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Chemical Structure| 479-41-4 Chemical Structure| 479-41-4

Structure of Indirubin
CAS No.: 479-41-4

Chemical Structure| 479-41-4

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CAS No.: 479-41-4

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Indirubin is a purple 3,2- bisindole and a stable isomer of indigo isolated from Indigo naturalis (Apiaceae) with anti-inflammatory and anticancer activities.

Synonyms: Couroupitine B; Indigo red; C.I. 73200, Couroupitine B, Indigo red, Indigopurpurin, NSC 105327

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Product Citations

Product Citations

Shriver, James A. ; Kaller, Kaylie S. ; Kinsey, Ally L. ; Wang, Katelyn R. ; Sterrenberg, Summer R. ; Van Vors, Madison K. , et al.

Abstract: The spontaneous conversion of 3-indoxyl to indigo was a well-established process used to produce indigo dyes. It was recently shown that some indoles, when reacted with molybdenum hexacarbonyl and cumyl peroxide, proceed through an indoxyl intermediate to produce significant amounts of indirubin through a competing mechanism. Modulation of this system to lower temperatures allows for careful tuning, leading to selective production of indirubins in a general process. A systematic assay of indoles show that electron deficient indoles work well when substituted at the 5 and 7 positions. In contrast, 6-substituted electron rich indoles give the best results whereas halogeno indoles work well in all cases. This process shows broad functional group tolerance for generally reactive carbonyl-containing compounds such as aldehydes and carboxylic acids.

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Product Details of Indirubin

CAS No. :479-41-4
Formula : C16H10N2O2
M.W : 262.26
SMILES Code : O=C1NC2=C(C=CC=C2)/C1=C3NC4=C(C=CC=C4)C\3=O
Synonyms :
Couroupitine B; Indigo red; C.I. 73200, Couroupitine B, Indigo red, Indigopurpurin, NSC 105327
MDL No. :MFCD00221745
InChI Key :JNLNPCNGMHKCKO-UHFFFAOYSA-N
Pubchem ID :10177

Safety of Indirubin

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P261-P305+P351+P338

Isoform Comparison

Biological Activity

Target

  • GSK-3β

    GSK-3β, IC50:0.6 μM

In Vitro:

Cell Line
Concentration Treated Time Description References
U87 glioma cells 5 μmol/L 48 hours Indirubin significantly inhibited the migration of U87 glioma cells, with complete inhibition at 5 μmol/L PMC4288480
GBM9 glioblastoma-derived neurosphere-initiating cells 5 μmol/L 48 hours Indirubin significantly inhibited the migration of GBM9 glioblastoma-derived neurosphere-initiating cells PMC4288480
U251 glioma cells 0.5 μmol/L 1 hour Indirubin significantly inhibited the migration of U251 glioma cells, with migration reduced to 48.7% at 0.5 μmol/L PMC4288480
U251 cells 1 μM 24 hours To investigate the effect of BiA on IDO1 expression, results showed that BiA almost completely suppressed IFNγ-induced IDO1 protein expression at a concentration of 1 μM. PMC10213750
HCMEC/D3 1 μM 24 hours To investigate the transcriptional alterations associated with BIA treatment of brain endothelium, results showed that BIA significantly down-regulated CDH5 gene expression and affected genes related to cell migration, angiogenesis, and endothelial proliferation. PMC11864199
HCMEC/D3 100 nM to 10 μM 24 hours To investigate the effects of BIA on brain endothelial cell barrier integrity, results showed that BIA significantly reduced barrier integrity. PMC11864199
NB4 cells 0.75 μM To investigate the effect of Indirubin alone or in combination with A and T on the differentiation of NB4 cells, results showed that Indirubin alone did not induce cell differentiation, but its combination with A and T significantly enhanced cell differentiation PMC2290784
NB4-R2 cells 0.75 μM To investigate the effect of Indirubin in combination with A and T on the differentiation of ATRA-resistant NB4-R2 cells, results showed that the combination significantly enhanced cell differentiation PMC2290784
Primary APL cells 0.75 μM To investigate the effect of Indirubin in combination with A and T on the differentiation of primary APL cells, results showed that the combination significantly enhanced cell differentiation PMC2290784

In Vivo:

Species
Animal Model
Administration Dosage Frequency Description References
nude mice GBM9 glioma intracranial xenograft model intraperitoneal injection 4 mg/kg/day Once daily for 4 weeks Indirubin significantly reduced intracranial invasion of GBM9 glioma cells and improved animal survival PMC4288480
mice GL261 and CT2A glioblastoma models intravenous injection 1 μM Single dose, observed for 96 hours To investigate the effect of PPRX-1701 on glioblastoma models, results showed that PPRX-1701 significantly prolonged the survival of GL261 model mice and reduced tumor volume. PMC10213750
Mice GBM xenograft model Intraperitoneal injection 20 mg/kg 3 times per week for 2 weeks To investigate the effects of BIA on drug accumulation in GBM tumor models, results showed that BIA significantly increased intratumoral cisplatin accumulation. PMC11864199
FVB/NJ mice APL mouse model Oral 20 mg/kg Single injection To investigate the therapeutic effect of Indirubin in combination with A and T on the APL mouse model, results showed that the combination significantly prolonged the survival of mice and induced cell differentiation PMC2290784

Protocol

Bio Calculators
Preparing Stock Solutions 1mg 5mg 10mg

1 mM

5 mM

10 mM

3.81mL

0.76mL

0.38mL

19.07mL

3.81mL

1.91mL

38.13mL

7.63mL

3.81mL
Dissolving Methods
Please choose the appropriate dissolution scheme according to your animal administration guide.For the following dissolution schemes, clear stock solution should be prepared according to in vitro experiments, and then cosolvent should be added in turn:

in order to ensure the reliability of the experimental results, the clarified stock solution can be properly preserved according to the storage conditions; The working fluid for in vivo experiment is recommended to be prepared now and used on the same day;

The percentage shown in front of the following solvent refers to the volume ratio of the solvent in the final solution; If precipitation or precipitation occurs in the preparation process, it can be assisted by heating and/or ultrasound.
Protocol 1

References

 

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