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MedKoo Cat#: 555618 | Name: Indirubin-3’-oxime
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Description:

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

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.

Chemical Structure

Indirubin-3’-oxime
Indirubin-3’-oxime
CAS#160807-49-8

Theoretical Analysis

MedKoo Cat#: 555618

Name: Indirubin-3’-oxime

CAS#: 160807-49-8

Chemical Formula: C16H11N3O2

Exact Mass: 277.0851

Molecular Weight: 277.28

Elemental Analysis: C, 69.31; H, 4.00; N, 15.15; O, 11.54

Price and Availability

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5mg USD 300.00 2 Weeks
10mg USD 550.00 2 Weeks
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Related CAS #
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Synonym
Indirubin-3’-oxime
IUPAC/Chemical Name
3-[1,3-dihydro-3-(hydroxyimino)-2H-indol-2-ylidene]-1,3-dihydro-2H-indol-2-one
InChi Key
HBDSHCUSXQATPO-BRNLPKLHSA-N
InChi Code
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-
SMILES Code
O=C1NC2=C(C=CC=C2)/C1=C3NC4=C(C=CC=C4)C/3=N/O
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
>3 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
Instruction
View handling instruction
Biological target:
Indirubin-3'-monoxime is a potent GSK-3β inhibitor, and weakly inhibits 5-Lipoxygenase, with IC50s of 22 nM and 7.8-10 µM, respectively; Indirubin-3'-monoxime also shows inhibitory activities against CDK5/p25 and CDK1/cyclin B, with IC50s of 100 and 180 nM.
In vitro activity:
The antibacterial activity results demonstrated that the synthesized indirubin-3'-monoximes 5a-5z and 5aa-5ad displayed good potency against S. aureus ATCC25923 (MIC = 0.4-25.6 μg mL-1). Reference: RSC Adv. 2022 Sep 2;12(38):25068-25080. https://pubmed.ncbi.nlm.nih.gov/36199871/
In vivo activity:
Xenograft-positive zebrafish embryos were divided randomly and treated with (a) DMSO (control group), (b) BTZ (10 nM), (c) I3MO (5 μM), and (d) I3MO/BTZ combination (10 nM and 5 μM, respectively). The tumor load was examined by quantification of Calcein-AM (green) positive areas in zebrafish, and compared in different groups after 24 h treatment. As Figure 3c–e showed, either monotherapy or combination therapy of I3MO eliminates the engraftment of MM cells in zebrafish embryos (P<0.05, t test). Reference: EBioMedicine. 2022 Apr;78:103950. https://pubmed.ncbi.nlm.nih.gov/35344764/
Solvent mg/mL mM
Solubility
DMF 10.0 36.06
DMSO 32.4 116.97
DMSO:PBS (pH 7.2) (1:5) 0.2 0.54
Ethanol 14.9 53.61
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 277.28 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.

Recalculate based on batch purity %
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. Yang FF, Shuai MS, Guan X, Zhang M, Zhang QQ, Fu XZ, Li ZQ, Wang DP, Zhou M, Yang YY, Liu T, He B, Zhao YL. Synthesis and antibacterial activity studies in vitro of indirubin-3'-monoximes. RSC Adv. 2022 Sep 2;12(38):25068-25080. doi: 10.1039/d2ra01035f. PMID: 36199871; PMCID: PMC9438470. 2. Choi S, Cha PH, Kim HY, Choi KY. Indirubin-3'-oxime stimulates chondrocyte maturation and longitudinal bone growth via activation of the Wnt/β-catenin pathway. Exp Mol Med. 2019 Sep 12;51(9):1-10. doi: 10.1038/s12276-019-0306-3. PMID: 31515471; PMCID: PMC6802626. 3. Yu Z, Wei X, Liu L, Sun H, Fang T, Wang L, Li Y, Sui W, Wang K, He Y, Zhao Y, Huang W, An G, Meng F, Huang C, Yu T, Anderson KC, Cheng T, Qiu L, Hao M. Indirubin-3'-monoxime acts as proteasome inhibitor: Therapeutic application in multiple myeloma. EBioMedicine. 2022 Apr;78:103950. doi: 10.1016/j.ebiom.2022.103950. Epub 2022 Mar 26. PMID: 35344764; PMCID: PMC8958548. 4. Ichimaru Y, Sano M, Kajiwara I, Tobe T, Yoshioka H, Hayashi K, Ijichi H, Miyairi S. Indirubin 3'-Oxime Inhibits Migration, Invasion, and Metastasis InVivo in Mice Bearing Spontaneously Occurring Pancreatic Cancer via Blocking the RAF/ERK, AKT, and SAPK/JNK Pathways. Transl Oncol. 2019 Dec;12(12):1574-1582. doi: 10.1016/j.tranon.2019.08.010. Epub 2019 Oct 28. PMID: 31671317; PMCID: PMC6835019.
In vitro protocol:
1. Yang FF, Shuai MS, Guan X, Zhang M, Zhang QQ, Fu XZ, Li ZQ, Wang DP, Zhou M, Yang YY, Liu T, He B, Zhao YL. Synthesis and antibacterial activity studies in vitro of indirubin-3'-monoximes. RSC Adv. 2022 Sep 2;12(38):25068-25080. doi: 10.1039/d2ra01035f. PMID: 36199871; PMCID: PMC9438470. 2. Choi S, Cha PH, Kim HY, Choi KY. Indirubin-3'-oxime stimulates chondrocyte maturation and longitudinal bone growth via activation of the Wnt/β-catenin pathway. Exp Mol Med. 2019 Sep 12;51(9):1-10. doi: 10.1038/s12276-019-0306-3. PMID: 31515471; PMCID: PMC6802626.
In vivo protocol:
1. Yu Z, Wei X, Liu L, Sun H, Fang T, Wang L, Li Y, Sui W, Wang K, He Y, Zhao Y, Huang W, An G, Meng F, Huang C, Yu T, Anderson KC, Cheng T, Qiu L, Hao M. Indirubin-3'-monoxime acts as proteasome inhibitor: Therapeutic application in multiple myeloma. EBioMedicine. 2022 Apr;78:103950. doi: 10.1016/j.ebiom.2022.103950. Epub 2022 Mar 26. PMID: 35344764; PMCID: PMC8958548. 2. Ichimaru Y, Sano M, Kajiwara I, Tobe T, Yoshioka H, Hayashi K, Ijichi H, Miyairi S. Indirubin 3'-Oxime Inhibits Migration, Invasion, and Metastasis InVivo in Mice Bearing Spontaneously Occurring Pancreatic Cancer via Blocking the RAF/ERK, AKT, and SAPK/JNK Pathways. Transl Oncol. 2019 Dec;12(12):1574-1582. doi: 10.1016/j.tranon.2019.08.010. Epub 2019 Oct 28. PMID: 31671317; PMCID: PMC6835019.
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 through Protein Interaction Profiles. Sci Rep. 2016 Nov 15;6:36969. doi: 10.1038/srep36969. PubMed PMID: 27845365; PubMed Central PMCID: PMC5109486.

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