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Synthesis and Spectra of a Kind of Novel Longer-Wavelength Benzoxazole Indole Styryl Cyanine Dye with a Carbazole-Bridged Chain

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Abstract

Based on cyanine dye probe oxazole yellow (YO) and Cy3, a series of novel styryl cyanine dyes were designed and synthesized. Carbazole was inserted into the structures of YO and Cy3 to act as a bridge to link the benzoxazole and indole group. This modification resulted in a novel kind of benzoxazole indole styryl cyanine dye with a carbazole-bridged chain. The dyes were characterized by 1HNMR and MS. The spectra of the novel dyes were also performed and the results showed that the maximum emission wavelength of the carbazole styryl cyanine dye was shifted red, the Stokes shift increased and the fluorescence intensity enhanced compared with those of YO and Cy3. These results indicated that the novel dye could be used as an excellent fluorescent probe in biological labeling.

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References

  1. Egawa T, Koide Y, Hanaoka K et al (2011) Chem Commun 47:4162–4164

    Article  CAS  Google Scholar 

  2. Umezawa K, Nakamura Y, Makino H et al (2008) J Am Chem Soc 130:1550–1551

    Article  PubMed  CAS  Google Scholar 

  3. Fu MY, Xiao Y, Qian XH et al (2008) Chem Commun :1780–1782

  4. Kurdyukova IV, Ishchenko AA (2012) Russ Chem Rev 81:258–290

    Article  CAS  Google Scholar 

  5. Opazo F, Rizzoli SO (2010) J Vis Exp 36:e1790

    Google Scholar 

  6. Fisher JA, Barchi JR, Welle CG et al (2008) J Neurophysiol 99:1545–1553

    Article  PubMed  Google Scholar 

  7. Rubner MM, Holzhauser C, Bohlander PR et al (2012) Chem Eur J 18:1299–1302

    Article  PubMed  CAS  Google Scholar 

  8. Ikeda S, Kubota T, Kino K et al (2008) Bioconjug Chem 19:1719–1725

    Article  PubMed  CAS  Google Scholar 

  9. Krieg R, Eitner A, Halbhuber KJ et al (2011) Acta Histochem 113:682–702

    Article  PubMed  CAS  Google Scholar 

  10. Deligeorgiev TG, Gadjev NI, Vasilev AA et al (2007) Dyes Pigments 75:466–473

    Article  CAS  Google Scholar 

  11. Dash S, Panigrahi M, Baliyarsingh S et al (2011) Curr Org Chem 15:2673–2689

    Article  CAS  Google Scholar 

  12. Tokar VP, Losytskyy MY, Ohulchanskyy TY et al (2010) J Fluoresc 20:865–872

    Article  PubMed  CAS  Google Scholar 

  13. Nizomov N, Kurtaliev EN, Nizamov SN et al (2009) J Mol Struct 936:199–205

    Article  CAS  Google Scholar 

  14. Kurtaliev EN (2011) J Fluoresc 21:1713–1719

    Article  PubMed  CAS  Google Scholar 

  15. Samanta A, Vendrell M, Yun SW et al (2011) Asian J 6:1353–1357

    Article  CAS  Google Scholar 

  16. Fei XN, Gu YC, Wang YQ et al (2010) Molecules 15:6983–6992

    Article  PubMed  CAS  Google Scholar 

  17. Pandey RK, James N, Chen Y et al (2008) Top Heterocycl Chem 14:41–74

    Article  CAS  Google Scholar 

  18. Fedyunyayeva IA, Klochko OP, Semenova OM et al (2011) Dyes Pigments 90:201–210

    Article  CAS  Google Scholar 

  19. He H, Lo PC, Yeung SL et al (2011) Chem Commun 47:4748–4750

    Article  CAS  Google Scholar 

  20. Bai M, Achilefu S (2011) Bioorg Med Chem Lett 21:280–284

    Article  PubMed  CAS  Google Scholar 

  21. Zhou LC, Zhao GJ, Liu JF et al (2007) J Photochem Photobiol A 187:305–310

    Article  CAS  Google Scholar 

  22. Scott W, Padilha LA, Hu HH et al (2008) J Lumin 128:1927–1936

    Article  Google Scholar 

  23. Zhang C, Liu T, Su YP et al (2010) Biomaterials 31:6612–6617

    Article  PubMed  CAS  Google Scholar 

  24. Freidzon AY, Bagatur’yants AA, Ushakov EN (2011) Int J Quantum Chem 111:2649–2662

    Article  CAS  Google Scholar 

  25. Song B, Zhang Q, Ma WH et al (2009) Dyes Pigments 82:396–400

    Article  CAS  Google Scholar 

  26. Fei XN, Gu YC, Li C et al (2012) J Fluoresc 22:807–814

    Article  PubMed  CAS  Google Scholar 

Download references

Acknowledgments

This work was financially supported by the National Natural Science Foundation of China (51178289), Technology Development Foundation Plan Project of Tianjin Colleges(No. 20110509).

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Correspondence to Xuening Fei.

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Fei, X., Gu, Y., Li, C. et al. Synthesis and Spectra of a Kind of Novel Longer-Wavelength Benzoxazole Indole Styryl Cyanine Dye with a Carbazole-Bridged Chain. J Fluoresc 23, 221–226 (2013). https://doi.org/10.1007/s10895-012-1137-y

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  • DOI: https://doi.org/10.1007/s10895-012-1137-y

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