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]
  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
2. [2]
  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
3. [3]
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4. [4]
  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
5. [5]
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6. [6]
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7. [7]
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8. [8]
  Lixian Fu , Yiyun Tan , Yue Ding , Weixia Qing , Yong Wang . Water–soluble and polarity–sensitive near–infrared fluorescent probe for long–time specific cancer cell membranes imaging and C. Elegans label. Chinese Chemical Letters, 2024, 35(4): 108886-. doi: 10.1016/j.cclet.2023.108886
9. [9]
  Zhen Dai , Linzhi Tan , Yeyu Su , Kerui Zhao , Yushun Tian , Yu Liu , Tao Liu . Site-specific incorporation of reduction-controlled guest amino acids into proteins for cucurbituril recognition. Chinese Chemical Letters, 2024, 35(5): 109121-. doi: 10.1016/j.cclet.2023.109121
10. [10]
  Gongcheng Ma , Qihang Ding , Yuding Zhang , Yue Wang , Jingjing Xiang , Mingle Li , Qi Zhao , Saipeng Huang , Ping Gong , Jong Seung Kim . Palladium-free chemoselective probe for in vivo fluorescence imaging of carbon monoxide. Chinese Chemical Letters, 2024, 35(9): 109293-. doi: 10.1016/j.cclet.2023.109293
11. [11]
  Xing Tian , Di Wu , Wanheng Wei , Guifu Dai , Zhanxian Li , Benhua Wang , Mingming Yu . A lipid droplets-targetable fluorescent probe for polarity detection in cells of iron death, inflammation and fatty liver tissue. Chinese Chemical Letters, 2024, 35(6): 108912-. doi: 10.1016/j.cclet.2023.108912
12. [12]
  Linfang Wang , Jing Liu , Minghao Ren , Wei Guo . A highly sensitive fluorescent HClO probe for discrimination between cancerous and normal cells/tissues. Chinese Chemical Letters, 2024, 35(6): 108945-. doi: 10.1016/j.cclet.2023.108945
13. [13]
  Yanjing Li , Jiayin Li , Yuqi Chang , Yunfeng Lin , Lei Sui . Tetrahedral framework nucleic acids promote the proliferation and differentiation potential of diabetic bone marrow mesenchymal stem cell. Chinese Chemical Letters, 2024, 35(9): 109414-. doi: 10.1016/j.cclet.2023.109414
14. [14]
  Liangji Chen , Zhen Yuan , Fudong Feng , Xin Zhou , Zhile Xiong , Wuji Wei , Hao Zhang , Banglin Chen , Shengchang Xiang , Zhangjing Zhang . A hydrogen-bonded organic framework containing fluorescent carbazole and responsive pyridyl units for sensing organic acids. Chinese Chemical Letters, 2024, 35(9): 109344-. doi: 10.1016/j.cclet.2023.109344
15. [15]
  Jianqiu Li , Yi Zhang , Songen Liu , Jie Niu , Rong Zhang , Yong Chen , Yu Liu . Cucurbit[8]uril-based non-covalent heterodimer realized NIR cell imaging through topological transformation from nanowire to nanorod. Chinese Chemical Letters, 2024, 35(10): 109645-. doi: 10.1016/j.cclet.2024.109645
16. [16]
  Xuejian Xing , Pan Zhu , E Pang , Shaojing Zhao , Yu Tang , Zheyu Hu , Quchang Ouyang , Minhuan Lan . D-A-D-structured boron-dipyrromethene with aggregation-induced enhanced phototherapeutic efficiency for near-infrared fluorescent and photoacoustic imaging-guided synergistic photodynamic and photothermal cancer therapy. Chinese Chemical Letters, 2024, 35(10): 109452-. doi: 10.1016/j.cclet.2023.109452
17. [17]
  Fang-Yuan Chen , Wen-Chao Geng , Kang Cai , Dong-Sheng Guo . Molecular recognition of cyclophanes in water. Chinese Chemical Letters, 2024, 35(5): 109161-. doi: 10.1016/j.cclet.2023.109161
18. [18]
  Zhiwen Li , Jingjing Zhang , Gao Li . Dynamic assembly of chiral golden knots. Chinese Journal of Structural Chemistry, 2024, 43(7): 100300-100300. doi: 10.1016/j.cjsc.2024.100300
19. [19]
  Caihong Mao , Yanfeng He , Xiaohan Wang , Yan Cai , Xiaobo Hu . Synthesis and molecular recognition characteristics of a tetrapodal benzene cage. Chinese Chemical Letters, 2024, 35(8): 109362-. doi: 10.1016/j.cclet.2023.109362
20. [20]
  Cheng-Da Zhao , Huan Yao , Shi-Yao Li , Fangfang Du , Li-Li Wang , Liu-Pan Yang . Amide naphthotubes: Biomimetic macrocycles for selective molecular recognition. Chinese Chemical Letters, 2024, 35(4): 108879-. doi: 10.1016/j.cclet.2023.108879

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