Citation: Junwei Chen, Na Wang, Hongjuan Tong, Chao Song, Huijuan Ma, Yajun Zhang, Feng Gao, Huan Xu, Wei Wang, Kaiyan Lou. A compact fluorescence/circular dichroism dual-modality probe for detection, differentiation, and detoxification of multiple heavy metal ions via bond-cleavage cascade reactions[J]. Chinese Chemical Letters, ;2021, 32(12): 3876-3881. doi: 10.1016/j.cclet.2021.05.047 shu

A compact fluorescence/circular dichroism dual-modality probe for detection, differentiation, and detoxification of multiple heavy metal ions via bond-cleavage cascade reactions

Junwei Chen ^a ,
Na Wang ^a ,
Hongjuan Tong ^b ,
Chao Song ^a ,
Huijuan Ma ^a ,
Yajun Zhang ^a ,
Feng Gao ^a ,
Huan Xu ^a ,
Wei Wang ^{a, c, *,} ,
Kaiyan Lou ^{a, **,}

a.
State Key Laboratory of Bioengineering Reactor, Shanghai Key Laboratory of New Drug Design, and Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science & Technology, Shanghai 200237, China
b.
School of Pharmacy, Collaborative Innovation Center of Green Manufacturing Technology for Traditional Chinese Medicine in Shaanxi Province, Shaanxi Institute of International Trade & Commerce, Xi'an 712046, China
c.
Department of Pharmacology and Toxicology and BIO5 Institute, University of Arizona, Tucson AZ 85721-0207, United States

wwang@pharmacy.arizona.edu

kylou@ecust.edu.cn

Received Date: 3 March 2021
Revised Date: 13 May 2021
Accepted Date: 20 May 2021
Available Online: 26 May 2021

Figures(6)

Selective detection of multiple analytes in a compact design with dual-modality and theranostic features presents great challenges. Herein, we wish to report a coumarin-thiazolidine masked D-penicillamine based dual-modality fluorescent probe COU-DPA-1 for selective detection, differentiation, and detoxification of multiple heavy metal ions (Ag⁺, Hg²⁺, Cu²⁺). The probe shows divergent fluorescence (FL) /circular dichroism (CD) responses via divergent bond-cleavage cascade reactions (metal ion promoted C-S cleavage and hydrolysis at two distinctive cleavage sites): FL "turn-off" and CD "turn-on" for Ag⁺ (no hydrolysis), FL "turn-on" and CD "turn-off" for Hg²⁺ (imine hydrolysis), and FL "self-threshold ratiometric" and CD "turn-off" for excess Cu²⁺ (lactone and imine hydrolysis), providing the first example of a fluorescence/CD dual-modality probe for multiple species with complimentary responses. Moreover, the bond-cleavage cascade reactions also lead to the formation of D-penicillamine heavy metal ion complexes for potential detoxification treatments.
- Fluorescent probe,
- Circular dichroism,
- Heavy metal ions,
- Dual-modality,
- Detoxification,
- Cascade reaction,
- Divergent responses
1. [1]
  A.P. de Silva, H.Q.N. Gunaratne, T. Gunnlaugsson, et al., Chem. Rev. 97(1997) 1515-1566. doi: 10.1021/cr960386p
2. [2]
  Y. Yang, Q. Zhao, W. Feng, F. Li, Chem. Rev. 113(2013) 192-270. doi: 10.1021/cr2004103
3. [3]
  W. Sun, M. Li, J. Fan, X. Peng, Acc. Chem. Res. 52(2019) 2818-2831. doi: 10.1021/acs.accounts.9b00340
4. [4]
  K.J. Bruemmer, S.W.M. Crossley, C.J. Chang, Angew. Chem. Int. Ed. 59(2020) 13734-13762. doi: 10.1002/anie.201909690
5. [5]
  J. Ohata, K.J. Bruemmer, C.J. Chang, Acc. Chem. Res. 52(2019) 2841-2848. doi: 10.1021/acs.accounts.9b00386
6. [6]
  Y. Yue, F. Huo, F. Cheng, et al., Chem. Soc. Rev. 48(2019) 4155-4177. doi: 10.1039/C8CS01006D
7. [7]
  J.L. Kolanowski, F. Liu, E.J. New, Chem. Soc. Rev. 47(2018) 195-208. doi: 10.1039/C7CS00528H
8. [8]
  J. Han, X. Liu, H. Xiong, et al., Anal. Chem. 92(2020) 5134-5142. doi: 10.1021/acs.analchem.9b05604
9. [9]
  L. Yang, Y. Zhang, X. Ren, et al., Anal. Chem. 92(2020) 4387-4394. doi: 10.1021/acs.analchem.9b05270
10. [10]
  W. Zhang, F. Huo, F. Cheng, C. Yin, J. Am. Chem. Soc. 142(2020) 6324-6331. doi: 10.1021/jacs.0c00992
11. [11]
  L. Yuan, W. Lin, Y. Xie, B. Chen, S. Zhu, J. Am. Chem. Soc. 134(2012) 1305-1315. doi: 10.1021/ja2100577
12. [12]
  J. Liu, Y.Q. Sun, Y. Huo, et al., J. Am. Chem. Soc. 136(2014) 574-577. doi: 10.1021/ja409578w
13. [13]
  C.X. Yin, K.M. Xiong, F.J. Huo, J.C. Salamanca, R.M. Strongin, Angew. Chem. Int. Ed. 56(2017) 13188-13198. doi: 10.1002/anie.201704084
14. [14]
  G. Yin, T. Niu, Y. Gan, et al., Angew. Chem. Int. Ed. 57(2018) 4991-4994. doi: 10.1002/anie.201800485
15. [15]
  A. Kumar Shaily, N. Ahmed, Ind. Eng. Chem. Res. 56(2017) 6358-6368. doi: 10.1021/acs.iecr.7b00188
16. [16]
  S. Areti, J.K. Khedkar, S. Bandaru, et al., Anal. Chim. Acta 873(2015) 80-87. doi: 10.1016/j.aca.2015.02.065
17. [17]
  M.A. Wani, P.K. Singh, R. Pandey, M.D. Pandey, J. Lumin. 171(2016) 159-165. doi: 10.1016/j.jlumin.2015.11.017
18. [18]
  K. Wang, W. Feng, Y. Wang, et al., Inorg. Chem. Commun. 71(2016) 102-104. doi: 10.1016/j.inoche.2016.07.013
19. [19]
  W. Lin, L. Yuan, X. Cao, Tetrahedron Lett. 49(2008) 6585-6588. doi: 10.1016/j.tetlet.2008.09.029
20. [20]
  N. Li, Y. Xiang, A. Tong, Chem. Commun. 46(2010) 3363-3365. doi: 10.1039/c001408g
21. [21]
  K. Li, N. Li, X. Chen, A. Tong, Anal. Chim. Acta 712(2012) 115-119. doi: 10.1016/j.aca.2011.10.066
22. [22]
  D.A. Lightner, Tech. Instrum. Anal. Chem. 14(1994) 131-174.
23. [23]
  W.M. Weigert, H. Offermanns, P. Scherberich, Angew. Chem. Int. Ed. 14(1975) 330-336. doi: 10.1002/anie.197503301
24. [24]
  M. Blanusa, V.M. Varnai, M. Piasek, K. Kostial, Curr. Med. Chem. 12(2005) 2771-2794. doi: 10.2174/092986705774462987
25. [25]
  H.T. Ratte, Environ. Toxicol. Chem. 18(1999) 89-108. doi: 10.1002/etc.5620180112
26. [26]
  T.W. Clarkson, L. Magos, G.J. Myers, N. Engl. J. Med. 349(2003) 1731-1737. doi: 10.1056/NEJMra022471
27. [27]
  U. Merle, M. Schaefer, P. Ferenci, W. Stremmel, Gut 56(2007) 115-120. doi: 10.1136/gut.2005.087262
28. [28]
  E. Gaggelli, H. Kozlowski, D. Valensin, G. Valensin, Chem. Rev. 106(2006) 1995-2044. doi: 10.1021/cr040410w
29. [29]
  B.O. Leung, F. Jalilehvand, V. Mah, M. Parvez, Q. Wu, Inorg. Chem. 52(2013) 4593-4602. doi: 10.1021/ic400192c
30. [30]
  B.O. Leung, F. Jalilehvand, V. Mah, Dalton Trans. (2007) 4666-4674. doi: 10.1039/B711436B
31. [31]
  Y. Sugiura, H. Tanaka, Chem. Pharm. Bull. 18(1970) 368-373. doi: 10.1248/cpb.18.368
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