Archives of Pharmacal Research

  • 제29권12호
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  • Pages.1091-1095
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  • 2006
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  • 0253-6269(pISSN)
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  • 1976-3786(eISSN)
대한약학회 (The Pharmaceutical Society of Korea)
권호 표지

Synthesis, Cytotoxicity and Structure-Activity Relationship Study of Terpyridines

  • 발행 : 2006.12.31
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초록

For the development of novel antitumor agents, we designed and synthesized terpyridines, and their biological activities were evaluated. Although most of the newly prepared terpyridines showed strong cytotoxicity against several human cancer cell lines, [2,2';6',2"]-terpyridine displayed the most significant cytotoxicity.

키워드

참고문헌

  1. Berger, J. M., Structure of DNA topoisomerases. Biochim. Biophys. Acta., 1400, 3-18 (1998) https://doi.org/10.1016/S0167-4781(98)00124-9
  2. Burden, D. A. and Osheroff, N., Mechanism of action of eukaryotic topoisomerase II and drugs target to the enzyme. Biochim. Biophys. Acta., 1400, 139-154 (1998) https://doi.org/10.1016/S0167-4781(98)00132-8
  3. Carter, P. J., Cheng, C. C., and Thorp, H. H., Oxidation of DNA and RNA by oxoruthenium (IV) metallointercalators: visualizing the recognition properties of dipyridophenazine by high-resolution electrophoresis. J. Am. Chem. Soc., 120, 632-642 (1998) https://doi.org/10.1021/ja9729589
  4. Donald, L. and Guise, J. L. E., An improved two-step synthesis of 2,2':6',2''-terpyridine. Tetahedron. Lett., 32, 1999-2002 (1991) https://doi.org/10.1016/S0040-4039(00)78891-5
  5. Fukuda, M., Nishio, K., Kanzawa, F., Ogasawara, H., Ishida, T., Arioka, H., Bojanowski, K., Oka, M., and Saijo, N., Synergism between cisplatin and topoisomerase I inhibitors, NB-506 and SN-38, in human small cell lung cancer cells. Cancer Res., 56, 789-793 (1996)
  6. Jennette, K. W., Lippard, S. J., Vassiliades, G. A., and Bauer, W. R., Metallointercalation Reagents. 2-Hydroxyethanethiolato (2,2',2''-terpyridine)-platinum(II) monocation binds strongly to DNA by intercalation. Proc. Nat. Acad. Sci. U.S.A., 71, 3839- 3943 (1974)
  7. Kim, D. S. H. L., Ashendel, C. L., Zhou, Q., Chang, C. -T., Lee, E. S., and Chang, C. -J., Novel protein kinase C inhibitor: ${\alpha}$- terthiophene derivatives. Bioorg. Med. Chem. Lett., 8, 2695- 2698 (1998) https://doi.org/10.1016/S0960-894X(98)00468-5
  8. Liu, H. Q., Cheung, T. C., Peng, S. M., and Che, C. M., Novel luminescent cyclometalated and terpyridine gold(III) complexes and DNA binding studies. J. Chem. Soc., Chem. Commun., 1787-1788 (1995)
  9. Lowe, G., Droz, A. S., Park, J. J., and Weaver, G. W., The Design and synthesis of bis-[4'-azido-2,2':6',2''-terpyridine platinum(II)] complexes with rigid and extended linker for study the topology of DNA by photoaffinity labeling. Bioorg. Chem., 27, 477-486 (1999) https://doi.org/10.1006/bioo.1999.1152
  10. McCoubrey, A., Latham, H. C., Cook, P. R., Rodger, A., and Lower, G., 4-Picoline-2,2':6',2''-terpyridine-platinum(II) – a potent intercalator of DNA. FEBS Letters, 380, 73-78 (1996) https://doi.org/10.1016/0014-5793(95)01537-X
  11. Mosmann, T., Rapid colormetric assay for cellular growth and survival: application to proliferation and cytotoxic assays. J. Immunol. Methods, 65, 55-63 (1983) https://doi.org/10.1016/0022-1759(83)90303-4
  12. Mukkala, V. M., Helenius, M., and Hemmila, I., Development of luminescent euripium(III) and terbium(III) chelates of 2,2': 6',2''-terpyridine derivatives for protein labeling. Helv. Chim. Acta., 76, 1361-1378 (1993) https://doi.org/10.1002/hlca.19930760323
  13. Pommier, Y., Pourquier, P., Fan, Y., and Strumberg, D., Mechanism of action of eukaryotic DNA topoisomerase I and drugs targeted to the enzyme. Biochim. Biophys. Acta 1400, 83-106 (1998) https://doi.org/10.1016/S0167-4781(98)00129-8
  14. Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warrenm, J. T., Bokesch, H., Kenney, S., and Boyd, M. R., New Colorimetric Cytotoxicity Assay for Anticancer-Drug Screening. J. Natl. Cancer Inst., 82, 1107-1112 (1990) https://doi.org/10.1093/jnci/82.13.1107
  15. Vliet, P. M. V., Toekimin, M. S., Haasnoot, J. G., Reedijk, J., Novakova, O., Vrana, O., and Brabec, V., mer-[Ru(terpy)Cl3] (terpy = 2,2':6',2''-terpyridine) shows biological activity, forms interstrand cross-links in DNA and binds two guanine derivatives in a trans configuration, Inorg. Chim. Acta., 231, 57-64 (1995) https://doi.org/10.1016/0020-1693(94)04320-U
  16. Wang, J. C., DNA Topoisomerases. Annu. Rev. Biochem., 65, 635-692 (1996) https://doi.org/10.1146/annurev.bi.65.070196.003223
  17. Zhao, L. X., Kim, T. S., Ahn, S. H., Kim, T. H., Kim, E.-K., Cho, W. J., Choi, H., Lee, C. S., Kim, J. A., Jeong, T. C., Chang, C.-J., and Lee, E. S., Synthesis, Topoisomerase I Inhibition and Antitumor Cytotoxicity of 2,2:62-,2,2:63- and 2,2:64- Terpyridine Derivatives. Bioorg. Med. Chem. Lett., 11, 2659- 2662 (2001) https://doi.org/10.1016/S0960-894X(01)00531-5
  18. Zhao, L. X., Moon, Y. S., Basnet, A., Kim, E.-k., Jahng, Y., Park, J. G., Jeong, T. C., Cho, W. J., Choi, S. U., Lee, C. O., Lee, S. Y., Lee, C. S., and Lee, E. S., Synthesis, topoisomerase I inhibition and structure-activity relationship study of 2,4,6- trisubstituted pyridine derivatives. Bioorg. Med. Chem. Lett., 14, 1333-1337 (2004) https://doi.org/10.1016/j.bmcl.2003.11.084