Atraric acid

Atraric acid
Product Name Atraric acid
CAS No.: 4707-47-5
Catalog No.: CFN98703
Molecular Formula: C10H12O4
Molecular Weight: 196.2 g/mol
Purity: >=98%
Type of Compound: Phenols
Physical Desc.: Powder
Targets: Androgen Receptor | PTP1B
Source: The fruits of Vitis vinifera L.
Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Price: $40/20mg
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.
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Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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    Anticancer Agents Med Chem. 2013 Jun;13(5):801-10.
    Computational and functional analysis of the androgen receptor antagonist atraric acid and its derivatives.[Pubmed: 23194423]
    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.
    METHODS AND RESULTS:
    Therefore, one objective of this study was to analyze the chemical/structural requirements for AR antagonism and to obtain predictions of where and how Atraric acid binds to the AR. Further, this study describes the chemical synthesis of 12 Atraric acid derivatives and their analysis using a combination of computational and functional assays. Functional analysis of Atraric acid derivatives indicated that none activated the AR. Both the para-hydroxyl group and the benzene ortho- and the meta-methyl groups of Atraric acid appeared to be essential to antagonize androgen-activated AR activity. Furthermore, extension of the hydrophobic side chain of Atraric acid led to slightly stronger AR antagonism. In silico data suggest that modifications to the basic Atraric acid structure change the hydrogen-bonding network with the AR ligand binding domain (LBD), so that the para-hydroxyl group of Atraric acid 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 Atraric acid interact with hydrophobic residues of the ligand pocket of AR, which might explain their functional importance for antagonism.
    CONCLUSIONS:
    Thus, these studies identify the chemical groups of Atraric acid that play key roles in allowing the Atraric acid-based chemical platform to act as an AR antagonist.
    Mycology An International Journal on Fungal Biology, 2011, 2(1):18-23.
    PTP1B inhibitory secondary metabolites from the Antarctic lichen Lecidella carpathica.[Reference: WebLink]
    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.
    METHODS AND RESULTS:
    Their structures were determined by analysis of NMR and MS data. Compounds 1–3 inhibited PTP1B activity in a dose-dependent manner with IC50 values of 3.7, 14.0 and 51.5 μM, respectively, and kinetic analyses of PTP1B inhibition by compounds 1 and 2 suggested that these compounds inhibit PTP1B activity in a competitive manner. In addition, 6,22-hopanediol (1) displayed some selectivity toward PTP1B over other protein tyrosine phosphatases, such as TCPTP (IC50 = 8.4 μM), SHP-2 (IC50 > 68 μM), LAR (IC50 > 68 μM), and CD45 (IC50 > 68 μM).
    J Cell Mol Med. 2009 Aug;13(8B):2210-23.
    The natural compound atraric acid is an antagonist of the human androgen receptor inhibiting cellular invasiveness and prostate cancer cell growth.[Pubmed: 18627423]
    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.
    METHODS AND RESULTS:
    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.
    CONCLUSIONS:
    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.
    Mol Cell Endocrinol. 2011 Jan 30;332(1-2):1-8.
    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]
    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.
    METHODS AND RESULTS:
    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.
    CONCLUSIONS:
    Both compounds are the first known natural, complete and specific AR antagonist.
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