Literature DB >> 18077159

Structural analogs of tylophora alkaloids may not be functional analogs.

Wenli Gao1, Annie Pei-Chun Chen, Chung-Hang Leung, Elizabeth A Gullen, Alois Fürstner, Qian Shi, Linyi Wei, Kuo-Hsiung Lee, Yung-Chi Cheng.   

Abstract

Phenanthroindolizidine-based tylophora alkaloids have been reported to have potential antitumor, anti-immuno and, anti-inflammatory activity. The structure-activity relationships of a series of tylophora alkaloids were studied to guide future drug design. Our results indicate that although these compounds are structural analogs, their potency of cytotoxicity, selectivity against NF-kappaB signaling pathway, and their inhibitory effects against protein and nucleic acid synthesis are different. Because they do not have an identical spectrum of targets, the studied compounds are structural, but may not be functional analogs.

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Year:  2007        PMID: 18077159      PMCID: PMC2701548          DOI: 10.1016/j.bmcl.2007.11.054

Source DB:  PubMed          Journal:  Bioorg Med Chem Lett        ISSN: 0960-894X            Impact factor:   2.823


  18 in total

1.  Phenanthroindolizidine alkaloids as cytotoxic substances in a Danaid butterfly, Ideopsis similis, against human cancer cells.

Authors:  H Komatsu; M Watanabe; M Ohyama; T Enya; K Koyama; T Kanazawa; N Kawahara; T Sugimura; K Wakabayashi
Journal:  J Med Chem       Date:  2001-05-24       Impact factor: 7.446

Review 2.  The IKK NF-kappa B system: a treasure trove for drug development.

Authors:  Michael Karin; Yumi Yamamoto; Q May Wang
Journal:  Nat Rev Drug Discov       Date:  2004-01       Impact factor: 84.694

3.  In vitro cytotoxic activity of phenanthroindolizidine alkaloids from Cynanchum vincetoxicum and Tylophora tanakae against drug-sensitive and multidrug-resistant cancer cells.

Authors:  Dan Staerk; Anne K Lykkeberg; Jette Christensen; Bogdan A Budnik; Fumiko Abe; Jerzy W Jaroszewski
Journal:  J Nat Prod       Date:  2002-09       Impact factor: 4.050

4.  Antitumor agents 251: synthesis, cytotoxic evaluation, and structure-activity relationship studies of phenanthrene-based tylophorine derivatives (PBTs) as a new class of antitumor agents.

Authors:  Linyi Wei; Arnold Brossi; Ross Kendall; Kenneth F Bastow; Susan L Morris-Natschke; Qian Shi; Kuo-Hsiung Lee
Journal:  Bioorg Med Chem       Date:  2006-06-30       Impact factor: 3.641

5.  Synthesis and structure-activity studies of antofine analogues as potential anticancer agents.

Authors:  Ye Fu; Sang Kook Lee; Hye-Young Min; Taeho Lee; Jaekwang Lee; Maosheng Cheng; Sanghee Kim
Journal:  Bioorg Med Chem Lett       Date:  2006-09-30       Impact factor: 2.823

6.  Total syntheses of the tylophora alkaloids cryptopleurine, (-)-antofine, (-)-tylophorine, and (-)-ficuseptine C.

Authors:  Alois Fürstner; Jason W J Kennedy
Journal:  Chemistry       Date:  2006-09-25       Impact factor: 5.236

7.  Abrogation of skin disease in LUPUS-prone MRL/FASlpr mice by means of a novel tylophorine analog.

Authors:  Jin-Young Choi; Wenli Gao; Jared Odegard; Her-Shyong Shiah; Michael Kashgarian; Jennifer M McNiff; David C Baker; Yung-Chi Cheng; Joseph Craft
Journal:  Arthritis Rheum       Date:  2006-10

8.  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

9.  Synthesis, in vitro and in vivo cytotoxicity of 6,7-diaryl-2,3,8,8a-tetrahydroindolizin-5(1H)-ones.

Authors:  F Scott Kimball; Ashok Rao Tunoori; Samuel F Victory; Dinah Dutta; Jonathan M White; Richard H Himes; Gunda I Georg
Journal:  Bioorg Med Chem Lett       Date:  2007-06-13       Impact factor: 2.823

10.  Structure-activity studies of phenanthroindolizidine alkaloids as potential antitumor agents.

Authors:  Wenli Gao; Scott Bussom; Susan P Grill; Elizabeth A Gullen; You-Cai Hu; Xueshi Huang; Sanbao Zhong; Conrad Kaczmarek; Julio Gutierrez; Samson Francis; David C Baker; Shishan Yu; Yung-Chi Cheng
Journal:  Bioorg Med Chem Lett       Date:  2007-05-16       Impact factor: 2.823

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  14 in total

Review 1.  Discovery and development of natural product-derived chemotherapeutic agents based on a medicinal chemistry approach.

Authors:  Kuo-Hsiung Lee
Journal:  J Nat Prod       Date:  2010-03-26       Impact factor: 4.050

2.  Total synthesis of (+)-antofine and (-)-cryptopleurine.

Authors:  Weijiang Ying; James W Herndon
Journal:  European J Org Chem       Date:  2013-05-01

3.  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

4.  Total syntheses of arylindolizidine alkaloids (+)-ipalbidine and (+)-antofine.

Authors:  Micah J Niphakis; Gunda I Georg
Journal:  J Org Chem       Date:  2010-09-03       Impact factor: 4.354

5.  Lead Optimization: Synthesis and Biological Evaluation of PBT-1 Derivatives as Novel Antitumor Agents.

Authors:  Lan Xie; Masuo Goto; Xiaoyan Chen; Susan L Morris-Natschke; Kuo-Hsiung Lee
Journal:  ACS Med Chem Lett       Date:  2021-11-17       Impact factor: 4.345

6.  DCB-3503, a tylophorine analog, inhibits protein synthesis through a novel mechanism.

Authors:  Ying Wang; Wenli Gao; Yuri V Svitkin; Annie Pei-Chun Chen; Yung-Chi Cheng
Journal:  PLoS One       Date:  2010-07-15       Impact factor: 3.240

7.  Phenanthrene-based tylophorine-1 (PBT-1) inhibits lung cancer cell growth through the Akt and NF-kappaB pathways.

Authors:  Jau-Chen Lin; Shuenn-Chen Yang; Tse-Ming Hong; Sung-Liang Yu; Qian Shi; Linyi Wei; Hsuan-Yu Chen; Pan-Chyr Yang; Kuo-Hsiung Lee
Journal:  J Med Chem       Date:  2009-04-09       Impact factor: 7.446

8.  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

9.  Impacts of baicalein analogs with modification of the 6th position of A ring on the activity toward NF-kappaB-, AP-1-, or CREB-mediated transcription.

Authors:  Sheng-Teng Huang; Yashang Lee; Elizabeth A Gullen; Yung-Chi Cheng
Journal:  Bioorg Med Chem Lett       Date:  2008-08-06       Impact factor: 2.823

10.  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

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