Startseite 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
Artikel
Lizenziert
Nicht lizenziert Erfordert eine Authentifizierung

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

  • Agata Głuszyńska EMAIL logo , Ewa Rajczak und Bernard Juskowiak
Veröffentlicht/Copyright: 28. Mai 2013
Veröffentlichen auch Sie bei De Gruyter Brill

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.

[1] Brooks, T, A., & Hurley, L. H. (2010). Targeting MYC expression through G-quadruplexes. Genes & Cancer, 1, 641–649. DOI: 10.1177/1947601910377493. http://dx.doi.org/10.1177/194760191037749310.1177/1947601910377493Suche in Google Scholar PubMed PubMed Central

[2] 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. 10.1002/jccs.200300026Suche in Google Scholar

[3] 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. http://dx.doi.org/10.1021/ac034789i10.1021/ac034789iSuche in Google Scholar PubMed

[4] 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. http://dx.doi.org/10.1002/cbdv.20049010010.1002/cbdv.200490100Suche in Google Scholar PubMed

[5] 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. http://dx.doi.org/10.1021/ac049510s10.1021/ac049510sSuche in Google Scholar PubMed

[6] 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. http://dx.doi.org/10.1021/ac052218f10.1021/ac052218fSuche in Google Scholar PubMed

[7] 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. http://dx.doi.org/10.1016/j.jlumin.2005.12.01610.1016/j.jlumin.2005.12.016Suche in Google Scholar

[8] 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. http://dx.doi.org/10.1093/nar/gkm15510.1093/nar/gkm155Suche in Google Scholar PubMed PubMed Central

[9] 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. 10.1007/978-1-59745-363-9Suche in Google Scholar

[10] 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. http://dx.doi.org/10.2174/138955703340550210.2174/1389557033405502Suche in Google Scholar PubMed

[11] 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. http://dx.doi.org/10.1021/ja00121a03410.1021/ja00121a034Suche in Google Scholar

[12] 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. http://dx.doi.org/10.1002/anie.20030058910.1002/anie.200300589Suche in Google Scholar

[13] 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. http://dx.doi.org/10.1016/j.biochi.2007.07.01110.1016/j.biochi.2007.07.011Suche in Google Scholar

[14] 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. http://dx.doi.org/10.1021/bi048474o10.1021/bi048474oSuche in Google Scholar

[15] 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. http://dx.doi.org/10.1016/j.biochi.2011.05.03510.1016/j.biochi.2011.05.035Suche in Google Scholar

[16] 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. http://dx.doi.org/10.1016/j.bbadis.2009.01.01410.1016/j.bbadis.2009.01.014Suche in Google Scholar

[17] 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. http://dx.doi.org/10.1002/ejoc.20080119610.1002/ejoc.200801196Suche in Google Scholar

[18] 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. http://dx.doi.org/10.1073/pnas.48.12.201310.1073/pnas.48.12.2013Suche in Google Scholar

[19] 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 http://dx.doi.org/10.1016/j.tetlet.2010.07.18010.1016/j.tetlet.2010.07.180Suche in Google Scholar

[20] 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. Suche in Google Scholar

[21] Haugland, R. P. (1996). Handbook of fluorescent probes and research chemicals (6th ed.). Eugene, OR, USA: Molecular Probes, Inc. Suche in Google Scholar

[22] 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. http://dx.doi.org/10.1016/S0223-5234(02)01349-110.1016/S0223-5234(02)01349-1Suche in Google Scholar

[23] 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. http://dx.doi.org/10.1158/1541-7786.MCR-07-026010.1158/1541-7786.MCR-07-0260Suche in Google Scholar

[24] 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. http://dx.doi.org/10.1021/bc200268a10.1021/bc200268aSuche in Google Scholar

[25] 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. http://dx.doi.org/10.1246/bcsj.72.26510.1246/bcsj.72.265Suche in Google Scholar

[26] Juskowiak, B., Chudak, M., Takagi, N., & Takagi, M. (2002). Photoisomerizable DNA ligands. Photoizomerization of anthrylvinylpyridinium derivatives. Polish Journal of Chemistry, 76, 83–93. Suche in Google Scholar

[27] 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. http://dx.doi.org/10.1016/j.ejca.2004.11.02410.1016/j.ejca.2004.11.024Suche in Google Scholar

[28] Kerwin, S. M. (2000). G-quadruplex DNA as a target for drug design. Current Pharmaceutical Design, 6, 441–471. http://dx.doi.org/10.2174/138161200340084910.2174/1381612003400849Suche in Google Scholar

[29] 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. http://dx.doi.org/10.1021/ma971155310.1021/ma9711553Suche in Google Scholar

[30] 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. http://dx.doi.org/10.1016/j.saa.2009.01.01910.1016/j.saa.2009.01.019Suche in Google Scholar

[31] 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. http://dx.doi.org/10.1002/cmdc.20070030010.1002/cmdc.200700300Suche in Google Scholar

[32] 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. http://dx.doi.org/10.1016/S0223-5234(99)80064-610.1016/S0223-5234(99)80064-6Suche in Google Scholar

[33] 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. http://dx.doi.org/10.1016/j.polymer.2008.06.03910.1016/j.polymer.2008.06.039Suche in Google Scholar

[34] 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. http://dx.doi.org/10.2174/156801104335274010.2174/1568011043352740Suche in Google Scholar PubMed

[35] 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. http://dx.doi.org/10.1016/j.tet.2006.04.05110.1016/j.tet.2006.04.051Suche in Google Scholar

[36] 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. http://dx.doi.org/10.1016/j.ejphar.2007.01.00510.1016/j.ejphar.2007.01.005Suche in Google Scholar PubMed

[37] 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. http://dx.doi.org/10.1002/chem.20080000810.1002/chem.200800008Suche in Google Scholar PubMed

[38] 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. http://dx.doi.org/10.1016/j.canlet.2009.02.02610.1016/j.canlet.2009.02.026Suche in Google Scholar PubMed

[39] 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. http://dx.doi.org/10.1021/jm970199z10.1021/jm970199zSuche in Google Scholar PubMed

[40] 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. http://dx.doi.org/10.1021/bi001236i10.1021/bi001236iSuche in Google Scholar PubMed

[41] 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. http://dx.doi.org/10.1046/j.1432-1327.2001.02242.x10.1046/j.1432-1327.2001.02242.xSuche in Google Scholar PubMed

[42] 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. http://dx.doi.org/10.1016/j.jlumin.2007.02.05410.1016/j.jlumin.2007.02.054Suche in Google Scholar

[43] 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. http://dx.doi.org/10.1016/j.bpc.2006.06.00610.1016/j.bpc.2006.06.006Suche in Google Scholar PubMed

[44] 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. http://dx.doi.org/10.1021/ja00195a08010.1021/ja00195a080Suche in Google Scholar

[45] 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. http://dx.doi.org/10.1002/ejoc.20060035610.1002/ejoc.200600356Suche in Google Scholar

[46] 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. http://dx.doi.org/10.1021/jp071963o10.1021/jp071963oSuche in Google Scholar

[47] 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. http://dx.doi.org/10.1016/j.bmcl.2010.01.15910.1016/j.bmcl.2010.01.159Suche in Google Scholar

[48] 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. http://dx.doi.org/10.1002/(SICI)1099-0518(199605)34:7<1359::AID-POLA26>3.0.CO;2-710.1002/(SICI)1099-0518(199605)34:7<1359::AID-POLA26>3.0.CO;2-7Suche in Google Scholar

Published Online: 2013-5-28
Published in Print: 2013-9-1

© 2013 Institute of Chemistry, Slovak Academy of Sciences

Artikel in diesem Heft

  1. Evaluation of waste products in the synthesis of surfactants by yeasts
  2. Investigation of CO2 and ethylethanolamine reaction kinetics in aqueous solutions using the stopped-flow technique
  3. Alkali pre-treatment of Sorghum Moench for biogas production
  4. Modelling of kinetics of microbial degradation of simulated leachate from tobacco dust waste
  5. Model predictive control-based robust stabilization of a chemical reactor
  6. Decomposition of meta- and para-phenylphenol during ozonation process
  7. Treatment of effluents from a membrane bioreactor by nanofiltration using tubular membranes
  8. Zeolite and potting soil sorption of CO2 and NH3 evolved during co-composting of grape and tobacco waste
  9. Liquid-solid equilibrium for the NaCl-NaHCO3-Na2CO3-H2O system at 45°C. Validation of mixed solvent electrolyte model
  10. Investigation of turbulent flow field in a Kenics static mixer by Laser Doppler Anemometry
  11. Effect of flow-rate on ethanol separation in membrane distillation process
  12. Preparation of aluminium ammonium calcium phosphates using microwave radiation
  13. Continuous dehydrochlorination of 1,3-dichloropropan-2-ol to epichlorohydrin: process parameters and by-products formation
  14. Preparation of sterically stabilized gold nanoparticles for plasmonic applications
  15. 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
  16. Microwave-assisted oxidation of alcohols by hydrogen peroxide catalysed by tetrabutylammonium decatungstate
  17. Dynamic shape and wall correction factors of cylindrical particles falling vertically in a Newtonian liquid
  18. Selective oxidation of metallic single-walled carbon nanotubes
Heruntergeladen am 27.11.2025 von https://www.degruyterbrill.com/document/doi/10.2478/s11696-013-0343-7/html
Button zum nach oben scrollen