Indirubin
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| 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 | |
| 479-41-4 | |
| ChemSpider | 4477010 |
| Jmol interactive 3D | Image |
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| Properties | |
| 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
- ↑ Zhang, Xiaoli; Song, Yajuan; Wu, Yuanyuan; Dong, Yanmin; Lai, Li; Zhang, Jing; Lu, Binbin; Dai, Fujun; He, Lijun (2011-11-15). "Indirubin inhibits tumor growth by antitumor angiogenesis via blocking VEGFR2-mediated JAK/STAT3 signaling in endothelial cell". International Journal of Cancer. Journal International Du Cancer 129 (10): 2502–2511. doi:10.1002/ijc.25909. ISSN 1097-0215. PMID 21207415.
- ↑ "Indirubin". Memorial Sloan Kettering Cancer Center.
- ↑ Williams, Shanté P.; Nowicki, Michal O.; Liu, Fang; Press, Rachael; Godlewski, Jakub; Abdel-Rasoul, Mahmoud; Kaur, Balveen; Fernandez, Soledad A.; Chiocca, E. Antonio (2011-08-15). "Indirubins Decrease Glioma Invasion by Blocking Migratory Phenotypes in Both the Tumor and Stromal Endothelial Cell Compartments". Cancer Research 71 (16): 5374–5380. doi:10.1158/0008-5472.CAN-10-3026. ISSN 0008-5472. PMC 4288480. PMID 21697283.
- ↑ Hideo Suzuki, Tsuyoshi Kaneko, Yuji Mizokami, Toshiaki Narasaka, Shinji Endo, Hirofumi Matsui, Akinori Yanaka, Aki Hirayama and Ichinosuke Hyodo (2013). "Therapeutic efficacy of the Qing Dai in patients with intractable ulcerative colitis". World J Gastroenterol 19 (17): 2718–2722. doi:10.3748/wjg.v19.i17.2718. PMC 3645393. PMID 23674882.