Citation: Ding Lele, Tian Zhenhao, Hou Jie, Dou Tongyi, Jin Qiang, Wang Dandan, Zou Liwei, Zhu Yadi, Song Yunqing, Cui Jingnan, Ge Guangbo. Sensing carboxylesterase 1 in living systems by a practical and isoformspecific fluorescent probe[J]. Chinese Chemical Letters, ;2019, 30(3): 558-562. doi: 10.1016/j.cclet.2018.12.013 shu

Sensing carboxylesterase 1 in living systems by a practical and isoformspecific fluorescent probe

Ding Lele ^a,1 ,
Tian Zhenhao ^a,1 ,
Hou Jie ^b,c ,
Dou Tongyi ^d ,
Jin Qiang ^b ,
Wang Dandan ^b ,
Zou Liwei ^b ,
Zhu Yadi ^b ,
Song Yunqing ^b ,
Cui Jingnan ^a,*, ,
Ge Guangbo ^b,*,

a.
State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116024, China
b.
Institute of Interdisciplinary Integrative Medicine Research, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China
c.
Biotechnology Department, College of Basic Medical Sciences, Dalian Medical University, Dalian 116044, China
d.
School of Life Science and Medicine, Dalian University of Technology, Panjin 124221, China

jncui@dlut.edu.cn

geguangbo@dicp.ac.cn

geguangbo@shutcm.edu.cn

Received Date: 15 November 2018
Revised Date: 11 December 2018
Accepted Date: 11 December 2018
Available Online: 12 March 2018

Figures(5)

Carboxylesterase 1 (CES1), one of the most abundant serine hydrolases in mammals, has drawn much attentions in recent years, owing to this enzyme involves in many physiological processes via hydrolysis of both endogenous esters and xenobiotic esters. Herein, to real-time monitor the activities of CES1 in various biological systems, a practical and isoform-specific fluorescent probe was developed on the basis of the substrate preference of CES1, as well as the structural and optical properties of BODIPY dyes. After screening of a panel of BODIPY ester derivatives, probe 1 displayed the best combination of specificity, sensitivity, enzymatic kinetics and applicability for monitoring CES1 activities in real samples. This probe was successfully used to detect CES1 activities in several biological systems including tissue preparations, living cells, tissue slices and zebrafish. Furthermore, the biomedical applications of probe 1 for screening of CES1 inhibitors were also demonstrated using tissue preparations or living cells as enzyme sources. In summary, a practical and broadly applicable tool for real-time monitoring CES1 in biological systems was developed and well-characterized, which held great promise for further investigations on CES1- associated drug discovery, clinical practice and fundamental research.
- Carboxylesterase 1,
- Fluorescent probe,
- Biological imaging,
- Living cells based inhibitors screening,
- BODIPY dyes
1. [1]
  S. Bencharit, C.C. Edwards, C.L. Morton, et al., J. Mol. Biol. 363(2006) 201-214. doi: 10.1016/j.jmb.2006.08.025
2. [2]
  J.S. Xu, Y.Y. Li, W.D. Chen, et al., Hepatology 59(2014) 1761-1771. doi: 10.1002/hep.26714
3. [3]
  D.D. Wang, L.W. Zou, Q. Jin, et al., Acta Pharm. Sin. B 8(2018) 699-712. doi: 10.1016/j.apsb.2018.05.005
4. [4]
  E. Dominguez, A. Galmozzi, J.W. Chang, et al., Nat. Chem. Biol. 10(2014) 113-121. doi: 10.1038/nchembio.1429
5. [5]
  L.W. Zou, Q. Jin, D.D. Wang, et al., Curr. Med. Chem. 25(2018) 1627-1649. doi: 10.2174/0929867325666171204155558
6. [6]
  D.D. Wang, L.W. Zou, Q. Jin, et al., Fitoterapia 117(2017) 84-95. doi: 10.1016/j.fitote.2017.01.010
7. [7]
  M.K. Ross, J.A. Crow, J. Biochem. Mol. Toxic. 21(2007) 187-196. doi: 10.1002/(ISSN)1099-0461
8. [8]
  T. Satoh, M. Hosokawa, Annu. Rev. Pharmacol. 38(1998) 257-288. doi: 10.1146/annurev.pharmtox.38.1.257
9. [9]
  W. Lacour, S. Adjili, J. Blaising, et al., Adv. Healthc. Mater. 5(2016) 2032-2044. doi: 10.1002/adhm.v5.16
10. [10]
  L.L. Zhang, H.K. Zhu, C.C. Zhao, et al., Chin. Chem. Lett. 28(2017) 218-221. doi: 10.1016/j.cclet.2016.07.008
11. [11]
  G.B. Ge, L. Feng, Q. Jin, et al., Anal. Chim. Acta 989(2017) 71-79. doi: 10.1016/j.aca.2017.07.048
12. [12]
  D.F. Yue, M.L. Wang, F. Deng, et al., Chin. Chem. Lett. 29(2018) 648-656. doi: 10.1016/j.cclet.2018.01.046
13. [13]
  B.A. Li, Z.S. He, H.X. Zhou, et al., Chin. Chem. Lett. 28(2017) 1929-1934. doi: 10.1016/j.cclet.2017.08.055
14. [14]
  Y. Wu, J. Wen, H.J. Li, et al., Chin. Chem. Lett. 28(2017) 1916-1924. doi: 10.1016/j.cclet.2017.09.032
15. [15]
  P. Zhang, Z.Q. Guo, C.X. Yan, et al., Chin. Chem. Lett. 28(2017) 1952-1956. doi: 10.1016/j.cclet.2017.08.038
16. [16]
  Q. Jin, L. Feng, D.D. Wang, et al., ACS Appl. Mater. Interfaces 7(2015) 28474-28481. doi: 10.1021/acsami.5b09573
17. [17]
  L. Feng, Z.M. Liu, J. Hou, et al., Biosens. Bioelectron. 65(2015) 9-15. doi: 10.1016/j.bios.2014.10.002
18. [18]
  Q. Jin, L. Feng, D.D. Wang, et al., Biosens. Bioelectron. 83(2016) 193-199. doi: 10.1016/j.bios.2016.04.075
19. [19]
  E.A. Halabi, Z. Thiel, N. Trapp, et al., J. Am. Chem. Soc. 139(2017) 13200-13207. doi: 10.1021/jacs.7b07748
20. [20]
  L. Liu, C.Q. Sun, J. Yang, et al., Chem.-Eur. J. 24(2018) 6148-6154. doi: 10.1002/chem.v24.23
21. [21]
  S.J. Park, Y.J. Kim, J.S. Kang, et al., Anal. Chem. 90(2018) 9465-9471. doi: 10.1021/acs.analchem.8b02101
22. [22]
  J.Z. Long, B.F. Cravatt, Chem. Rev. 111(2011) 6022-6063. doi: 10.1021/cr200075y
23. [23]
  T. Fukami, M. Kariya, T. Kurokawa, et al., Eur. J. Pharm. Sci. 78(2015) 47-53. doi: 10.1016/j.ejps.2015.07.006
24. [24]
  Z.M. Liu, L. Feng, G.B. Ge, et al., Biosens. Bioelectron. 57(2014) 30-35. doi: 10.1016/j.bios.2014.01.049
25. [25]
  D.D. Wang, Q. Jin, J. Hou, et al., J. Chromatogr. B 1008(2016) 212-218. doi: 10.1016/j.jchromb.2015.11.046
26. [26]
  A. Loudet, K. Burgess, Chem. Rev. 107(2007) 4891-4932. doi: 10.1021/cr078381n
27. [27]
  G. Ulrich, R. Ziessel, A. Harriman, Angew. Chem. Int. Ed. 47(2008) 1184-1201. doi: 10.1002/(ISSN)1521-3773
28. [28]
  S. Kim, J. Bouffard, Y. Kim, Chem.-Eur. J. 21(2015) 17459-17465. doi: 10.1002/chem.201503040
29. [29]
  M. Taketani, M. Shii, K. Ohura, et al., Life. Sci. 81(2007) 924-932. doi: 10.1016/j.lfs.2007.07.026
30. [30]
  L.L. Ding, Z.H. Tian, J. Hou, et al., Acta Pharm. Sin. 52(2017) 58-65.
31. [31]
  G.B. Ge, J. Ning, L.H. Hu, et al., Chem. Commun. 49(2013) 9779-9781. doi: 10.1039/c3cc45250f
32. [32]
  Z.R. Dai, L. Feng, Q. Jin, et al., Chem. Sci. 8(2017) 2795-2803. doi: 10.1039/C6SC03970G
33. [33]
  L.W. Zou, P. Wang, X.K. Qian, et al., Biosens. Bioelectron. 90(2017) 283-289. doi: 10.1016/j.bios.2016.11.068
34. [34]
  D.S. Shi, J. Yang, D.F. Yang, et al., J. Pharmacol. Exp. Ther. 319(2006) 1477-1484. doi: 10.1124/jpet.106.111807
35. [35]
  Y. Sato, A. Miyashita, T. Iwatsubo, et al., Drug Metab. Dispos. 40(2012) 1389-1396. doi: 10.1124/dmd.112.045054
36. [36]
  H.B. Rasmussen, D. Bjerre, K. Linnet, et al., Pharmacogenomics 16(2015) 649-665. doi: 10.2217/pgs.15.7
37. [37]
  B.A. Barut, L.I. Zon, Physiol. Genomics 2(2000) 49-51. doi: 10.1152/physiolgenomics.2000.2.2.49
38. [38]
  S.P. Choksi, D. Babu, D. Lau, et al., Development 141(2014) 3410-3419. doi: 10.1242/dev.108209
39. [39]
  J.M. Nussbaum, L.H.J. Liu, S.A. Hasan, et al., Hepatology 58(2013) 1326-1338. doi: 10.1002/hep.v58.4
40. [40]
  N. Fujiyama, M. Miura, S. Kato, et al., Drug Metab. Dispos. 38(2010) 2210-2217. doi: 10.1124/dmd.110.034249
41. [41]
  Y. Chen, Q.Q. Wiu, Z.H. Zhang, et al., China J. Chin. Mater. Med. 36(2011) 988-991.
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