Anacardic Acid Inhibits Estrogen Receptor α–DNA Binding and Reduces Target Gene Transcription and Breast Cancer Cell Proliferation

Schultz, David J.; Wickramasinghe, Nalinie S.; Ivanova, Margarita; Isaacs, Susan M.; Dougherty, Susan; Imbert-Fernandez, Yoannis; Cunningham, Albert R.; Chen, Chun‐Yuan; Klinge, Carolyn M.

doi:10.1158/1535-7163.mct-09-0978

Cited by 48 publications

(75 citation statements)

References 43 publications

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“…Meanwhile, it has shown certain antitumor activities (7,8) by inhibiting histone acetyltransferase (9)(10)(11)(12)(13) and transcriptional factor nuclear factor-κB (14) in cell and animal models. In addition, it may efficiently inhibit the proliferation of breast carcinoma cells (15).…”

Section: Introductionmentioning

confidence: 99%

Anacardic acid (6-pentadecylsalicylic acid) induces apoptosis of prostate cancer cells through inhibition of androgen receptor and activation of p53 signaling

Jing¹,

Tan²,

Binghai³

et al. 2012

Chin. J. Cancer Res.

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Anacardic acid (AA) is a mixture of 2-hydroxy-6-alkylbenzoic acid homologs. It is widely regarded as a non-specific histone acetyltransferase inhibitor of p300. The effects and the mechanisms of AA in LNCaP cells (prostate cancer cells) remain unknown. To investigate the effect of AA on LNCaP cells, we had carried out several experiments and found that AA inhibits LNCaP cell proliferation, induces G1/S cell cycle arrest and apoptosis of LNCaP cell. The mechanisms via which AA acts on LNCaP cells may be due to the following aspects. First, AA can regulate p300 transcription and protein level except for its mechanisms regulating function of p300 through post-translational modification in LNCaP cells. Second, AA can activate p53 through increasing the phosphorylation of p53 on Ser15 in LNCaP cells. AA can selectively activate p21 (target genes of p53). Third, AA can down-regulates androgen receptor (AR) through supressing p300. Our study suggests that AA has multiple anti-tumor activities in LNCaP cells and warrants further investigation. Chin J Cancer Res 2012;24(4):275-283 www.thecjcr.org culture medium when necessary. DMEM, growth factorreduced matrigel and fetalbovine serum (FBS) were bought from BD Corporation (San Jose, CA). The Lipofectamine™ 2000 and the Total RNA Extraction kit were purchased from Invitrogen (Carlsbad, CA). The MTT Cell Proliferation and Cytotoxicity Assay kit and the Annexin V-FITC & PI Apoptosis Detection kit were purchased from KeyGen Biotech (Nanjing, China). SYBR Green PCR Master Mix were purchased from Fermentas (Burlington, Ontario, Canada). The Total Protein Extraction kit was purchased from ProMab (Changsha, China). Primary antibodies for p300, p21, p53, AR, cyclin D1 and siRNA specifically for p300 were bought from Santa Cruz Biotechnology (Santa Cruz, CA). Primary antibody for phospho-p53 (Ser 15) was purchased from Cell Signaling Technology. RPMI 1640 was purchased from GIBCO. Cell lines and cell cultureLNCaP was purchased from Yinrun (Changsha, China). LNCaP is a classical metastatic prostate adenocarcinoma cell line, derived from metastatic lymph nodes. LNCaP was cultured with both RPMI 1640 and 10% FBS, and subcultured weekly (37 ℃, 5% CO 2 ). p300 siRNA transfectionT h e L n c a p c e l l s w e r e s e e d e d i n t o 6 -w e l l p l a t e s (4×10 4 -5×10 4 cells/well) and cultured in 2 mL basic culture medium containing 10% FBS overnight until the cells were 70% confluent. Cells were transiently transfected with a validated scrambled control siRNA, or p300 siRNA by using InterferinTM transfection reagent. The mixture of siRNA and InterferinTM transfection reagent was incubated for 10 min, added to each well of the 6-well plates and incubated at 37 ℃ for 24 h before drug treatment. Detecting the inhibition of cell growth using MTT assaysLncap cells were treated with AA or transfected with p300 siRNA before drug treatment. Cells were incubated at various concentrations (0, 5, 25, and 125 μmol/L) at a series of time points (0, 4, 24 and 28 h). Then, 5 mg/mL of MTT so...

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Section: Introductionmentioning

confidence: 99%

Anacardic acid (6-pentadecylsalicylic acid) induces apoptosis of prostate cancer cells through inhibition of androgen receptor and activation of p53 signaling

Jing¹,

Tan²,

Binghai³

et al. 2012

Chin. J. Cancer Res.

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“…4 Its activity has been shown on melanoma 5 and colon, breast, lung, cervical, and kidney cancers. 6 It can also inhibit the growth of hormone-dependent tumors, by suppressing the activity of androgen 7 and estrogen 8 receptors. Due to the amphipathic properties of AA, it can be incorporated easily into the liposome bilayer for the purpose of delivery.…”

Section: Introductionmentioning

confidence: 99%

Anacardic acid enhances the anticancer activity of liposomal mitoxantrone towards melanoma cell lines – in vitro studies

Legut¹,

Lipka²,

Filipczak³

et al. 2014

IJN

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This paper describes a novel formulation of antineoplastic drug: mitoxantrone loaded into liposomal carriers enriched with encapsulated anacardic acid in the liposomal bilayer using a vitamin C gradient. Anacardic acid is a potent epigenetic agent with anticancer activity. This is the first liposomal formulation to combine an actively encapsulated drug and anacardic acid. The liposomes were characterized in terms of basic parameters, such as size, zeta potential, optimal drug-to-lipid ratio, loading time and temperature, and stability at 4°C and in human plasma in vitro. The formulation was found to be stable, and the loading process was rapid and efficient (drug-to-lipid ratio of up to 0.3 with over 90% efficiency in 5 minutes). The cytotoxicity of these formulations was assessed using the human melanoma cell lines A375 and Hs294T and the normal human dermal fibroblast line. The results showed that anacardic acid and to a smaller extent vitamin C significantly increased the cytotoxicity of the drug towards melanoma compared to ammonium sulfate liposomes. On the other hand, vitamin C and anacardic acid both protected normal cells from damage caused by the drug. The formulation combining anacardic acid, vitamin C, and mitoxantrone showed promising results in terms of cytotoxicity and cytoprotection. Therefore, it has potential for anticancer treatment.

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“…Otherwise, caspase-independent apoptosis inhibition in pituitary adenoma and lung adenocarcinoma cells (Seong et al, 2013) and histone acetyltransferases and nuclear factor kappa B (NF-κB) may be a potential target in chemotherapy (Sung et al, 2008). There are other evidences for its anticancer activity (Schultz et al, 2010;Wu et al, 2011;Huang et al, 2014); where the benzamide derivatives, 2-isopropoxy-6-pentadecyl-Npyridin-4-ylbenzamide, 2-ethoxy-N-nitrophenyl) -6-pentadecylbenzamide and 2-ethoxy-6-pentadecyl-Npyridin-4-ylbenzamide strongly inhibit HeLa cell lines (Chandregowda et al, 2009). …”

Section: A Occidentale and Its Biological Rolesmentioning

confidence: 99%

Pharmacological properties of cashew (Anacardium occidentale)

Leite¹,

Islam²,

Junior³

et al. 2016

Afr. J. Biotechnol.

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Anacardium occidentale L. is a tree native to Brazil, which is rich in phenolic lipids. Nowadays, the cashew bark (Cashew Nut Shell Liquid) has received great attention in the pharmaceutical industry, due to its economy, abundance and important chemical compounds. Net of cashew nut shell is classified according to the method of production of: (1) net of the shell of natural cashew nut (60-65% anacardic acid; 15-20% cardol and 10% of cardanol) and (2) liquid from the technical cashew nut shell (60-65% of cardanol, 15-20% cardol and 10% of polymeric material). This work aims to report the pharmacological properties of liquids from cashew nut shells. Results suggest that both liquids have antifungal, antibacterial, antiparasitic, anti-tumor, antiulcerogenic, molluscicides, antimutagenic and antioxidant activities. Natural cashew nut liquid is non-genotoxic, whereas technical liquid is genotoxic in prokaryotes and eukaryotes, although there is no evidence of their mutagenic effects on eukaryotic cells. In conclusion, the excellent antioxidant and non-mutagenic activities of cashew nut shell liquid (CNSL) provide opportunities for CNSL in the cosmetic and/or pharmaceutical industries, but continuous study is needed to allow safe and efficacious preparations.

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Anacardic Acid Inhibits Estrogen Receptor α–DNA Binding and Reduces Target Gene Transcription and Breast Cancer Cell Proliferation

Abstract: Anacardic acid (AnAc; 2-hydroxy-6-alkylbenzoic acid) is a dietary and medicinal phytochemical with established anticancer activity in cell and animal models. The mechanisms by which AnAc inhibits cancer cell proliferation remain undefined.

Cited by 48 publications

References 43 publications

Anacardic acid (6-pentadecylsalicylic acid) induces apoptosis of prostate cancer cells through inhibition of androgen receptor and activation of p53 signaling

Anacardic acid (6-pentadecylsalicylic acid) induces apoptosis of prostate cancer cells through inhibition of androgen receptor and activation of p53 signaling

Anacardic acid enhances the anticancer activity of liposomal mitoxantrone towards melanoma cell lines – in vitro studies

Pharmacological properties of cashew (Anacardium occidentale)

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Anacardic Acid Inhibits Estrogen Receptor α–DNA Binding and Reduces Target Gene Transcription and Breast Cancer Cell Proliferation

Abstract: Anacardic acid (AnAc; 2-hydroxy-6-alkylbenzoic acid) is a dietary and medicinal phytochemical with established anticancer activity in cell and animal models. The mechanisms by which AnAc inhibits cancer cell proliferation remain undefined.

Cited by 48 publications

References 43 publications

Anacardic acid (6-pentadecylsalicylic acid) induces apoptosis of prostate cancer cells through inhibition of androgen receptor and activation of p53 signaling

Anacardic acid (6-pentadecylsalicylic acid) induces apoptosis of prostate cancer cells through inhibition of androgen receptor and activation of p53 signaling

Anacardic acid enhances the anticancer activity of liposomal mitoxantrone towards melanoma cell lines &ndash; in vitro studies

Pharmacological properties of cashew (Anacardium occidentale)

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Product

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Anacardic acid enhances the anticancer activity of liposomal mitoxantrone towards melanoma cell lines – in vitro studies