Citation: Chuan-Zhi Ni, Ruo-Ming Li, Fang-Qi Zhang, Qu-Ao-Wei Li, Yuan-Yuan Zhu, Jie Zeng, Shuang-Xi Gu. A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells[J]. Chinese Chemical Letters, ;2024, 35(10): 109862. doi: 10.1016/j.cclet.2024.109862 shu

A chiral fluorescent probe for molecular recognition of basic amino acids in solutions and cells

Chuan-Zhi Ni ^{a, 1} ,
Ruo-Ming Li ^{a, b, 1} ,
Fang-Qi Zhang ^a ,
Qu-Ao-Wei Li ^a ,
Yuan-Yuan Zhu ^{a, *,} ,
Jie Zeng ^{a, *,} ,
Shuang-Xi Gu ^{a, *,}

a.
School of Chemistry and Environmental Engineering, School of Chemical Engineering & Pharmacy, Pharmaceutical Research Institute, Hubei Key Laboratory of Novel Reactor and Green Chemical Technology, Wuhan Institute of Technology, Wuhan 430205, China
b.
Nanjing Pusheng Biomedical Co., Ltd., Nanjing 210033, China

yyzhu531@163.com

jiezeng116964@163.com

shuangxigu@163.com

Received Date: 17 February 2024
Revised Date: 29 March 2024
Accepted Date: 6 April 2024
Available Online: 29 April 2024

Figures(10)

A novel and readily available binaphthyl-based fluorescent probe (S)-1 was designed and synthesized. (S)-1 can be used to not only chemoselectively discriminate 3 basic amino acids out of common amino acids, but also enantioselectively recognize histidine. Encouragingly, enantioselective imaging of histidine in cells was achieved for the first time by the probe (S)-1. These performances endowed it potential application in the chiral analysis of basic amino acids in asymmetric synthesis and cell imaging for diagnosis of diseases caused by racemization of histidine. Nuclear magnetic resonance (NMR) and mass spectrometry investigations suggested that different reaction extent of (S)-1 with l/d-histidine and different product structures generated the observed enantioselective fluorescent response. The molecular structures and thermodynamic stability of the complexes, formed from (S)-1 + Zn²⁺ and enantiomers of histidine, were calculated by Gaussian 16 based on density functional theory (DFT) to validate the above action mechanism.
- Fluorescent probe,
- Chiral recognition,
- Enantioselectivity,
- Chemoselectivity,
- Basic amino acids,
- Cell imaging
1. [1]
  T. Vellai, Nature 596 (2021) 192–194. doi: 10.1038/d41586-021-01943-7
2. [2]
  S.F. Oh, T. Praveena, H. Song, et al., Nature 600 (2021) 302–307. doi: 10.1038/s41586-021-04083-0
3. [3]
  S.X. Gu, H.F. Wang, Y.Y. Zhu, et al., Pharm. Front. 2 (2020) e79–e87. doi: 10.1055/s-0040-1713820
4. [4]
  J. Gambardella, W. Khondkar, M.B. Morelli, et al., Biomedicines 8 (2020) 277. doi: 10.3390/biomedicines8080277
5. [5]
  N. Kanarek, H.R. Keys, J.R. Cantor, et al., Nature 559 (2018) 632. doi: 10.1038/s41586-018-0316-7
6. [6]
  A. Pinson, L. Xing, T. Namba, et al., Science 377 (2022) abl6422. doi: 10.1126/science.abl6422
7. [7]
  G. Murtas, L. Pollegioni, Int. J. Mol. Sci. 24 (2023) 3274. doi: 10.3390/ijms24043274
8. [8]
  M. Abdulbagi, L. Wang, O. Siddig, et al., Biomolecules 11 (2021) 1716. doi: 10.3390/biom11111716
9. [9]
  J.J.A.J. Bastings, H.M. Van Eijk, S.W. Olde Damink, et al., Nutrients 11 (2019) 2205. doi: 10.3390/nu11092205
10. [10]
  Y. Shi, Z. Hussain, Y. Zhao, Int. J. Mol. Sci. 23 (2022) 10794. doi: 10.3390/ijms231810794
11. [11]
  F. Nie, K.-Z. Wang, D. Yan, Nat. Commun. 14 (2023) 1654. doi: 10.1038/s41467-023-37331-0
12. [12]
  J. Cai, A.A. Liu, X.H. Shi, et al., J. Am. Chem. Soc. 145 (2023) 24375–24385. doi: 10.1021/jacs.3c09448
13. [13]
  R. Izzo, V. Trimarco, P. Mone, et al., Pharmacol. Res. 183 (2022) 106360. doi: 10.1016/j.phrs.2022.106360
14. [14]
  A. Bongioanni, M.S. Bueno, B.A. Mezzano, et al., Int. J. Pharm. 613 (2022) 121375. doi: 10.1016/j.ijpharm.2021.121375
15. [15]
  S. Mandal, S. Mallik, A. Bhoumick, et al., ChemBioChem (2024) e202300834.
16. [16]
  M.S. Roy, X.F. Meng, K. Koda, et al., Org. Biomol. Chem. 21 (2023) 1422–1434. doi: 10.1039/d2ob01908f
17. [17]
  Y. Ke, J. Zhao, U.H. Verkerk, et al., J. Phys. Chem. B 111 (2007) 14318–14328. doi: 10.1021/jp0746648
18. [18]
  B.M. Paget, K.V. Ram, S.Y. Zhang, et al., Sensor. Actuat. B: Chem. 400 (2024) 134828. doi: 10.1016/j.snb.2023.134828
19. [19]
  M. Xie, J. Chen, Y. Wang, et al., Chin. Chem. Lett. 35 (2024) 108575. doi: 10.1016/j.cclet.2023.108575
20. [20]
  H. Niu, J. Liu, H.M. O’Connor, et al., Chem. Soc. Rev. 52 (2023) 2322–2357. doi: 10.1039/d1cs01097b
21. [21]
  Y. Xu, C. Li, S. Lu, et al., Nat. Commun. 13 (2022) 2009. doi: 10.1080/13658816.2022.2048834
22. [22]
  L. Pu, Chem. Commun. 58 (2022) 8038–8048. doi: 10.1039/d2cc02363f
23. [23]
  J. Li, N. Du, R. Guan, et al., ACS Appl. Mater. Interface. 15 (2023) 23642–23652. doi: 10.1021/acsami.3c02423
24. [24]
  J. Yang, L. Jiang, J. Tian, S, et al., Org. Lett. 24 (2022) 9327–9331. doi: 10.1021/acs.orglett.2c03962
25. [25]
  Y. Mao, E. Thomae, S. Davis, et al., Org. Lett. 25 (2023) 2157–2161. doi: 10.1021/acs.orglett.3c00692
26. [26]
  L. Pu, Acc. Chem. Res. 45 (2012) 150–163. doi: 10.1021/ar200048d
27. [27]
  J.M. Brunel, Chem. Rev. 105 (2005) 857–898. doi: 10.1021/cr040079g
28. [28]
  Z. Huang, S. Yu, K. Wen, et al., Chem. Sci. 5 (2014) 3457–3462. doi: 10.1039/C4SC00818A
29. [29]
  Y.Y. Zhu, X.D. Wu, S.X. Gu, et al., J. Am. Chem. Soc. 141 (2019) 175–181. doi: 10.1021/jacs.8b07803
30. [30]
  Y.Y. Zhu, X.D. Wu, M. Abed, et al., Chem. Eur. J. 25 (2019) 7866–7873. doi: 10.1002/chem.201900880
31. [31]
  M.X. Sun, C.Z. Ni, F.Q. Zhang, et al., Chin. Chem. Lett. 34 (2023) 108345. doi: 10.1016/j.cclet.2023.108345
1. [1]
  Cong Gao , Zijian Zhu , Siwei Li , Zheng Xi , Qingqing Sun , Jie Han , Rong Guo . Chiral supramolecular catalysts of helical nanoribbon: More twist, higher enantioselectivity. Chinese Chemical Letters, 2025, 36(3): 109968-. doi: 10.1016/j.cclet.2024.109968
2. [2]
  Qian Ren , Xue Dai , Ran Cen , Yang Luo , Mingyang Li , Ziyun Zhang , Qinghong Bai , Zhu Tao , Xin Xiao . A cucurbit[8]uril-based supramolecular phosphorescent assembly: Cell imaging and sensing of amino acids in aqueous solution. Chinese Chemical Letters, 2024, 35(12): 110022-. doi: 10.1016/j.cclet.2024.110022
3. [3]
  Huamei Zhang , Jingjing Liu , Mingyue Li , Shida Ma , Xucong Zhou , Aixia Meng , Weina Han , Jin Zhou . Imaging polarity changes in pneumonia and lung cancer using a lipid droplet-targeted near-infrared fluorescent probe. Chinese Chemical Letters, 2024, 35(12): 110020-. doi: 10.1016/j.cclet.2024.110020
4. [4]
  Han-Min Wang , Yan-Chen Li , Lu-Lu Sun , Ming-Ye Tang , Jia Liu , Jiahao Cai , Lei Dong , Jia Li , Yi Zang , Hai-Hao Han , Xiao-Peng He . Protein-encapsulated long-wavelength fluorescent probe hybrid for imaging lipid droplets in living cells and mice with non-alcoholic fatty liver. Chinese Chemical Letters, 2024, 35(11): 109603-. doi: 10.1016/j.cclet.2024.109603
5. [5]
  Yiming Yang , Lichao Sun , Qingfeng Zhang . Plasmonic nanocrystals with intrinsic chirality: Biomolecule-directed synthesis and applications. Chinese Journal of Structural Chemistry, 2025, 44(1): 100467-100467. doi: 10.1016/j.cjsc.2024.100467
6. [6]
  Boran Cheng , Lei Cao , Chen Li , Fang-Yi Huo , Qian-Fang Meng , Ganglin Tong , Xuan Wu , Lin-Lin Bu , Lang Rao , Shubin Wang . Fluorine-doped carbon quantum dots with deep-red emission for hypochlorite determination and cancer cell imaging. Chinese Chemical Letters, 2024, 35(6): 108969-. doi: 10.1016/j.cclet.2023.108969
7. [7]
  Zhixue Liu , Haiqi Chen , Lijuan Guo , Xinyao Sun , Zhi-Yuan Zhang , Junyi Chen , Ming Dong , Chunju Li . Luminescent terphen[3]arene sulfate-activated FRET assemblies for cell imaging. Chinese Chemical Letters, 2024, 35(9): 109666-. doi: 10.1016/j.cclet.2024.109666
8. [8]
  Yudi Cheng , Xiao Wang , Jiao Chen , Zihan Zhang , Jiadong Ou , Mengyao She , Fulin Chen , Jianli Li . A near-infrared fluorescent probe for visualizing transformation pathway of Cys/Hcy and H₂S and its applications in living system. Chinese Chemical Letters, 2024, 35(5): 109156-. doi: 10.1016/j.cclet.2023.109156
9. [9]
  Tao Liu , Xuwei Han , Xueyi Sun , Weijie Zhang , Ke Gao , Runan Min , Yuting Tian , Caixia Yin . An activated fluorescent probe to monitor NO fluctuation in Parkinson’s disease. Chinese Chemical Letters, 2025, 36(3): 110170-. doi: 10.1016/j.cclet.2024.110170
10. [10]
  Fan Zheng , Runsha Xiao , Shuai Huang , Zhikang Chen , Chen Lai , Anyao Bi , Heying Yao , Xueping Feng , Zihua Chen , Wenbin Zeng . Accurate visualization colorectal cancer by monitoring viscosity variations with a novel mitochondria-targeted fluorescent probe. Chinese Chemical Letters, 2025, 36(2): 109876-. doi: 10.1016/j.cclet.2024.109876
11. [11]
  Zhixiao Xiong , Shanni Qiu , Yuyu Wang , Houna Duan , Yi Xiao , Yufang Xu , Weiping Zhu , Xuhong Qian . Photocalibrated NO release from the zinc ion fluorescent probe based on naphthalimide and its application in living cells. Chinese Chemical Letters, 2025, 36(4): 110002-. doi: 10.1016/j.cclet.2024.110002
12. [12]
  Jiayu Zeng , Minhui Liu , Ting Yang , Jia Huang , Songjiao Li , Wanting Zhang , Dan Cheng , Longwei He , Jia Zhou . Two-dimensional design strategy to construct smart dual-responsive fluorescent probe for the precise tracking of ischemic stroke. Chinese Chemical Letters, 2025, 36(5): 110166-. doi: 10.1016/j.cclet.2024.110166
13. [13]
  Chuanfeng Fan , Jian Gao , Yingkai Gao , Xintong Yang , Gaoning Li , Xiaochun Wang , Fei Li , Jin Zhou , Haifeng Yu , Yi Huang , Jin Chen , Yingying Shan , Li Chen . A non-peptide-based chymotrypsin-targeted long-wavelength emission fluorescent probe with large Stokes shift and its application in bioimaging. Chinese Chemical Letters, 2024, 35(10): 109838-. doi: 10.1016/j.cclet.2024.109838
14. [14]
  Lei Shen , Hongmei Liu , Ming Jin , Jinchao Zhang , Caixia Yin , Shuxiang Wang , Yutao Yang . “Three-in-one” strategy of trifluoromethyl regulated blood-brain barrier permeable fluorescent probe for peroxynitrite and antiepileptic evaluation of edaravone. Chinese Chemical Letters, 2024, 35(10): 109572-. doi: 10.1016/j.cclet.2024.109572
15. [15]
  Wenping Dong , Mo Ma , Jingkang Li , Lanlan Xu , Dejiang Gao , Pinyi Ma , Daqian Song . Near-infrared fluorescent probe with large Stokes shift and long emission wavelength for rapid diagnosis of lung cancer via aerosol inhalation delivery. Chinese Chemical Letters, 2025, 36(5): 110147-. doi: 10.1016/j.cclet.2024.110147
16. [16]
  Meiling Zhao , Yao Lu , Yutao Zhang , Haoyun Xue , Zhiqian Guo . Ultra-high signal-to-noise ratio near-infrared chemiluminescent probe for in vivo sensing singlet oxygen. Chinese Chemical Letters, 2025, 36(5): 110105-. doi: 10.1016/j.cclet.2024.110105
17. [17]
  Xiaohui Fu , Yanping Zhang , Juan Liao , Zhen-Hua Wang , Yong You , Jian-Qiang Zhao , Mingqiang Zhou , Wei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688
18. [18]
  Jiajun Lu , Zhehui Liao , Tongxiang Cao , Shifa Zhu . Synergistic Brønsted/Lewis acid catalyzed atroposelective synthesis of aryl-β-naphthol. Chinese Chemical Letters, 2025, 36(1): 109842-. doi: 10.1016/j.cclet.2024.109842
19. [19]
  Jieshuai Xiao , Yuan Zheng , Yue Zhao , Zhuangzhi Shi , Minyan Wang . Asymmetric Nozaki-Hiyama-Kishi (NHK)-type reaction of isatins with aromatic iodides by cobalt catalysis. Chinese Chemical Letters, 2025, 36(5): 110243-. doi: 10.1016/j.cclet.2024.110243
20. [20]
  Jia-Mei Qin , Xue Li , Wei Lang , Fu-Hao Zhang , Qian-Yong Cao . An AIEgen nano-assembly for simultaneous detection of ATP and H₂S. Chinese Chemical Letters, 2024, 35(6): 108925-. doi: 10.1016/j.cclet.2023.108925

Get Citation

PDF

XML

Metrics

PDF Downloads(5)
Abstract views(830)
HTML views(34)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142