First synthesis and biological evaluation of novel spin-labeled derivatives of deoxypodophyllotoxin

European Journal of Medicinal Chemistry

Volumn 45, Issue 4, 2010, Pages 1673-1677

  Zhang, Zhi Wei ^a   Zhang, Jia Qiang ^a   Hui, Ling ^c   Chen, Shi Wu ^a,b   Tian, Xuan ^a  

^a LANZHOU UNIVERSITY   (China)

^b LANZHOU UNIVERSITY   (China)

^c LANZHOU GENERAL HOSPITAL   (China)

Author keywords

Antioxidative activity; Antitumor activity; Deoxypodophyllotoxin; Spin labeled

Indexed keywords

(1 OXYL 2,2,6,6 TETRAMETHYL 4 PIPERIDINYLOXYCARBONYL)LEVO TYROSINE 4 DEMETHYL 4 DEOXYPODOPHYLLIC ESTER; 4' DEMETHYL 4 DEOXYPODOPHYLLOTOXIN; DEOXYPODOPHYLLOTOXIN; ETOPOSIDE; N (1 OXYL 2,2,6,6 TETRAMETHYL 4 PIPERIDINYLOXYCARBONYL)ALANINE 4' DEMETHYL 4 DEOXYPODOPHYLLIC ESTER; N (1 OXYL 2,2,6,6 TETRAMETHYL 4 PIPERIDINYLOXYCARBONYL)GLYCIN 4' DEMETHYL 4 DEOXYPODOPHYLLIC ESTER; N (1 OXYL 2,2,6,6 TETRAMETHYL 4 PIPERIDINYLOXYCARBONYL)ISOLEUCINE 4' DEMETHYL 4 DEOXYPODOPHYLLIC ESTER; N (1 OXYL 2,2,6,6 TETRAMETHYL 4 PIPERIDINYLOXYCARBONYL)LEUCINE 4' DEMETHYL 4 DEOXYPODOPHYLLIC ESTER; N (1 OXYL 2,2,6,6 TETRAMETHYL 4 PIPERIDINYLOXYCARBONYL)PHENYLALANINE 4' DEMETHYL 4 DEOXYPODOPHYLLIC ESTER; N (1 OXYL 2,2,6,6 TETRAMETHYL 4 PIPERIDINYLOXYCARBONYL)PROLINE 4' DEMETHYL 4 DEOXYPODOPHYLLIC ESTER; N (1 OXYL 2,2,6,6 TETRAMETHYL 4 PIPERIDINYLOXYCARBONYL)VALINE 4' DEMETHYL 4 DEOXYPODOPHYLLIC ESTER; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; APOPTOSIS; ARTICLE; BIOLOGICAL ACTIVITY; CELL CYCLE ARREST; CELL CYCLE G2 PHASE; CELL CYCLE M PHASE; CELL STRAIN HL 60; CONTROLLED STUDY; CYTOTOXICITY; DRUG SYNTHESIS; MICROTUBULE ASSEMBLY; NONHUMAN; RAT; TUMOR CELL LINE;

ANIMALS; ANTIOXIDANTS; CELL LINE; HUMANS; PODOPHYLLOTOXIN; RATS; RATS, SPRAGUE-DAWLEY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, INFRARED; SPIN LABELS;

EID: 77649183584     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.12.032     Document Type: Article

References (41)

1. Ayres D.C., and Loike J.D. Lignans, Chemical, Biological and Clinical Properties (1990), Cambridge University Press, Cambridge (Chapters 3 and 4)
2. Thorpe E.P., Chaplin D.J., and David C. Cancer Res. 63 (2003) 1144-1147
3. Gordaliza M., Garcia P.A., Miguel del Corral J.M., Castro M.A., and Gomez-Zurita M.A. Toxicon 44 (2004) 431-440
4. Hande K.R. Eur. J. Cancer 34 (1998) 1514-1521
5. Jardine I. Anticancer Agents Based on Natural Products Models vol. 16 (1980), Academic Press, New York pp. 319-351
6. Issell B.F. Cancer Chemother. Pharmacol. 7 (1982) 73-80
7. Gordaliza M., Castro M.A., Miguel Del Corral J.M., and San Feliciano A. Curr. Pharm. Des. 6 (2000) 1811-1839
8. Van Vliet D.S., Tachibana Y., Bastow K.F., Huang E.S., and Lee K.H. J. Med. Chem. 44 (2001) 1422-1428
9. Schacter L. Semin. Oncol. 23 (1996) 1-7
10. Ikeda R., Nagao T., Okabe H., Nakano Y., Matsunaga H., Katano M., and Mori M. Chem. Pharm. Bull. 46 (1998) 871-874
11. Subrahmanyam D., Renuka B., Kumar G.S., Vandana V., and Deevi D.S. Bioorg. Med. Chem. Lett. (1999) 2131-2134
12. Kim Y., Kim S.B., You Y.J., and Ahn B.Z. Planta Med. 68 (2002) 271-274
13. Masuda T., Oyama Y., Yonemori S., Takeda Y., Yamazaki Y., Mizuguchi S., Nakata M., Tanaka T., Chikahisa L., Inabak Y., and Okada Y. Phytother. Res. 16 (2002) 353-358
14. Muto N., Tomokuni T., Haramoto M., Tatemoto H., Nakanishi T., Inatomi Y., Murata H., and Inada A. Biosci. Biotechnol. Biochem. 72 (2008) 477-484
15. Lee S.H., Son M.J., Ju H.K., Lin C.X., Moon T.C., Choi H.G., Son J.K., and Chang H.W. Biol. Pharm. Bull. 27 (2004) 786-788
16. Sudo K., Konno K., Shigeta S., and Yokota T. Antivir. Chem. Chemother. 9 (1998) 263-267
17. Suh S.J., Kim J.R., Jin U.H., Choi H.S., Chang Y.C., Lee Y.C., Kim S.H., Lee I.S., Moon T.S., Chang H.W., and Kim C.H. Vasc. Pharmcol. 51 (2009) 13-20
18. Yong Y.J., Shin S.Y., Lee Y.H., and Lim Y.H. Bioorg. Med. Chem. Lett. 19 (2009) 4367-4371
19. Kim Y., You Y.J., Nam N.H., and Ahn B.Z. Bioorg. Med. Chem. Lett. 12 (2002) 3435-3438
20. You Y.J., Kim Y., Nam N.H., Bang S.C., and Ahn B.Z. Eur. J. Med. Chem. 39 (2004) 189-193
21. Sosnovsky G., and Li S.W. Life Sci. 36 (1985) 1479-1483
22. Zheleva A.M., and Gadjeva V.G. Int. J. Pharm. 212 (2001) 257-266
23. Sosnovsky G. J. Pharm. Sci. 81 (1992) 496-499
24. Sosnovsky G. Pure Appl. Chem. 62 (1990) 289-294
25. Tian X., Zhang F.M., and Li W.G. Life Sci. 70 (2002) 2433-2443
26. Jin Y., Chen S.W., and Tian X. Bioorg. Med. Chem. 14 (2006) 3062-3068
27. Liu Y.Q., and Tian X. Synth. Commun. 35 (2005) 2749-2758
28. Tian X., Yang M.G., and Chen Y.Z. Life Sci. 60 (1997) 511-517
29. Chen S.W., Tian X., and Tu Y.Q. Bioorg. Med. Chem. Lett. 14 (2004) 5063-5066
30. Chen S.W., Xiang R., Liu J., and Tian X. Bioorg. Med. Chem. 17 (2009) 3111-3117
31. Zhang F.M., and Tian X. Acta Chim. Sinica 60 (2002) 720-724
32. Zhang F.M., Yao X.J., Tian X., and Tu Y.Q. Molecules 11 (2006) 849-857
33. Chen S.W., Wang Y.H., Jin Y., Tian X., Zheng Y.T., Luo D.Q., and Tu Y.Q. Bioorg. Med. Chem. Lett. 17 (2007) 2091-2095
34. Chen S.W., Yang R., and Tian X. Helv. Chim. Acta 92 (2009) 1568-1574
35. Rozantsev E.G. Izv. Akad. Nauk. SSSR. Ser. Kim. (1964) 2187-2191
36. Staab H.A., and Mannschreck A. Chem. Ber. 95 (1962) 1284-1297
37. Hankovszky H.O., Hideg K., and Lex L. Synthesis (1979) 530-531
38. Gensler W.J., Judge J.F.X., and Leeding M.V. J. Org. Chem. 37 (1972) 1062-1065
39. Xiao Z.Y., Han S.Q., Bastow K.F., and Lee K.H. Bioorg. Med. Chem. 14 (2004) 1581-1584
40. Mosmann T. J. Immunol. Methods 65 (1983) 55-63
41. Ohkawa H., Ohnishi N., and Yaki K. Anal. Biochem. 95 (1979) 351-358