xu Y, Zhu W, Zeng B, Yang C, Wu B, Qian X (2011) Org Biomol Chem 9:8284
Choi JY, Kim D, Yoon J (2013) Dyes Pigm 96:176–179
Ambrosi G, Fanelli M, Paoli P, Formica M, Paderni D, Rossi P, Micheloni M, Giorgi G, Fusi L (2020) Dalton Trans 49:7496–7506
Pourfallah G, Lou X (2016) Sens Actuators B-Chem 233:379–387
Shyamal M, Mazumdar P, Maity S, Sahoo GP, Salgado-Morán G, Misra A (2016) J Phys Chem A 120:210–220
Park GJ, Lee JJ, You GR, Nguyen L, Noh I, Kim C (2016) Sens Actuat B-Chem 223:509–519
Acknowledgements
This work was supported by the National Natural Science Foundation of China (21807058) and the Research Foundation of Education Bureau of Hunan Province (21A0279).
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Yu, QY., Wei, CW., Wang, XJ. et al. A fluorescent probe based on a phenylalanine derivative is capable of sequential detection of Zn2+ and Cys/His. J Biol Inorg Chem 28, 205–211 (2023). https://doi.org/10.1007/s00775-022-01984-x
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DOI: https://doi.org/10.1007/s00775-022-01984-x