Journal of Fluorescence

, Volume 22, Issue 3, pp 807–814 | Cite as

Study on Synthesis and Spectrum of Novel Styryl Cyanine Dyes with a Carbazole Bridged Chain

Original Paper


Based on the frequently-used cyanine dye probe thiazole orange (TO), a novel kind of cyanine dye was designed and synthesized. Carbazole was inserted into the methylidyne structure of TO as a bridge to afford a kind of novel styryl cyanine dye with carbazole bridged chain. The dyes were characterized by HNMR and MS. The spectra of the novel dyes were also studied and the results showed that the fluorescent wavelength of novel carbzole dye shifted red for 100 nm, stock shift increased by 70 nm and the fluorescent intensity enhanced by 70 times compared to that of TO. When the novel dye was labeled by BSA, its fluorescent wavelength changed little and the intensity enhanced. It is indicated that it can be used as an excellent fluorescent probe in biological labeling.


Carbazole Bridge chain Novel styryl cyanine dye Fluorescence Probe 



This work was financially supported by the National Natural Science Foundation of China (No. 21072147, 51178289), Key Project of Science and Technology Committee of Tianjin (10JCYBJC10500). The work in the article also supported by Technology Development Foundation Plan Project of Tianjin Colleges(No. 20100503).


  1. 1.
    Bailly C (2000) Topoisomerase I poisons and suppressors as anticancer drugs. Curr Med Chem 7(1):39–58PubMedGoogle Scholar
  2. 2.
    Zhang PQ et al (2008) Synthesis, antioxidation activity of 5-[2-(8-Hydroxy-quinolin-2-yl)-vinyl]-2-methyl-quinolin-8-ol and its induction proliferation of mesenchymal stem cells. Chin J Org Chem 28(6):1035–1039Google Scholar
  3. 3.
    Wang GR et al (2009) Synthesis, antioxidation activity of (E)-9-p-Tolyl-3-[2-(8-hydroxy-qui-nol-2-yl)vinyl]-carbazole and (E)-9-(p-Anisyl)-3-[2-(8-hydroxy-qui-nol-2-yl)vinyl]-carbazole and their induction proliferation of mesenchymal stem cells. Acta Chimica Sinica 67(9):974–982Google Scholar
  4. 4.
    Lee LG et al (1986) Thiazole orange: a new dye for reticulocyte analysis. Cytometry 7:508–517PubMedCrossRefGoogle Scholar
  5. 5.
    Nygren J et al (1998) The interactions between the fluorescent dye thiazole orange and DNA. Biopolymers 46:39–51PubMedCrossRefGoogle Scholar
  6. 6.
    Timtcheva I et al (2000) Homodimeric monomethine cyanine dyes as fluoresecent probes of biopolymers. J Photochem Photobiol B 58:130–135PubMedCrossRefGoogle Scholar
  7. 7.
    Rye HS et al (1992) Stable fluorescent complexes of double-stranded DNA with bis-intercalating asymmetric cyanine dyes-properties and applications. Nucleic Acids Res 20(11):2803–2812PubMedCrossRefGoogle Scholar
  8. 8.
    Netze TL et al (1995) Base-content dependence of emission enhancements, quantum yields, and lifetimes for cyanine dyes bound to double-strand DNA: photophysical properties of monomeric and bichromomphoric DNA stains. J Phys Chem 99:17936–17947CrossRefGoogle Scholar
  9. 9.
    Kohler O et al (2003) Thiazole orange as fluorescent universal base in peptide nucleic acids. Chem Comm 7:2938–2939CrossRefGoogle Scholar
  10. 10.
    Svanvik N et al (2001) Free-probe fluorescence of light-up probes. J Am Chem Soc 123:803–809PubMedCrossRefGoogle Scholar
  11. 11.
    El-Shishtawy RM et al (2007) New amino and acetamido monomethine cyanine dyes for the detection of DNA in agarose gels. Bioorg Med Chem 15(16):5537–5542PubMedCrossRefGoogle Scholar
  12. 12.
    Carreon JR et al (2007) Cyanine dye conjugates as probes for live cell imaging. Bioorg Med Chem Lett 17(18):5182–5185PubMedCrossRefGoogle Scholar
  13. 13.
    Ikeda S et al (2008) Sequence dependence of fluorescence emission and quenching of doubly thiazole orange labeled DNA: effective design of a hybridization-sensitive probe. Bioconjugate Chem 19(8):1719–1725CrossRefGoogle Scholar
  14. 14.
    Kubota T et al (2009) Doubly thiazole orange-labeled DNA for live cell rna imaging. Bull Chem Soc Jpn 82(1):110–117CrossRefGoogle Scholar
  15. 15.
    Pei R et al (2009) Light-up properties of complexes between thiazole orange-small molecule conjugates and aptamers. Nucleic Acids Res 37(8):e59PubMedCrossRefGoogle Scholar
  16. 16.
    Li K et al (2009) Conjugated polyelectrolyte amplified thiazole orange emission for label free sequence specific DNA detection with single nucleotide polymorphism selectivity. Anal Chem 81(10):4099–4105PubMedCrossRefGoogle Scholar
  17. 17.
    Koide Y et al (2009) Design and development of enzymatically activatable photosensitizer based on unique characteristics of thiazole orange. J Am Chem Soc 131(17):6058–6059PubMedCrossRefGoogle Scholar
  18. 18.
    Fei XN et al (2009) Thiazole orange derivatives: synthesis, fluorescence properties, and labeling cancer cells. Bioorg Med Chem 17:585–591PubMedCrossRefGoogle Scholar
  19. 19.
    Fei XN et al (2010) Targeted thiazole orange derivative with folate: synthesis, fluorescence and in vivo fluorescence imaging. Molecules 15:6983–6992PubMedCrossRefGoogle Scholar
  20. 20.
    Fei XN et al (2011) Preparation and fluorescent properties of a complex probe based on inorganic QDs and organic dye. J Lumin 131:291–296CrossRefGoogle Scholar
  21. 21.
    Gu YC et al (2010) Synthesis, crystal structure and spectral properties of thiazole orange derivative. Chalcogenide Lett 7(5):305–312Google Scholar

Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  1. 1.School of Chemical Engineering and Technology, TianJin UniversityTianjinChina
  2. 2.Department of Material Science and EngineeringTianJin Institute of Urban ConstructionTianjinChina
  3. 3.Tianjin Institute of Urban ConstructionTianjinChina

Personalised recommendations