Design, synthesis, and evaluation of a water-soluble antofine analogue with high antiproliferative and antitumor activity

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 4, 2013, Pages 1006-1017

  Kwon, Yongseok ^a   Song, Jayoung ^a   Lee, Boeun ^a   In, Jinkyung ^a   Song, Hohyun ^b   Chung, Hwa Jin ^a   Lee, Sang Kook ^a   Kim, Sanghee ^a  

^a Seoul National University   (South Korea)

^b Ewha Womans University   (South Korea)

Author keywords

Antitumor activity; Antofine; Hydrophilic analogue; Multidrug resistance; Phenanthroindolizidine

Indexed keywords

(2,3,6 TRIMETHOXY 9,11,12,13 TETRAHYDRO 10H 9A AZACYCLOPENTA[B]TRIPHENYL EN 12A YL)METHANOL; 13A HYDROXYMETHYLANTOFINE; 2,3,6 TRIMETHOXY 9,11,12,13 TETRAHYDRO 10H 9A AZACYCLOPENTA[B]TRIPHENYLE NE 12A CARBOXYLIC ACID; 2,3,6 TRIMETHOXY 9,11,12,13 TETRAHYDRO 10H 9A AZACYCLOPENTA[B]TRIPHENYLE NE 12A CARBOXYLIC ACID METHYL ESTER; ANTINEOPLASTIC AGENT; ANTOFINE DERIVATIVE; MAMMALIAN TARGET OF RAPAMYCIN; MULTIDRUG RESISTANCE PROTEIN; PACLITAXEL; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; AQUEOUS SOLUTION; ARTICLE; CANCER CELL; CANCER INHIBITION; CANCER RESISTANCE; CELL CYCLE ARREST; CELL STRAIN; CELL STRAIN A549; CONTROLLED STUDY; DRUG DESIGN; DRUG POTENTIATION; DRUG SCREENING; DRUG SOLUBILITY; DRUG SYNTHESIS; FEMALE; G0 PHASE CELL CYCLE CHECKPOINT; G1 PHASE CELL CYCLE CHECKPOINT; HUMAN; HUMAN CELL; LUNG CANCER; MOUSE; NONHUMAN; PROTEIN EXPRESSION; SIGNAL TRANSDUCTION; STRUCTURE ACTIVITY RELATION; TUMOR XENOGRAFT;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; DRUG RESISTANCE, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; G1 PHASE CELL CYCLE CHECKPOINTS; HCT116 CELLS; HEK293 CELLS; HUMANS; INDOLES; LUNG NEOPLASMS; MICE; MICE, NUDE; PHENANTHROLINES; SIGNAL TRANSDUCTION; STEREOISOMERISM; TOR SERINE-THREONINE KINASES; TRANSPLANTATION, HETEROLOGOUS; WATER;

MUS MUSCULUS;

EID: 84873309785     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.11.039     Document Type: Article

References (47)

1. E. Gellert S.W. Pelletier, Alkaloids: Chemical and Biological Perspectives 1987 Academic Press New York 55 132
2. M. Suffness, and G.A. Cordell A. Brossi, The Alkaloids, Chemistry and Pharmacology Vol. 25 1985 Academic Press New York 3 355
3. E. Gellert J. Nat. Prod. 45 1982 50
4. D. Staerk, A.K. Lykkeberg, J. Christensen, B.A. Budnik, F. Abe, and J.W. Jaroszewski J. Nat. Prod. 65 2002 1299
5. S.K. Lee, K.-A. Nam, and Y.-H. Heo Planta Med. 69 2003 21
6. S.R. Chemler Curr. Bioact. Compd. 5 2009 2
7. For recent reviews, see J.P. Michael Nat. Prod. Rep. 25 2008 139
8. J.P. Michael Nat. Prod. Rep. 24 2007 191
9. J.P. Michael Nat. Prod. Rep. 22 2005 603
10. Z. Li, Z. Jin, and R. Huang Synthesis 16 2001 2365
11. For recent representative examples, see: X. Yang, Q. Shi, C.-Y. Lai, C.-Y. Chen, E. Ohkoshi, S.-C. Yang, C.-Y. Wang, K.F. Bastow, T.-S. Wu, S.-L. Pan, C.-M. Teng, P.-C. Yang, and K.-H. Lee J. Med. Chem. 55 2012 6751
12. X. Yang, Q. Shi, S.-C. Yang, C.-Y. Chen, S.-L. Yu, K.F. Bastow, S.L. Morris-Natschke, P.-C. Wu, C.-Y. Lai, T.-S. Wu, S.-L. Pan, C.-M. Teng, J.-C. Lin, P.-C. Yang, and K.-H. Lee J. Med. Chem. 54 2011 5097
13. T. Ikeda, T. Yaegashi, T. Matsuzaki, R. Yamazaki, S. Hashimoto, and S. Sawada Bioorg. Med. Chem. Lett. 21 2011 5978
14. K. Wang, W. Wang, Q. Wang, and R. Huang Lett. Org. Chem. 5 2008 383
15. C.-R. Su, A.G. Damu, P.-C. Chiang, K.F. Bastow, S.L. Morris-Natschke, K.-H. Lee, and T.-S. Wu Bioorg. Med. Chem. 16 2008 6233
16. W. Gao, S. Bussom, S.P. Grill, E.A. Gullen, Y.-C. Hu, X. Huang, S. Zhong, C. Kaczmarek, J. Gutierrez, S. Francis, D.C. Baker, S. Yu, and Y.-C. Cheng Bioorg. Med. Chem. Lett. 17 2007 4338
17. Y. Fu, S.K. Lee, H.-Y. Min, T. Lee, J. Lee, M. Cheng, and S. Kim Bioorg. Med. Chem. Lett. 17 2007 97
18. T.-H. Chuang, S.-J. Lee, C.-W. Yang, and P.-L. Wu Org. Biomol. Chem. 4 2006 860
19. M. Suffness, and J. Douros J.M. Cassady, J.D. Douros, Anticancer Agents Based on Natural Product Models 1980 Academic Press London 465 487
20. C. Gopalakrishnan, D. Shankaranarayan, L. Kameswaran, and S. Natarajan Indian J. Med. Res. 69 1979 513
21. S.A. Hitchcock, and L.D. Pennington J. Med. Chem. 49 2006 7559
22. M. Ishikawa, and Y. Hashimoto J. Med. Chem. 54 2011 1539
23. D.E. Clark J. Pharm. Sci. 88 1999 815
24. The theoretical solubility was calculated using Discovery Studio (DS) 2.55 software. (Accerlys, San Diego, CA, USA).
25. During the preparation of this manuscript, compounds 4a and 4b were reported as a synthetic intermediate of the proposed structure of hypoestestatin 1. See B. Su, C. Cai, and Q. Wang J. Org. Chem. 77 2012 7981
26. S. Kim, J. Lee, T. Lee, H.-g. Park, and D. Kim Org. Lett. 5 2003 2703
27. For previous alkylation of N-Boc-proline methyl ester, see P.S. Baran, B.D. Hafensteiner, N.B. Ambhaikar, C.A. Guerrero, and J.D. Gallagher J. Am. Chem. Soc. 128 2006 8678
28. S.K. Lee, B. Cui, R.R. Mehta, A.D. Kinghorn, and J.M. Pezzuto Chem. Biol. Interact. 115 1998 215
29. S.K. Lee, K.A. Nam, Y.H. Hoe, H.-Y. Min, E.-Y. Kim, H. Ko, S. Song, T. Lee, and S. Kim Arch. Pharm. Res. 26 2003 253
30. S.H. Song, H.Y. Min, and S.K. Lee Biomol. Ther. 18 2010 402
31. A. Avdeef, and B. Testa Cell. Mol. Life Sci. 59 2002 1681
32. D. Seebach, M. Boes, R. Naef, and W.B. Schweizer J. Am. Chem. Soc. 105 1983 5390
33. H. Wang, and J.P. Germanas Synlett 1999 33
34. A. Jemal, R. Siegel, J. Xu, and E. Ward CA Cancer J. Clin. 60 2010 277
35. J.-Y. Hong, H.-J. Chung, H.-J. Lee, H.-J. Park, and S.K. Lee J. Nat. Prod. 74 2011 2102
36. N. Hay, and N. Sonenberg Genes Dev. 18 2004 1926
37. M.A. Bjornsti, and P.J. Houghton Cancer Cell 5 2004 519 523
38. R.H. Giles, J.H. van Es, and H. Clevers Biochim. Biophys. Acta 1653 2003 1
39. Kang, Y.-J.; Park, H. J.; Chung, H.-J.; Min, H.-Y.; Park, E. J.; Lee, M. A.; Shin, Y.; Lee, S. K. Mol. Pharmacol. [Online early access]. http://dx.doi.org/10.1124/mol.112.078535. Published Online: May 1, 2012.
40. B.S. Burns, M.L. Edin, G.E. Lester, H.G. Tuttle, M.E. Wall, M.C. Wani, and G.D. Bos Clin. Orthop. Relat. Res. 383 2001 259
41. P. Reinecke, M. Schmitz, E.M. Schneider, H.E. Gabbert, and C.D. Gerharz Cancer Invest. 18 2000 614
42. E.-H. Kim, H.-Y. Min, H.-J. Chung, J. Song, H.-J. Park, S. Kim, and S.K. Lee Food Chem. Toxicol. 50 2012 1060
43. J.E. Frampton, and S.E. Easthope Drugs 64 2004 2475
44. T. Kitazaki, M. Oka, Y. Nakamura, J. Tsurutani, S. Doi, M. Yasunaga, M. Takemura, H. Yabuuchi, H. Soda, and S. Kohno Lung Cancer 49 2005 337
45. M. Leggas, J.C. Panetta, Y. Zhuang, J.D. Schuetz, B. Johnston, F. Bai, B. Sorrentino, S. Zhou, P.J. Houghton, and C.F. Stewart Cancer Res. 66 2006 4802
46. C. Ludescher, J. Thaler, D. Drach, J. Drach, M. Spitaler, C. Gattringer, H. Huber, and J. Hofmann Br. J. Haematol. 82 1992 161
47. T.C. Chou Pharmacol. Rev. 58 2006 621