Design, synthesis and biological evaluation of E-ring modifi ed evodiamine derivatives as novel antitumor agents

Kun Fang Guo-Qiang Dong Hai Gong Na Liu Zhen-Gang Li Shi-Ping Zhu Zhen-Yuan Miao Jian-Zhong Yao Wan-Nian Zhang Chun-Quan Sheng

Citation:  Kun Fang, Guo-Qiang Dong, Hai Gong, Na Liu, Zhen-Gang Li, Shi-Ping Zhu, Zhen-Yuan Miao, Jian-Zhong Yao, Wan-Nian Zhang, Chun-Quan Sheng. Design, synthesis and biological evaluation of E-ring modifi ed evodiamine derivatives as novel antitumor agents[J]. Chinese Chemical Letters, 2014, 25(7): 978-982. doi: 10.1016/j.cclet.2014.03.043 shu

Design, synthesis and biological evaluation of E-ring modifi ed evodiamine derivatives as novel antitumor agents

    通讯作者: Chun-Quan Sheng,
  • 基金项目:

    This work was supported by National Natural Science Foundation of China (Nos. 81222044, 81373278) (Nos. 81222044, 81373278)

    Technology of Shanghai (No. 11431920402) (No. 11431920402)

    the National Basic Research Program of China (No. 2014CB541800) (No. 2014CB541800)

    Shanghai Rising-Star Program (No. 12QH1402600) (No. 12QH1402600)

    Shanghai Municipal Health Bureau (No. XYQ2011038). (No. XYQ2011038)

摘要: A series of novel E-ring modified evodiamine derivatives were designed and synthesized as antitumor agents. Their capacity to interfere with the catalytic activity of topoisomerase I and II was evaluated by the relaxation assay. In vitro antitumor activity results revealed that compound 12 showed good antitumor activity with a broad spectrum. Its binding modes with topoisomerase I and II were clarified by molecular docking.

English

  • 
    1. [1] G.M. Cragg, P.G. Grothaus, D.J. Newman, Impact of natural products on developing new anti-cancer agents, Chem. Rev. 109 (2009) 3012-3043.[1] G.M. Cragg, P.G. Grothaus, D.J. Newman, Impact of natural products on developing new anti-cancer agents, Chem. Rev. 109 (2009) 3012-3043.

    2. [2] D.J. Newman, G.M. Cragg, Natural products as sources of new drugs over the 30 years from 1981 to 2010, J. Nat. Prod. 75 (2012) 311-335.[2] D.J. Newman, G.M. Cragg, Natural products as sources of new drugs over the 30 years from 1981 to 2010, J. Nat. Prod. 75 (2012) 311-335.

    3. [3] D.J. Newman, G.M. Cragg, Natural products as sources of new drugs over the last 25 years, J. Nat. Prod. 70 (2007) 461-477.[3] D.J. Newman, G.M. Cragg, Natural products as sources of new drugs over the last 25 years, J. Nat. Prod. 70 (2007) 461-477.

    4. [4] N.H. Oberlies, D.J. Kroll, Camptothecin and taxol: historic achievements in natural products research, J. Nat. Prod. 67 (2004) 129-135.[4] N.H. Oberlies, D.J. Kroll, Camptothecin and taxol: historic achievements in natural products research, J. Nat. Prod. 67 (2004) 129-135.

    5. [5] J. Jiang, C. Hu, Evodiamine: a novel anti-cancer alkaloid from Evodia rutaecarpa, Molecules 14 (2009) 1852-1859.[5] J. Jiang, C. Hu, Evodiamine: a novel anti-cancer alkaloid from Evodia rutaecarpa, Molecules 14 (2009) 1852-1859.

    6. [6] Z.G. Yang, A.Q. Chen, B. Liu, Antiproliferation and apoptosis induced by evodiamine in human colorectal carcinoma cells (COLO-205), Chem. Biodivers. 6 (2009) 924-933.[6] Z.G. Yang, A.Q. Chen, B. Liu, Antiproliferation and apoptosis induced by evodiamine in human colorectal carcinoma cells (COLO-205), Chem. Biodivers. 6 (2009) 924-933.

    7. [7] G. Dong, C. Sheng, S. Wang, et al., Selection of evodiamine as a novel topoisomerase I inhibitor by structure-based virtual screening and hit optimization of evodiamine derivatives as antitumor agents, J. Med. Chem. 53 (2010) 7521-7531.[7] G. Dong, C. Sheng, S. Wang, et al., Selection of evodiamine as a novel topoisomerase I inhibitor by structure-based virtual screening and hit optimization of evodiamine derivatives as antitumor agents, J. Med. Chem. 53 (2010) 7521-7531.

    8. [8] G. Dong, S. Wang, Z. Miao, et al., New tricks for an old natural product: discovery of highly potent evodiamine derivatives as novel antitumor agents by systemic structure-activity relationship analysis and biological evaluations, J. Med. Chem. 55 (2012) 7593-7613.[8] G. Dong, S. Wang, Z. Miao, et al., New tricks for an old natural product: discovery of highly potent evodiamine derivatives as novel antitumor agents by systemic structure-activity relationship analysis and biological evaluations, J. Med. Chem. 55 (2012) 7593-7613.

    9. [9] H. Huang, Q. Chen, X. Ku, et al., A series of alpha-heterocyclic carboxaldehyde thiosemicarbazones inhibit topoisomerase IIa catalytic activity, J. Med. Chem. 53 (2010) 3048-3064.[9] H. Huang, Q. Chen, X. Ku, et al., A series of alpha-heterocyclic carboxaldehyde thiosemicarbazones inhibit topoisomerase IIa catalytic activity, J. Med. Chem. 53 (2010) 3048-3064.

    10. [10] L. Du, H.C. Liu, W. Fu, et al., Unprecedented citrinin trimer tricitinol B functions as a novel topoisomerase IIa inhibitor, J. Med. Chem. 54 (2011) 5796-5810.[10] L. Du, H.C. Liu, W. Fu, et al., Unprecedented citrinin trimer tricitinol B functions as a novel topoisomerase IIa inhibitor, J. Med. Chem. 54 (2011) 5796-5810.

    11. [11] G. Jones, P. Willett, R.C. Glen, et al., Development and validation of a genetic algorithm for flexible docking, J. Mol. Biol. 267 (1997) 727-748.[11] G. Jones, P. Willett, R.C. Glen, et al., Development and validation of a genetic algorithm for flexible docking, J. Mol. Biol. 267 (1997) 727-748.

    12. [12] B.L. Staker, M.D. Feese, M. Cushman, et al., Structures of three classes of anticancer agents bound to the human topoisomerase I-DNA covalent complex, J. Med. Chem. 48 (2005) 2336-2345.[12] B.L. Staker, M.D. Feese, M. Cushman, et al., Structures of three classes of anticancer agents bound to the human topoisomerase I-DNA covalent complex, J. Med. Chem. 48 (2005) 2336-2345.

    13. [13] H. Wei, A.J. Ruthenburg, S.K. Bechis, G.L. Verdine, Nucleotide-dependent domain movement in the ATPase domain of a human type IIA DNA topoisomerase, J. Biol. Chem. 280 (2005) 37041-37047.[13] H. Wei, A.J. Ruthenburg, S.K. Bechis, G.L. Verdine, Nucleotide-dependent domain movement in the ATPase domain of a human type IIA DNA topoisomerase, J. Biol. Chem. 280 (2005) 37041-37047.

    14. [14] Accelrys Software Inc., Discovery Studio Modeling Environment, Release 3.0, Accelrys Software Inc., San Diego, 2010.[14] Accelrys Software Inc., Discovery Studio Modeling Environment, Release 3.0, Accelrys Software Inc., San Diego, 2010.

    15. [15] K. Chikamori, A.G. Grozav, T. Kozuki, et al., DNA topoisomerase II enzymes as molecular targets for cancer chemotherapy, Curr. Cancer Drug. Targets 10 (2010) 758-771.[15] K. Chikamori, A.G. Grozav, T. Kozuki, et al., DNA topoisomerase II enzymes as molecular targets for cancer chemotherapy, Curr. Cancer Drug. Targets 10 (2010) 758-771.

    16. [16] A.T. Baviskar, C. Madaan, R. Preet, et al., N-fused imidazoles as novel anticancer agents that inhibit catalytic activity of topoisomerase IIa and induce apoptosis in G1/S phase, J. Med. Chem. 54 (2011) 5013-5030.[16] A.T. Baviskar, C. Madaan, R. Preet, et al., N-fused imidazoles as novel anticancer agents that inhibit catalytic activity of topoisomerase IIa and induce apoptosis in G1/S phase, J. Med. Chem. 54 (2011) 5013-5030.

  • 加载中
计量
  • PDF下载量:  0
  • 文章访问数:  1378
  • HTML全文浏览量:  23
文章相关
  • 收稿日期:  2013-12-04
  • 网络出版日期:  2014-03-07
通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索

/

返回文章