Literature DB >> 22823514

Antitumor agents 295. E-ring hydroxylated antofine and cryptopleurine analogues as antiproliferative agents: design, synthesis, and mechanistic studies.

Xiaoming Yang1, Qian Shi, Chin-Yu Lai, Chi-Yuan Chen, Emika Ohkoshi, Shuenn-Chen Yang, Chih-Ya Wang, Kenneth F Bastow, Tian-Shung Wu, Shiow-Lin Pan, Che-Ming Teng, Pan-Chyr Yang, Kuo-Hsiung Lee.   

Abstract

Various E-ring hydroxylated antofine and cryptopleurine analogues were designed, synthesized, and tested against five human cancer cell lines. Interesting structure-activity relationship (SAR) correlations were found among these new compounds. The most potent compound 13b was further tested against a series of nonsmall cell lung cancer (NSCLC) cell lines in which it showed impressive antiproliferative activity. Mechanistic studies revealed that 13b is able to down-regulate HSP90 and β-catenin in A549 lung adenocarcinoma cells in a dose-dependent manner, suggesting a potential use for treating hedgehog pathway-driven tumorigenesis.

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Year:  2012        PMID: 22823514      PMCID: PMC3422873          DOI: 10.1021/jm3001218

Source DB:  PubMed          Journal:  J Med Chem        ISSN: 0022-2623            Impact factor:   7.446


  17 in total

1.  Mode of action of tylocrebrine: effects on protein and nucleic acid synthesis.

Authors:  M T Huang; A P Grollman
Journal:  Mol Pharmacol       Date:  1972-09       Impact factor: 4.436

2.  Antitumor agents 288: design, synthesis, SAR, and biological studies of novel heteroatom-incorporated antofine and cryptopleurine analogues as potent and selective antitumor agents.

Authors:  Xiaoming Yang; Qian Shi; Shuenn-Chen Yang; Chi-Yuan Chen; Sung-Liang Yu; Kenneth F Bastow; Susan L Morris-Natschke; Pei-Chi Wu; Chin-Yu Lai; Tian-Shung Wu; Shiow-Lin Pan; Che-Ming Teng; Jau-Chen Lin; Pan-Chyr Yang; Kuo-Hsiung Lee
Journal:  J Med Chem       Date:  2011-06-28       Impact factor: 7.446

3.  Antitumor agents. 274. A new synthetic strategy for E-ring SAR study of antofine and cryptopleurine analogues.

Authors:  Xiaoming Yang; Qian Shi; Kenneth F Bastow; Kuo-Hsiung Lee
Journal:  Org Lett       Date:  2010-04-02       Impact factor: 6.005

4.  Inhibition of dihydrofolate reductase and cell growth activity by the phenanthroindolizidine alkaloids pergularinine and tylophorinidine: the in vitro cytotoxicity of these plant alkaloids and their potential as antimicrobial and anticancer agents.

Authors:  K N Rao; S R Venkatachalam
Journal:  Toxicol In Vitro       Date:  2000-02       Impact factor: 3.500

5.  Phenanthroindolizidines and Phenanthroquinolizidines: Promising Alkaloids for Anti-Cancer Therapy.

Authors:  Sherry R Chemler
Journal:  Curr Bioact Compd       Date:  2009-03-01

6.  Antitumor agents 268. Design, synthesis, and mechanistic studies of new 9-substituted phenanthrene-based tylophorine analogues as potent cytotoxic agents.

Authors:  Xiaoming Yang; Qian Shi; Yi-Nan Liu; Guiyu Zhao; Kenneth F Bastow; Jau-Chen Lin; Shuenn-Chen Yang; Pan-Chyr Yang; Kuo-Hsiung Lee
Journal:  J Med Chem       Date:  2009-08-27       Impact factor: 7.446

7.  Novel mode of action of tylophorine analogs as antitumor compounds.

Authors:  Wenli Gao; Wing Lam; Sanbao Zhong; Conrad Kaczmarek; David C Baker; Yung-Chi Cheng
Journal:  Cancer Res       Date:  2004-01-15       Impact factor: 12.701

8.  Antitumor agents 253. Design, synthesis, and antitumor evaluation of novel 9-substituted phenanthrene-based tylophorine derivatives as potential anticancer agents.

Authors:  Linyi Wei; Qian Shi; Kenneth F Bastow; Arnold Brossi; Susan L Morris-Natschke; Kyoko Nakagawa-Goto; Tian-Shung Wu; Shiow-Lin Pan; Che-Ming Teng; Kuo-Hsiung Lee
Journal:  J Med Chem       Date:  2007-06-22       Impact factor: 7.446

9.  Mutants of CHO cells resistant to the protein synthesis inhibitors, cryptopleurine and tylocrebrine: genetic and biochemical evidence for common site of action of emetine, cryptopleurine, tylocrebine, and tubulosine.

Authors:  R S Gupta; L Siminovitch
Journal:  Biochemistry       Date:  1977-07-12       Impact factor: 3.162

10.  Anti-proliferative activity of heat shock protein (Hsp) 90 inhibitors via beta-catenin/TCF7L2 pathway in adult T cell leukemia cells.

Authors:  Ryosuke Kurashina; Junko H Ohyashiki; Chiaki Kobayashi; Ryoko Hamamura; Yu Zhang; Toshihiko Hirano; Kazuma Ohyashiki
Journal:  Cancer Lett       Date:  2009-05-21       Impact factor: 8.679

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  6 in total

1.  Multidrug resistance-selective antiproliferative activity of Piper amide alkaloids and synthetic analogues.

Authors:  Yue-Hu Wang; Masuo Goto; Li-Ting Wang; Kan-Yen Hsieh; Susan L Morris-Natschke; Gui-Hua Tang; Chun-Lin Long; Kuo-Hsiung Lee
Journal:  Bioorg Med Chem Lett       Date:  2014-09-06       Impact factor: 2.823

2.  Targeting a ribonucleoprotein complex containing the caprin-1 protein and the c-Myc mRNA suppresses tumor growth in mice: an identification of a novel oncotarget.

Authors:  Ya-Qi Qiu; Cheng-Wei Yang; Yue-Zhi Lee; Ruey-Bing Yang; Chih-Hao Lee; Hsing-Yu Hsu; Chien-Chung Chang; Shiow-Ju Lee
Journal:  Oncotarget       Date:  2015-02-10

3.  Screening of Phenanthroquinolizidine Alkaloid Derivatives for Inducing Cell Death of L1210 Leukemia Cells with Negative and Positive P-glycoprotein Expression.

Authors:  Jana Kubíčková; Katarína Elefantová; Lucia Pavlikova; Martin Cagala; Mário Šereš; Peter Šafář; Štefan Marchalín; Kamila Ďurišová; Viera Boháčová; Zdena Sulova; Boris Lakatoš; Albert Breier; Petra Olejníková
Journal:  Molecules       Date:  2019-06-05       Impact factor: 4.411

4.  Structure-activity relationships of cryptopleurine analogs with E-ring modifications as anti-hepatitis C virus agents.

Authors:  Ying Wang; Shao-Ru Chen; Xiaoming Yang; Kuo-Hsiung Lee; Yung-Chi Cheng
Journal:  Bioorg Med Chem       Date:  2017-12-20       Impact factor: 3.641

5.  Cryptopleurine analogs with modification of e ring exhibit different mechanism to rac-cryptopleurine and tylophorine.

Authors:  Ying Wang; Hui-Chyn Wong; Elizabeth A Gullen; Wing Lam; Xiaoming Yang; Qian Shi; Kuo-Hsiung Lee; Yung-Chi Cheng
Journal:  PLoS One       Date:  2012-12-10       Impact factor: 3.240

6.  Use of chiral-pool approach into epi-thieno analogues of the scarce bioactive phenanthroquinolizidine alkaloids.

Authors:  Peter Šafář; Štefan Marchalín; Nadežda Prónayová; Viktor Vrábel; Ata Martin Lawson; Mohamed Othman; Adam Daïch
Journal:  Tetrahedron       Date:  2016-04-21       Impact factor: 2.457

  6 in total

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