Atraric acidCAS# 4707-47-5 |
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| Cas No. | 4707-47-5 | SDF | Download SDF |
| PubChem ID | 78435 | Appearance | Powder |
| Formula | C10H12O4 | M.Wt | 196.2 |
| Type of Compound | Phenols | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | methyl 2,4-dihydroxy-3,6-dimethylbenzoate | ||
| SMILES | CC1=CC(=C(C(=C1C(=O)OC)O)C)O | ||
| Standard InChIKey | UUQHKWMIDYRWHH-UHFFFAOYSA-N | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Atraric acid derivatives as a new chemical lead structure for novel therapeutic compounds as AR antagonists, that can be used for prophylaxis or treatment of prostatic diseases. It inhibits PTP1B activity in a dose-dependent manner with IC50 values of 51.5 uM, suggest that atraric acid has potential to treat diabetes. |
| Targets | Androgen Receptor | PTP1B |
| In vitro | Computational and functional analysis of the androgen receptor antagonist atraric acid and its derivatives.[Pubmed: 23194423]Anticancer Agents Med Chem. 2013 Jun;13(5):801-10.Androgen receptor (AR) antagonists are important compounds for the treatment of prostate cancer (PCa). The Atraric acid (AA), a natural compound, binds to the AR and acts as a specific AR antagonist. Interestingly, Atraric acid represents a novel chemical platform that could serve as a potential basis for new AR antagonists. PTP1B inhibitory secondary metabolites from the Antarctic lichen Lecidella carpathica.[Reference: WebLink]Mycology An International Journal on Fungal Biology, 2011, 2(1):18-23.Protein tyrosine phosphatase 1B (PTP1B) is an attractive therapeutic target for diabetes, playing a major role in negative regulation of the insulin signaling pathway. Bioassay-guided investigations of an MeOH extract of the Antarctic lichen, Lecidella carpathica, afforded three PTP1B inhibitory metabolites: hopane-6α,22-diol (1), brialmontin 1 (2), and Atraric acid (3), along with two aromatic metabolites (4 and 5) previously isolated from a different Antarctic lichen species. |
| Kinase Assay | The natural compounds atraric acid and N-butylbenzene-sulfonamide as antagonists of the human androgen receptor and inhibitors of prostate cancer cell growth.[Pubmed: 20965230]The natural compound atraric acid is an antagonist of the human androgen receptor inhibiting cellular invasiveness and prostate cancer cell growth.[Pubmed: 18627423]J Cell Mol Med. 2009 Aug;13(8B):2210-23.Extracts from Pygeum africanum are used in the treatment of prostatitis, benign prostatic hyperplasia and prostate cancer (Pca), major health problems of men in Western countries. The ligand-activated human androgen receptor (AR) supports the growth of the prostate gland. Inhibition of human AR by androgen ablation therapy and by applying synthetic anti-androgens is therefore the primary goal in treatment of patients. Mol Cell Endocrinol. 2011 Jan 30;332(1-2):1-8.Extracts from the plant Pygeum africanum are widely used in the therapy of benign prostate hyperplasia (BPH) and in combinational therapy for prostate cancer, the second leading cause of cancer death and the mostly diagnosed form of cancer in men. |
Atraric acid Dilution Calculator
Atraric acid Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 5.0968 mL | 25.4842 mL | 50.9684 mL | 101.9368 mL | 127.421 mL |
| 5 mM | 1.0194 mL | 5.0968 mL | 10.1937 mL | 20.3874 mL | 25.4842 mL |
| 10 mM | 0.5097 mL | 2.5484 mL | 5.0968 mL | 10.1937 mL | 12.7421 mL |
| 50 mM | 0.1019 mL | 0.5097 mL | 1.0194 mL | 2.0387 mL | 2.5484 mL |
| 100 mM | 0.051 mL | 0.2548 mL | 0.5097 mL | 1.0194 mL | 1.2742 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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The natural compound atraric acid is an antagonist of the human androgen receptor inhibiting cellular invasiveness and prostate cancer cell growth.[Pubmed:18627423]
J Cell Mol Med. 2009 Aug;13(8B):2210-23.
Extracts from Pygeum africanum are used in the treatment of prostatitis, benign prostatic hyperplasia and prostate cancer (Pca), major health problems of men in Western countries. The ligand-activated human androgen receptor (AR) supports the growth of the prostate gland. Inhibition of human AR by androgen ablation therapy and by applying synthetic anti-androgens is therefore the primary goal in treatment of patients. Here, we show that Atraric acid (AA) isolated from bark material of Pygeum africanum has anti-androgenic activity, inhibiting the transactivation mediated by the ligand-activated human AR. This androgen antagonistic activity is receptor specific and does not inhibit the closely related glucocorticoid or progesterone receptors. Mechanistically, AA inhibits nuclear transport of AR. Importantly, AA is able to efficiently repress the growth of both the androgen-dependent LNCaP and also the androgen-independent C4-2 Pca cells but not that of PC3 or CV1 cells lacking AR. In line with this, AA inhibits the expression of the endogenous prostate specific antigen gene in both LNCaP und C4-2 cells. Analyses of cell invasion revealed that AA inhibits the invasiveness of LNCaP cells through extracellular matrix. Thus, this study provides a molecular insight for AA as a natural anti-androgenic compound and may serve as a basis for AA derivatives as a new chemical lead structure for novel therapeutic compounds as AR antagonists, that can be used for prophylaxis or treatment of prostatic diseases.
Computational and functional analysis of the androgen receptor antagonist atraric acid and its derivatives.[Pubmed:23194423]
Anticancer Agents Med Chem. 2013 Jun;13(5):801-10.
Androgen receptor (AR) antagonists are important compounds for the treatment of prostate cancer (PCa). The Atraric acid (AA), a natural compound, binds to the AR and acts as a specific AR antagonist. Interestingly, AA represents a novel chemical platform that could serve as a potential basis for new AR antagonists. Therefore, one objective of this study was to analyze the chemical/structural requirements for AR antagonism and to obtain predictions of where and how AA binds to the AR. Further, this study describes the chemical synthesis of 12 AA derivatives and their analysis using a combination of computational and functional assays. Functional analysis of AA derivatives indicated that none activated the AR. Both the para-hydroxyl group and the benzene ortho- and the meta-methyl groups of AA appeared to be essential to antagonize androgen-activated AR activity. Furthermore, extension of the hydrophobic side chain of AA led to slightly stronger AR antagonism. In silico data suggest that modifications to the basic AA structure change the hydrogen-bonding network with the AR ligand binding domain (LBD), so that the para-hydroxyl group of AA forms a hydrogen bond with the LBD, confirming the functional importance of this group for AR antagonism. Moreover, in silico modeling also suggested that the ortho- and meta- methyl groups of AA interact with hydrophobic residues of the ligand pocket of AR, which might explain their functional importance for antagonism. Thus, these studies identify the chemical groups of AA that play key roles in allowing the AA-based chemical platform to act as an AR antagonist.
The natural compounds atraric acid and N-butylbenzene-sulfonamide as antagonists of the human androgen receptor and inhibitors of prostate cancer cell growth.[Pubmed:20965230]
Mol Cell Endocrinol. 2011 Jan 30;332(1-2):1-8.
Extracts from the plant Pygeum africanum are widely used in the therapy of benign prostate hyperplasia (BPH) and in combinational therapy for prostate cancer, the second leading cause of cancer death and the mostly diagnosed form of cancer in men. The androgen receptor (AR) plays a crucial role in the development of the prostate as well as in prostate diseases. Even though the extracts from P. africanum are considered as beneficial for prostate diseases in clinical trials, and some active compounds for treatment of BPH could be identified, compounds responsible for AR inhibition and the molecular mechanism for inhibition of prostatitis need to be identified. Recently, Atraric acid and N-butylbenzene-sulfonamide were isolated from a selective dichlormethane extract of P. africanum as two novel AR antagonistic compounds. The molecular mechanisms of AR inhibition were analyzed and are summarized here. Both compounds are the first known natural, complete and specific AR antagonist.
