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BioAssay: AID 658958

Antiproliferative activity against estrogen-deficient human MCF7 cells after 72 hrs by MTT assay

Biochanin A (BCA), a major isoflavone in red clover and many other legumes, has been reported to display estrogenic as well as cancer chemopreventive properties. Ingested BCA is known to display low bioavailability due to poor solubility, extensive metabolism and rapid clearance. Esters of bioactive isoflavones are known to increase metabolic stability and bioavailability following local rather more ..
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 Tested Compounds
 Tested Compounds
All(6)
 
 
Active(6)
 
 
 Tested Substances
 Tested Substances
All(6)
 
 
Active(6)
 
 
 Related BioAssays
 Related BioAssays
AID: 658958
Data Source: ChEMBL (816030)
BioAssay Type: Confirmatory, Concentration-Response Relationship Observed
Depositor Category: Literature, Extracted
BioAssay Version:
Deposit Date: 2013-05-16
Modify Date: 2014-05-26

Data Table ( Complete ):           View Active Data    View All Data
BioActive Compounds: 6
Description:
Title: Ester and carbamate ester derivatives of Biochanin A: synthesis and in vitro evaluation of estrogenic and antiproliferative activities.

Abstract: Biochanin A (BCA), a major isoflavone in red clover and many other legumes, has been reported to display estrogenic as well as cancer chemopreventive properties. Ingested BCA is known to display low bioavailability due to poor solubility, extensive metabolism and rapid clearance. Esters of bioactive isoflavones are known to increase metabolic stability and bioavailability following local rather than systemic administration. We synthesized BCA from phloroglucinol and p-methoxy-phenylacetic acid by a Friedel-Crafts reaction and cyclization. We also synthesized esters (1, 3) and carbamate esters (2, 4, 5) at position 7 of BCA using short aliphatic chains bearing a chlorine (1, 2) or a bromine atom (3, 4) or long aliphatic chains without such atoms (5). We tested the estrogenic and antiproliferative activities of 1-5 and BCA using human breast and endometrial adenocarcinoma cells. We found that 5 affects MCF-7 and Ishikawa cells in a manner providing for induction of gene expression to a level similar to 17beta-estradiol and BCA but, unlike both of the latter, for suppression of cell proliferation as well. In addition, 5 appeared to display higher stability compared to 1-4 and BCA in both MCF-7 and Ishikawa cells. The inference is that 5 may represent a safer than BCA alternative to hormone replacement therapy.
(PMID: 22464681)
Comment
Compounds with activity <= 50uM or explicitly reported as active by ChEMBL are flagged as active in this PubChem assay presentation.
Putative Target:
ChEMBL Target ID: 80224
Target Type: CELL-LINE
Cell Line: MCF7
Tissue: Breast carcinoma cells
Pref Name: MCF7
Organism: Homo sapiens
Tax ID: 9606
Confidence: Target assigned is non-molecular
Relationship Type: Non-molecular target assigned
Categorized Comment - additional comments and annotations
From ChEMBL:
Assay Type: Functional
Assay Data Source: Scientific Literature
BAO: Assay Format: cell-based format
Assay Cell Type: MCF7
Result Definitions
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TIDNameDescriptionHistogramTypeUnit
OutcomeThe BioAssay activity outcomeOutcome
1EC50*EC50 PubChem standard valueFloatμM
2EC50 activity commentEC50 activity commentString
3EC50 standard flagEC50 standard flagInteger
4EC50 qualifierEC50 qualifierString
5EC50 published valueEC50 published valueFloatpM
6EC50 standard valueEC50 standard valueFloatnM
7EC50 data validityEC50 data validityString
8EC50 activity commentEC50 activity commentString
9EC50 standard flagEC50 standard flagInteger
10EC50 qualifierEC50 qualifierString
11EC50 published valueEC50 published valueFloatμM
12EC50 standard valueEC50 standard valueFloatnM
13EC50 data validityEC50 data validityString

* Activity Concentration.

Data Table (Concise)
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