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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
Chemical Compound Review

Idronoxil     3-(4-hydroxyphenyl)-2H- chromen-7-ol

Synonyms: Phenoxodiol, Dehydroequol, Haganin E, Haginin E, NV-06, ...
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Disease relevance of Haginin E


High impact information on Haginin E

  • These data therefore indicate that phenoxodiol promotes G(1)-S arrest by the specific loss in cdk2 activity due to p53-independent p21(WAF1) induction [6].
  • Analysis of in vitro purified cyclin-dependent kinase (cdk) activity showed that phenoxodiol did not inhibit cdk activity [6].
  • In contrast, cellular cdk2 activity obtained from HN12 cell lines exposed to phenoxodiol for 12 hours decreased by 60%, whereas cdk6 activity remained unaltered, suggesting that the loss of cdk2 activity was specific [6].
  • Moreover, clear evidence of cell death as determined by nuclear morphology and plasmatic membrane damage occur despite ZVAD, suggesting that another mechanism besides caspase-dependent apoptosis is required for clonogenic death induced by phenoxodiol [6].
  • To assess the role of p21(WAF1) induction by phenoxodiol, we used HCT116 isogenic cell lines and showed that phenoxodiol induced G(1) arrest together with p21(WAF1) expression in wild-type clones [6].

Biological context of Haginin E


Anatomical context of Haginin E

  • To determine the mechanism of antiproliferative effects of phenoxodiol, we examined its effects in a battery of human cell lines [6].
  • We show that phenoxodiol inhibits hallmarks of endothelial cell activation, namely TNF or IL-1 induced E-selectin and VCAM-1 expression and IL-8 secretion [9].
  • METHODS AND RESULTS: Responses to brachial artery infusion of dehydroequol (0.1, 0.3, 1 and 3 micromol/min) in forearm resistance arteries were obtained in six healthy males [10].
  • Variation in sensitivity to Phenoxodiol appeared related to events upstream of the mitochondria and the degree of conformational change in Bax [3].
  • Isoflavone treatment for 24 weeks had no effect on the total area of atherosclerotic plaques in the whole aorta, but DeE reduced the plaque thickness in the aortic arch by 29%, although this did not reach statistical significance [11].

Associations of Haginin E with other chemical compounds


Gene context of Haginin E

  • In addition, it was demonstrated that phenoxodiol is capable of inducing apoptosis by: 1) the activation of the mitochondrial pathway through caspase-2 and Bid signaling, and 2) the proteasomal degradation of the anti-apoptotic protein XIAP [8].
  • BACKGROUND: Previously, it was demonstrated that phenoxodiol induces apoptosis in epithelial ovarian carcinoma (EOC) cells and that it is capable of sensitizing these cells to Fas-mediated apoptosis [8].
  • Together, these studies suggest that Phenoxodiol induces apoptosis of melanoma cells by induction of p53-dependent BH3 proteins (Bad, PUMA and Noxa) and the p53-independent Bim protein, resulting in activation of Bax and its downstream events [3].

Analytical, diagnostic and therapeutic context of Haginin E

  • METHODS: Phenoxodiol given by intravenous infusion continuously for 7 days on 14-day cycles was dose-escalated on an inter-patient basis at dosages of 0.65,1.3, 3.3, 20.0, and 27.0 mg/kg/day (three to four patients per stratum) [2].
  • Tumour latency was increased from 70.4 days in the control group to 92.9 (P=0.04) days and 97.8 (P=0.03) days in the groups that were fed 50 and 75 mg/kg phenoxodiol, respectively [12].


  1. Phenoxodiol--an isoflavone analog--induces apoptosis in chemoresistant ovarian cancer cells. Kamsteeg, M., Rutherford, T., Sapi, E., Hanczaruk, B., Shahabi, S., Flick, M., Brown, D., Mor, G. Oncogene (2003) [Pubmed]
  2. Phase I trial of phenoxodiol delivered by continuous intravenous infusion in patients with solid cancer. Choueiri, T.K., Mekhail, T., Hutson, T.E., Ganapathi, R., Kelly, G.E., Bukowski, R.M. Ann. Oncol. (2006) [Pubmed]
  3. Involvement of BH3-only proapoptotic proteins in mitochondrial-dependent Phenoxodiol-induced apoptosis of human melanoma cells. Yu, F., Watts, R.N., Zhang, X.D., Borrow, J.M., Hersey, P. Anticancer Drugs (2006) [Pubmed]
  4. Flavonoid compounds in maintenance of prostate health and prevention and treatment of cancer. Brown, D.M., Kelly, G.E., Husband, A.J. Mol. Biotechnol. (2005) [Pubmed]
  5. Growth of LNCaP cells in monoculture and coculture with osteoblasts and response to tNOX inhibitors. Axanova, L., Morré, D.J., Morré, D.M. Cancer Lett. (2005) [Pubmed]
  6. Phenoxodiol, a novel isoflavone, induces G1 arrest by specific loss in cyclin-dependent kinase 2 activity by p53-independent induction of p21WAF1/CIP1. Aguero, M.F., Facchinetti, M.M., Sheleg, Z., Senderowicz, A.M. Cancer Res. (2005) [Pubmed]
  7. X-linked inhibitor of apoptosis (XIAP) confers human trophoblast cell resistance to Fas-mediated apoptosis. Straszewski-Chavez, S.L., Abrahams, V.M., Funai, E.F., Mor, G. Mol. Hum. Reprod. (2004) [Pubmed]
  8. Molecular mechanism of phenoxodiol-induced apoptosis in ovarian carcinoma cells. Alvero, A.B., O'Malley, D., Brown, D., Kelly, G., Garg, M., Chen, W., Rutherford, T., Mor, G. Cancer (2006) [Pubmed]
  9. Phenoxodiol, an experimental anticancer drug, shows potent antiangiogenic properties in addition to its antitumour effects. Gamble, J.R., Xia, P., Hahn, C.N., Drew, J.J., Drogemuller, C.J., Brown, D., Vadas, M.A. Int. J. Cancer (2006) [Pubmed]
  10. The isoflavone metabolite dehydroequol produces vasodilatation in human resistance arteries via a nitric oxide-dependent mechanism. Chin-Dusting, J.P., Boak, L., Husband, A., Nestel, P.J. Atherosclerosis (2004) [Pubmed]
  11. Cardiovascular protective effects of synthetic isoflavone derivatives in apolipoprotein e-deficient mice. Jiang, F., Jones, G.T., Husband, A.J., Dusting, G.J. J. Vasc. Res. (2003) [Pubmed]
  12. Phenoxodiol, a novel isoflavone derivative, inhibits dimethylbenz[a]anthracene (DMBA)-induced mammary carcinogenesis in female Sprague-Dawley rats. Constantinou, A.I., Mehta, R., Husband, A. Eur. J. Cancer (2003) [Pubmed]
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