WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H540233
CAS#: 961-29-5
Description: Isoliquiritigenin is a SIRT activator, GABA to-A receptor positive modulator, and inhibitor of NMDA receptors, VEGFR2, and HDACs. It increases Nrf2 expression, downregulates expression of COX-2 and PLA2 , and induces apoptosis in breast cancer cells.
Hodoodo Cat#: H540233
Name: Isoliquiritigenin
CAS#: 961-29-5
Chemical Formula: C15H12O4
Exact Mass: 256.07
Molecular Weight: 256.250
Elemental Analysis: C, 70.31; H, 4.72; O, 24.97
Synonym: 4,2',4'-Trihydroxychalcone; GU-17; GU17; GU 17, Isoliquiritigenin
IUPAC/Chemical Name: (E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one
InChi Key: DXDRHHKMWQZJHT-FPYGCLRLSA-N
InChi Code: InChI=1S/C15H12O4/c16-11-4-1-10(2-5-11)3-8-14(18)13-7-6-12(17)9-15(13)19/h1-9,16-17,19H/b8-3+
SMILES Code: O=C(C1=CC=C(O)C=C1O)/C=C/C2=CC=C(O)C=C2
Appearance: Solid powder
Purity: >97% (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: 2914.50.3000
More Info:
| Biological target: | Isoliquiritigenin inhibits aldose reductase with an IC50 of 320 nM. |
| In vitro activity: | This study showed that hASC-derived WACs were able to transdifferentiate to a beige or brown adipocyte by expressing both UCP1 and PRDM16 in response to low-dose ILG (Isoliquiritigenin) treatments (Figure 4A,B). Previously, UCP1 and PRDM16 were shown to be master regulators for brown adipogenesis, and their overexpression could induce browning in stem cells. These results confirmed that the expression levels of UCP1 and PRDM16 increased in beige and brown adipocytes after ILG treatment of WACs. However, it is thought that WACs contain beige-like adipocytes, because UCP-1 is expressed in WACs even if it is a small amount. Importantly, JNK phosphorylation was downregulated during increasing beige and brown adipocyte differentiation of WACs. Consistently, immunofluorescence staining confirmed a significant increase in UCP1, while p-JNK expression was downregulated in WACs after ILG treatment (Figure 4C,D). Reference: Molecules. 2020 Dec; 25(23): 5660. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7730955/ |
| In vivo activity: | In addition, the number of nodule distribution in abdominal cavity of nude mice in the ISL group was lower than in the control group (Figure 7f). The results showed that ISL decreased the expression levels of N-cadherin (p < 0.05, Figure 8d), vimentin (Figure 8e), α-SMA (Figure 8f), p-Smad2/3 (p < 0.05, Figure 8g), and TWIST1/2 (p < 0.05, Figure 8h), while increased E-cadherin (p < 0.05, Figure 8c) and TGFβRI (Figure 8i) expression levels compared with those of the control group. In addition, the total serum level of TGF-β1 in ISL group was markedly lower than the control group (mean, 5598 pg/mL vs. 25916 pg/mL; p < 0.05, Figure 8j). Collectively, these results demonstrated that ISL inhibited the tumor metastasis via up-regulating the E-cadherin and down-regulating the N-cadherin, p-Smad2/3, and TWIST1/2 protein expression in the xenograft animal model. Reference: Cancers (Basel). 2021 Mar; 13(6): 1236. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8001359/ |
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| DMSO | 44.0 | 171.71 | |
| DMSO:PBS (pH 7.2) (1:10) | 0.1 | 0.39 | |
| DMF | 20.0 | 78.05 | |
| Ethanol | 43.7 | 170.42 |
The following data is based on the product molecular weight 256.25 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. Moon H, Choi JW, Song BW, Kim IK, Lim S, Lee S, Hwang KC, Kim SW. Isoliquiritigenin Enhances the Beige Adipocyte Potential of Adipose-Derived Stem Cells by JNK Inhibition. Molecules. 2020 Dec 1;25(23):5660. doi: 10.3390/molecules25235660. PMID: 33271769; PMCID: PMC7730955. 2. Gómez-Sierra T, Medina-Campos ON, Solano JD, Ibarra-Rubio ME, Pedraza-Chaverri J. Isoliquiritigenin Pretreatment Induces Endoplasmic Reticulum Stress-Mediated Hormesis and Attenuates Cisplatin-Induced Oxidative Stress and Damage in LLC-PK1 Cells. Molecules. 2020 Sep 27;25(19):4442. doi: 10.3390/molecules25194442. PMID: 32992605; PMCID: PMC7582730. 3. Chen HY, Chiang YF, Huang JS, Huang TC, Shih YH, Wang KL, Ali M, Hong YH, Shieh TM, Hsia SM. Isoliquiritigenin Reverses Epithelial-Mesenchymal Transition Through Modulation of the TGF-β/Smad Signaling Pathway in Endometrial Cancer. Cancers (Basel). 2021 Mar 11;13(6):1236. doi: 10.3390/cancers13061236. PMID: 33799801; PMCID: PMC8001359. 4. Huang X, Shi Y, Chen H, Le R, Gong X, Xu K, Zhu Q, Shen F, Chen Z, Gu X, Chen X, Chen X. Isoliquiritigenin prevents hyperglycemia-induced renal injuries by inhibiting inflammation and oxidative stress via SIRT1-dependent mechanism. Cell Death Dis. 2020 Dec 7;11(12):1040. doi: 10.1038/s41419-020-03260-9. PMID: 33288747; PMCID: PMC7721869. |
| In vitro protocol: | 1. Moon H, Choi JW, Song BW, Kim IK, Lim S, Lee S, Hwang KC, Kim SW. Isoliquiritigenin Enhances the Beige Adipocyte Potential of Adipose-Derived Stem Cells by JNK Inhibition. Molecules. 2020 Dec 1;25(23):5660. doi: 10.3390/molecules25235660. PMID: 33271769; PMCID: PMC7730955. 2. Gómez-Sierra T, Medina-Campos ON, Solano JD, Ibarra-Rubio ME, Pedraza-Chaverri J. Isoliquiritigenin Pretreatment Induces Endoplasmic Reticulum Stress-Mediated Hormesis and Attenuates Cisplatin-Induced Oxidative Stress and Damage in LLC-PK1 Cells. Molecules. 2020 Sep 27;25(19):4442. doi: 10.3390/molecules25194442. PMID: 32992605; PMCID: PMC7582730. |
| In vivo protocol: | 1. Chen HY, Chiang YF, Huang JS, Huang TC, Shih YH, Wang KL, Ali M, Hong YH, Shieh TM, Hsia SM. Isoliquiritigenin Reverses Epithelial-Mesenchymal Transition Through Modulation of the TGF-β/Smad Signaling Pathway in Endometrial Cancer. Cancers (Basel). 2021 Mar 11;13(6):1236. doi: 10.3390/cancers13061236. PMID: 33799801; PMCID: PMC8001359. 2. Huang X, Shi Y, Chen H, Le R, Gong X, Xu K, Zhu Q, Shen F, Chen Z, Gu X, Chen X, Chen X. Isoliquiritigenin prevents hyperglycemia-induced renal injuries by inhibiting inflammation and oxidative stress via SIRT1-dependent mechanism. Cell Death Dis. 2020 Dec 7;11(12):1040. doi: 10.1038/s41419-020-03260-9. PMID: 33288747; PMCID: PMC7721869. |
1: Zhao S, Chang H, Ma P, Gao G, Jin C, Zhao X, Zhou W, Jin B. Inhibitory effect of DNA topoisomerase inhibitor isoliquiritigenin on the growth of glioma cells. Int J Clin Exp Pathol. 2015 Oct 1;8(10):12577-82. eCollection 2015. PubMed PMID: 26722447; PubMed Central PMCID: PMC4680392.
2: Choi YH, Kim YJ, Chae HS, Chin YW. In vivo gastroprotective effect along with pharmacokinetics, tissue distribution and metabolism of isoliquiritigenin in mice. Planta Med. 2015 May;81(7):586-93. doi: 10.1055/s-0035-1545914. Epub 2015 Apr 15. PubMed PMID: 25875506.
3: Peng F, Du Q, Peng C, Wang N, Tang H, Xie X, Shen J, Chen J. A Review: The Pharmacology of Isoliquiritigenin. Phytother Res. 2015 Jul;29(7):969-77. doi: 10.1002/ptr.5348. Epub 2015 Apr 24. Review. PubMed PMID: 25907962.
4: Li ZX, Li J, Li Y, You K, Xu H, Wang J. Novel insights into the apoptosis mechanism of DNA topoisomerase I inhibitor isoliquiritigenin on HCC tumor cell. Biochem Biophys Res Commun. 2015 Aug 21;464(2):548-53. doi: 10.1016/j.bbrc.2015.07.003. Epub 2015 Jul 6. PubMed PMID: 26159926.
5: Lee YK, Chin YW, Bae JK, Seo JS, Choi YH. Pharmacokinetics of isoliquiritigenin and its metabolites in rats: low bioavailability is primarily due to the hepatic and intestinal metabolism. Planta Med. 2013 Nov;79(17):1656-65. doi: 10.1055/s-0033-1350924. Epub 2013 Oct 9. PubMed PMID: 24108436.
6: Gong H, Zhang BK, Yan M, Fang PF, Li HD, Hu CP, Yang Y, Cao P, Jiang P, Fan XR. A protective mechanism of licorice (Glycyrrhiza uralensis): isoliquiritigenin stimulates detoxification system via Nrf2 activation. J Ethnopharmacol. 2015 Mar 13;162:134-9. doi: 10.1016/j.jep.2014.12.043. Epub 2014 Dec 31. PubMed PMID: 25557030.
7: Honda H, Nagai Y, Matsunaga T, Okamoto N, Watanabe Y, Tsuneyama K, Hayashi H, Fujii I, Ikutani M, Hirai Y, Muraguchi A, Takatsu K. Isoliquiritigenin is a potent inhibitor of NLRP3 inflammasome activation and diet-induced adipose tissue inflammation. J Leukoc Biol. 2014 Dec;96(6):1087-100. doi: 10.1189/jlb.3A0114-005RR. Epub 2014 Sep 10. PubMed PMID: 25210146.
8: Mahalingam S, Gao L, Eisner J, Helferich W, Flaws JA. Effects of isoliquiritigenin on ovarian antral follicle growth and steroidogenesis. Reprod Toxicol. 2016 Dec;66:107-114. doi: 10.1016/j.reprotox.2016.10.004. Epub 2016 Oct 20. PubMed PMID: 27773742; PubMed Central PMCID: PMC5125911.
9: Lu H, Fang ZZ, Cao YF, Hu CM, Hong M, Sun XY, Li H, Liu Y, Fu X, Sun H. Isoliquiritigenin showed strong inhibitory effects towards multiple UDP-glucuronosyltransferase (UGT) isoform-catalyzed 4-methylumbelliferone (4-MU) glucuronidation. Fitoterapia. 2013 Jan;84:208-12. doi: 10.1016/j.fitote.2012.12.002. Epub 2012 Dec 10. PubMed PMID: 23237733.
10: Wu S, Xue J, Yang Y, Zhu H, Chen F, Wang J, Lou G, Liu Y, Shi Y, Yu Y, Xia C, Hu Y, Chen Z. Isoliquiritigenin Inhibits Interferon-γ-Inducible Genes Expression in Hepatocytes through Down-Regulating Activation of JAK1/STAT1, IRF3/MyD88, ERK/MAPK, JNK/MAPK and PI3K/Akt Signaling Pathways. Cell Physiol Biochem. 2015;37(2):501-14. doi: 10.1159/000430372. Epub 2015 Aug 28. PubMed PMID: 26315837.
11: Link P, Wetterauer B, Fu Y, Wink M. Extracts of Glycyrrhiza uralensis and isoliquiritigenin counteract amyloid-β toxicity in Caenorhabditis elegans. Planta Med. 2015 Mar;81(5):357-62. doi: 10.1055/s-0035-1545724. Epub 2015 Mar 17. PubMed PMID: 25782036.
12: Wang N, Wang Z, Wang Y, Xie X, Shen J, Peng C, You J, Peng F, Tang H, Guan X, Chen J. Dietary compound isoliquiritigenin prevents mammary carcinogenesis by inhibiting breast cancer stem cells through WIF1 demethylation. Oncotarget. 2015;6(12):9854-76. PubMed PMID: 25918249; PubMed Central PMCID: PMC4496402.
13: Li Y, Zhao H, Wang Y, Zheng H, Yu W, Chai H, Zhang J, Falck JR, Guo AM, Yue J, Peng R, Yang J. Isoliquiritigenin induces growth inhibition and apoptosis through downregulating arachidonic acid metabolic network and the deactivation of PI3K/Akt in human breast cancer. Toxicol Appl Pharmacol. 2013 Oct 1;272(1):37-48. doi: 10.1016/j.taap.2013.05.031. Epub 2013 Jun 5. PubMed PMID: 23747687.
14: Zhao Z, Park SM, Guan L, Wu Y, Lee JR, Kim SC, Kim YW, Zhao R. Isoliquiritigenin attenuates oxidative hepatic damage induced by carbon tetrachloride with or without buthionine sulfoximine. Chem Biol Interact. 2015 Jan 5;225:13-20. doi: 10.1016/j.cbi.2014.10.030. Epub 2014 Nov 6. PubMed PMID: 25450236.
15: Yang EJ, Kim M, Woo JE, Lee T, Jung JW, Song KS. The comparison of neuroprotective effects of isoliquiritigenin and its Phase I metabolites against glutamate-induced HT22 cell death. Bioorg Med Chem Lett. 2016 Dec 1;26(23):5639-5643. doi: 10.1016/j.bmcl.2016.10.072. Epub 2016 Oct 26. PubMed PMID: 27815122.
16: Wang N, Wang Z, Peng C, You J, Shen J, Han S, Chen J. Dietary compound isoliquiritigenin targets GRP78 to chemosensitize breast cancer stem cells via β-catenin/ABCG2 signaling. Carcinogenesis. 2014 Nov;35(11):2544-54. doi: 10.1093/carcin/bgu187. Epub 2014 Sep 6. PubMed PMID: 25194164.
17: Fu H, Zhang Y, Wang X, Han Y, Peng X, Efferth T, Fu Y. Synthesis and anti-tumor activity of novel aminomethylated derivatives of isoliquiritigenin. Molecules. 2014 Oct 31;19(11):17715-26. doi: 10.3390/molecules191117715. PubMed PMID: 25365296.
18: Hirchaud F, Hermetet F, Ablise M, Fauconnet S, Vuitton DA, Prétet JL, Mougin C. Isoliquiritigenin induces caspase-dependent apoptosis via downregulation of HPV16 E6 expression in cervical cancer Ca Ski cells. Planta Med. 2013 Nov;79(17):1628-35. doi: 10.1055/s-0033-1350956. Epub 2013 Nov 8. PubMed PMID: 24214831.
19: Tian WW, Zhao L, Ma KT, Li L, Si JQ. [Isoliquiritigenin relaxes the cerebral basilar artery by enhancing BKCa current in spontaneously hypertensive rat: role of sGC/cGMP]. Sheng Li Xue Bao. 2015 Jun 25;67(3):329-34. Chinese. PubMed PMID: 26109306.
20: Ma X, Fang F, Song M, Ma S. The effect of isoliquiritigenin on learning and memory impairments induced by high-fat diet via inhibiting TNF-α/JNK/IRS signaling. Biochem Biophys Res Commun. 2015 Sep 4;464(4):1090-5. doi: 10.1016/j.bbrc.2015.07.081. Epub 2015 Jul 17. PubMed PMID: 26188513.
