Indirubin-3’-oxime
Indirubin-3’-oxime is a potent inhibitor of glycogen synthase kinase 3β (GSK3β; IC50 = 22 nM).1 As GSK3β phosphorylates tau protein, indirubin-3’-oxime prevents tau phosphorylation both in vitro and in vivo at Alzheimer’s disease-relevant sites.
For research use only. We do not sell to patients.
Chemical Information
| Name | Indirubin-3’-oxime |
|---|---|
| Iupac Chemical Name | 3-[1,3-dihydro-3-(hydroxyimino)-2H-indol-2-ylidene]-1,3-dihydro-2H-indol-2-one |
| Synonyms | Indirubin-3’-oxime |
| Molecular Formula | C16H11N3O2 |
| Molecular Weight | 277.28 |
| Smile | O=C1NC2=C(C=CC=C2)/C1=C3NC4=C(C=CC=C4)C/3=N/O |
| InChiKey | HBDSHCUSXQATPO-BRNLPKLHSA-N |
| InChi | InChI=1S/C16H11N3O2/c20-16-13(9-5-1-3-7-11(9)18-16)15-14(19-21)10-6-2-4-8-12(10)17-15/h1-8,17,21H,(H,18,20)/b15-13-,19-14- |
| CAS Number | 160807-49-8 |
| Related CAS |
Ordering Information
| Packaging | Price | Availability | Purity | Shipping Time |
|---|---|---|---|---|
| Bulk | Enquiry | Enquiry | Enquiry |
| Formulation | Solid powder |
|---|---|
| Purity | 98% Min. |
| Storage | 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 |
| Handling | |
| 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. |
| HS Code |
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| Mechanism | |
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| Clinical study |
1: Choudhary SA, Bora N, Banerjee D, Arora L, Das AS, Yadav R, Klotz KN, Pal D, Jha AN, Dasgupta S. A novel small molecule A(2A) adenosine receptor agonist, indirubin-3'-monoxime, alleviates lipid-induced inflammation and insulin resistance in 3T3-L1 adipocytes. Biochem J. 2019 Aug 30;476(16):2371-2391. doi: 10.1042/BCJ20190251. PubMed PMID: 31409652.
2: Zhang Y, Song L, Li J, Zhang Y, Lu X, Zhang B. Inhibitory effects of indirubin-3'-monoxime against human osteosarcoma. IUBMB Life. 2019 May 3. doi: 10.1002/iub.2058. [Epub ahead of print] PubMed PMID: 31050877.
3: Sathiya Priya C, Vidhya R, Kalpana K, Anuradha CV. Indirubin-3'-monoxime prevents aberrant activation of GSK-3β/NF-κB and alleviates high fat-high fructose induced Aβ-aggregation, gliosis and apoptosis in mice brain. Int Immunopharmacol. 2019 May;70:396-407. doi: 10.1016/j.intimp.2019.02.053. Epub 2019 Mar 8. PubMed PMID: 30856390.
4: Tchoumtchoua J, Halabalaki M, Gikas E, Tsarbopoulos A, Fotaki N, Liu L, Nam S, Jove R, Skaltsounis LA. Preliminary pharmacokinetic study of the anticancer 6BIO in mice using an UHPLC-MS/MS approach. J Pharm Biomed Anal. 2019 Feb 5;164:317-325. doi: 10.1016/j.jpba.2018.10.039. Epub 2018 Oct 25. PubMed PMID: 30412805.
5: Lee MY, Li YZ, Huang KJ, Huang HC, Lin CY, Lee YR. Indirubin-3'-oxime suppresses human cholangiocarcinoma through cell-cycle arrest and apoptosis. Eur J Pharmacol. 2018 Nov 15;839:57-65. doi: 10.1016/j.ejphar.2018.09.023. Epub 2018 Sep 27. PubMed PMID: 30267650.
6: Chan MC, Chan RW, Mok CK, Mak NK, Wong RN. Indirubin-3'-oxime as an antiviral and immunomodulatory agent in treatment of severe human influenza virus infection. Hong Kong Med J. 2018 Oct;24 Suppl 6(5):45-47. PubMed PMID: 30229739.
7: Otten C, Knox J, Boulday G, Eymery M, Haniszewski M, Neuenschwander M, Radetzki S, Vogt I, Hähn K, De Luca C, Cardoso C, Hamad S, Igual Gil C, Roy P, Albiges-Rizo C, Faurobert E, von Kries JP, Campillos M, Tournier-Lasserve E, Derry WB, Abdelilah-Seyfried S. Systematic pharmacological screens uncover novel pathways involved in cerebral cavernous malformations. EMBO Mol Med. 2018 Oct;10(10). pii: e9155. doi: 10.15252/emmm.201809155. PubMed PMID: 30181117; PubMed Central PMCID: PMC6180302.
8: Tanaka T, Kasai M, Kobayashi S. Mechanism responsible for inhibitory effect of indirubin 3'-oxime on anticancer agent-induced YB-1 nuclear translocation in HepG2 human hepatocellular carcinoma cells. Exp Cell Res. 2018 Sep 15;370(2):454-460. doi: 10.1016/j.yexcr.2018.07.009. Epub 2018 Jul 5. PubMed PMID: 29981748.
9: Uhrin P, Wang D, Mocan A, Waltenberger B, Breuss JM, Tewari D, Mihaly-Bison J, Huminiecki Ł, Starzyński RR, Tzvetkov NT, Horbańczuk J, Atanasov AG. Vascular smooth muscle cell proliferation as a therapeutic target. Part 2: Natural products inhibiting proliferation. Biotechnol Adv. 2018 Nov 1;36(6):1608-1621. doi: 10.1016/j.biotechadv.2018.04.002. Epub 2018 Apr 17. Review. PubMed PMID: 29678389.
10: Teodoro JS, Varela AT, Duarte FV, Gomes AP, Palmeira CM, Rolo AP. Indirubin and NAD(+) prevent mitochondrial ischaemia/reperfusion damage in fatty livers. Eur J Clin Invest. 2018 Jun;48(6):e12932. doi: 10.1111/eci.12932. Epub 2018 Apr 16. PubMed PMID: 29603199.
11: Liu C, Jiang P, Xu Y, Zheng M, Qiao J, Zhou X, Huang D, Bian M. Inhibition of Suicidal Erythrocyte Death by Indirubin-3'-Monoxime. Cell Physiol Biochem. 2018;45(3):1108-1120. doi: 10.1159/000487352. Epub 2018 Feb 7. PubMed PMID: 29439254.
12: Tanaka T, Ohashi S, Saito H, Wada T, Aoyama T, Ichimaru Y, Miyairi S, Kobayashi S. Indirubin 3'-oxime inhibits anticancer agent-induced YB-1 nuclear translocation in HepG2 human hepatocellular carcinoma cells. Biochem Biophys Res Commun. 2018 Jan 29;496(1):7-11. doi: 10.1016/j.bbrc.2017.12.106. Epub 2017 Dec 21. PubMed PMID: 29274785.
13: Liu K, Li J, Wu X, Chen M, Luo F, Li J. GSK-3β inhibitor 6-bromo-indirubin-3'-oxime promotes both adhesive activity and drug resistance in colorectal cancer cells. Int J Oncol. 2017 Dec;51(6):1821-1830. doi: 10.3892/ijo.2017.4163. Epub 2017 Oct 16. PubMed PMID: 29039496.
14: Sklirou AD, Gaboriaud-Kolar N, Papassideri I, Skaltsounis AL, Trougakos IP. 6-bromo-indirubin-3'-oxime (6BIO), a Glycogen synthase kinase-3β inhibitor, activates cytoprotective cellular modules and suppresses cellular senescence-mediated biomolecular damage in human fibroblasts. Sci Rep. 2017 Sep 15;7(1):11713. doi: 10.1038/s41598-017-11662-7. PubMed PMID: 28916781; PubMed Central PMCID: PMC5601901.
15: Medina-Moreno S, Dowling TC, Zapata JC, Le NM, Sausville E, Bryant J, Redfield RR, Heredia A. Targeting of CDK9 with indirubin 3'-monoxime safely and durably reduces HIV viremia in chronically infected humanized mice. PLoS One. 2017 Aug 17;12(8):e0183425. doi: 10.1371/journal.pone.0183425. eCollection 2017. PubMed PMID: 28817720; PubMed Central PMCID: PMC5560554.
16: Ichimaru Y, Fujii T, Saito H, Sano M, Uchiyama T, Miyairi S. 5-Bromoindirubin 3'-(O-oxiran-2-ylmethyl)oxime: A long-acting anticancer agent and a suicide inhibitor for epoxide hydrolase. Bioorg Med Chem. 2017 Sep 1;25(17):4665-4676. doi: 10.1016/j.bmc.2017.07.009. Epub 2017 Jul 8. PubMed PMID: 28743492.
17: Minges A, Groth G. Small-molecule inhibition of pyruvate phosphate dikinase targeting the nucleotide binding site. PLoS One. 2017 Jul 10;12(7):e0181139. doi: 10.1371/journal.pone.0181139. eCollection 2017. PubMed PMID: 28700696; PubMed Central PMCID: PMC5507339.
18: Sano M, Ichimaru Y, Kurita M, Hayashi E, Homma T, Saito H, Masuda S, Nemoto N, Hemmi A, Suzuki T, Miyairi S, Hao H. Induction of cell death in pancreatic ductal adenocarcinoma by indirubin 3'-oxime and 5-methoxyindirubin 3'-oxime in vitro and in vivo. Cancer Lett. 2017 Jul 1;397:72-82. doi: 10.1016/j.canlet.2017.03.031. Epub 2017 Mar 24. PubMed PMID: 28347789.
19: Zhang X, Castanotto D, Nam S, Horne D, Stein C. 6BIO Enhances Oligonucleotide Activity in Cells: A Potential Combinatorial Anti-androgen Receptor Therapy in Prostate Cancer Cells. Mol Ther. 2017 Jan 4;25(1):79-91. doi: 10.1016/j.ymthe.2016.10.017. Epub 2017 Jan 4. PubMed PMID: 28129131; PubMed Central PMCID: PMC5363309.
20: Vilar S, Quezada E, Uriarte E, Costanzi S, Borges F, Viña D, Hripcsak G. Computational Drug Target Screening
Chemical Structure
