Synthesis, characterization, and anticancer activity of novel lipophilic emodin cationic derivatives - Details

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Abstract：

Seventeen　novel　emodin　derivatives　were　synthesized,　and　the　structures　were　confirmed　by　IR,　H　NMR,　MS,　and　elemental　analysis.　The　cytotoxic　activity　of　the　derivatives　was　evaluated　against　A375,　BGC-823,　HepG2,　and　HELF　cells　by　MTT　assay.　Compound　9a　with　highest　potency　and　low　toxicity　was　selected　to　further　investigate　its　detailed　molecular　mechanism.　The　lead　compound　9a　induced　a　loss　of　the　mitochondrial　transmembrane　potential　(ΔΨm),　an　increase　in　reactive　oxygen　species　(ROS),　release　of　cytochrome　c　and　activation　of　caspase-3　and　caspase-9.　In　addition,　the　confocal　study　showed　that　emodin　derivative　9a　(containing　asymmetric　hydrocarbon　tails)　was　mainly　localized　in　mitochondria,　demonstrating　a　key　role　of　the　mitochondria-mediated　apoptosis　pathway　in　cancer　cells.　Taken　together,　the　results　demonstrate　that　embodin　derivative　9a　preferentially　regulates　the　ROS-mediated　apoptosis　in　A375　cells　through　the　induction　of　cytochrome　c　expression　and　activation　of　caspase-3　and　caspase-9　proteins.　Seventeen　novel　emodin　derivatives　were　synthesized　and　the　cytotoxic　activity　were　evaluated.　Compound　9a　with　highest　potency　and　low　toxicity　was　selected　to　further　investigate　its　detailed　molecular　mechanism.　Compound　9a　induced　a　loss　of　the　mitochondrial　transmemberane　potential,　an　increase　of　reactive　oxygen　species,　release　of　cytochrome　c　and　activation　of　caspase　3　and　9.　©　2015　John　Wiley　&　Sons　A/S.

Keyword：

apoptosis; emodin derivative; reactive oxygen species; synthesis

Community：

[ 1 ] [Yang, X.]College of Chemistry, Fuzhou University, Fuzhou, Fujian, 350108, China
[ 2 ] [Zhao, W.]College of Chemistry, Fuzhou University, Fuzhou, Fujian, 350108, China
[ 3 ] [Hu, X.]College of Chemistry, Fuzhou University, Fuzhou, Fujian, 350108, China
[ 4 ] [Hao, X.]College of Chemistry, Fuzhou University, Fuzhou, Fujian, 350108, China
[ 5 ] [Hong, F.]College of Chemistry, Fuzhou University, Fuzhou, Fujian, 350108, China
[ 6 ] [Wang, J.]College of Chemistry, Fuzhou University, Fuzhou, Fujian, 350108, China
[ 7 ] [Xiang, L.]College of Chemistry, Fuzhou University, Fuzhou, Fujian, 350108, China
[ 8 ] [Zhu, Y.]College of Chemistry, Fuzhou University, Fuzhou, Fujian, 350108, China
[ 9 ] [Yuan, Y.]College of Chemistry, Fuzhou University, Fuzhou, Fujian, 350108, China
[ 10 ] [Yuan, Y.]Research Institute of Photocatalysis, State Key Laboratory of Photocatalysis on Energy and Environment, Fuzhou, Fujian, 350002, China
[ 11 ] [Ho, R.J.Y.]College of Chemistry, Fuzhou University, Fuzhou, Fujian, 350108, China
[ 12 ] [Ho, R.J.Y.]Department of Pharmaceutics, University of Washington, Seattle, WA 98105, United States
[ 13 ] [Wang, W.]College of Chemistry, Fuzhou University, Fuzhou, Fujian, 350108, China
[ 14 ] [Wang, W.]Research Institute of Photocatalysis, State Key Laboratory of Photocatalysis on Energy and Environment, Fuzhou, Fujian, 350002, China
[ 15 ] [Shao, J.]College of Chemistry, Fuzhou University, Fuzhou, Fujian, 350108, China
[ 16 ] [Shao, J.]Research Institute of Photocatalysis, State Key Laboratory of Photocatalysis on Energy and Environment, Fuzhou, Fujian, 350002, China
[ 17 ] [Shao, J.]Department of Pharmaceutics, University of Washington, Seattle, WA 98105, United States

Reprint 's Address：

[Wang, W.]College of Chemistry, Fuzhou UniversityChina

Email：

wangwf@fzu.edu.cn

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Source ：

Chemical Biology and Drug Design

ISSN： 1747-0277

Year： 2015

Issue： 6

Volume： 86

Page： 1451-1457

2 . 8 0 2

JCR@2015

3 . 2 0 0

JCR@2023

ESI HC Threshold：268

JCR Journal Grade：2

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SCOPUS Cited Count：

ESI Highly Cited Papers on the List： 0 Unfold All

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Chinese Cited Count：

30 Days PV： 1

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