Indirubin | CAS#479-41-4 | MedKoo Biosciences

MedKoo Cat#: 206023 | Name: Indirubin

Featured

Description:

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

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.

Chemical Structure

Indirubin

CAS#479-41-4

Theoretical Analysis

MedKoo Cat#: 206023

Name: Indirubin

CAS#: 479-41-4

Chemical Formula: C16H10N2O2

Exact Mass: 262.0742

Molecular Weight: 262.26

Elemental Analysis: C, 73.27; H, 3.84; N, 10.68; O, 12.20

Price and Availability

Size	Price	Availability
25mg	USD 350.00	2 Weeks
50mg	USD 600.00	2 Weeks
100mg	USD 950.00	2 Weeks
250mg	USD 1,650.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

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

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).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Indirubin (Couroupitine B) is a bis-indole alkaloid and has remarkable anticancer activity against chronic myelocytic leukemia.

In vitro activity:

The effects Indirubin of the migration potential of the U87 and U118 glioma cells was assessed by wound heal assay. The results showed that the treatment of U87 and U118 cells with Indirubin for 24 h caused reduction in the migration of these cells as evident from the wound width (Fig. 5). Reference: AMB Express. 2020 Sep 25;10(1):171. https://pubmed.ncbi.nlm.nih.gov/32975633/

In vivo activity:

Consistently, this study also determined the hydroxyproline content in the lung homogenates, a marker correlated with fibrosis severity, and found that indirubin treatment significantly attenuated the levels of hydroxyproline in the lung following BLM injection (Fig. 2F). Furthermore, the survival condition of mice was monitored during the course of 14 days. Interestingly, the survival rate of the bleomycin-treated mice at day 14 was significantly lower than that of the control mice and the indirubin-treated mice (Fig. 2G). Taken together, these results indicate that indirubin effectively alleviates BLM-induced lung injury and fibrosis in mice. Reference: Biomed Pharmacother. 2020 Nov;131:110715. https://pubmed.ncbi.nlm.nih.gov/32927253/

	Solvent	mg/mL	mM
Solubility
	DMSO	19.3	73.72

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 262.26 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. Li Z, Wang H, Wei J, Han L, Guo Z. Indirubin exerts anticancer effects on human glioma cells by inducing apoptosis and autophagy. AMB Express. 2020 Sep 25;10(1):171. doi: 10.1186/s13568-020-01107-2. PMID: 32975633; PMCID: PMC7519025. 2. Liu SG, Luo GP, Qu YB, Chen YF. Indirubin inhibits Wnt/β-catenin signal pathway via promoter demethylation of WIF-1. BMC Complement Med Ther. 2020 Aug 14;20(1):250. doi: 10.1186/s12906-020-03045-9. PMID: 32795328; PMCID: PMC7427955. 3. Wang Q, Yu J, Hu Y, Chen X, Zhang L, Pan T, Miao K, Mou Y, Xu Y, Xiong W, Wang Y. Indirubin alleviates bleomycin-induced pulmonary fibrosis in mice by suppressing fibroblast to myofibroblast differentiation. Biomed Pharmacother. 2020 Nov;131:110715. doi: 10.1016/j.biopha.2020.110715. Epub 2020 Sep 11. PMID: 32927253. 4. Wei G, Sun H, Liu JL, Dong K, Liu J, Zhang M. Indirubin, a small molecular deriving from connectivity map (CMAP) screening, ameliorates obesity-induced metabolic dysfunction by enhancing brown adipose thermogenesis and white adipose browning. Nutr Metab (Lond). 2020 Mar 16;17:21. doi: 10.1186/s12986-020-00440-4. PMID: 32190098; PMCID: PMC7076951.

In vitro protocol:

In vivo protocol:

1. Wang Q, Yu J, Hu Y, Chen X, Zhang L, Pan T, Miao K, Mou Y, Xu Y, Xiong W, Wang Y. Indirubin alleviates bleomycin-induced pulmonary fibrosis in mice by suppressing fibroblast to myofibroblast differentiation. Biomed Pharmacother. 2020 Nov;131:110715. doi: 10.1016/j.biopha.2020.110715. Epub 2020 Sep 11. PMID: 32927253. 2. Wei G, Sun H, Liu JL, Dong K, Liu J, Zhang M. Indirubin, a small molecular deriving from connectivity map (CMAP) screening, ameliorates obesity-induced metabolic dysfunction by enhancing brown adipose thermogenesis and white adipose browning. Nutr Metab (Lond). 2020 Mar 16;17:21. doi: 10.1186/s12986-020-00440-4. PMID: 32190098; PMCID: PMC7076951.

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.