Citation: Yang Yangyang, Zhang Chen, Pan Rizhao, Zhang Shiwei, Yao Shengtao, Tang Yao, Zhu Weilong, Wang Liyue, Zhu Weiping, Xu Yufang, Qian Xuhong. A ratiometric fluorescent probe for alkaline phosphatase with high sensitivity[J]. Chinese Chemical Letters, ;2020, 31(1): 125-128. doi: 10.1016/j.cclet.2019.04.037 shu

A ratiometric fluorescent probe for alkaline phosphatase with high sensitivity

Yang Yangyang ^a,*, ,
Zhang Chen ^a ,
Pan Rizhao ^a ,
Zhang Shiwei ^a ,
Yao Shengtao ^a ,
Tang Yao ^a ,
Zhu Weilong ^a ,
Wang Liyue ^a ,
Zhu Weiping ^a ,
Xu Yufang ^a,*, ,
Qian Xuhong ^a,b,**,

a.
Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai 200237, China
b.
State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai 200237, China

triyang@ecust.edu.cn

yfxu@ecust.edu.cn

xhqian@ecust.edu.cn

Received Date: 12 March 2019
Revised Date: 15 April 2019
Accepted Date: 15 April 2019
Available Online: 16 January 2019

Figures(5)

Alkaline phosphatase (ALP) is one of essential biomarkers in mammalian tissue. Here we report a ratiometric probe for ALP, which is rationally designed and synthesized by employing ESIPT fluorophore N-(3-(benzo[d]thiazol-2-yl)-4-hydroxyphenyl)benzamide (BTHPB). The enzymatic dephosphorylation converts the probe to BTHPB, which exhibits a large spectral red-shift (120 nm), allowing extremely high sensitivity of ALP sensing at 0.004 mU/mL. The probe also shows excellent biocompatibility and has been applied for monitoring the endogenic ALP in living cells.
- Fluorescent probe,
- Alkaline phosphatase,
- Ratiometric,
- ESIPT,
- Biomarker
1. [1]
  J.L. Millán, Mammalian Alkaline Phosphatases: FromBiology to Applications in Medicine and Biotechnology, Wiley-VCH, Weinheim, 2006.
2. [2]
  R.B. McComb, G.N. Bowers, S. Posen, Alkaline Phosphatase, Plenum Press, New York, 1979.
3. [3]
  G. Ramaswamy, V.R. Rao, L. Krishnamoorthy, et al., Indian J. Clin. Biochem. 15 (2000) 110-113.
4. [4]
  D. Goltzman, D. Miao, Encyclopedia Endocr. Dis. 1 (2004) 164-169.
5. [5]
  Z. Xu, X. Huang, X. Han, et al., Chem 7 (2018) 1609-1628.
6. [6]
  W. Chen, Y. Pan, J. Chen, et al., Chin. Chem. Lett. 29 (2018) 1429-1435. doi: 10.1016/j.cclet.2018.08.011
7. [7]
  Han X, Y. Liu, G. Liu, et al., Chem. -Asian J. 14 (2019) 890-895. doi: 10.1002/asia.201801854
8. [8]
  Z. Xu, J. Chen, L.L. Hu, et al., Chin. Chem. Lett. 28 (2017) 1935-1942. doi: 10.1016/j.cclet.2017.07.018
9. [9]
  Z. Xu, L. Xu, J. Zhou, et al., Chem. Commun. (Camb.) 48 (2012) 10871-10873. doi: 10.1039/c2cc36141h
10. [10]
  B. Li, Z. He, H. Zhou, H. Zhang, T. Cheng, Chin. Chem. Lett. 28 (2017) 1929-1934. doi: 10.1016/j.cclet.2017.08.055
11. [11]
  J. Zhu, P. Jia, N. Li, et al., Chin. Chem. Lett. 29 (2018) 1445-1450. doi: 10.1016/j.cclet.2018.09.002
12. [12]
  D. Yue, M. Wang, F. Deng, et al., Chin. Chem. Lett. 29 (2018) 648-656. doi: 10.1016/j.cclet.2018.01.046
13. [13]
  J. Park, Y. Kim, Bioorg. Med. Chem. Lett. 23 (2013) 2332-2335. doi: 10.1016/j.bmcl.2013.02.063
14. [14]
  H. Gong, G. Little, M. Cradduck, et al., Talanta 84 (2011) 941-946. doi: 10.1016/j.talanta.2011.02.035
15. [15]
  Z.G. Song, R.T.K. Kwok, E.G. Zhao, et al., ACS Appl. Mater. Interfaces 6 (2014) 17245-17254. doi: 10.1021/am505150d
16. [16]
  X.B. Wang, Z.Y. Zhang, X.Y. Ma, et al., Talanta 137 (2015) 156-160. doi: 10.1016/j.talanta.2015.01.028
17. [17]
  X. Zhou, Y. Jiang, X. Zhao, Y. Zhu, Molecules 21 (2016) 1619-1628. doi: 10.3390/molecules21121619
18. [18]
  M.H. Lee, J.S. Kim, J.L. Sessler, Chem. Soc. Rev. 44 (2015) 4185-4191. doi: 10.1039/C4CS00280F
19. [19]
  Y. Tan, L. Zhang, K. Man, et al., ACS Appl. Mater. Interfaces 9 (2017) 6796-6803. doi: 10.1021/acsami.6b14176
20. [20]
  C. Chen, J. Zhao, Y. Lu, J. Su, X. Yang, Anal. Chem. 90 (2018) 3505-3511. doi: 10.1021/acs.analchem.7b05325
21. [21]
  P. Ou, R. Zhang, Z. Liu, et al., Angew. Chem. Int. Ed. 58 (2019) 2261-2265. doi: 10.1002/anie.201811391
22. [22]
  H. Wang, Z. Feng, S.J.D. Signore, A.A. Rodal, B. Xu, J. Am. Chem. Soc. 140 (2018) 3505-3509. doi: 10.1021/jacs.7b13307
23. [23]
  J. Zhao, S. Ji, Y. Chen, H. Guo, P. Yang, Phys. Chem. Chem. Phys. 14 (2012) 8803-8817. doi: 10.1039/C2CP23144A
24. [24]
  S. Goswami, S. Das, K. Aich, et al., Org. Lett. 15 (2013) 5412-5415. doi: 10.1021/ol4026759
25. [25]
  G. Li, D. Zhu, Q. Liu, L. Xue, H. Jiang, Org. Lett. 15 (2013) 924-927. doi: 10.1021/ol4000845
26. [26]
  T. Kim, H. Kang, G. Han, S. Chung, Y. Kim, Chem. Commun. 2 (2009) 5895-5897.
27. [27]
  D. Murale, H. Kim, W. Choi, D. Churchill, Org. Lett. 15 (2013) 3946-3949. doi: 10.1021/ol4017222
28. [28]
  C. Fan, S. Luo, H. Qi, Luminescence 31 (2016) 423-427. doi: 10.1002/bio.2977
29. [29]
  J. Li, L. Si, J. Bao, Z. Wang, Z. Dai, Anal. Chem. 89 (2017) 3681-3685. doi: 10.1021/acs.analchem.6b05112
30. [30]
  W. Zhang, H. Yang, N. Li, N. Zhao, RSC Adv. 8 (2018) 14995-15000. doi: 10.1039/C8RA01786G
31. [31]
  R. Hu, S. Li, Y. Zeng, et al., Phys. Chem. Chem. Phys. 13 (2011) 2044-2051. doi: 10.1039/C0CP01181A
32. [32]
  S. Li, Q. Wang, Y. Qian, et al., J. Phys. Chem. A 111 (2007) 11793-11800. doi: 10.1021/jp075301a
33. [33]
  S.R. Grando, C.M. Pessoa, M.R. Gallas, et al., Langmuir 25 (2009) 13219-13223. doi: 10.1021/la902242y
34. [34]
  R. Hu, J. Feng, D. Hu, et al., Angew. Chem. Int. Ed. 49 (2010) 4915-4918. doi: 10.1002/anie.201000790
35. [35]
  L. Cui, W. Zhu, Y. Xu, X. Qian, Anal. Chim. Acta 786 (2013) 139-145. doi: 10.1016/j.aca.2013.05.011
36. [36]
  M. Santra, B. Roy, K.H. Ahn, Org. Lett. 13 (2011) 3422-3425. doi: 10.1021/ol2011693
37. [37]
  E. Barni, P. Savarino, M. Marzona, M. Piva, J. Heterocycl. Chem. 20 (1983) 1517-1521. doi: 10.1002/jhet.5570200616
38. [38]
  M. Fosset, D. Chappelet-Tordo, M. Lazdunski, Biochemistry 13 (1974) 1783-1788. doi: 10.1021/bi00706a001
39. [39]
  H.N. Fernley, P.D. Boyer (Eds.), The Enzymes, Vol. 4, Academic Press, New York, 1971, pp. 417-447.
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