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Synthesis, Cytotoxicity and Structure-Activity Relationship Study of Terpyridines  

Zhao, Long-Xuan (Department of Chemistry, Liaoning Normal University)
Sherchan, Jyoti (College of Pharmacy, Yeungnam University)
Park, Jung-Ki (College of Pharmacy, Yeungnam University)
Jahng, Yurng-Dong (College of Pharmacy, Yeungnam University)
Jeong, Byeong-Seon (College of Pharmacy, Yeungnam University)
Jeong, Tae-Cheon (College of Pharmacy, Yeungnam University)
Lee, Chong-Soon (Department of Biochemistry, Yeungnam University)
Lee, Eung-Seok (College of Pharmacy, Yeungnam University)
Publication Information
Archives of Pharmacal Research / v.29, no.12, 2006 , pp. 1091-1095 More about this Journal
Abstract
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.
Keywords
Terpyridines; Cytotoxicity; Topoisomerase I inhibition; Antitumor agent; Synthesis;
Citations & Related Records

Times Cited By Web Of Science : 20  (Related Records In Web of Science)
Times Cited By SCOPUS : 16
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1 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)   DOI   ScienceOn
2 Donald, L. and Guise, J. L. E., An improved two-step synthesis of 2,2':6',2''-terpyridine. Tetahedron. Lett., 32, 1999-2002 (1991)   DOI   ScienceOn
3 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)   DOI   ScienceOn
4 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)   DOI
5 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)   DOI   ScienceOn
6 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)   DOI   ScienceOn
7 Berger, J. M., Structure of DNA topoisomerases. Biochim. Biophys. Acta., 1400, 3-18 (1998)   DOI   ScienceOn
8 Wang, J. C., DNA Topoisomerases. Annu. Rev. Biochem., 65, 635-692 (1996)   DOI   ScienceOn
9 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)   DOI   ScienceOn
10 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)
11 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)   DOI   ScienceOn
12 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)
13 Mosmann, T., Rapid colormetric assay for cellular growth and survival: application to proliferation and cytotoxic assays. J. Immunol. Methods, 65, 55-63 (1983)   DOI   ScienceOn
14 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)   DOI
15 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)   DOI   ScienceOn
16 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)   DOI   ScienceOn
17 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)   DOI   ScienceOn
18 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)