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Chemical Compound Review

Indinol     1H-indol-3-ylmethanol

Synonyms: CPDQT-428, PubChem7265, zlchem 356, S2313_Selleck, CHEMBL155625, ...
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Disease relevance of AI3-60090


Psychiatry related information on AI3-60090

  • The CYP1A1 enzyme that catalyzes 2-hydroxyestrone (2-OHE1) formation is inducible by dietary modification and supplementation with the active components of cruciferous vegetables, indole-3-carbinol (I-3-C), or diindolylmethane (DIM) [5].

High impact information on AI3-60090


Chemical compound and disease context of AI3-60090


Biological context of AI3-60090


Anatomical context of AI3-60090


Associations of AI3-60090 with other chemical compounds


Gene context of AI3-60090


Analytical, diagnostic and therapeutic context of AI3-60090

  • Indole-3-carbinol (I3C), a natural constituent of cruciferous vegetables, is an inhibitor in several experimental animal models of carcinogenesis by polynuclear aromatic hydrocarbons or aflatoxin B1 (AFB1) when administered prior to or during carcinogen exposure [31].
  • Adjunct medical treatments, aimed at containing the virus and growth of tumours, include indole-3-carbinol or its dimer diindolylmethane, interferon, photodynamic therapy and others [32].
  • Anticarcinogenic activity of indole-3-carbinol acid products: ultrasensitive bioassay by trout embryo microinjection [33].
  • The relative contribution of indole-3-carbinol (I3C) and its acid condensation products to the anticarcinogenic activity of this crucifer phytochemical has been studied using trout embryo microinjection [33].
  • We hypothesized that the phytochemical, indole-3-carbinol (I3C), and some of its acid-condensation derivatives may inhibit P-glycoprotein-mediated transport due to their aromatic and nitrogen components, thus increasing the accumulation and efficacy of anticancer drugs and acting as a dietary adjuvant to conventional chemotherapy [8].


  1. Selective responsiveness of human breast cancer cells to indole-3-carbinol, a chemopreventive agent. Tiwari, R.K., Guo, L., Bradlow, H.L., Telang, N.T., Osborne, M.P. J. Natl. Cancer Inst. (1994) [Pubmed]
  2. Indole-3-carbinol suppresses NF-kappaB and IkappaBalpha kinase activation, causing inhibition of expression of NF-kappaB-regulated antiapoptotic and metastatic gene products and enhancement of apoptosis in myeloid and leukemia cells. Takada, Y., Andreeff, M., Aggarwal, B.B. Blood (2005) [Pubmed]
  3. A new indole-3-carbinol tetrameric derivative inhibits cyclin-dependent kinase 6 expression, and induces G1 cell cycle arrest in both estrogen-dependent and estrogen-independent breast cancer cell lines. Brandi, G., Paiardini, M., Cervasi, B., Fiorucci, C., Filippone, P., De Marco, C., Zaffaroni, N., Magnani, M. Cancer Res. (2003) [Pubmed]
  4. Chemoprevention of spontaneous endometrial cancer in female Donryu rats by dietary indole-3-carbinol. Kojima, T., Tanaka, T., Mori, H. Cancer Res. (1994) [Pubmed]
  5. Estrogen metabolism and the diet-cancer connection: rationale for assessing the ratio of urinary hydroxylated estrogen metabolites. Lord, R.S., Bongiovanni, B., Bralley, J.A. Alternative medicine review : a journal of clinical therapeutic. (2002) [Pubmed]
  6. Multiple dietary factors in the enhancement of dimethylhydrazine carcinogenesis: main effect of indole-3-carbinol. Pence, B.C., Buddingh, F., Yang, S.P. J. Natl. Cancer Inst. (1986) [Pubmed]
  7. Indole-3-carbinol and tamoxifen cooperate to arrest the cell cycle of MCF-7 human breast cancer cells. Cover, C.M., Hsieh, S.J., Cram, E.J., Hong, C., Riby, J.E., Bjeldanes, L.F., Firestone, G.L. Cancer Res. (1999) [Pubmed]
  8. Reversal of multidrug resistance in vivo by dietary administration of the phytochemical indole-3-carbinol. Christensen, J.G., LeBlanc, G.A. Cancer Res. (1996) [Pubmed]
  9. Inhibition of nuclear translocation of nuclear factor-{kappa}B contributes to 3,3'-diindolylmethane-induced apoptosis in breast cancer cells. Rahman, K.W., Sarkar, F.H. Cancer Res. (2005) [Pubmed]
  10. Effects of indole-3-carbinol on lung tumorigenesis and DNA methylation induced by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and on the metabolism and disposition of NNK in A/J mice. Morse, M.A., LaGreca, S.D., Amin, S.G., Chung, F.L. Cancer Res. (1990) [Pubmed]
  11. Tryptophan side chain oxidase from Pseudomonas. Oxidation of skatole to indole-3-carboxaldehyde via indole-3-methanol. Ushiro, H., Takai, K., Noda, Y., Narumiya, S., Tokuyama, T., Hayaishi, O. J. Biol. Chem. (1978) [Pubmed]
  12. Dietary indole-3-carbinol promotes endometrial adenocarcinoma development in rats initiated with N-ethyl-N'-nitro-N-nitrosoguanidine, with induction of cytochrome P450s in the liver and consequent modulation of estrogen metabolism. Yoshida, M., Katashima, S., Ando, J., Tanaka, T., Uematsu, F., Nakae, D., Maekawa, A. Carcinogenesis (2004) [Pubmed]
  13. Translocation of Bax to mitochondria induces apoptotic cell death in indole-3-carbinol (I3C) treated breast cancer cells. Rahman, K.M., Aranha, O., Glazyrin, A., Chinni, S.R., Sarkar, F.H. Oncogene (2000) [Pubmed]
  14. Pharmacokinetics and tissue disposition of indole-3-carbinol and its acid condensation products after oral administration to mice. Anderton, M.J., Manson, M.M., Verschoyle, R.D., Gescher, A., Lamb, J.H., Farmer, P.B., Steward, W.P., Williams, M.L. Clin. Cancer Res. (2004) [Pubmed]
  15. Dietary agent indole-3-carbinol protects female rats against the hepatotoxicity of the antitumor drug ET-743 (trabectidin) without compromising efficacy in a rat mammary carcinoma. Donald, S., Verschoyle, R.D., Greaves, P., Colombo, T., Zucchetti, M., Falcioni, C., Zaffaroni, M., D'Incalci, M., Manson, M.M., Jimeno, J., Steward, W.P., Gescher, A.J. Int. J. Cancer (2004) [Pubmed]
  16. Salt-sensitive hypertension develops after transient induction of ANG II-dependent hypertension in Cyp1a1-Ren2 transgenic rats. Howard, L.L., Patterson, M.E., Mullins, J.J., Mitchell, K.D. Am. J. Physiol. Renal Physiol. (2005) [Pubmed]
  17. Indole-3-carbinol activates the ATM signaling pathway independent of DNA damage to stabilize p53 and induce G1 arrest of human mammary epithelial cells. Brew, C.T., Aronchik, I., Hsu, J.C., Sheen, J.H., Dickson, R.B., Bjeldanes, L.F., Firestone, G.L. Int. J. Cancer (2006) [Pubmed]
  18. Inhibition of phosphatidylinositol 3-kinase/protein kinase B signaling is not sufficient to account for indole-3-carbinol-induced apoptosis in some breast and prostate tumor cells. Howells, L.M., Hudson, E.A., Manson, M.M. Clin. Cancer Res. (2005) [Pubmed]
  19. Mechanism of action of dietary chemoprotective agents in rat liver: induction of phase I and II drug metabolizing enzymes and aflatoxin B1 metabolism. Manson, M.M., Ball, H.W., Barrett, M.C., Clark, H.L., Judah, D.J., Williamson, G., Neal, G.E. Carcinogenesis (1997) [Pubmed]
  20. Enhancement by indole-3-carbinol of liver and thyroid gland neoplastic development in a rat medium-term multiorgan carcinogenesis model. Kim, D.J., Han, B.S., Ahn, B., Hasegawa, R., Shirai, T., Ito, N., Tsuda, H. Carcinogenesis (1997) [Pubmed]
  21. Indole-3-carbinol inhibition of androgen receptor expression and downregulation of androgen responsiveness in human prostate cancer cells. Hsu, J.C., Zhang, J., Dev, A., Wing, A., Bjeldanes, L.F., Firestone, G.L. Carcinogenesis (2005) [Pubmed]
  22. Stimulation of insulin secretion from isolated rat islets by SaRI 59-801. Hanson, R.L., Isaacson, C.M., Boyajy, L.D. Diabetes (1985) [Pubmed]
  23. Cytostatic effects of 3,3'-diindolylmethane in human endometrial cancer cells result from an estrogen receptor-mediated increase in transforming growth factor-alpha expression. Leong, H., Firestone, G.L., Bjeldanes, L.F. Carcinogenesis (2001) [Pubmed]
  24. Inhibition of amyloid fibril formation and cytotoxicity by hydroxyindole derivatives. Cohen, T., Frydman-Marom, A., Rechter, M., Gazit, E. Biochemistry (2006) [Pubmed]
  25. Protection by chlorophyllin and indole-3-carbinol against 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP)-induced DNA adducts and colonic aberrant crypts in the F344 rat. Guo, D., Schut, H.A., Davis, C.D., Snyderwine, E.G., Bailey, G.S., Dashwood, R.H. Carcinogenesis (1995) [Pubmed]
  26. Anti-mutagenesis and anti-promotion by apigenin, robinetin and indole-3-carbinol. Birt, D.F., Walker, B., Tibbels, M.G., Bresnick, E. Carcinogenesis (1986) [Pubmed]
  27. Expression of the human aryl hydrocarbon receptor complex in yeast. Activation of transcription by indole compounds. Miller, C.A. J. Biol. Chem. (1997) [Pubmed]
  28. Indole-3-carbinol (I3C) inhibits cyclin-dependent kinase-2 function in human breast cancer cells by regulating the size distribution, associated cyclin E forms, and subcellular localization of the CDK2 protein complex. Garcia, H.H., Brar, G.A., Nguyen, D.H., Bjeldanes, L.F., Firestone, G.L. J. Biol. Chem. (2005) [Pubmed]
  29. Indole-3-carbinol selectively uncouples expression and activity of estrogen receptor subtypes in human breast cancer cells. Sundar, S.N., Kerekatte, V., Equinozio, C.N., Doan, V.B., Bjeldanes, L.F., Firestone, G.L. Mol. Endocrinol. (2006) [Pubmed]
  30. Inhibition of MUC1 expression by indole-3-carbinol. Lee, I.J., Han, F., Baek, J., Hisatsune, A., Kim, K.C. Int. J. Cancer (2004) [Pubmed]
  31. Enhancement of carcinogenesis by the natural anticarcinogen indole-3-carbinol. Bailey, G.S., Hendricks, J.D., Shelton, D.W., Nixon, J.E., Pawlowski, N.E. J. Natl. Cancer Inst. (1987) [Pubmed]
  32. Therapy for recurrent respiratory papillomatosis. Auborn, K.J. Antivir. Ther. (Lond.) (2002) [Pubmed]
  33. Anticarcinogenic activity of indole-3-carbinol acid products: ultrasensitive bioassay by trout embryo microinjection. Dashwood, R.H., Fong, A.T., Arbogast, D.N., Bjeldanes, L.F., Hendricks, J.D., Bailey, G.S. Cancer Res. (1994) [Pubmed]
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