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

MedKoo CAT#: 206023

CAS#: 479-41-4

Description: Indirubin is a potent and selective CDK inhibitor. Indirubin is the active ingredient of Danggui Longhui Wan, a mixture of plants that is used in traditional Chinese medicine to treat chronic diseases. Indirubin has been used to treat the symptoms of leukemia. Further biological explorations revealed the ability of indirubin to bind cyclin-dependent kinases and 6-bromoindirubin, extracted from mollusks, to bind glycogen synthase kinase-3. Studies have shown that Indirubin can help keep cancer cells from reproducing in rats. Indirubin also appears to reduce inflammation by inhibiting part of the immune response.


Price and Availability

Size
Price

25mg
USD 360
Size
Price

Size
Price

Indirubin, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 206023
Name: Indirubin
CAS#: 479-41-4
Chemical Formula: C16H10N2O2
Exact Mass: 262.07423
Molecular Weight: 262.2628
Elemental Analysis: C, 73.27; H, 3.84; N, 10.68; O, 12.20


Synonym: Indirubin; C.I. 73200, Couroupitine B, Indigo red, Indigopurpurin, NSC 105327; NSC-105327; NSC105327.

IUPAC/Chemical Name: 3-(1,3-Dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-2H-indol-2-one

InChi Key: CRDNMYFJWFXOCH-YPKPFQOOSA-N

InChi Code: InChI=1S/C16H10N2O2/c19-15-10-6-2-4-8-12(10)17-14(15)13-9-5-1-3-7-11(9)18-16(13)20/h1-8,17H,(H,18,20)/b14-13-

SMILES Code: O=C1NC2=C(C=CC=C2)/C1=C3NC4=C(C=CC=C4)C/3=O


Technical Data

Appearance:
Red 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, not soluble in water.

Shelf Life:
>5 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).

Harmonized System Code:
293490


Additional Information

  
 
 
 


References

1: Park MH, Lee YY, Cho KH, La S, Lee HJ, Yim DS, Ban S, Park MY, Kim YC, Kim YG, Shin YG. Validation of a liquid chromatography-triple quadrupole mass spectrometric method for the determination of 5-Nitro-5'-Hydroxy-Indirubin-3'-Oxime (AGM-130) in human plasma and its application to microdose clinical trial. Biomed Chromatogr. 2015 Jul 2. doi: 10.1002/bmc.3551. [Epub ahead of print] PubMed PMID: 26139072.

2: Hu Z, Tu Y, Xia Y, Cheng P, Sun W, Shi Y, Guo L, He H, Xiong C, Chen S, Zhang X. Rapid Identification and Verification of Indirubin-Containing Medicinal Plants. Evid Based Complement Alternat Med. 2015;2015:484670. doi: 10.1155/2015/484670. Epub 2015 May 18. PubMed PMID: 26089942; PubMed Central PMCID: PMC4451998.

3: Yan L, Lai F, Chen X, Xiao Z. Discovery of novel indirubin-3'-monoxime derivatives as potent inhibitors against CDK2 and CDK9. Bioorg Med Chem Lett. 2015 Jun 1;25(11):2447-51. doi: 10.1016/j.bmcl.2015.03.066. Epub 2015 Mar 31. PubMed PMID: 25908517.

4: Gaboriaud-Kolar N, Vougogiannopoulou K, Skaltsounis AL. Indirubin derivatives: a patent review (2010 - present). Expert Opin Ther Pat. 2015 May;25(5):583-93. doi: 10.1517/13543776.2015.1019865. PubMed PMID: 25887337.

5: Ameria SP, Jung HS, Kim HS, Han SS, Kim HS, Lee JH. Characterization of a flavin-containing monooxygenase from Corynebacterium glutamicum and its application to production of indigo and indirubin. Biotechnol Lett. 2015 Aug;37(8):1637-44. doi: 10.1007/s10529-015-1824-2. Epub 2015 Apr 8. PubMed PMID: 25851950.

6: Wang L, Li X, Liu X, Lu K, Chen NA, Li P, Lv X, Wang X. Enhancing effects of indirubin on the arsenic disulfide-induced apoptosis of human diffuse large B-cell lymphoma cells. Oncol Lett. 2015 Apr;9(4):1940-1946. Epub 2015 Feb 9. PubMed PMID: 25789073; PubMed Central PMCID: PMC4356417.

7: Song JH, Lee JE, Cho KM, Park SH, Kim HJ, Kim YC, Kim TS. 5-diphenylacetamido-indirubin-3'-oxime as a novel mitochondria-targeting agent with anti-leukemic activities. Mol Carcinog. 2015 Mar 18. doi: 10.1002/mc.22307. [Epub ahead of print] PubMed PMID: 25788004.

8: Wongsaroj L, Sallabhan R, Dubbs JM, Mongkolsuk S, Loprasert S. Cloning of Toluene 4-Monooxygenase Genes and Application of Two-Phase System to the Production of the Anticancer Agent, Indirubin. Mol Biotechnol. 2015 Mar 18. [Epub ahead of print] PubMed PMID: 25779640.

9: Ichimaru Y, Saito H, Uchiyama T, Metori K, Tabata K, Suzuki T, Miyairi S. Indirubin 3'-(O-oxiran-2-ylmethyl)oxime: a novel anticancer agent. Bioorg Med Chem Lett. 2015 Apr 1;25(7):1403-6. doi: 10.1016/j.bmcl.2015.02.053. Epub 2015 Feb 28. PubMed PMID: 25765906.

10: Gao X, Zhou Y, Wu KX, Ding YH, Fan DM, Yang M, Zhang YZ, Zhang YJ, Xiong DS. Inhibitory effects of indirubin derivative PHII-7 on invasion and migration in metastatic cancer. Neoplasma. 2015;62(2):209-29. doi: 10.4149/neo_2015_026. PubMed PMID: 25591586.

11: Lee JJ, Han JH, Jung SH, Lee SG, Kim IS, Cuong NM, Huong TT, Khanh PN, Kim YH, Yun YP, Ma JY, Myung CS. Antiplatelet action of indirubin-3'-monoxime through suppression of glycoprotein VI-mediated signal transduction: a possible role for ERK signaling in platelets. Vascul Pharmacol. 2014 Dec;63(3):182-92. doi: 10.1016/j.vph.2014.10.005. Epub 2014 Nov 5. PubMed PMID: 25451564.

12: Jung DW, Hong YJ, Kim SY, Kim WH, Seo S, Lee JE, Shen H, Kim YC, Williams DR. 5-Nitro-5'hydroxy-indirubin-3'oxime is a novel inducer of somatic cell transdifferentiation. Arch Pharm (Weinheim). 2014 Nov;347(11):806-18. doi: 10.1002/ardp.201400223. Epub 2014 Sep 2. PubMed PMID: 25363410.

13: Sharma S, Taliyan R. Neuroprotective role of Indirubin-3'-monoxime, a GSKβ inhibitor in high fat diet induced cognitive impairment in mice. Biochem Biophys Res Commun. 2014 Oct 3;452(4):1009-15. doi: 10.1016/j.bbrc.2014.09.034. Epub 2014 Sep 16. PubMed PMID: 25234596.

14: Braig S, Bischoff F, Abhari BA, Meijer L, Fulda S, Skaltsounis L, Vollmar AM. The pleiotropic profile of the indirubin derivative 6BIO overcomes TRAIL resistance in cancer. Biochem Pharmacol. 2014 Sep 15;91(2):157-67. doi: 10.1016/j.bcp.2014.07.009. Epub 2014 Jul 25. PubMed PMID: 25069048.

15: Tanaka T, Ohashi S, Saito H, Higuchi T, Tabata K, Kosuge Y, Suzuki T, Miyairi S, Kobayashi S. Indirubin derivatives alter DNA binding activity of the transcription factor NF-Y and inhibit MDR1 gene promoter. Eur J Pharmacol. 2014 Oct 15;741:83-9. doi: 10.1016/j.ejphar.2014.07.035. Epub 2014 Jul 24. PubMed PMID: 25066113.

16: Huang M, Lin HS, Lee YS, Ho PC. Evaluation of meisoindigo, an indirubin derivative: in vitro antileukemic activity and in vivo pharmacokinetics. Int J Oncol. 2014 Oct;45(4):1724-34. doi: 10.3892/ijo.2014.2548. Epub 2014 Jul 21. PubMed PMID: 25050545.

17: Heshmati N, Cheng X, Dapat E, Sassene P, Eisenbrand G, Fricker G, Müllertz A. In vitro and in vivo evaluations of the performance of an indirubin derivative, formulated in four different self-emulsifying drug delivery systems. J Pharm Pharmacol. 2014 Nov;66(11):1567-75. doi: 10.1111/jphp.12286. Epub 2014 Jun 24. PubMed PMID: 24961657.

18: Efstathiou A, Gaboriaud-Kolar N, Smirlis D, Myrianthopoulos V, Vougogiannopoulou K, Alexandratos A, Kritsanida M, Mikros E, Soteriadou K, Skaltsounis AL. An inhibitor-driven study for enhancing the selectivity of indirubin derivatives towards leishmanial Glycogen Synthase Kinase-3 over leishmanial cdc2-related protein kinase 3. Parasit Vectors. 2014 May 20;7:234. doi: 10.1186/1756-3305-7-234. PubMed PMID: 24886176; PubMed Central PMCID: PMC4039064.

19: Zahoor M, Cha PH, Choi KY. Indirubin-3'-oxime, an activator of Wnt/β-catenin signaling, enhances osteogenic commitment of ST2 cells and restores bone loss in high-fat diet-induced obese male mice. Bone. 2014 Aug;65:60-8. doi: 10.1016/j.bone.2014.05.003. Epub 2014 May 9. PubMed PMID: 24815917.

20: Mok CK, Kang SS, Chan RW, Yue PY, Mak NK, Poon LL, Wong RN, Peiris JS, Chan MC. Anti-inflammatory and antiviral effects of indirubin derivatives in influenza A (H5N1) virus infected primary human peripheral blood-derived macrophages and alveolar epithelial cells. Antiviral Res. 2014 Jun;106:95-104. doi: 10.1016/j.antiviral.2014.03.019. Epub 2014 Apr 6. PubMed PMID: 24717263.