| 2-Hydroxyestradiolanti-cancer agent acting as an angiogenesis inhibitor via the HIF-1a pathway |
Sample solution is provided at 25 µL, 10mM.
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Chemical structure
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| Cas No. | 362-05-0 | SDF | Download SDF |
| Synonyms | 2-HE2,NSC 61711 | ||
| Chemical Name | estra-1,3,5(10)-triene-2,3,17β-triol | ||
| Canonical SMILES | OC1=C(O)C=C(CC[C@]2([H])[C@]3([H])CC[C@@]4(C)[C@@]2([H])CC[C@@H]4O)C3=C1 | ||
| Formula | C18H24O3 | M.Wt | 288.4 |
| Solubility | ≤20mg/ml in ethanol;20mg/ml in DMSO;20mg/ml in dimethyl formamide | Storage | Store at -20°C |
| Physical Appearance | A crystalline solid | Shipping Condition | Evaluation sample solution : ship with blue ice.All other available size:ship with RT , or blue ice upon request |
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. | ||
2-Hydroxyestradiol is an angiogenesis inhibitor via the HIF-1a pathway.
HIF-1a, a basic helix-loop-helix PAS domain containing protein, is reported as the master transcriptional regulator of cellular and developmental response to hypoxia.
In vitro: In vitro evidences suggested that most of the cellular effects of 2-hydroxyestradiol were mediated by 2-methoxyestradiol, a metabolite of 2-hydroxyestradiol as an anti-cancer agent acting as an angiogenesis inhibitor via the HIF-1a pathway. Inhibition of catechol-O-methyltransferase (COMT), the enzyme methylating 2-hydroxyestradiol to 2-methoxyestradiol, blocked the ability of 2-hydroxyestradiol to inhibit growth of vascular smooth muscle cells, cardiac fibroblasts, as well as renal mesangial cells. Moreover, 2-hydroxyestradiol could inhibit vascular smooth muscle cell growth in cells obtained from wild-type mice but not in cells cultured from COMT knockout mice. In contrast to 2OHE, treatment of vascular smooth muscle cells with 2-methoxyestradiol inhibited serum-induced growth of cells from both wild-type and COMTknockout mice [1].
In vivo: Animal study showed that after administration of 2-hydroxyestradiol, plasma levels of 2-hydroxyestradiol declined extremely rapidly. Concomitant with the disappearance of 2-hydroxyestradiol, 2-methoxyestradiol occurred and then declined. After administration of 2-methoxyestradiol, plasma levels of 2MEOE declined with a plasma CL of 50 ml min(-1) kg(-1). We could not detect 2-hydroxyestradiol in plasma from rats receiving 2-methoxyestradiol. Thus, the authors conclude that the conversion of 2-hydroxyestradiol to 2-methoxyestradiol was so efficient, and the administration of 2-hydroxyestradiol is bioequivalent to administration of 2-methoxyestradiol itself [1].
Clinical trial: So far, no clinical study has been conducted.
Reference:[1] Zacharia, L. C.,Piché, C.A.,Fielding, R.M., et al. 2-hydroxyestradiol is a prodrug of 2-methoxyestradiol. Journal of Pharmacology and Experimental Therapeutics 309(3), 1093-1097 (2004).
