Skip to main content
Log in

Synthesis and spectroscopic characterisation of (E)-2-(2-(9-(4-(1H-1,2,4-triazol-1-yl)butyl)-9H-carbazol-3-yl)vinyl)-3-ethylbenzo[d]thiazol-3-ium, a new ligand and potential DNA intercalator

  • Original Paper
  • Published:
Chemical Papers Aims and scope Submit manuscript

Abstract

Three new compounds based on carbazole planar skeleton were synthesised. Among them there is a new ligand and a potential DNA intercalator which contains a benzothiazolium moiety connected to the carbazole ring by a vinyl bridge. The absorption and emission spectral properties of this new ligand have been studied by spectroscopic methods.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Brooks, T, A., & Hurley, L. H. (2010). Targeting MYC expression through G-quadruplexes. Genes & Cancer, 1, 641–649. DOI: 10.1177/1947601910377493.

    Article  CAS  Google Scholar 

  • Chang, C. C., Wu, J. Y., & Chang, T. C. (2003a). A carbazole derivative synthesis for stabilizing the quadruplex structure. Journal of the Chinese Chemical Society, 50, 185–188.

    CAS  Google Scholar 

  • Chang, C. C., Wu, J. Y., Chien, C. W., Wu, W. S., Liu, H., Kang, C. C., Yu, L. J., & Chang, T. C. (2003b). A fluorescent carbazole derivative: High sensitivity for quadruplex DNA. Analytical Chemistry, 75, 6177–6183. DOI: 10.1021/ac034789i.

    Article  CAS  Google Scholar 

  • Chang, C. C., Kuo, I. C., Lin, J. J., Lu, Y. C., Chen, C. T., Back, H. T., Lou, P. J., & Chang, T. C. (2004a). A novel carbazole derivative, BMVC: a potential antitumor agent and fluorescence marker of cancer cells. Chemistry & Biodiversity, 1, 1377–1384. DOI: 10.1002/cbdv.200490100.

    Article  CAS  Google Scholar 

  • Chang, C. C., Kuo, I. C., Ling, I. F., Chen, H. T., Chen, H. C., Lou, P. J., Lin, J. J., & Chang, T. C. (2004b). Detection of quadruplex DNA structures in human telomeres by a fluorescent carbazole derivative. Analytical Chemistry, 76, 4490–4494. DOI: 10.1021/ac049510s.

    Article  CAS  Google Scholar 

  • Chang, C. C., Chu J. F., Kao, F. J., Chiu, Y. C., Lou, P. J., Chen, H. C., & Chang, T. C. (2006a). Verification of antiparallel G-quadruplex structure in human telomeres by using two-photon excitation fluorescence lifetime imaging microscopy of the 3,6-bis(1-methyl-4-vinylpyridinium)carbazole diiodide molecule. Analytical Chemistry, 78, 2810–2815. DOI: 10.1021/ac052218f.

    Article  CAS  Google Scholar 

  • Chang, C. C., Chu, J. F., Kuo H. H., Kang, C. C., Lin, S. H., & Chang, T. C. (2006b). Solvent effect on photophysical properties of a fluorescence probe: BMVC. Journal of Luminescence, 119–120, 84–90. DOI: 10.1016/j.jlumin.2005.12.016.

    Article  Google Scholar 

  • Chang, C. C., Chien, C. W., Lin, Y. H., Kang, C. C., & Chang, T. C. (2007). Investigation of spectral conversion of d(TTAGGG)4 and d(TTAGGG)13 upon potassium titration by a G-quadruplex recognizer BMVC molecule. Nucleic Acids Research, 35, 2846–2860. DOI: 10.1093/nar/gkm155.

    Article  CAS  Google Scholar 

  • Chang, T. C., & Chang, C. C. (2010). Detection of Gquadruplexes in cells and investigation of G-quadruplex structure of d(T2AG3)4 in K+ solution by a carbazole derivative: BMVC. In P. Baumann (Ed.), G-quadruplex DNA: Methods and protocols (Series: Methods in molecular biology, Vol. 608, pp. 183–206). New York, NY, USA: Humana Press. DOI: 10.1007/978-1-59745-363-9 12.

    Google Scholar 

  • Cuesta, J., Read, M. A., & Neidle, S. (2003). The design of G-quadruplex ligands as telomerase inhibitors. Mini-Reviews in Medicinal Chemistry, 3, 11–21.

    Article  CAS  Google Scholar 

  • Czarny, A., Boykin, D. W., Wood, A. A., Nunn, C. M., Neidle, S., Zhao, M., & Wilson, W. D. (1995). Analysis of van der Waals and electrostatic contributions in the interactions of minor groove binding benzimidazoles with DNA. Journal of the American Chemical Society, 117, 4716–4717. DOI: 10.1021/ja00121a034.

    Article  CAS  Google Scholar 

  • Davis, J. T. (2004). G-quartets 40 years later: From 5′-GMP to molecular biology and supramolecular chemistry. Angewandte Chemie International Edition, 43, 668–698. DOI: 10.1002/anie.200300589.

    Article  CAS  Google Scholar 

  • De Cian, A., Lacroix, L., Douarre, C., Temime-Smaali, N., Trentesaux, C., Riou, J. F., & Mergny, J. L. (2008). Targeting telmeres and telomerase. Biochimie, 90, 131–155. DOI: 10.1016/j.biochi.2007.07.011.

    Article  Google Scholar 

  • Dias, N., Jacquemard, U., Baldeyrou, B., Tardy, C., Lansiaux, A., Colson, P., Tanious, F., Wilson, W. D., Routier, S., Mérour, J. Y., & Bailly, C. (2004). Targeting DNA with novel diphenylcarbazoles. Biochemistry, 43, 15169–15178. DOI: 10.1021/bi048474o.

    Article  CAS  Google Scholar 

  • Dumat, B., Bordeau, G., Faurel-Paul, E., Mahuteau-Betzer, F., Saettel, N., Bombled, M., Metgé, G., Charra, F., Fiorini-Debuisschert, C., & Teulade-Fichou, M. P. (2011). N-phenylcarbazole-based two-photon fluorescent probes: Strong sequence dependence of the duplex vs quadruplex selectivity. Biochimie, 93, 1209–1218. DOI: 10.1016/j.biochi.2011.05.035.

    Article  CAS  Google Scholar 

  • Folini, M., Gandellini, P., & Zaffaroni, N. (2009). Targeting the telosome: Therapeutic implications. Biochimica et Biophysica Acta, 1792, 309–316. DOI: 10.1016/j.bbadis.2009.01.014.

    Article  CAS  Google Scholar 

  • Franceschin, M. (2009). G-quadruplex DNA structures and organic chemistry: More than one connection. European Journal of Organic Chemistry, 2009, 2225–2238. DOI: 10.1002/ejoc.200801196.

    Article  Google Scholar 

  • Gellert, M., Lipsett, M. N., & Davies, D. R. (1962). Helix formation by guanylic acid. Proceedings of the National Academy of Sciences of the United States of America, 48, 2013–2018.

    Article  CAS  Google Scholar 

  • Głuszyńska, A., Bajor, K., Czerwińska, I., Kalet, D., & Juskowiak, B. (2010). The synthesis and spectral properties of new DNA binding ligands. Tetrahedron Letters, 51, 5415–5418. DOI: 10.1016/j.tetlet.2010.07.180

    Article  Google Scholar 

  • Głuszyńska, A., Rajczak, E., & Juskowiak, B. (2012). The synthesis and spectral properties of new carbazole ligand, potential DNA intercalator. In J. Markoš (Ed.), Proceedings of the 39th International Conference of the Slovak Society of Chemical Engineering, May 21–25, 2012 (P. 098, pp 1349–1354). Tatranské Matliare, Slovakia: Slovak Society of Chemical Engineering.

    Google Scholar 

  • Haugland, R. P. (1996). Handbook of fluorescent probes and research chemicals (6th ed.). Eugene, OR, USA: Molecular Probes, Inc.

    Google Scholar 

  • Hotzel, C., Marotto, A., & Pindur, U. (2002). Design, synthesis, DNA-binding and cytotoxicity evaluation of new potential combilexines. European Journal of Medicinal Chemistry, 37, 367–378. DOI: 10.1016/s0223-5234(02)01349-1.

    Article  CAS  Google Scholar 

  • Huang, F. C., Chang, C. C., Lou, P. J., Kuo, I. C., Chien, C. W., Chen, C. T., Shieh, F. Y., Chang, T. C., & Lin, J. J. (2008). G-quadruplex stabilizer 3,6-bis(1-methyl-4-vinylpyridinium)carbazole diiodide induces accelerated senescence and inhibits tumorigenic properties in cancer cells. Molecular Cancer Research, 6, 955–964. DOI: 10.1158/1541-7786.MCR-07-0260.

    Article  CAS  Google Scholar 

  • Jain, A. K., & Bhattacharya, S. (2011). Interaction of G-quadruplexes with nonintercalating duplex-DNA minor groove binding ligands. Bioconjugate Chemistry, 22, 2355–2368. DOI: 10.1021/bc200268a.

    Article  CAS  Google Scholar 

  • Juskowiak, B., Ohba, M., Sato, M., Takenaka, S., Takagi, M., & Kondo, H. (1999). Photoisomerizable DNA ligands. Spectral and electrochemical properties and base-pair selectivity of binding of bis[2-(1-alkylpyridinium-4-yl)vinyl]benzene dyes. Bulletin of the Chemical Society of Japan, 72, 265–277. DOI: 10.1246/bcsj.72.265.

    Article  CAS  Google Scholar 

  • Juskowiak, B., Chudak, M., Takagi, N., & Takagi, M. (2002). Photoisomerizable DNA ligands. Photoizomerization of anthrylvinylpyridinium derivatives. Polish Journal of Chemistry, 76, 83–93.

    CAS  Google Scholar 

  • Kelland, L. R. (2005). Overcoming the immortality of tumour cells by telomere and telomerase based cancer therapeutics — current status and future prospects. European Journal of Cancer, 41, 971–979. DOI: 10.1016/j.ejca.2004.11.024.

    Article  CAS  Google Scholar 

  • Kerwin, S. M. (2000). G-quadruplex DNA as a target for drug design. Current Pharmaceutical Design, 6, 441–471.

    Article  CAS  Google Scholar 

  • Kim, H. K., Ryu, M. K., Kim, K. D., Lee, S. M., Cho, S. W., & Park, J. W. (1998). Tunable electroluminescence from silicon-containing poly(p-phenylenevinylene)-related copolymers with well-defined structures. Macromolecules, 31, 1114–1123. DOI: 10.1021/ma9711553.

    Article  CAS  Google Scholar 

  • Li, J., Li, D., Han, Y., Shuang, S., & Dong, C. (2009). Synthesis of 1-phenyl-3-biphenyl-5-(N-ethylcarbazole-3-yl)-2-pyrazoline and its use as DNA probe. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 73, 221–225. DOI: 10.1016/j.saa.2009.01.019.

    Article  Google Scholar 

  • Ou, T. M., Lu, Y. J., Tan, J. H., Huang, Z. S., Wong, K. Y., & Gu, L. Q. (2008). G-quadruplexes: Targets in anticancer drug design. ChemMedChem, 3, 690–713. DOI: 10.1002/cmdc.200700300.

    Article  CAS  Google Scholar 

  • Patrick, D. A., Boykin, D. W., Wilson, W. D., Tanious, F. A., Spychala, J., Bender, B. C., Hall, J. E., Dykstra, C. C., Ohemeng, K. A., & Tidwell, R. R. (1997). Anti-Pneumocystis carinii pneumonia activity of dicationic carbazoles. European Journal of Medicinal Chemistry, 32, 781–793. DOI: 10.1016/s0223-5234(99)80064-6.

    Article  CAS  Google Scholar 

  • Qu, J., Morita, R., Ashitaka, H., Ogata, N., & Masuda, T. (2008). DNA-lipid complexes carrying carbazole and triphenylamine moieties: Synthesis, and chiroptical and photoelectronic properties. Polymer, 49, 3663–3670. DOI: 10.1016/j.polymer.2008.06.039.

    Article  CAS  Google Scholar 

  • Riou, J. F. (2004). G-quadruplex interacting agents targeting the telomeric G-overhang are more than simple telomerase inhibitors. Current Medicinal Chemistry — Anti-Cancer Agents, 4, 439–443. DOI: 10.2174/1568011043352740.

    Article  CAS  Google Scholar 

  • Ryu, H., Subramanian, L. R., & Hanack, M. (2006). Photoand electroluminescent properties of cyano-substituted styryl derivatives and synthesis of CN-PPV model compounds containing an alkoxy spacer for OLEDs. Tetrahedron, 62, 6236–6247. DOI: 10.1016/j.tet.2006.04.051.

    Article  CAS  Google Scholar 

  • Saengkhae, C., Salerno, M., Adès, D., Siove, A., Le Moyec, L., Migonney, V., & Garnier-Suillerot, A. (2007). Ability of carbazole salts, inhibitors of Alzheimer β-amyloid fibril formation, to cross cellular membranes. European Journal of Pharmacology, 559, 124–131. DOI: 10.1016/j.ejphar.2007.01.005.

    Article  CAS  Google Scholar 

  • Song, Y., Di, C. A., Wei, Z., Zhao, T., Xu, W., Liu, Y., Zhang, D., & Zhu, D. (2008). Synthesis, characterization, and field-effect transistor properties of carbazolenevinylene oligomers: From linear to cyclic architectures. Chemistry — A European Journal, 14, 4731–4740. DOI: 10.1002/chem.200800008.

    Article  CAS  Google Scholar 

  • Spychała, J. (2009). Selective cytostatic and cytotoxic anticancer effects of bisfunctional agents: A strategy for the design of DNA binding agents. Cancer Letters, 281, 203–212. DOI: 10.1016/j.canlet.2009.02.026.

    Article  Google Scholar 

  • Sun, D., Thompson, B., Cathers, B. E., Salazar, M., Kerwin, S. M., Trent, J. O., Jenkins, T. C., Neidle, S., & Hurley, L. H. (1997). Inhibition of human telomerase by a G-quadruplexinteractive compound. Journal of Medicinal Chemistry, 40, 2113–2116. DOI: 10.1021/jm970199z.

    Article  CAS  Google Scholar 

  • Tanious, F. A., Ding, D., Patrick, D. A., Bailly, C., Tidwell, R. R., & Wilson, W. D. (2000). Effects of compound structure on carbazole dication-DNA complexes: Tests of the minor-groove complex models. Biochemistry, 39, 12091–12101. DOI: 10.1021/bi001236i.

    Article  CAS  Google Scholar 

  • Tanious, F. A., Wilson, W. D., Patrick, D. A., Tidwell, R. R., Colson, P., Houssier, C., Tardy, C., & Bailly, C. (2001). Sequence-dependent binding of bis-amidine carbazole dications to DNA. European Journal of Biochemistry, 268, 3455–3464. DOI: 10.1046/j.1432-1327.2001.02242.x.

    Article  CAS  Google Scholar 

  • Tsai, Y. L., Chang, C. C., Kang, C. C., & Chang, T. C. (2007). Effect of different electronic properties on 9-aryl-substituted BMVC derivatives for new fluorescence probes. Journal of Luminescence, 127, 41–47. DOI: 10.1016/j.jlumin.2007.02.054.

    Article  CAS  Google Scholar 

  • White, E. W., Tanious, F., Ismail, M. A., Reszka, A. P., Neidle, S., Boykin, D.W., & Wilson, W. D. (2007). Structure-specific recognition of quadruplex DNA by organic cations: Influence of shape, substituents and charge. Biophysical Chemistry, 126, 140–153. DOI: 10.1016/j.bpc.2006.06.006.

    Article  CAS  Google Scholar 

  • Wilson, W. D., Tanious, F. A., Barton, H. J., Jones, R., Strekowski, L., & Boykin, D. W. (1989). Binding of 4′,6-diamidino-2-phenylindole (DAPI) to GC and mixed sequences in DNA: Intercalation of a classical groove-binding molecule. Journal of the American Chemical Society, 111, 5008–5010. DOI: 10.1021/ja00195a080.

    Article  CAS  Google Scholar 

  • Xu, T. H., Lu, R., Qiu, X. P., Liu, X. L., Xue, P. C., Tan, C. H., Bao, C. Y., & Zhao, Y. Y. (2006). Synthesis and characterization of carbazole-based dendrimers with porphyrin cores. European Journal of Organic Chemistry, 2006, 4014–4020. DOI: 10.1002/ejoc.200600356.

    Article  Google Scholar 

  • Yang, D. Y., Chang, T. C., & Sheu, S. Y. (2007). Interaction between human telomere and a carbazole derivative: A molecular dynamics simulation of a quadruplex stabilizer and telomerase inhibitor. The Journal of Physical Chemistry A, 111, 9224–9232. DOI: 10.1021/jp071963o.

    Article  CAS  Google Scholar 

  • Zhang, F. F., Gan, L. L., & Zhou, C. H. (2010). Synthesis, antibacterial and antifungal activities of some carbazole derivatives. Bioorganic & Medicinal Chemistry Letters, 20, 1881–1884. DOI: 10.1016/j.bmcl.2010.01.159.

    Article  CAS  Google Scholar 

  • Zhang, Y., Wang, L., Wada, T., & Sasabe, H. (1996). Synthesis and characterization of novel hyperbranched polymer with dipole carbazole moieties for multifunctional materials. Journal of Polymer Science: Part A: Polymer Chemistry, 34, 1359–1363. DOI: 10.1002/(SICI)1099-0518(199605)34:7<1359::AID-POLA26>3.0.CO;2-7.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Agata Głuszyńska.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Głuszyńska, A., Rajczak, E. & Juskowiak, B. Synthesis and spectroscopic characterisation of (E)-2-(2-(9-(4-(1H-1,2,4-triazol-1-yl)butyl)-9H-carbazol-3-yl)vinyl)-3-ethylbenzo[d]thiazol-3-ium, a new ligand and potential DNA intercalator. Chem. Pap. 67, 1231–1239 (2013). https://doi.org/10.2478/s11696-013-0343-7

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.2478/s11696-013-0343-7

Keywords

Navigation