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biochanin A, biochanin A, 14C-labeled, genistein 4-methyl ether

No.	Title	Href
1	The combination of Biochanin A and SB590885 potentiates the inhibition of tumour progression in hepatocellular carcinoma. Cancer Cell Int. 2020 Aug 5;20:371. doi: 10.1186/s12935-020-01463-w.	`Click`
2	The natural isoflavone Biochanin-A synergizes 5-fluorouracil anticancer activity in vitro and in vivo in Ehrlich solid-phase carcinoma model. Phytother Res. 2022 Mar;36(3):1310-1325. doi: 10.1002/ptr.7388.	`Click`
3	Combination of Biochanin A and Temozolomide Impairs Tumor Growth by Modulating Cell Metabolism in Glioblastoma Multiforme. Anticancer Res. 2019 Jan;39(1):57-66. doi: 10.21873/anticanres.13079.	`Click`

No.

Title

Href

The combination of Biochanin A and SB590885 potentiates the inhibition of tumour progression in hepatocellular carcinoma. Cancer Cell Int. 2020 Aug 5;20:371. doi: 10.1186/s12935-020-01463-w.

Click

The natural isoflavone Biochanin-A synergizes 5-fluorouracil anticancer activity in vitro and in vivo in Ehrlich solid-phase carcinoma model. Phytother Res. 2022 Mar;36(3):1310-1325. doi: 10.1002/ptr.7388.

Click

Combination of Biochanin A and Temozolomide Impairs Tumor Growth by Modulating Cell Metabolism in Glioblastoma Multiforme. Anticancer Res. 2019 Jan;39(1):57-66. doi: 10.21873/anticanres.13079.

Click

Name	Biochanin A
PubChem CID	5280373
Molecular Weight	284.26g/mol
Synonyms	biochanin A, biochanin A, 14C-labeled, genistein 4-methyl ether
Formula	C₁₆H₁₂O₅
SMILES	COC1=CC=C(C=C1)C2=COC3=CC(=CC(=C3C2=O)O)O
InChI	1S/C16H12O5/c1-20-11-4-2-9(3-5-11)12-8-21-14-7-10(17)6-13(18)15(14)16(12)19/h2-8,17-18H,1H3
InChIKey	WUADCCWRTIWANL-UHFFFAOYSA-N
CAS Number	491-80-5
ChEMBL ID	CHEMBL131921
ChEBI ID	CHEBI:17574
Drug Bank ID	DB15334
KEGG ID	C00814
Toxicity	Organism	Test Type	Route(Dose)
	rat	LD50	intraperitoneal(165 mg/kg)
	mouse	LD50	intraperitoneal(254 mg/kg)
	rat	LD50	oral(322 mg/kg)
Structure			Download 2D MOL 3D MOL

Chineses Pinyin	HongCheYouCao
Use Part	Flower and inflorescence
Habitat	China
Species	>Kingdom: Viridiplantae 　-->Phylum: Streptophyta 　　-->Class: Equisetopsida 　　　-->Order: Fabales 　　　　-->Family: Fabaceae 　　　　　-->Genus: Trifolium 　　　　　　-->Species: Trifolium pratense

Pair Name	Biochanin A, Fluorouracil
Partner Name	Fluorouracil
Disease Info	[ICD-11: 2C60]	Breast cancer		Investigative
Biological Phenomena	Induction-->Apoptosis
Gene Regulation	Down-regulation	Expression	AKT1	hsa207
	Down-regulation	Expression	BIRC5	hsa332
	Down-regulation	Expression	CCND1	hsa595
	Down-regulation	Expression	ESR1	hsa2099
	Down-regulation	Expression	MMP2	hsa4313
	Down-regulation	Expression	VEGFA	hsa7422
In Vitro Model	MCF-7	Invasive breast carcinoma of no special type	Homo sapiens (Human)	CVCL_0031
In Vitro Model	MDA-MB-231	Breast adenocarcinoma	Homo sapiens (Human)	CVCL_0062
In Vivo Model	Ehrlich solid-phase carcinoma was inducedviathe subcutane-ous inoculation of 0.2 ml of ascetic fluid, containing 2.5×10⁶ EACcells, into the right thigh of the hind limb of each mouse.
Result	The synergistic antitumor effect of Bio-A/ 5-FU combination can be, at least partly, attributed to Bio-A-mediated suppression of ER-α/Akt axis and the augmentation of 5-FU-mediated proapoptotic effects.

Pair Name	Biochanin A, Temozolomide
Partner Name	Temozolomide
Disease Info	[ICD-11: 2A00]	Glioblastoma multiforme		Investigative
Biological Phenomena	Induction-->Glycolytic to oxidative phosphorylation
Gene Regulation	Down-regulation	Phosphorylation	AKT1	hsa207
	Down-regulation	Expression	EGFR	hsa1956
	Down-regulation	Phosphorylation	MAPK3	hsa5595
	Down-regulation	Expression	MYC	hsa4609
	Up-regulation	Phosphorylation	TP53	hsa7157
In Vitro Model	U-87MG ATCC	Glioblastoma	Homo sapiens (Human)	CVCL_0022
In Vitro Model	T98G	Glioblastoma	Homo sapiens (Human)	CVCL_0556
Result	Chanin A significantly enhanced the anticancer efficacy of temozolomide in GBM cells.

Pair Name	Biochanin A, SB590885
Partner Name	SB590885
Disease Info	[ICD-11: 2C12]	Hepatocellular carcinoma		Investigative
Biological Phenomena	Induction-->Apoptosis
Gene Regulation	Up-regulation	Expression	BAX	hsa581
	Down-regulation	Expression	BCL2	hsa596
	Up-regulation	Cleavage	CASP9	hsa842
	Down-regulation	Expression	CCND1	hsa595
	Up-regulation	Expression	CDKN1A	hsa1026
	Down-regulation	Phosphorylation	MAP2K7	hsa5609
	Down-regulation	Phosphorylation	MAPK1	hsa5594
	Up-regulation	Cleavage	PARP1	hsa142
	Up-regulation	Expression	PSMD9	hsa5715
	Down-regulation	Phosphorylation	RPS6	hsa6194
	Down-regulation	Phosphorylation	RPS6KB1	hsa6198
In Vitro Model	BEL-7402	Human papillomavirus-related cervical adenocarcinoma	Homo sapiens (Human)	CVCL_5492
In Vitro Model	SK-HEP-1	Liver and intrahepatic bile duct epithelial neoplasm	Homo sapiens (Human)	CVCL_0525
In Vivo Model	5×10⁶ Bel-7402 cells were injected subcutaneously into the right flank near the hind leg of each nude mouse until the tumor volume was ~ 100 mm3.
Result	The results identify an effective combination therapy for the most aggressive form of HCC and provide the possibility of therapeutic improvement for patients with advanced HCC.