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]
  Yi-Xin Zhang , Fang-Qi Zhang , Ao-Pei Peng , Tao Jiang , Ya-Xi Meng , Yang Li , Shuang-Xi Gu , Yuan-Yuan Zhu . Enantioselective recognition of amino acids in water using emission-tunable chiral fluorescent probes. Chinese Chemical Letters, 2026, 37(1): 111500-. doi: 10.1016/j.cclet.2025.111500
2. [2]
  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
3. [3]
  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
4. [4]
  Wanxin Li , Wenxing Gao , Mengyao Wen , Zecheng He , Li Shang . Controllable synthesis of selenolate ligand-costabilized water-soluble near-infrared fluorescent gold nanoclusters for cell imaging. Chinese Chemical Letters, 2025, 36(10): 110803-. doi: 10.1016/j.cclet.2024.110803
5. [5]
  Qian Pang , Fangjun Huo , Yongkang Yue , Caixia Yin . ONOO⁻ and viscosity dual-response fluorescent probe for arthritis imaging in vivo. Chinese Chemical Letters, 2025, 36(9): 110713-. doi: 10.1016/j.cclet.2024.110713
6. [6]
  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
7. [7]
  Yi Tao , Jie Pan , Wenting Yin , Qinglong Qiao , Zhaochao Xu . An LPS-targeted fluorescent probe for dynamic super-resolution imaging of Gram-negative bacterial outer membranes. Chinese Chemical Letters, 2026, 37(7): 112611-. doi: 10.1016/j.cclet.2026.112611
8. [8]
  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
9. [9]
  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
10. [10]
  Chunhong Liu , Xiaotong Liang , Wanhua Wu , Zhouyu Wang , Cheng Yang . Recent advances in chiral recognition with macrocyclic hosts. Chinese Chemical Letters, 2026, 37(7): 112279-. doi: 10.1016/j.cclet.2025.112279
11. [11]
  Jie Pan , Shurui Hu , Wenchao Jiang , Junyu Xiao , Xiaogang Liu , Qinglong Qiao , Zhaochao Xu . Phenylethynyl-bridged naphthalimide probe for super-resolution imaging and polarity decoding of lipid droplets. Chinese Chemical Letters, 2026, 37(9): 112618-. doi: 10.1016/j.cclet.2026.112618
12. [12]
  Chong Wang , Hao Xie , Rulan Xia , Xuewei Liao , Jin Wang , Huajun Yang , Chen Wang . Nanofluidic ion rectification sensor for enantioselective recognition and detection. Chinese Chemical Letters, 2025, 36(8): 110642-. doi: 10.1016/j.cclet.2024.110642
13. [13]
  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
14. [14]
  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
15. [15]
  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
16. [16]
  Meng-Juan Tang , Zhong-Hong Zhu , Hai-Ling Wang , Fu-Pei Liang , Hua-Hong Zou . Mitochondria-targeted and magnetic resonance imaging of water-stable trilobate-shaped nonanuclear lanthanide clusters. Chinese Chemical Letters, 2026, 37(9): 112126-. doi: 10.1016/j.cclet.2025.112126
17. [17]
  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
18. [18]
  Shuairu Wang , Dongsheng Lian , Chuyang Sun , Minghao Xu , Mingming Zhu , Chenxu Yan , Zhiqian Guo . High selective NIR-Ⅱ fluorescent probe for sensing phosgene in plants. Chinese Chemical Letters, 2026, 37(7): 111744-. doi: 10.1016/j.cclet.2025.111744
19. [19]
  Wenchao Chen , Xiaoting Niu , Xinyu Liang , Guanghao Zhu , Xue Zhang , Qing Gong , Cen Xie , Guangbo Ge , Ping Wang , Yuqi He . Rationally engineered a universal far-red fluorogenic substrate of bile salt hydrolase for functional imaging and inhibitor screening. Chinese Chemical Letters, 2026, 37(4): 111320-. doi: 10.1016/j.cclet.2025.111320
20. [20]
  Junbin Li , Min Dai , Tianxin Zhang , Xindi Sun , Du Lian , Mengyi Xiong , Yibo Zhou , Zhihe Qing . Activable chimeric bioluminescent sensors via electrostatic protein engineering for field-deployable imaging of wound infection. Chinese Chemical Letters, 2026, 37(9): 112449-. doi: 10.1016/j.cclet.2026.112449

Get Citation

PDF

XML

Metrics

PDF Downloads(10)
Abstract views(2762)
HTML views(155)

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