- Novel anthraquinone compounds inhibit colon cancer cell proliferation via the reactive oxygen species/JNK pathway
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A series of amide anthraquinone derivatives, an important component of some traditional Chinese medicines, were structurally modified and the resulting antitumor activities were evaluated. The compounds showed potent anti-proliferative activities against eight human cancer cell lines, with no noticeable cytotoxicity towards normal cells. Among the candidate compounds, 1-nitro-2-acyl anthraquinone-leucine (8a) showed the greatest inhibition of HCT116 cell activity with an IC50 of 17.80 μg/mL. In addition, a correlation model was established in a three-dimensional quantitative structure-activity relationship (3D-QSAR) study using Comparative Molecular Field Analysis (CoMFA) and comparative molecular similarity index analysis (CoMSIA). Moreover, compound 8a effectively killed tumor cells by reactive oxygen species (ROS)-JNK activation, causing an increase in ROS levels, JNK phosphorylation, and mitochondrial stress. Cytochrome c was then released into cytoplasm, which, in turn activated the cysteine protease pathway and ultimately induced tumor cell apoptosis, suggesting a potential use of this compound for colon cancer treatment.
- Chen, Tinggui,Feng, Liheng,Guan, Yingying,Guo, Fang,Li, Yuying,Liu, Yaoming,Ma, Kaiqing,Su, Qiang,Wang, Zhuanhua,Zhang, Liwei,Zhou, Yuzhi
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supporting information
(2020/04/10)
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- Design, Synthesis, Molecular Docking, and Biological Evaluation of New Emodin Anthraquinone Derivatives as Potential Antitumor Substances
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The emodin anthraquinone derivatives are generally used in traditional Chinese medicine due to their various pharmacological activities. In the present study, a series of emodin anthraquinone derivatives have been designed and synthesized, among which 1,3-dihydroxy-6,8-dimethoxyanthracene-9,10-dione is a natural compound that has been synthesized for the very first time, and 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione is a compound that has never been reported earlier. Interestingly, while total seven of these compounds showed neuraminidase inhibitory activity in influenza virus with inhibition rate more than 50 %, specific four compounds exhibited significant inhibition of tumor cell proliferation. The further results demonstrate that 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione showed the best anticancer activity among all the synthesized compounds by inducing highest apoptosis rate to HCT116 cancer cells and arresting their G0/G1 cell cycle phase, through elevation of intracellular level of reactive oxygen species (ROS). Moreover, the binding of 1,3-dimethoxy-5,8-dimethylanthracene-9,10-dione with BSA protein has thoroughly been investigated. Altogether, this study suggests the neuraminidase inhibitory activity and antitumor potential of the new emodin anthraquinone derivatives.
- Li, Yuying,Guo, Fang,Chen, Tinggui,Zhang, Liwei,Wang, Zhuanhua,Su, Qiang,Feng, Liheng
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- Preparation of 1-nitroanthraquinone-2-carboxylic acids
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1-Nitroanthraquinone-2-carboxylic acids of the general formula I STR1 where X is hydrogen, chlorine or bromine, are prepared by oxidizing a 1-nitro-2-methylanthraquinone of the general formula II STR2 with nitric acid in an organic reaction medium.
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- REACTION OF α-HALOGENO- AND α-NITROANTHRAQUINONES WITH THE ANIONS OF CH ACIDS IV. REACTION OF 1-NITROANTHRAQUINONE-2-CARBOXYLIC ACID WITH CYANOACETIC ESTER AND MALONONITRILE
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The reaction of 1-nitroanthraquinone-2-carboxylic acid with cyanoacetic ester and malononitrile in the presence of a base leads to nucleophilic substitution of the nitro group and acylation of the CH acid molecule by the carboxyl group to the corresponding 1-alkyl-2-acylanthraquinones.Subsequent treatment of the latter with sulfuric acid leads to 2-hydroxy-7H-dibenzoquinoline-3,4-dicarboxylic acid.The N-phenylamide of the latter is produced by the reaction of 1-nitroanthraquinone-2-carbanilide with cyanoacetic ester.
- Gorelik, M. V.,Lomzakova, V. I.
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p. 2053 - 2055
(2007/10/02)
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- Preparation of 1-nitroanthraquinone-2-carboxylic acid
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1-Nitroanthraquinone-2-carboxylic acid of the formula I STR1 is prepared by treating novel 2-substituted 1-nitroanthraquinones of the general formula II STR2 where R is --CH=CH--R1 or --CH2 --CHO, where R1 is C1 -C5 -dialkylamino or a cyclic 5- or 6-membered amine which may contain further hetero atoms, with oxidizing agents free of heavy metal.
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- Preparation and Evaluation of 2-Substituted Anthraquinones Based on the Anthracyclines
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Anthraquinones substituted at the 2 position with a basic side chain were prepared, and their binding to DNA was evaluated.All compounds showed an intercalative mode of binding to DNA; 1,4-dihydroxy derivatives bound more strongly than 1-hydroxy or nonhydroxylated compounds.Greatest DNA-binding activity was found where there were five atoms between the anthraquinone ring and the basic nitrogen.
- Bennett, Stephen,Sharples, Derek,Brown, Jeffrey R.
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p. 369 - 373
(2007/10/02)
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