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446-72-0

446-72-0 structure
446-72-0 structure
  • Name: Genistein
  • Chemical Name: genistein
  • CAS Number: 446-72-0
  • Molecular Formula: C15H10O5
  • Molecular Weight: 270.237
  • Catalog: Biochemical Natural product
  • Create Date: 2018-02-04 08:00:00
  • Modify Date: 2024-01-02 11:38:49
  • Genistein, a soy isoflavone, is a multiple tyrosine kinases inhibitor which acts as a chemotherapeutic agent against different types of cancer, mainly by altering apoptosis, the cell cycle, and angiogenesis and inhibiting metastasis.
Name genistein
Synonyms 5-18-04-00594 (Beilstein Handbook Reference)
5,7,4'-trihydroxyisoflavone
4',5,7-trihydroxyisoflavone
Genistein
GeniVida
4H-1-Benzopyran-4-one, 5,7-dihydroxy-3-(4-hydroxyphenyl)-
prunetol
EINECS 207-174-9
genisteol
Bonistein
NPI 031L
MFCD00016952
5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Genestein
sophoricol
GLYCITEN
Description Genistein, a soy isoflavone, is a multiple tyrosine kinases inhibitor which acts as a chemotherapeutic agent against different types of cancer, mainly by altering apoptosis, the cell cycle, and angiogenesis and inhibiting metastasis.
Related Catalog
Target

EGFR:0.6 μM (IC50, Cell Assay)

In Vitro Genistein inhibits serum-stimulated growth of MCF-7 and T47D ER+ cells with IC50 values of 7.6 and 8.7 μg/mL by dye exclusion, respectively, and 8.7 and 10.6 μg/mL by [3H]thymidmne incorporation, respectively. These values are similar to the IC50 values of 9.4 and 7 μg/mL for MCF-7 and T47D ER+ cells, respectively, obtained with the MTT assay. Additionally, Genistein at concentrations up to 20 μg/mL does not alter MTT mitochondrial reduction when compared to control cells in an 8 h incubation period. Furthermore, neither biochanin A or daidzein are found to interfere with the MTT assay at IC50 concentrations. Therefore, the MTT assay is valid for determining growth inhibition by Genistein at concentrations under 20 μg/mL in the systems studied[1].
In Vivo In the present study, the effective dose of morphine caused a significant decrease in testis weight of mice compared to Saline group (p=0.00). Moreover, testis weight are significantly increase in treated animals with Genistein and Genistein plus morphine in all doses in comparison with morphine group (p=0.028). Morphine caused a significant decrease in the testosterone, LH and FSH hormones compared to saline group (p=0.00). In addition, the testosterone, LH and FSH hormones increased significantly in Genistein (p<0.05) and Genistein plus morphine in all groups administration compared to morphine group (p=0.024)[2]. Bisphenol A (BPA) treatment alone and combined with Genistein had no significant effect on the protein expression of LC3II and PPARα in liver of STD- or HFD-fed rats (P>0.05; P>0.05). Significant decreasing of the protein expression of PPARγ in liver is observed when Genistein is added to rats, compared to either HFD group or HFD-BPA group[3].
Cell Assay The IC50 values for Genistein are determined by the MTT assay. Briefly, the MTT assay is a colorimetric assay that is based on the ability of living but not dead cells to reduce a tetrazolium-based compound to a blue formazan product. The formazan crystals are solubilized in DMSO, and the absorbance is measured at 540 nm. The absorbance at 540 nm is proportional to the number of viable cells. The lC50 values obtained with the MTT assay are compared with the lC50 values obtained by counting viable cells using trypan blue dye exclusion and by tritiated thymidine incorporation into DNA[1].
Animal Admin Mice[2] Balb/c male mice are used. Genistein is administered as follows: On days 1-30, Genistein once daily, interaperitoneally injecting. Morphine plus Genistein is administered as follows: On days 1-30, Genistein once daily plus morphine, interaperitoneally injecting (17, 18). The same volume of saline is administered. Mice are randomly divided into 8 groups (n=6). 1) Normal saline group (1 mL DW/daily); 2) Morphine treated group; 3) Genistein 1 mg/kg treated group; 4) Genistein 2 mg/kg treated group 5) Genistein 4 mg/kg treated group; 6) Morphine plus Genistein 1 mg/kg treated group; 7) Morphine plus Genistein 2 mg/kg treated group; 8) Morphine plus Genistein 4 mg/kg treated group. Rats[3] Male 8-week-old Wistar rats (150-180g) are used. After one week acclimation, all rats are randomly divided into 8 groups with 10 rats per group and treated for 35 weeks as follows: (1) STD group is fed with rodent standard chow diet (STD); (2) STD-BPA group is fed with STD and administered with BPA (50 μg/kg/day); (3) STD-(BPA+G) group is fed with STD and administered with BPA (50 μg/kg/day) plus Genistein (10 mg/kg/day); (4) STD-G group is fed with STD and administered with Genistein (10 mg/kg/day); (5) HFD group received high-fat diet (HFD); (6) HFD-BPA group is fed with HFD and administered with BPA (50 μg/kg/day); (7) STD-(BPA+G) group is fed with HFD and administered with BPA (50 μg/kg/day) plus Genistein (10 mg/kg/day); (8) HFD-G group is fed with HFD and administrated with Genistein (10 mg/kg/day). All the male genitors are treated for 35 weeks consecutively. The details of BPA (50 μg/kg/day) and Genistein (10 mg/kg/day) treatment methods have been described previously: BPA is dissolved in corn oil and diluted with three stock solutions (20, 40, 80, and 120 μg/mL).
References

[1]. Peterson G, et al. Genistein inhibits both estrogen and growth factor-stimulated proliferation of human breast cancer cells. Cell Growth Differ. 1996 Oct;7(10):1345-51.

[2]. Jalili C, et al. Effect of Genistein on reproductive parameter and serum nitric oxide levels in morphine-treated mice. Int J Reprod Biomed (Yazd). 2016 Feb;14(2):95-102.

[3]. Ding S, et al. Environmentally Relevant Dose of Bisphenol A Does Not Affect Lipid Metabolism and Has No Synergetic or Antagonistic Effects on Genistein's Beneficial Roles on Lipid Metabolism. PLoS One. 2016 May 12;11(5):e0155352.
Density 1.5±0.1 g/cm3
Boiling Point 555.5±50.0 °C at 760 mmHg
Melting Point 297-298 °C
Molecular Formula C15H10O5
Molecular Weight 270.237
Flash Point 217.1±23.6 °C
Exact Mass 270.052826
PSA 90.90000
LogP 2.96
Vapour Pressure 0.0±1.6 mmHg at 25°C
Index of Refraction 1.732
Storage condition −20°C
Stability Light Sensitive
Water Solubility insoluble

CHEMICAL IDENTIFICATION

RTECS NUMBER :
NR2392000
CHEMICAL NAME :
Isoflavone, 4',5,7-trihydroxy-
CAS REGISTRY NUMBER :
446-72-0
BEILSTEIN REFERENCE NO. :
0263823
LAST UPDATED :
199801
DATA ITEMS CITED :
12
MOLECULAR FORMULA :
C15-H10-O5
MOLECULAR WEIGHT :
270.25
WISWESSER LINE NOTATION :
T66 BO EVT&J CR DQ& IQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>500 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
125 mg/kg
SEX/DURATION :
female 16-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - urogenital system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
625 mg/kg
SEX/DURATION :
female 16-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1680 mg/kg
SEX/DURATION :
female 21 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Maternal Effects - other effects
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
13200 mg/kg
SEX/DURATION :
male 22 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
18600 mg/kg
SEX/DURATION :
female 31 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Effects on Newborn - stillbirth

MUTATION DATA

TYPE OF TEST :
Mutation in mammalian somatic cells
TEST SYSTEM :
Rodent - hamster Lung
DOSE/DURATION :
25 umol/L
REFERENCE :
FCTOD7 Food and Chemical Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.20- 1982- Volume(issue)/page/year: 35,605,1997
Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302
Precautionary Statements P301 + P312 + P330
Personal Protective Equipment Eyeshields;Faceshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes Xi: Irritant;
Risk Phrases R36/38
Safety Phrases S26-S24/25-S22
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS NR2392000
HS Code 2932999099
HS Code 2932999099
Summary 2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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