Chlorogenic AcidA Bcr-Abl inhibitor

Chlorogenic Acid (CAS 327-97-9)

Chlorogenic Acid | CAS 327-97-9 is rated 4.0 out of 5 by 1.
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Synonym: 3-O-Caffeoylquinic acid
Application: A Bcr-Abl inhibitor
CAS Number: 327-97-9
Purity: ≥95%
Molecular Weight: 354.31
Molecular Formula: C16H18O9
* Refer to Certificate of Analysis for lot specific data (including water content).
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Chlorogenic Acid is an analog of caffeic acid (sc-200499) that displays antioxidant, analgesic, antipyretic and chemopreventive activity. Chlorogenic acid inhibits Bcr-Abl (the fusion protein of Bcr and c-Abl) tyrosine kinase and triggers MAP kinases p38-dependent apoptosis. Chlorogenic acid has been documented to inhibit growth of A549 human cancer cells in vitro. In a dose dependent manner chlorogenic acid suppressed 12-O-tetradecanoylphorbol-13- acetate (TPA)-induced neoplastic transformation of JB6 P+ cells. When JB6 P+ cells were pretreated with chlorogenic acid, UVB- or TPA-induced transactivation of AP-1 and NF-κ B were blocked and at lower doses, chlorogenic acid decreased the phosphorylation of c-Jun NH2-terminal kinases, MAPK kinase 4, and p38 kinase. In the same study, chlorogenic acid also increased the activities of GST and NAD(P)H. In IL-1 induced HUVEC cells Chlorogenic acid dose-dependently suppressed IL-1 beta-induced mRNA expression of endothelial cell selectin, VCAM-1, and ICAM-1, production of ROS, and attenuated or blocked IL-1 beta-induced nuclear translocation of NF-κ B subunits p50 and p65, which in turn transcriptionally attenuated CAM. In addition to all of these actions, chlorogenic acid, in a dose-response manner, was observed to markedly reduce the adhesion of human monocyte cells to IL-1 β-treated HUVEC cells. The compound has also been observed to inhibit in vitro DNA methylation.


References

1. Huang, M.T., et al. 1988. Cancer Res. 48: 5941-5946. PMID: 3139287
2. Huang, M.T., et al. 1991. Cancer Res. 51: 813-819. PMID: 1899046
3. Feng, R., et al. 2005. J. Biol. Chem. 280: 27888-27895. PMID: 15944151
4. dos Santos, M.D., et al. 2006. Biol. Pharm. Bull. 29: 2236-2240. PMID: 17077520
5. Lee, W.J. and Zhu, B.T. 2006. Carcinogenesis. 27: 269-277. PMID: 16081510
6. Chang, W.C., et al. 2010. Eur J Nutr. 49: 267-275. PMID: 19937041

Physical State :
Solid
Solubility :
25mg/ml soluble in 100% ethanol, DMSO, dimethyl formamide or PBS (pH 7.2).
Storage :
Store at -20° C
Melting Point :
210° C (lit.)(dec.)
Boiling Point :
~665.0° C at 760 mmHg (Predicted)
Density :
1.28 g/cm3 (lit.)
Refractive Index :
n20D 1.69 (Predicted)
Optical Activity :
α20/D -36.5°±1.5°, c = 1 in water
pK Values :
pKa: 2.66 at 27° C
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
GU8480000
PubChem CID :
1794427
Merck Index :
14: 2142
MDL Number :
MFCD00003862
EC Number :
206-325-6
Beilstein Registry :
2708407
SMILES :
C1[C@H]([C@H]([C@@H](C[C@@]1(C(=O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)O

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Certificate of Analysis

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Date published: 2015-04-20
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