Biochanin AA nitric oxide synthase inhibitor and apoptosis inducer

Biochanin A (CAS 491-80-5)

Biochanin A | CAS 491-80-5 is rated 5.0 out of 5 by 1.
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Synonym: 5,7-Dihydroxy-4'-methoxyisoflavone; 4'-Methylgenistein
Application: A nitric oxide synthase inhibitor and apoptosis inducer
CAS Number: 491-80-5
Purity: ≥98%
Molecular Weight: 284.27
Molecular Formula: C16H12O5
* Refer to Certificate of Analysis for lot specific data (including water content).
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Biochanin A, an isoflavone, is a natural plant phytoestrogen which has been reported to be an antiproliferative and anti-inflammatory agent. Studies show that this compound inhibits iNOS expression and lipopolysacharide (LPS)-induced nitric oxide production in macrophages. Additionally, Biochanin A displays the ability to block phosphorylation of IκBα and p38 MAPK, which prevents NF-κB activation. Furthermore, Biochanin A has been observed to suppress IL-6, IL-1β, and TNF-α production.


References

1. Chae, Y.H. et al. 1992. Chem. Biol. Interact. 82(2): 181-193. PMID: 1568269

2. Jing, Y. and Waxman, S. 1995. Anticancer Res. 15(4): 1147-1152. PMID: 7653993

3. Rooke, N. et al. 2000. J. Med. Chem. 43(22): 4169-4179. PMID: 11063613

4. Khan, I.A. et al. 2000. J. Nat. Prod. 63(10): 1414-1416. PMID: 11076565

5. Tasdemir, D. et al. 2006. J. Med. Chem. 49(11): 3345-3353. PMID: 16722653

6. Salem, M.M. and Werbovetz, K.A. 2006. J. Nat. Prod. 69(1): 43-49. PMID: 16441066

7. Schuster, D. et al. 2008. J. Med. Chem. 51(14): 4188-4199. PMID: 18533708

8. Thors, L. et al. 2010. Br. J. Pharmacol. 160(3): 549-560. PMID: 20590565

9. Kole, L. et al. 2011. Eur. J. Pharmacol. 653(1-3): 8-15. PMID: 21147093

Appearance :
Powder
Physical State :
Solid
Solubility :
Soluble in water (<1 mg/ml at 25° C), chloroform, methanol, DMSO (57 mg/ml at 25° C), and ethanol (9 mg/ml at 25° C).
Storage :
Store at 4° C
Melting Point :
210-213° C
Boiling Point :
518.6° C at 760 mmHg (Predicted)
Density :
1.4 g/cm3 (Predicted)
Refractive Index :
n20D 1.67 (Predicted)
IC50 :
MAO: IC50 = 0.4 µM (human); Fatty acid synthase: IC50 = 8 µM (plasmodium falciparum); 17β-HSD2: IC50 = 9.9 µM (human); Trypanosoma brucei brucei: IC50 = 12.3 µM; Giardia intestinalis: IC50 = 3.5 µg/ml
Ki Data :
Carbonyl reductase 1: Ki= 2.03 µM (human); CYP19: Ki= 12 µM (human)
pK Values :
pKa: 6.5 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
DJ3002500
PubChem CID :
5280373
Merck Index :
14: 10423
MDL Number :
MFCD00006839
EC Number :
207-744-7
Beilstein Registry :
278107
SMILES :
COC1=CC=C(C=C1)C2=COC3=CC(=CC(=C3C2=O)O)O

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Certificate of Analysis

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Can you provide the references for the IC50 data listed for Biochanin A?

Asked by: ChemSynth123
Thank you for your question. Here are some citations for Biochanin A, sc-205603, IC50 data: http://europepmc.org/abstract/MED/11076565 12/21/2016: IC50 values were pulled from https://www.ebi.ac.uk/chembl/bioactivity/results/1/cmpd_chemblid/asc/tab/display. J. Med. Chem. (2000) 43:4169-4179 - https://www.ebi.ac.uk/chembl/doc/inspect/CHEMBL1133504 J. Med. Chem. (2008) 51:4188-4199 - https://www.ebi.ac.uk/chembl/doc/inspect/CHEMBL1157467 J. Nat. Prod. (2006) 69:43-49 - https://www.ebi.ac.uk/chembl/doc/inspect/CHEMBL1157220 J. Nat. Prod. (2000) 63:1414-1416 - https://www.ebi.ac.uk/chembl/doc/inspect/CHEMBL1155607 J. Med. Chem. (2006) 49:3345-3353 - https://www.ebi.ac.uk/chembl/doc/inspect/CHEMBL1148505
Answered by: TechService7
Date published: 2016-12-23
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Rated 5 out of 5 by from Wang Wang, J. et al. (PubMed 26394281) reported that Biochanin A protects dopaminergic neurons against lipopolysaccharide-induced damage and oxidative stress in a rat model of Parkinson's disease. -SCBT Publication Review
Date published: 2015-03-26
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