A phytochemical with antiradiation and chemopreventative effects
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3,3'-Diindolylmethane

Item No. 15927

Technical Information
Formal Name
3,3'-methylenebis-1H-indole
CAS Number
1968-05-4
Synonyms
  • DIM
Molecular Formula
C17H14N2
Formula Weight
Purity
≥98%
Formulation
A crystalline solid
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS(pH 7.2) (1:4): 0.2 mg/mlEthanol: 15 mg/ml
λmax
225, 283 nm
SMILES
C12=CC=CC=C1C(CC3=CNC4=C3C=CC=C4)=CN2
InChi Code
InChI=1S/C17H14N2/c1-3-7-16-14(5-1)12(10-18-16)9-13-11-19-17-8-4-2-6-15(13)17/h1-8,10-11,18-19H,9H2
InChi Key
VFTRKSBEFQDZKX-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    3,3’-Diindolylmethane (DIM) is a bioactive metabolite of indole-3-carbinol, a phytochemical produced by the breakdown of the glucosinolate glucobrassicin found in cruciferous vegetables. At 10-30 µM, it demonstrates anticancer and chemopreventative effects involving Nrf2 induction of Phase 2 enzymes, promotion of apoptosis, induction of cell cycle arrest, inhibition of cell proliferation, and inhibition of histone deacetylases and DNA methylation activities.1,2,3 Furthermore, at 0.3 µM DIM was shown to act as a potent radioprotector and mitigator of the effects of ionizing radiation exposure by stimulating an ATM-driven DNA damage-like response and NF-κB survival signaling in cultured epithelial cells.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wong, C.P., Hsu, A., Buchanan, A., et alEffects of sulforaphane and 3,3'-diindolylmethane on genome-wide promoter methylation in normal prostate epithelial cells and prostate cancer cells. PLoS One 9(1), (2014).

    2. Wu, T.Y., Khor, T.O., Su, Z.Y., et alEpigenetic modifications of Nrf2 by 3,3'-diindolylmethane in vitro in TRAMP C1 cell line and in vivo TRAMP prostate tumors. AAPS J. 15(3), 864-874 (2013).

    3. Xu, Y., Zhang, J., Shi, W., et alAnticancer effects of 3,3'-diindolylmethane are associated with G1 arrest and mitochondria-dependent apoptosis in human nasopharyngeal carcinoma cells. Oncol. Lett. 5(2), 655-662 (2013).

    4. Fan, S., Meng, Q., Xu, J., et alDIM (3,3'-diindolylmethane) confers protection against ionizing radiation by a unique mechanism. Proc. Natl. Acad. Sci. USA 110(46), 18650-18655 (2013).