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A Dicyanomethylene-4H-Pyran Based NIR Ratiometric Fluorescent Probe for Diazane and its Bioimaging

  • Gongchun Li
  • Yongxiang Liu
  • Xiaopeng Yang
  • Yong Ye
ORIGINAL ARTICLE
  • 58 Downloads

Abstract

A near-infrared ICT-based fluorescent probe LX was successfully obtained. LX which detection limit is low as 22.2 nm shows excellent selectivity and high sensitivity to diazane. LX can selectively detected diazane from other species over a wide pH (3–10) range. A obvious color change of solution from yellow to orange can be found, allowing the naked eye to detect. The sensing mechanism was reasonably detected by ESI-MS and DFT calculations. In addition, LX succeed in the visualization of diazane in living cells and the detection of diazane in water samples.

Keywords

Fluorescent probe Diazane NIR ICT 

Notes

Acknowledgements

This work was financially supported by NSFC (No. 21572209) and Program for Innovative Research Team (in Science and Technology) in University of Henan Province (No. 17IRTSTHN002).

Supplementary material

10895_2018_2328_MOESM1_ESM.doc (1.6 mb)
ESM 1 (DOC 1605 kb)

References

  1. 1.
    Ragnarsson U (2001) Synthetic methodologyfor alkyl substituted hydrazines. Chem Soc Rev 30:205–213CrossRefGoogle Scholar
  2. 2.
    Wang J, Chen L (1995) Hydrazine detection using a tyrosinase-based inhibition biosensor. Anal Chem 67:3824–3827CrossRefGoogle Scholar
  3. 3.
    Zelnick SD, Mattie DR, Stepaniak PC (2003) Occupational exposure to hydrazines: treatment of acute central nervous system toxicity. Aviat Space Environ Med 74:1285–1291PubMedGoogle Scholar
  4. 4.
    Zhang B, Yang X, Zhang R, Liu Y, Ren X, Xian M, Ye Y, Zhao Y (2017) A lysosomal-targeted two-photon fluorescent probe to sense hypochlorous acid in live cells. Anal Chem 89:10384–10390CrossRefGoogle Scholar
  5. 5.
    Brown AB, Gibson TL, Baum JC, Ren T, Smith TM (2005) Fluorescence-enhancement sensingof ammonia andhydrazines via disruption of the internal hydrogen bond in a carbazolopyridinophane. Sensors Actuators B Chem 110:8–12CrossRefGoogle Scholar
  6. 6.
    Feng W, Qiao Q, Leng S, Miao L, Xu Z (2016) A 1,8-naphthalimide-derived turn-on fluorescentprobe for imaging lysosomal nitric oxide in living cells. Chin Chem Lett 27:1554–1558CrossRefGoogle Scholar
  7. 7.
    Li J, Yang X, Zhang D, Liu Y, Tang J, Li Y, Zhao Y, Ye Y (2018) A fluorescein-based “turn-on” fluorescence probe for hypochlorous acid detection and its application in cell imaging. Sensors Actuators B Chem 265:84–90CrossRefGoogle Scholar
  8. 8.
    Batchelor-McAuley C, Banks CE, Simm AO, Jones TGJ, Compton RG (2006) The electroanalytical detection of hydrazine: a comparison of the use of palladium nanoparticles supported on boron-doped diamond and palladium platedBDD microdisc array. Analyst 131:106–110CrossRefGoogle Scholar
  9. 9.
    Collins GE, Latturner S, Rose-Pehrsson SL (1995) Chemiluminescence detection of hydrazine vapor. Talanta 42:543–551CrossRefGoogle Scholar
  10. 10.
    Safavi A, Baezzat MR (1998) Flow injection chemiluminescence determination ofhydrazine. Anal Chim Acta 358:121–125CrossRefGoogle Scholar
  11. 11.
    Collins GE, Rose- Pehrsson SL (1993) Sensitive, fluorescent detection of hydrazine via derivatization with 2,3-naphthalene dicarboxaldehyde. Anal Chim Acta 284:207–215CrossRefGoogle Scholar
  12. 12.
    Collins GE, Rose-Pehrsson SL (1994) Fluorescent detection of hydrazine, monomethylhydrazine, and1,1-dimethylhydrazine by derivatization with aromatic dicarbaldehydes. Analyst 119:1907–1913CrossRefGoogle Scholar
  13. 13.
    Elder DP, Snodin D, Teasdale A (2011) Control and analysis of hydrazine, hydrazides and hydrazones- genotoxic impurities in active pharmaceutical ingredients (APIs) and drug products. J Pharm Biomed Anal 54:900–910CrossRefGoogle Scholar
  14. 14.
    Sun M, Bai L, Lui DQ (2009) A generic approach for the determination of trace hydrazine in drug substances using in situ derivatization-headspace GC–MS. J Pharm Biomed Anal 49:529–533CrossRefGoogle Scholar
  15. 15.
    Li S, Zhang D, Xie X, Ma S, Liu Y, Xu Z, Gao Y, Ye Y (2016) A novel solvent-dependently bifunctional NIR absorptive and fluorescent ratiometric probefor detecting Fe3+/Cu2+ and its application in bioimaging. Sensors Actuators B Chem 224:661–667CrossRefGoogle Scholar
  16. 16.
    Liu J, Zhou W, You T, Li F, Wang E, Dong S (1996) Detection of hydrazine, methylhydrazine, and isoniazid by capillary electrophoresis with a palladium- modified microdisk array electrode. Anal Chem 68:3350–3353CrossRefGoogle Scholar
  17. 17.
    Goswami S, Aich K, Das S, Roy SB, Pakhira B, Sarkar S (2014) A reaction based colorimetric as well as fluorescence 'turn on' probe for the rapid detection of hydrazine. RSC Adv 4:14210–14214CrossRefGoogle Scholar
  18. 18.
    Qian Y, Lin J, Han L, Lin L, Zhu H (2014) A resorufin-based colorimetric and fluorescent probefor live-cell monitoring ofhydrazine. Biosens Bioelectron 58:282–286CrossRefGoogle Scholar
  19. 19.
    Yang X, Liu Y, Wu Y, Ren X, Zhang D, Ye Y (2017) A NIR ratiometric probe for hydrazine “naked eye” detection and its imaging in living cell. Sensors Actuators B Chem 253:488–494CrossRefGoogle Scholar
  20. 20.
    Xiao L, Tu J, Sun S, Pei Z, Pei Y, Pang Y, Xu Y (2014) A fluorescent probe for hydrazine and its in vivo applications. RSC Adv 4:41807–41811CrossRefGoogle Scholar
  21. 21.
    Zhang L, Zhu H, Zhao C, Gu X (2017) A near-infrared fluorescent probe for monitoring fluvastatin-stimulated endogenous H2S production. Chin Chem Lett 28:218–221CrossRefGoogle Scholar
  22. 22.
    Zhao Z, Zhang G, Gao Y, Yang X, Li Y (2011) A novel detection technique of hydrazine hydrate: modality change of hydrogen bonding-induced rapidand ultrasensitive colorimetric assay. Chem Commun 47:12816–12818CrossRefGoogle Scholar
  23. 23.
    Choi M, Moon J, Bae J, Lee J, Chang S (2013) Dual signaling of hydrazine by selective deprotection of dichlorofluorescein and resorufin acetates. Org Biomol Chem 11:2961–2965CrossRefGoogle Scholar
  24. 24.
    Jin X, Liu C, Wang X, Huang H, Zhang X, Zhu H (2015) A flavone-based ESIPT fluorescent sensorfor detection of N2H4 in aqueous solution and gas state and its imaging in living cells. Sensors Actuators B Chem 216:141–149CrossRefGoogle Scholar
  25. 25.
    Yu S, Wang S, Yu H, Feng Y, Zhang S, Zhu M, Yin H, Meng X (2015) A ratiometric two-photon fluorescent probefor hydrazine and its applications. Sensors Actuators B 220:1338–1345CrossRefGoogle Scholar
  26. 26.
    Lee MH, Yoon B, Kim JS, Sessler JL (2013) Naphthalimide trifluoroacetyl acetonate:a hydrazine selective chemodosimetric sensor. Chem Sci 4:4121–4126CrossRefGoogle Scholar
  27. 27.
    Chen W, Liu W, Liu XJ, Kuang YQ, Yu RQ, Jiang JH (2017) A novel fluorescent probe for sensitive detection and imaging of hydrazine in living cells. Talanta 162:225–231CrossRefGoogle Scholar
  28. 28.
    Yuan L, Lin W, Zhao S, Gao W, Chen B, He L, Zhu S (2012) A unique approach to development of near- infrared fluorescent sensorsfor in vivo imaging. J Am Chem Soc 134:13510–13523CrossRefGoogle Scholar
  29. 29.
    Guo Z, Park S, Yoon J, Shin I (2014) Recent progress in the development of near-infrared fluorescent probesfor bioimaging applications. Chem Soc Rev 43:16–29CrossRefGoogle Scholar
  30. 30.
    Hu C, Sun W, Cao J, Gao P, Wang J, Fan J, Song F, Sun S, Peng X (2013) A ratiometric near-infrared fluorescent probe for hydrazine and its in vivo applications. Org Lett 15:4022–4025CrossRefGoogle Scholar
  31. 31.
    Zhang J, Ning L, Liu J, Wang J, Yu B, Liu X, Yao X, Zhang Z, Zhang H (2015) Naked-eye and near- infrared fluorescence probe for hydrazine and its applications in in vitro and in vivo bioimaging. Anal Chem 87:9101–9107CrossRefGoogle Scholar
  32. 32.
    Fan J, Sun W, Hu M, Cao J, Cheng G, Dong H, Song K, Liu Y, Sun S, Peng X (2012) An ICT-based ratiometric probe for hydrazine and its application in live cells. Chem Commun 48:8117–8119CrossRefGoogle Scholar
  33. 33.
    Wang C, Liu Y, Cheng J, Song J, Zhao Y, Ye Y (2015) Efficient FRET-based fluorescent ratiometric chemosensors for Fe3+ and its application in living cells. J Lumin 157:143–148CrossRefGoogle Scholar

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© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Key laboratory of Chemo/Biosensing and Detection, College of Chemistry and Chemical EngineeringXuchang UniversityXuchangChina
  2. 2.College of Chemistry and Molecular EngineeringZhengzhou UniversityZhengzhouChina

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