Indirubin

Indirubin

Names
IUPAC name (3Z)-3-(3-Oxo-1,3-dihydro-2H-indol-2-ylidene)-1,3-dihydro-2H-indol-2-one
Other names Indigo red
Identifiers
CAS Number	479-41-4
3D model (Jmol)	Interactive image
ChemSpider	4477010
ECHA InfoCard	100.119.646
InChI 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- Key: CRDNMYFJWFXOCH-YPKPFQOOSA-N
SMILES c1ccc2c(c1)/C(=C/3\C(=O)c4ccccc4N3)/C(=O)N2
Properties
Chemical formula	C16H10N2O2
Molar mass	262.27 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Indirubin is a chemical compound most often produced as a byproduct of bacterial metabolism. For instance, it is one of the compounds responsible for the generally benign condition purple urine bag syndrome, resulting from bacteria metabolizing indoxyl sulfate found naturally in urine.

Indirubin is a chemical constituent of indigo naturalis (also known as qing dai), which has been used for hundreds of years in traditional Chinese medicine. It is produced by collecting the waste products from the bacterial degradation of specific forms of vegetation.

Research

Indirubin exerts its effects on the human body by downregulating expression of genes. Genes Plk1 and Pin1, both oncogenic, have been shown to be affected by indirubin. Indirubin has, in vitro and in vivo, been shown to reduce expression of the CDC25B gene, which codes for production of CDC25B enzyme. CDC stands for cell-division-cycle, and is used in cellular reproduction. Studies suggest that mouse cells are viable after the CDC25B (and CDC25C) genes are "knocked out", but removal of CDC25A results in non-viable cells.

Indirubin shows anti-inflammatory and anti-angiogenesis properties.^[1]

Indirubin has not been shown to prevent or treat cancer in humans.^[2] However, it is being studied for treatment of small-cell lung cancer, glioblastoma,^[3] and chronic myeloid leukemia, either alone or in conjunction with more typical cancer management treatments.

Indirubin, in the form of indigo naturalis, has been used for many years in the treatment of plaque psoriasis. It is applied topically or ingested for systemic effects. Results in the treatment of ulcerative colitis, another immune-modulated disease process, shows promise as well.^[4]

References