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479-41-4

479-41-4 structure
479-41-4 structure
  • Name: Indirubin
  • Chemical Name: Indirubin
  • CAS Number: 479-41-4
  • Molecular Formula: C16H10N2O2
  • Molecular Weight: 262.263
  • Catalog: API Antineoplastic agents Natural source antineoplastic agents
  • Create Date: 2018-04-14 08:00:00
  • Modify Date: 2024-01-02 22:38:37
  • Indirubin(Couroupitine B) is a purple 3,2- bisindole and a stable isomer of indigo isolated from Indigo naturalis (Apiaceae); anti-inflammatory and anticancer activities.IC50 value:Target:in vitro: The activation of EGF receptor, known to be highly expressed in psoriatic lesions, was inhibited by indigo naturalis or indirubin. The cell proliferation and CDC25B expression of epidermal keratinocytes were induced by EGF alone and confirmed to be inhibited by indigo naturalis or indirubin [2]. indirubin inhibited prostate tumor growth through inhibiting tumor angiogenesis. indirubin inhibited angiogenesis in vivo. We also showed the inhibition activity of indirubin in endothelial cell migration, tube formation and cell survival in vitro [3].in vivo: Indirubin treatment suppressed skin inflammation in DNCB-exposed mice. The skin lesions were significantly thinner in the Indirubin-treated group than in untreated controls, and the hyperkeratosis disappeared. Indirubin reduced the total serum IgE level and cytokines production. In addition, it normalized NF-κB, IκB-α and MAP kinase expression [1]. Indirubin dose-dependently inhibited intersegmental vessel formation in zebrafish embryos. It also inhibited HUVEC proliferation by the induction of cellular apoptosis and cell-cycle arrest at the G0/G1 phase [4].
Name Indirubin
Synonyms Indirubin
(3Z)-3-(3-Oxo-1,3-dihydro-2H-indol-2-ylidene)-1,3-dihydro-2H-indol-2-one
Indigo Red
2-ylidene)-1,3-dihydro
COUROUPITINE B
[2,3'-Biindolinylidene]-2',3-dione
MFCD00221745
INDIGOPURPURIN
2H-Indol-2-one, 3-(1,3-dihydro-3-oxo-2H-indol-2-ylidene)-1,3-dihydro-, (3Z)-
Description Indirubin(Couroupitine B) is a purple 3,2- bisindole and a stable isomer of indigo isolated from Indigo naturalis (Apiaceae); anti-inflammatory and anticancer activities.IC50 value:Target:in vitro: The activation of EGF receptor, known to be highly expressed in psoriatic lesions, was inhibited by indigo naturalis or indirubin. The cell proliferation and CDC25B expression of epidermal keratinocytes were induced by EGF alone and confirmed to be inhibited by indigo naturalis or indirubin [2]. indirubin inhibited prostate tumor growth through inhibiting tumor angiogenesis. indirubin inhibited angiogenesis in vivo. We also showed the inhibition activity of indirubin in endothelial cell migration, tube formation and cell survival in vitro [3].in vivo: Indirubin treatment suppressed skin inflammation in DNCB-exposed mice. The skin lesions were significantly thinner in the Indirubin-treated group than in untreated controls, and the hyperkeratosis disappeared. Indirubin reduced the total serum IgE level and cytokines production. In addition, it normalized NF-κB, IκB-α and MAP kinase expression [1]. Indirubin dose-dependently inhibited intersegmental vessel formation in zebrafish embryos. It also inhibited HUVEC proliferation by the induction of cellular apoptosis and cell-cycle arrest at the G0/G1 phase [4].
Related Catalog
References

[1]. Kim MH, et al. Indirubin, a purple 3,2- bisindole, inhibited allergic contact dermatitis via regulating T helper (Th)-mediated immune system in DNCB-induced model. J Ethnopharmacol. 2013 Jan 9;145(1):214-9.

[2]. Hsieh WL, et al. Indirubin, an acting component of indigo naturalis, inhibits EGFR activation and EGF-induced CDC25B gene expression in epidermal keratinocytes. J Dermatol Sci. 2012 Aug;67(2):140-6.

[3]. Zhang X, et al. Indirubin inhibits tumor growth by antitumor angiogenesis via blocking VEGFR2-mediated JAK/STAT3 signaling in endothelial cell. Int J Cancer. 2011 Nov 15;129(10):2502-11.

[4]. Alex D, et al. Indirubin shows anti-angiogenic activity in an in vivo zebrafish model and an in vitro HUVEC model. J Ethnopharmacol. 2010 Sep 15;131(2):242-7.
Density 1.4±0.1 g/cm3
Boiling Point 496.6±45.0 °C at 760 mmHg
Melting Point 350 °C
Molecular Formula C16H10N2O2
Molecular Weight 262.263
Flash Point 207.0±28.9 °C
Exact Mass 262.074219
PSA 58.20000
LogP 2.48
Vapour Pressure 0.0±1.3 mmHg at 25°C
Index of Refraction 1.709

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DU2995000
CHEMICAL NAME :
(delta(sup 2,3')-Biindoline)-2',3-dione
CAS REGISTRY NUMBER :
479-41-4
BEILSTEIN REFERENCE NO. :
0088279
LAST UPDATED :
199612
DATA ITEMS CITED :
3
MOLECULAR FORMULA :
C16-H10-N2-O2
MOLECULAR WEIGHT :
262.28

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
10 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
CTYAD8 Zhongcaoyao. Chinese Traditional and Herbal Medicine. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.11- 1980- Volume(issue)/page/year: 13,24,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1100 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 9,266,1984 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
36400 mg/kg/26W-I
TOXIC EFFECTS :
Gastrointestinal - hypermotility, diarrhea Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Related to Chronic Data - death
REFERENCE :
CTYAD8 Zhongcaoyao. Chinese Traditional and Herbal Medicine. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.11- 1980- Volume(issue)/page/year: 12,75,1981
Hazard Codes N
Risk Phrases R20/21/22
Safety Phrases S36/37
HS Code 2933990090
HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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title: CAS No. 479-41-4 | Chemsrc address: https://www.chemsrc.com/en/baike/314514.html

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