Design, synthesis, biological evaluation and molecular modeling studies of 1-aryl-6-(3,4,5-trimethoxyphenyl)-3(Z)-hexen-1,5-diynes as a new class of potent antitumor agents

Yu Hsiang Lo, Ying Ting Lin, Yu Peng Liu, Tsai Hui Duh, Pei-Jung Lu, Ming Jung Wu

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

A series of novel enediyne-containing molecules, 1-aryl-6-(3,4,5- trimethoxyphenyl)-3(Z)-hexen-1,5-diynes, were synthesized and displayed significant IC50 values of 10-7 to 10-6 M against various cancer cell lines. Of these compounds, 1-(2-pyridinyl)-6-(3,4,5- trimethoxyphenyl)-3(Z)-hexen-1,5-diyne (8) demonstrated the greatest growth inhibition activity. Compound 8 also arrested cancer cells in the G2/M phase and induced apoptosis via activation of Caspase-3. In addition to the G2/M block, compound 8 caused microtubule depolymerization at low concentrations and markedly decreased tumor size in xenographic studies.

Original languageEnglish
Pages (from-to)526-533
Number of pages8
JournalEuropean Journal of Medicinal Chemistry
Volume62
DOIs
Publication statusPublished - 2013 Apr 1

Fingerprint

Diynes
Molecular modeling
Antineoplastic Agents
Enediynes
Cells
Depolymerization
Caspase 3
Tumors
Neoplasms
G2 Phase
Chemical activation
Apoptosis
Microtubules
Cell Division
Inhibitory Concentration 50
Molecules
Cell Line
Growth

All Science Journal Classification (ASJC) codes

  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

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title = "Design, synthesis, biological evaluation and molecular modeling studies of 1-aryl-6-(3,4,5-trimethoxyphenyl)-3(Z)-hexen-1,5-diynes as a new class of potent antitumor agents",
abstract = "A series of novel enediyne-containing molecules, 1-aryl-6-(3,4,5- trimethoxyphenyl)-3(Z)-hexen-1,5-diynes, were synthesized and displayed significant IC50 values of 10-7 to 10-6 M against various cancer cell lines. Of these compounds, 1-(2-pyridinyl)-6-(3,4,5- trimethoxyphenyl)-3(Z)-hexen-1,5-diyne (8) demonstrated the greatest growth inhibition activity. Compound 8 also arrested cancer cells in the G2/M phase and induced apoptosis via activation of Caspase-3. In addition to the G2/M block, compound 8 caused microtubule depolymerization at low concentrations and markedly decreased tumor size in xenographic studies.",
author = "Lo, {Yu Hsiang} and Lin, {Ying Ting} and Liu, {Yu Peng} and Duh, {Tsai Hui} and Pei-Jung Lu and Wu, {Ming Jung}",
year = "2013",
month = "4",
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Design, synthesis, biological evaluation and molecular modeling studies of 1-aryl-6-(3,4,5-trimethoxyphenyl)-3(Z)-hexen-1,5-diynes as a new class of potent antitumor agents. / Lo, Yu Hsiang; Lin, Ying Ting; Liu, Yu Peng; Duh, Tsai Hui; Lu, Pei-Jung; Wu, Ming Jung.

In: European Journal of Medicinal Chemistry, Vol. 62, 01.04.2013, p. 526-533.

Research output: Contribution to journalArticle

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AU - Lo, Yu Hsiang

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AU - Lu, Pei-Jung

AU - Wu, Ming Jung

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AB - A series of novel enediyne-containing molecules, 1-aryl-6-(3,4,5- trimethoxyphenyl)-3(Z)-hexen-1,5-diynes, were synthesized and displayed significant IC50 values of 10-7 to 10-6 M against various cancer cell lines. Of these compounds, 1-(2-pyridinyl)-6-(3,4,5- trimethoxyphenyl)-3(Z)-hexen-1,5-diyne (8) demonstrated the greatest growth inhibition activity. Compound 8 also arrested cancer cells in the G2/M phase and induced apoptosis via activation of Caspase-3. In addition to the G2/M block, compound 8 caused microtubule depolymerization at low concentrations and markedly decreased tumor size in xenographic studies.

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