Phenoxodiol
(Synonyms: 脱氢雌马酚,Idronoxil; Dehydroequol; Haginin E) 目录号 : GC36895
A phenol with anticancer activity
Cas No.:81267-65-4
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Idronoxil is a phenol and derivative of genistein that has been found in B. tournefortii and has anticancer activity.1,2,3 It reduces the viability of R182S, R127, Hey, CP70, A2780, R187, R188, and R207 primary ovarian cancer cells, but not non-cancerous ovarian surface epithelial (OSE) cells, when used at a concentration of 10 ?g/ml.2 Idronoxil (1 ?g/ml) reduces colony formation and induces apoptosis in R127 and CP70 primary ovarian cancer cells, respectively, and restores sensitivity to Fas-mediated apoptosis in CP70 cells. In vivo, idronoxil (50 and 75 mg/kg) increases latency to tumor formation and reduces tumor multiplicity in a rat model of mammary carcinogenesis induced by dimethylbenz[a]anthracene (DMBA).3
1.Rahmani, R., Bouajila, J., Jouaidi, M., et al.African mustard (Brassica tournefortii) as source of nutrients and nutraceuticals propertiesJ. Food Sci.85(6)1856-1871(2020) 2.Kamsteeg, M., Rutherford, T., Sapi, E., et al.Phenoxodiol – an isoflavone analog – induces apoptosis in chemoresistant ovarian cancer cellsOncogene22(17)2611-2620(2003) 3.Constantinou, A.I., Mehta, R., and Husband, A.Phenoxodiol, a novel isoflavone derivative, inhibits dimethylbenz[a]anthracene (DMBA)-induced mammary carcinogenesis in female Sprague–Dawley ratsEur. J. Cancer39(7)1012-1018(2004)
| Cas No. | 81267-65-4 | SDF | |
| 别名 | 脱氢雌马酚,Idronoxil; Dehydroequol; Haginin E | ||
| Canonical SMILES | OC1=CC=C2C=C(C3=CC=C(O)C=C3)COC2=C1 | ||
| 分子式 | C15H12O3 | 分子量 | 240.25 |
| 溶解度 | DMSO: ≥ 100 mg/mL (416.23 mM); Water: < 0.1 mg/mL (insoluble) | 储存条件 | Store at -20°C,protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.1623 mL | 20.8117 mL | 41.6233 mL |
| 5 mM | 0.8325 mL | 4.1623 mL | 8.3247 mL |
| 10 mM | 0.4162 mL | 2.0812 mL | 4.1623 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Phenoxodiol: pharmacology and clinical experience in cancer monotherapy and in combination with chemotherapeutic drugs
Expert Opin Pharmacother 2009 Apr;10(6):1059-67.PMID:19364253DOI:10.1517/14656560902837980.
Background: Phenoxodiol is a synthetic derivative of the naturally occurring plant isoflavone genistein. The observation that an inverse relationship exists between dietary intake of isoflavones and cancer incidence has led to the evaluation of these compounds in cancer therapy. Objective: This article reviews the mechanisms of action of Phenoxodiol and the completed and ongoing clinical studies evaluating this drug. Results/conclusions: By altering the chemical structure of genistein, the new compound Phenoxodiol showed increased anticancer activity without any increase in toxicity. In addition to its direct cytotoxic activity against different cancers, Phenoxodiol sensitizes chemoresistant ovarian cancer cells to platinum and taxane drugs, as well as gemcitabine and topotecan. The US Food and Drug Administration has granted 'fast track' status to the development of Phenoxodiol as chemosensitizer for platinum and taxane drugs used in the treatment of recurrent ovarian cancer.
Phenoxodiol: isoflavone analog with antineoplastic activity
Curr Oncol Rep 2006 Mar;8(2):104-7.PMID:16507219DOI:10.1007/s11912-006-0044-2.
Phenoxodiol, a synthetic analog of the plant isoflavone genistein, represents a new generation of oncology drugs acting as multiple signal transduction regulators. Phenoxodiol exerts its effect mainly by the induction of apoptosis through multiple mechanisms resulting in degradation of antiapoptotic proteins, with increased levels being linked to chemoresistance in tumor cells. Preclinical studies with this agent showed promising anticancer activity leading to a potential role in the treatment of a wide range of solid and hematologic cancers. Early clinical studies, especially in chemotherapy-resistant ovarian cancer, showed minimal toxicity with minor antitumor activity. Hormone-refractory prostate cancer is another promising area in which Phenoxodiol is being actively tested. Studies are ongoing to define the optimal use of this novel anticancer agent.
Flavonoids, Phenoxodiol, and a novel agent, triphendiol, for the treatment of pancreaticobiliary cancers
Expert Opin Investig Drugs 2009 Apr;18(4):469-79.PMID:19278301DOI:10.1517/13543780902762835.
Flavonoids, in particular the isoflavones, are naturally occurring compounds found in soy and textured vegetables that have antiproliferative effects on a variety of cancer types. Phenoxodiol is a derivative of the isoflavone genisten that is 5-20 times more potent than genisten. Triphendiol is a derivative of Phenoxodiol that has superior anticancer activity against pancreatic and bile duct cancers. This review will focus on the mechanisms of action and activity of two isoflavone derivatives, Phenoxodiol and triphendiol, in various tumor types, especially pancreaticobiliary cancers. Triphendiol induces apoptosis in pancreatic cell lines by both caspase-mediated and caspase-independent mechanisms. The addition of triphendiol to gemcitabine is synergistic in in vitro and in vivo models of pancreatic cancer and represents a novel combination of drugs for pancreatic cancer patients.
Phenoxodiol, a novel approach for the treatment of ovarian cancer
Curr Opin Investig Drugs 2006 Jun;7(6):542-8.PMID:16784025doi
Epithelial ovarian cancer is the fourth leading cause of cancer-related deaths in women and is the most lethal of the gynecological malignancies. Thle high mortality rate arises from difficulties in the early detection of the disease and the widespread development of chemoresistance. Phenoxodiol, a novel isoflavone derivative, has demonstrated antitumor activity. In addition, it has been shown to induce cell death in chemoresistant epithelial ovarian cancer cells. Moreover, suboptimal exposure of these cells to Phenoxodiol lowered the IC50 value of numerous chemotherapeutic agents. In this review, the current understanding of the mechanism of action of Phenoxodiol, its potential clinical application for the treatment of ovarian cancer and the concept of chemosensitization are discussed.
Enzymatic synthesis of novel unnatural Phenoxodiol glycosides with a glycosyl donor flexible glycosyltransferase MeUGT1
Enzyme Microb Technol 2022 Nov;161:110113.PMID:35998478DOI:10.1016/j.enzmictec.2022.110113.
Isoflavonoids are of great interest due to their human health-promoting properties, which have resulted in studies on exploiting these phytochemicals as hotspots in diverse bio -industries. Biocatalytic glycosylation of isoflavonoid aglycones to glycosides has attracted marked interests because it enable the biosynthesis of isoflavonoid glycosides with high selectivity under mild conditions, and also provide an environmentally friendly option for the chemical synthesis. Thus, these inspired us to exploit new flexible and effective glycosyltransferases from microbes for making glycosides attractive compounds that are in high demand in several industries. Most recently, we have reported the functional characterization of a bacterial-origin recombinant glycosyltransferase (MeUGT1). Herein, more detailed kinetic characteristics of this biocatalyst, using a number of glycosyl donor substrates, were examined for further investigation of its biocatalytic applicability, enabling it feasible to biosynthesize new glycosides; phenoxodiol-4'-O-α-glucuronide, phenoxodiol-4'-O-α-(2''-N-acetyl)glucosaminide, phenoxodiol-4'-O-α-galactoside, phenoxodiol-4'-O-α-(2''-N-acetyl)galactosaminide and phenoxodiol-4'-O-α-(2''-deoxy)glucoside. The thorough kinetic analyses revealed that while the recombinant enzyme can utilize, albeit with different substrate preference and catalytic efficiency, a total five different nucleotide sugars as glycosyl donors, exhibiting its promiscuity towards glycosyl donors. This is the first report that a recombinant glycosyltransferase MeUGT1 that can regio-specifically glycosylate C4'-hydroxyl function of semi-synthetic Phenoxodiol isoflavene to biosynthesize a series of unnatural phenoxodiol-4'-O-α-glycosides.