Citation: Tong Hongjuan, Zhang Yajun, Ma Shengnan, Zhang Minghao, Wang Na, Wang Rui, Lou Kaiyan, Wang Wei. A pinacol boronate caged NIAD-4 derivative as a near-infrared fluorescent probe for fast and selective detection of hypochlorous acid[J]. Chinese Chemical Letters, ;2018, 29(1): 139-142. doi: 10.1016/j.cclet.2017.07.007 shu

A pinacol boronate caged NIAD-4 derivative as a near-infrared fluorescent probe for fast and selective detection of hypochlorous acid

Tong Hongjuan ^a ,
Zhang Yajun ^a ,
Ma Shengnan ^a ,
Zhang Minghao ^a ,
Wang Na ^a ,
Wang Rui ^a ,
Lou Kaiyan ^a,, ,
Wang Wei ^a,b,,

a.
Shanghai Key Laboratory of New Drug Design, Shanghai Key Laboratory of Chemical Biology, School of Pharmacy; State Key Laboratory of Bioengineering Reactor, East China University of Science & Technology, Shanghai 200237, China
b.
Department of Chemistry and Chemical Biology, University of New Mexico, Albuquerque, NM 87131-0001, USA

Corresponding author: Lou Kaiyan, kylou@ecust.edu.cn Wang Wei, wwang@unm.edu
Received Date: 23 March 2017
Revised Date: 13 May 2017
Accepted Date: 5 July 2017
Available Online: 8 January 2017

Figures(5)

Hypochlorous acid (HOCl) is one of highly reactive oxygen species (ROS). It is involved in both immune defense against invading microbes and the progression of many diseases including cardiovascular disease and neurodegeneration disorders. It is generated from hydrogen peroxide (H₂O₂) and chloride ions in the presence of myeloperoxidase in activated neutrophils. To illustrate HOCl's biological functions, fluorescent probes, particularly those fluorescence emissions are in the near-infrared range, are highly needed for in vivo applications. Herein, we reported the design of a pinacol boronate caged near-infrared (NIR) fluorescent probe 1 derived from an Aβ binding fluorophore NIAD-4 for fast and selective detection of HOCl/ClO^- over other ROS. Upon exposure to HOCl/ClO^-, the pinacol boronate caging group of the probe 1 was quickly converted to electron-donating hydroxyl group, which increased intramolecular charge transfer (ICT) in the excited state and resulted in the red-shift and intensity enhancement of fluorescence emission. The probe bears several unique features:(1) It could be used as either a ratiomatic or turn-on fluorescent probe; (2) Reaction of the caging group boronate with HOCl is very fast and finishes within seconds, which provides the selectivity over H₂O₂; (3) The NIAD-4 fluorophore provides additional selectivity for detection of HOCl over peroxynitrite. Moreover, the utility of the probe in imaging HOCl/ClO^- was demonstrated in in vitro phantom imaging studies using mouse brain homogenate as biological relevant media.
- Fluorescent probe,
- Hypochlorous acid,
- Boronate,
- Reactive oxygen species (ROS),
- Near-infrared (NIR) imaging
1. [1]
  S.G. Rhee, Science 312(2006) 1882-1883. doi: 10.1126/science.1130481
2. [2]
  R. von Bernhardi, J. Eugenin, Antioxid. Redox Signal. 16(2012) 974-1031. doi: 10.1089/ars.2011.4082
3. [3]
  D. Roos, C.C. Winterbourn, Science 296(2002) 669-671. doi: 10.1126/science.1071271
4. [4]
  D.I. Pattison, M.J. Davies, Biochemistry 45(2006) 8152-8162. doi: 10.1021/bi060348s
5. [5]
  Y.W. Yap, M. Whiteman, N.S. Cheung, Cell. Signal. 19(2007) 219-228. doi: 10.1016/j.cellsig.2006.06.013
6. [6]
  M.V. Avshalumov, L. Bao, J.C. Patel, M.E. Rice, Antioxid. Redox Signal. 9(2007) 219-231. doi: 10.1089/ars.2007.9.219
7. [7]
  A.P. de Silva, H.Q.N. Gunaratne, T. Gunnlaugsson, et al., Chem. Rev. 97(1997) 1515-1566. doi: 10.1021/cr960386p
8. [8]
  X. Qian, Y. Xiao, Y. Xu, et al., Chem. Commun. 46(2010) 6418-6436. doi: 10.1039/c0cc00686f
9. [9]
  Y. Yang, Q. Zhao, W. Feng, F. Li, Chem. Rev. 113(2013) 192-270. doi: 10.1021/cr2004103
10. [10]
  Y. Yue, F. Huo, C. Yin, J.O. Escobedo, R.M. Strongin, Analyst 141(2016) 1859-1873. doi: 10.1039/C6AN00158K
11. [11]
  X. Chen, F. Wang, J.Y. Hyun, et al., Chem. Soc. Rev. 45(2016) 2976-3016. doi: 10.1039/C6CS00192K
12. [12]
  M. Sun, H. Yu, H. Zhu, et al., Anal. Chem. 86(2014) 671-677. doi: 10.1021/ac403603r
13. [13]
  F. Tian, Y. Jia, Y. Zhang, et al., Biosens. Bioelectron. 86(2016) 68-74. doi: 10.1016/j.bios.2016.06.039
14. [14]
  L. Yuan, W. Lin, H. Chen, Biomaterials 34(2013) 9566-9571. doi: 10.1016/j.biomaterials.2013.08.081
15. [15]
  L. Yuan, W. Lin, Y. Yang, H. Chen, J. Am. Chem. Soc. 134(2012) 1200-1211. doi: 10.1021/ja209292b
16. [16]
  G. Cheng, J. Fan, W. Sun, et al., Chem. Commun. 50(2014) 1018-1020. doi: 10.1039/C3CC47864E
17. [17]
  J.O. Escobedo, O. Rusin, S. Lim, R.M. Strongin, Curr. Opin. Chem. Biol. 14(2010) 64-70. doi: 10.1016/j.cbpa.2009.10.022
18. [18]
  E.E. Nesterov, J. Skoch, B.T. Hyman, et al., Angew. Chem. Int. Ed. 44(2005) 5452-5456. doi: 10.1002/(ISSN)1521-3773
19. [19]
  A. Sikora, J. Zielonka, M. Lopez, J. Joseph, B. Kalyanaraman, Free Radic. Biol. Med. 47(2009) 1401-1407. doi: 10.1016/j.freeradbiomed.2009.08.006
20. [20]
  S.P.G. Costa, R.M.F. Batista, M.M.M. Raposo, Tetrahedron 64(2008) 9733-9737. doi: 10.1016/j.tet.2008.07.096
21. [21]
  J. Yang, J. Yang, S.H. Liang, et al., Sci. Rep. 6(2016) 35613. doi: 10.1038/srep35613
22. [22]
  Y.W. Yap, M. Whiteman, B.H. Bay, et al., J. Neurochem. 98(2006) 1597-1609. doi: 10.1111/jnc.2006.98.issue-5
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