AscochlorinAn inhibitor of matrix metalloproteinase-9 activity

Ascochlorin (CAS 26166-39-2)

Ascochlorin | CAS 26166-39-2 is rated 5.0 out of 5 by 1.
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Application: An inhibitor of matrix metalloproteinase-9 activity
CAS Number: 26166-39-2
Purity: >95%
Molecular Weight: 404.9
Molecular Formula: C23H29CIO4
* Refer to Certificate of Analysis for lot specific data (including water content).
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Ascochlorin is a prenylphenol natural product isolated from the Ascochyta viciae fungus that blocks the expression of MMP-9 (matrix metalloproteinase-9) by suppressing activation of the MMP-9 gene. Matrix metalloproteinases are implicated in the behavior of invading and metastatic cells, as these proteins are responsible for modification and degradation of the extracellular matrix. Ascochlorin is shown to blockade the activation of nuclear transcription factor AP-1 (activator protein-1) on the Fra-1 protein, which leads to a suppression of MMP-9 gene expression downstream. This activity is exploited against the growth of MX-1 cells (estrogen receptor-negative cancer cells), where blockade of AP-1 by Ascochlorin provides a crucial cytotoxic handle in the absence of the estrogen receptor chemotherapeutic target. Ascochlorin has also been observed to bind nuclear hormone receptors, and a library of Ascochlorin derivatives showed activity as peroxisome proliferator activated receptor gamma (PPARγ) agonists. Ascochlorin is an activator of p53.


References

1. Togashi, M., et al. 2003. J. Med. Chem. 46: 4113-4123. PMID: 12954063
2. Sakaguchi, K., et al. 2005. Biochem. Biophys. Res. Commun. 329: 46-50. PMID: 15721271
3. Hong, S., et al. 2005. J. Biol. Chem. 280: 25202-25209. PMID: 15863510

Appearance :
Powder
Physical State :
Solid
Derived From :
Acremonium sp.
Solubility :
Soluble in ethanol, methanol, DMF, DMSO (0.9-1.1 mg/ml), chloroform, and ethyl acetate. Insoluble in water.
Storage :
Store at -20° C
Melting Point :
226.87° C (Predicted)
Boiling Point :
556.91° C at 760 mmHg (Predicted)
Density :
1.20 g/cm3 (Predicted)
Refractive Index :
n20D 1.60 (Predicted)
IC50 :
C3H 10T1/2: IC50 = 1 µM (mouse)
pK Values :
pKa: 6.26 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
VH3707560
PubChem CID :
11258227
MDL Number :
MFCD01939947
SMILES :
C[C@@H]1CCC(=O)[C@@H]([C@@]1(C)/C=C/C(=C/CC2=C(C(=C(C(=C2O)Cl)C)C=O)O)/C)C

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Certificate of Analysis

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Rated 5 out of 5 by from Hong et al Hong et al. (PubMed ID 15863510) found that Ascochlorin inhibited metalloproteinase-9 expression by suppressing activator protein-1-mediated gene expression via the ERK1/2 signaling pathway. -SCBT Publication Review
Date published: 2015-01-29
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