Genisterin | CAS#446-72-0 | topoisomerase inhibitor

MedKoo Cat#: 529319 | Name: Genisterin

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Genistein, a naturally occurring isoflavone primarily found in soy products, exhibits a wide range of bioactivities, especially notable for its anti-cancer, anti-inflammatory, and antioxidant properties. It functions as a protein tyrosine kinase inhibitor and modulates multiple signaling pathways, including PI3K/Akt, NF-κB, and estrogen receptors (ER). In vitro, genistein inhibits the proliferation of various cancer cell lines such as MCF-7 (breast cancer) with IC₅₀ values ranging from 10–50 µM, and induces apoptosis in prostate (LNCaP, PC3) and colon cancer cells. It has been shown to downregulate cyclin D1 and upregulate p21^WAF1/CIP1, leading to cell cycle arrest. Additionally, genistein reduces pro-inflammatory cytokines such as TNF-α and IL-6 in LPS-stimulated macrophages. Its antioxidant effect is linked to scavenging free radicals and upregulating endogenous antioxidant enzymes like superoxide dismutase (SOD). Despite promising preclinical data, genistein’s bioavailability and potential estrogenic effects remain considerations in clinical translation.

Chemical Structure

Genisterin

CAS#446-72-0

Theoretical Analysis

MedKoo Cat#: 529319

Name: Genisterin

CAS#: 446-72-0

Chemical Formula: C15H10O5

Exact Mass: 270.0528

Molecular Weight: 270.24

Elemental Analysis: C, 66.67; H, 3.73; O, 29.60

Price and Availability

Size	Price	Availability	Quantity
1g	USD 250.00	2 Weeks
5g	USD 450.00	2 Weeks

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Synonym

Genistein, 4',5,7-Trihydroxyisoflavone; Prunetol; Genisterin; CI-75610; C.I.-75610; NSC 36586; NSC36586; NSC-36586;

IUPAC/Chemical Name

5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one

InChi Key

TZBJGXHYKVUXJN-UHFFFAOYSA-N

InChi Code

InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H

SMILES Code

O=C1C(C2=CC=C(O)C=C2)=COC3=CC(O)=CC(O)=C13

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A25M06B17C

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Genistein, a soy isoflavone, is a multiple tyrosine kinases (e.g., EGFR) inhibitor which acts as a chemotherapeutic agent against different types of cancer, mainly by altering apoptosis, the cell cycle, and angiogenesis and inhibiting metastasis.

In vitro activity:

Although not exhibiting any visible toxicity on the HEK-cGASlow cells at the doses used, Genistein treatment reduced cell proliferation above 30 μM (Fig. S1A). To circumvent this, this study normalized the number of cGAMP-producing cells after Genistein treatment and confirmed a dose-dependent inhibition of cGAMP transactivation of cocultured LL171 cells by Genistein (Fig. 1C). Similarly, pretreatment of connexin (CX) expressing human MG-63 cells with Genistein, that were subsequently transfected with an immunostimulatory DNA (ISD) to activate cGAS, significantly decreased ISRE-luciferase expression from cocultured LL171 cells (Fig. 1D). It is noteworthy that intracellular levels of cGAMP were increased by Genistein in HEK cGASlow cells (Fig. 1E), indicating an inhibition of GJIC aligned with the accumulating cGAMP levels observed. Reference: mBio. 2022 Aug 30;13(4):e0206422. https://pubmed.ncbi.nlm.nih.gov/35924852/

In vivo activity:

The mfn2 expression and mitochondrial membrane potential in DN group were significantly higher than those in control group, which were also increased in each treatment group with genistein in a dose-dependent manner (Figs. 3a and 3b). It shows that genistein supplementation improves nephropathy likely via modulation of the mitochondrial fusion and function in DN rats. Reference: Acta Cir Bras. 2022 Aug 15;37(6):e370601. https://pubmed.ncbi.nlm.nih.gov/35976278/

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	111.01
	DMSO	61.3	226.96
	DMSO:PBS (pH 7.2) (1:6)	1.0	3.70
	Ethanol	4.0	14.80

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 270.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Ullah TR, Balka KR, Ambrose RL, Pépin G, Wilce MCJ, Wilce JA, Thomas BJ, De Nardo D, Williams BRG, Gantier MP. Genistein Targets STING-Driven Antiviral Responses. mBio. 2022 Aug 30;13(4):e0206422. doi: 10.1128/mbio.02064-22. Epub 2022 Aug 4. PMID: 35924852; PMCID: PMC9426420. 2. Cong L, Xie X, Liu S, Xiang L, Fu X. Genistein promotes M1 macrophage apoptosis and reduces inflammatory response by disrupting miR-21/TIPE2 pathway. Saudi Pharm J. 2022 Jul;30(7):934-945. doi: 10.1016/j.jsps.2022.05.009. Epub 2022 May 23. PMID: 35903524; PMCID: PMC9315303. 3. Li Y, Ou S, Liu Q, Gan L, Zhang L, Wang Y, Qin J, Liu J, Wu W. Genistein improves mitochondrial function and inflammatory in rats with diabetic nephropathy via inhibiting MAPK/NF-κB pathway. Acta Cir Bras. 2022 Aug 15;37(6):e370601. doi: 10.1590/acb370601. PMID: 35976278; PMCID: PMC9377651. 4. Siriviriyakul P, Sriko J, Somanawat K, Chayanupatkul M, Klaikeaw N, Werawatganon D. Genistein attenuated oxidative stress, inflammation, and apoptosis in L-arginine induced acute pancreatitis in mice. BMC Complement Med Ther. 2022 Aug 4;22(1):208. doi: 10.1186/s12906-022-03689-9. PMID: 35927726; PMCID: PMC9351145.

In vitro protocol:

In vivo protocol:

1. Li Y, Ou S, Liu Q, Gan L, Zhang L, Wang Y, Qin J, Liu J, Wu W. Genistein improves mitochondrial function and inflammatory in rats with diabetic nephropathy via inhibiting MAPK/NF-κB pathway. Acta Cir Bras. 2022 Aug 15;37(6):e370601. doi: 10.1590/acb370601. PMID: 35976278; PMCID: PMC9377651. 2. Siriviriyakul P, Sriko J, Somanawat K, Chayanupatkul M, Klaikeaw N, Werawatganon D. Genistein attenuated oxidative stress, inflammation, and apoptosis in L-arginine induced acute pancreatitis in mice. BMC Complement Med Ther. 2022 Aug 4;22(1):208. doi: 10.1186/s12906-022-03689-9. PMID: 35927726; PMCID: PMC9351145.

1: Sekar V, Anandasadagopan SK, Ganapasam S. Genistein regulates tumor microenvironment and exhibits anticancer effect in dimethyl hydrazine-induced experimental colon carcinogenesis. Biofactors. 2016 Nov 12;42(6):623-637. doi: 10.1002/biof.1298. PubMed PMID: 27255553. 2: Froyen EB, Steinberg FM. Genistein decreases basal hepatic cytochrome P450 1A1 protein expression and activity in Swiss Webster mice. Nutr Res. 2016 May;36(5):430-9. doi: 10.1016/j.nutres.2016.01.001. PubMed PMID: 27101761. 3: Rahman Mazumder MA, Hongsprabhas P. Genistein as antioxidant and antibrowning agents in in vivo and in vitro: A review. Biomed Pharmacother. 2016 Aug;82:379-92. doi: 10.1016/j.biopha.2016.05.023. Review. PubMed PMID: 27470376. 4: Incir S, Bolayirli IM, Inan O, Aydın MS, Bilgin IA, Sayan I, Esrefoglu M, Seven A. The effects of genistein supplementation on fructose induced insulin resistance, oxidative stress and inflammation. Life Sci. 2016 Aug 1;158:57-62. doi: 10.1016/j.lfs.2016.06.014. PubMed PMID: 27350161. 5: Moskot M, Gabig-Cimińska M, Jakóbkiewicz-Banecka J, Węsierska M, Bocheńska K, Węgrzyn G. Cell cycle is disturbed in mucopolysaccharidosis type II fibroblasts, and can be improved by genistein. Gene. 2016 Jul 1;585(1):100-3. doi: 10.1016/j.gene.2016.03.029. PubMed PMID: 27016302. 6: Zhang HP, Zhao JH, Yu HX, Guo DX. Genistein ameliorated endothelial nitric oxidase synthase uncoupling by stimulating sirtuin-1 pathway in ox-LDL-injured HUVECs. Environ Toxicol Pharmacol. 2016 Mar;42:118-24. doi: 10.1016/j.etap.2016.01.011. PubMed PMID: 26829290. 7: Patel S, Peretz J, Pan YX, Helferich WG, Flaws JA. Genistein exposure inhibits growth and alters steroidogenesis in adult mouse antral follicles. Toxicol Appl Pharmacol. 2016 Feb 15;293:53-62. doi: 10.1016/j.taap.2015.12.026. PubMed PMID: 26792615; PubMed Central PMCID: PMC4744102. 8: Choi EY, Bae SH, Ha MH, Choe SH, Hyeon JY, Choi JI, Choi IS, Kim SJ. Genistein suppresses Prevotella intermedia lipopolysaccharide-induced inflammatory response in macrophages and attenuates alveolar bone loss in ligature-induced periodontitis. Arch Oral Biol. 2016 Feb;62:70-9. doi: 10.1016/j.archoralbio.2015.11.019. PubMed PMID: 26655950. 9: Wu B, Liang Y, Tan Y, Xie C, Shen J, Zhang M, Liu X, Yang L, Zhang F, Liu L, Cai S, Huai D, Zheng D, Zhang R, Zhang C, Chen K, Tang X, Sui X. Genistein-loaded nanoparticles of star-shaped diblock copolymer mannitol-core PLGA-TPGS for the treatment of liver cancer. Mater Sci Eng C Mater Biol Appl. 2016 Feb;59:792-800. doi: 10.1016/j.msec.2015.10.087. PubMed PMID: 26652434. 10: Cui S, Hassan RY, Heintz-Buschart A, Bilitewski U. Regulation of Candida albicans Interaction with Macrophages through the Activation of HOG Pathway by Genistein. Molecules. 2016 Jan 28;21(2):162. doi: 10.3390/molecules21020162. PubMed PMID: 26828477. 11: Baechler SA, Soukup ST, Molzberger AF, Kulling SE, Diel P, Marko D. Topoisomerase poisoning by genistein in the intestine of rats. Toxicol Lett. 2016 Jan 22;243:88-97. doi: 10.1016/j.toxlet.2015.12.009. PubMed PMID: 26723871. 12: Oktem C, Oto S, Toru S, Bakar C, Ozdemir H, Akova YA. Suramin, Genistein and Collagen Matrix (DuraGen) for Delayed Adjustment after Strabismus Surgery: Which One is Best? Curr Eye Res. 2016;41(3):417-24. doi: 10.3109/02713683.2015.1020171. PubMed PMID: 25859732. 13: Ganai AA, Husain M. Genistein attenuates D-GalN induced liver fibrosis/chronic liver damage in rats by blocking the TGF-β/Smad signaling pathways. Chem Biol Interact. 2017 Jan 5;261:80-85. doi: 10.1016/j.cbi.2016.11.022. PubMed PMID: 27876602. 14: Russo M, Russo GL, Daglia M, Kasi PD, Ravi S, Nabavi SF, Nabavi SM. Understanding genistein in cancer: The "good" and the "bad" effects: A review. Food Chem. 2016 Apr 1;196:589-600. doi: 10.1016/j.foodchem.2015.09.085. Review. PubMed PMID: 26593532. 15: Yu L, Ham K, Gao X, Castro L, Yan Y, Kissling GE, Tucker CJ, Flagler N, Dong R, Archer TK, Dixon D. Epigenetic regulation of transcription factor promoter regions by low-dose genistein through mitogen-activated protein kinase and mitogen-and-stress activated kinase 1 nongenomic signaling. Cell Commun Signal. 2016 Aug 31;14(1):18. doi: 10.1186/s12964-016-0141-2. PubMed PMID: 27582276; PubMed Central PMCID: PMC5007815. 16: Wu TC, Lin YC, Chen HL, Huang PR, Liu SY, Yeh SL. The enhancing effect of genistein on apoptosis induced by trichostatin A in lung cancer cells with wild type p53 genes is associated with upregulation of histone acetyltransferase. Toxicol Appl Pharmacol. 2016 Feb 1;292:94-102. doi: 10.1016/j.taap.2015.12.028. PubMed PMID: 26768552. 17: Ha YR, Kang YJ, Lee SJ. In vivo study on splenomegaly inhibition by genistein in Plasmodium berghei-infected mice. Parasitol Int. 2015 Oct;64(5):369-76. doi: 10.1016/j.parint.2015.05.013. PubMed PMID: 26004668. 18: Qin J, Teng J, Zhu Z, Chen J, Huang WJ. Genistein induces activation of the mitochondrial apoptosis pathway by inhibiting phosphorylation of Akt in colorectal cancer cells. Pharm Biol. 2016;54(1):74-9. doi: 10.3109/13880209.2015.1014921. PubMed PMID: 25880142. 19: Silvestre MA, Vicente-Fiel S, Raga E, Salvador I, Soler C, Yániz JL. Effect of genistein added to bull semen after thawing on pronuclear and sperm quality. Anim Reprod Sci. 2015 Dec;163:120-7. doi: 10.1016/j.anireprosci.2015.10.006. PubMed PMID: 26552873. 20: Salleh N, Ismail N, Muniandy S, Korla PK, Giribabu N. Combinatorial effects of genistein and sex-steroids on the level of cystic fibrosis transmembrane regulator (CFTR), adenylate cyclase (AC) and cAMP in the cervix of ovariectomised rats. Reprod Toxicol. 2015 Dec;58:194-202. doi: 10.1016/j.reprotox.2015.10.017. PubMed PMID: 26529183.