Merck
  • Home
  • Search Results
  • Synthesis, antitumor activity, and mechanism of action of 6-acrylic phenethyl ester-2-pyranone derivatives.

Synthesis, antitumor activity, and mechanism of action of 6-acrylic phenethyl ester-2-pyranone derivatives.

Organic & biomolecular chemistry (2015-03-25)
Sai Fang, Lei Chen, Miao Yu, Bao Cheng, Yongsheng Lin, Susan L Morris-Natschke, Kuo-Hsiung Lee, Qiong Gu, Jun Xu
ABSTRACT

Based on the scaffolds of caffeic acid phenethyl ester (CAPE) as well as bioactive lactone-containing compounds, 6-acrylic phenethyl ester-2-pyranone derivatives were synthesized and evaluated against five tumor cell lines (HeLa, C6, MCF-7, A549, and HSC-2). Most of the new derivatives exhibited moderate to potent cytotoxic activity. Moreover, HeLa cell lines showed higher sensitivity to these compounds. In particular, compound showed potent cytotoxic activity (IC50 = 0.50-3.45 μM) against the five cell lines. Further investigation on the mechanism of action showed that induced apoptosis, arrested the cell cycle at G2/M phases in HeLa cells, and inhibited migration through disruption of the actin cytoskeleton. In addition, ADMET properties were also calculated in silico, and compound showed good ADMET properties with good absorption, low hepatotoxicity, and good solubility, and thus, could easily be bound to carrier proteins, without inhibition of CYP2D6. A structure-activity relationship (SAR) analysis indicated that compounds with ortho-substitution on the benzene ring exhibited obviously increased cytotoxic potency. This study indicated that compound is a promising compound as an antitumor agent.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Aluminum oxide, mesoporous, MSU-X (wormhole), average pore size 3.8 nm
Sigma-Aldrich
Bicinchoninic acid disodium salt hydrate, ≥98% (HPLC)
Supelco
4-tert-Octylphenol monoethoxylate solution, 10 μg/mL in acetone, analytical standard
Sigma-Aldrich
1,3-Propylene sulfite, 99%
Sigma-Aldrich
Aluminum oxide, activated, acidic, Brockmann I, free-flowing, Redi-Dri
Sigma-Aldrich
Aluminum oxide, activated, neutral, Brockmann I, free-flowing, Redi-Dri
Sigma-Aldrich
Aluminum oxide, nanopowder, 13 nm primary particle size (TEM), 99.8% trace metals basis
Sigma-Aldrich
Aluminum oxide, nanoparticles, <50 nm particle size (DLS), 20 wt. % in isopropanol
Sigma-Aldrich
Aluminum oxide, 99.997% trace metals basis
Sigma-Aldrich
Aluminum oxide, nanowires, diam. × L 2-6 nm × 200-400 nm
Sigma-Aldrich
Aluminum oxide, nanopowder, <50 nm particle size (TEM)
Supelco
Aluminum oxide, activated, neutral, Brockmann Activity I
Supelco
Aluminum oxide, for the determination of hydrocarbons
Sigma-Aldrich
Aluminum oxide, activated, basic, Brockmann I
Sigma-Aldrich
Aluminum oxide, activated, acidic, Brockmann I
Sigma-Aldrich
Aluminum oxide, activated, neutral, Brockmann I
Sigma-Aldrich
Aluminum oxide, Type CG-20
Sigma-Aldrich
Aluminum oxide, fused, powder, primarily α-phase, 100-200 mesh
Sigma-Aldrich
Aluminum oxide, Corundum, α-phase, -100 mesh
Sigma-Aldrich
Aluminum oxide, pellets, 3 mm
Sigma-Aldrich
Aluminum oxide, pore size 58 Å, ~150 mesh
Sigma-Aldrich
Aluminum oxide, Type WN-6, Neutral, Activity Grade Super I
Sigma-Aldrich
Aluminum oxide, powder, primarily α phase, ≤10 μm avg. part. size, 99.5% trace metals basis
Sigma-Aldrich
Aluminum oxide, fused, powder, primarily α-phase, -325 mesh
Sigma-Aldrich
Aluminum oxide, powder, 99.99% trace metals basis
Sigma-Aldrich
Aluminum oxide, calcined, powder, primarily α-phase, 100-325 mesh
Sigma-Aldrich
Aluminum oxide, nanoparticles, 30-60 nm particle size (TEM), 20 wt. % in H2O
Sigma-Aldrich
Aluminum oxide, single crystal substrate, <0001>