Monatshefte für Chemie - Chemical Monthly

, Volume 149, Issue 6, pp 1003–1008 | Cite as

An NBD–NH2 fluorescent probe for bioimaging: existence of a specific detection of ClO

  • Yunxia Yang
  • Di Zhang
  • Mengsheng Xu
  • Jianhong Wang
  • Jipeng Chen
  • Le Wang
Original Paper


A fluorescent probe 4-amino-7-nitrobenz-2-oxa-1,3-diazole NBD–NH2 for critical sensing hypochlorous (ClO) has been developed in this paper. Probe NBD–NH2 exhibited excellent sensitivity and high selectivity toward detection of ClO in CH3CH2OH/HEPES solution (1:4, v/v, 10 mM, pH 7.4), where the detection limit as low as 40 nM. The green fluorescence of NBD–NH2 was distinctly quenched by addition of ClO. In addition, the new probe was also applied for bioimaging using HeLa cells and exist a critical detection of ClO in living cells.

Graphical abstract


NBD–NH2 Fluorescent probe Hypochlorous 



The authors thank Professor Zhihua Sun and Li-June Ming for carefully reading the manuscript and for constructive comments. We are grateful for financial support from the Natural Science Foundation of Shanghai (No. 17ZR1412000) and the Scientific and Technological Project of Henan Province of China (162102310352).

Supplementary material

706_2018_2143_MOESM1_ESM.doc (218 kb)
Supplementary material 1 (DOC 218 kb)


  1. 1.
    Gomes A, Fernandes E, Lima JLFC (2005) J Biochem Biophys Methods 65:45CrossRefPubMedGoogle Scholar
  2. 2.
    Fiedler TJ, Davey CA, Fenna RE (2000) J Biol Chem 275:11964CrossRefPubMedGoogle Scholar
  3. 3.
    Hammerschmidt S, Büchler N, Wahn H (2001) Chest 121:573CrossRefGoogle Scholar
  4. 4.
    Yap YW, Whiteman M, Cheung NS (2007) Cell Signal 19:219CrossRefPubMedGoogle Scholar
  5. 5.
    Pullar JM, Vissers MCM, Winterbourn CC (2000) IUBMB Life 50:259CrossRefPubMedGoogle Scholar
  6. 6.
    Dickinson BC, Chang CJ (2011) Nat Chem Biol 7:504CrossRefPubMedPubMedCentralGoogle Scholar
  7. 7.
    Wu SM, Pizzo SV (2001) Arch Biochem Biophys 391:119CrossRefPubMedGoogle Scholar
  8. 8.
    Maruyama Y, Lindholm B, Stenvinkel P (2004) J Nephrol 17(Suppl 8):72Google Scholar
  9. 9.
    Hasegawa T, Malle E, Farhood A, Jaeschke H (2005) Am J Physiol Gastrointest Liver Physiol 289:760CrossRefGoogle Scholar
  10. 10.
    Soldatkin AP, Gorchkov DV, Martelet C, Jaffrezic-Renault N (1997) Sens Actuators B 43:99CrossRefGoogle Scholar
  11. 11.
    Ballesta Claver J, Valencia Mirón MC, Capitán-Vallvey LF (2004) Anal Chim Acta 522:267CrossRefGoogle Scholar
  12. 12.
    Ordeig O, Mas R, Gonzalo J, Campo F, Muñoz F, Haro C (2005) Electroanalysis 17:1641CrossRefGoogle Scholar
  13. 13.
    Zhan XQ, Yan JH, Su JH, Wang YC, He J, Wang SY, Zheng H, Xu JG (2010) Sens Actuators B 150:774CrossRefGoogle Scholar
  14. 14.
    Chen X, Wang F, Hyun JY, Wei T, Qiang J, Ren X, Shin I, Yoon J (2016) Chem Soc Rev 45:2976CrossRefPubMedGoogle Scholar
  15. 15.
    Zhang Z, Zheng Y, Hang W, Yan X, Zhao Y (2011) Talanta 85:779CrossRefPubMedGoogle Scholar
  16. 16.
    Zhang YR, Liu Y, Feng X, Zhao BX (2017) Sens Actuators B 240:18CrossRefGoogle Scholar
  17. 17.
    Wang B, Li P, Yu F, Song P, Sun X, Yang S, Lou Z, Han K (2013) Chem Commun 49:1014CrossRefGoogle Scholar
  18. 18.
    Hu JJ, Wong NK, Lu MY, Chen X, Ye S, Zhao AQ, Gao P, YiTsun Kao R, Shen J, Yang D (2016) Chem Sci 7:2094CrossRefPubMedPubMedCentralGoogle Scholar
  19. 19.
    Cheng X, Jia H, Long T, Feng J, Qin J, Li Z (2011) Chem Commun 47:11978CrossRefGoogle Scholar
  20. 20.
    Yin W, Zhu H, Wang R (2014) Dyes Pigm 107:127CrossRefGoogle Scholar
  21. 21.
    Chang C, Wang F, Qiang J, Zhang Z, Chen Y, Zhang W, Wang Y, Chen X (2017) Sens Actuators B 243:22CrossRefGoogle Scholar
  22. 22.
    Lv J, Wang F, Wei T, Chen X (2017) Ind Eng Chem Res 56:3757CrossRefGoogle Scholar
  23. 23.
    Chen X, Lee KA, Ren X, Ryu JC, Kim G, Ryu JH, Lee WJ, Yoon J (2016) Nat Prot 11:1219CrossRefGoogle Scholar
  24. 24.
    Wang B, Chen D, Kambam S, Wang F, Wang Y, Zhang W, Yin J, Chen H, Chen X (2015) Dyes Pigm 120:22CrossRefGoogle Scholar
  25. 25.
    Oushiki D, Kojima H, Terai T, Arita M, Hanaoka K, Urano Y, Nagano T (2010) J Am Chem Soc 132:2795CrossRefPubMedGoogle Scholar
  26. 26.
    Wang L, Hu Y, Qu Y, Xu J, Cao J (2016) Dyes Pigm 128:54CrossRefGoogle Scholar
  27. 27.
    Zhou G, Wang H, Ma Y, Chen X (2013) Tetrahedron 69:867CrossRefGoogle Scholar
  28. 28.
    Ma Z, Wang X, Sun Y, Liu J, Tong Y, Liu Z (2016) J Fluoresc 26:1917CrossRefPubMedGoogle Scholar
  29. 29.
    Farnoudiyan-Habibi A, Massoumi B, Jaymand M (2017) Spectrochim Acta A 177:14CrossRefGoogle Scholar
  30. 30.
    Zhang D, Wang M, Chai M, Chen X, Ye Y, Zhao Y (2012) Sens Actuators B 168:200CrossRefGoogle Scholar
  31. 31.
    Zhang D, Liu W, Chen K, Cheng J, Zhao Y, Ye Y (2016) RSC Adv 6:103905CrossRefGoogle Scholar
  32. 32.
    Liu D, Pang T, Ma K, Jiang W, Bao X (2014) RSC Adv 4:2563CrossRefGoogle Scholar
  33. 33.
    Cui K, Zhang DQ, Zhang GX, Zhu DB (2010) Tetrahedron Lett 51:6052CrossRefGoogle Scholar
  34. 34.
    Li JF, Huo FJ, Yin CX (2014) RSC Adv 4:44610CrossRefGoogle Scholar
  35. 35.
    Xiong K, Huo F, Yin C, Chao J, Zhang Y, Xu M (2015) Sens Actuators B 221:1508CrossRefGoogle Scholar
  36. 36.
    Cheng G, Fan J, Sun W, Cao J, Hu C, Peng X (2014) Chem Commun 50:5018Google Scholar
  37. 37.
    Xu Q, Heo CH, Kim JA, Lee HS, Hu Y, Kim D, Swamy KMK, Kim G, Nam SJ, Kim HM, Yoon J (2016) Anal Chem 88:6615CrossRefPubMedGoogle Scholar
  38. 38.
    Li J, Yin C, Huo F, Xiong K, Chao J, Zhang Y (2016) Sens Actuators B 231:547CrossRefGoogle Scholar
  39. 39.
    Xiong K, Huo F, Yin C, Chu Y, Yang Y, Chao J, Zheng A (2016) Sens Actuators B 224:307CrossRefGoogle Scholar
  40. 40.
    Tibiletti F, Simonetti M, Nicholas KM, Palmisano G, Parravicini M, Imbesi F, Tollari S, Penoni A (2010) Tetrahedron 66:1280CrossRefGoogle Scholar
  41. 41.
    Koide Y, Urano Y, Hanaoka K, Terai T, Nagano T (2011) J Am Chem Soc 133:5680CrossRefPubMedGoogle Scholar
  42. 42.
    Defoin A (2004) Cheminform 35:706CrossRefGoogle Scholar
  43. 43.
    Yang YK, Cho HJ, Lee J, Shin I, Tae J (2009) Org Lett 11:859CrossRefPubMedGoogle Scholar
  44. 44.
    Cheng J, Song J, Niu H, Tang J, Zhang D, Zhao Y, Ye Y (2016) New J Chem 40:6384CrossRefGoogle Scholar
  45. 45.
    Zhang W, Liu W, Li P, Kang J, Wang J, Wang H, Tang B (2015) Chem Commun 51:10150CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  • Yunxia Yang
    • 1
  • Di Zhang
    • 2
  • Mengsheng Xu
    • 1
  • Jianhong Wang
    • 1
  • Jipeng Chen
    • 1
  • Le Wang
    • 1
  1. 1.College of Chemistry and Chemical EngineeringShanghai University of Engineering ScienceShanghaiChina
  2. 2.Henan Cereal Quality and Safety Testing Key Laboratory, Institute of Quality Standards and Testing Technology for Agro-ProductsHenan Academy of Agricultural SciencesZhengzhouChina

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