2-Methoxyestradiol 2-甲氧基雌二醇

CAS 362-07-2 MFCD00010489

化学结构图

362-07-2
SMILES: COc1cc2c(cc1O)CC[C@@H]1[C@@H]2CC[C@]2(C)[C@@H](O)CC[C@@H]12

化学属性

Mol. FormulaC19H26O3
Mol. Weight302
Appearance crystalline white solid powder
SolubilitySoluble in DMSO, not in water
Melting Point186.0 to 190.0 deg-C

别名和识别编码

Chemical Name2-Methoxyestradiol
Synonym (17B)-2-METHOXYESTRA-1,3,5(10)-TRIENE-3,17-DIOL 1,3,5(10)-ESTRATRIEN-2,3,17-BETA-TRIOL 2-METHYL ETHER 1,3,5(10)-ESTRATRIENE-2,3,17BETA-TRIOL 2-METHYL ETHER 1,3,5(10)-Estratriene-2,3,17-triol 2-methyl ether 1,3,5(10)-Estratriene-2,3,17-triol 2-methyl ether 2,3,17β-Trihydroxy-1,3,5(10)-estratriene 2-methyl ether 2-Hydroxyestradiol 2-methyl ether 3,17β-Dihydroxy-2-methoxy-1,3,5(10)-estratriene 1,3,5[10]-ESTRATRIENE-2,3,17-TRIOL 2-METHYL ETHER 2,3,17β-Trihydroxy-1,3,5(10)-estratriene 2-methyl ether 2,3,17BETA-TRIHYDROXY-1,3,5[10]-ESTRATRIENE 2-METHYL ETHER 2-Hydroxyestradiol 2-methyl ether 2-ME2;(8R,9S,13S,14S,17S)-2-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol 2-ME2;(8R,9S,13S,14S,17S)-2-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol;2-MeOE2;2-甲氧基雌二醇
CAS Number362-07-2
PubChem Substance ID66414
MDL NumberMFCD00010489
Beilstein Registry Number3147966
Chemical Name Translation2-甲氧基雌二醇
Reaxys-RN3147966
LabNetwork Molecule IDLN01303091
InChIInChI=1S/C19H26O3/c1-19-8-7-12-13(15(19)5-6-18(19)21)4-3-11-9-16(20)17(22-2)10-14(11)12/h9-10,12-13,15,18,20-21H,3-8H2,1-2H3/t12-,13+,15-,18-,19-/m0/s1
FormulaC19H26O3
IUPAC Name(8R,9S,13S,14S,17S)-2-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,17-diol
InChIKeyCQOQDQWUFQDJMK-SSTWWWIQSA-N
Canonical SMILESOC1=C(OC)C=C2[C@@]3([H])CC[C@]4(C)[C@@H](O)CC[C@@]4([H])[C@]3([H])CCC2=C1
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分类

  • {SNA} Angiogenesis Inhibitors, Anti-proliferative Agents, Bioactive Small Molecule Alphabetical Index, Cytokines, Growth Factors and Hormones, Enzyme Inhibitors, Enzyme Inhibitors by Enzyme, Hormones, M, Other Steroid Products, R to Z, Steroid Hormones, Superoxide dismutase, 化学预防剂, 生化试剂, 生物活性小分子, 癌症研究, 细胞信号转导和神经科学, 细胞生物学, 血管生成, 酶、抑制剂和底物
  • Angiogenesis, Angiogenesis Inhibitors, Anti-proliferative Agents, Bioactive Small Molecules, Biochemicals and Reagents, Cancer Research,

产品应用

  • 2-methoxyestradiol, also known as 2-ME, is an orally bioavailable estradiol metabolite with potential antineoplastic activity. 2-Methoxyestradiol inhibits angiogenesis by reducing endothelial cell proliferation and inducing endothelial cell apoptosis. This agent also inhibits tumor cell growth by binding to tubulin, resulting in antimitotic activity, and by inducing caspase activation, resulting in cell cycle arrest in the G2 phase, DNA fragmentation, and apoptosis.

相关文献及参考

  • [2]. Aquino-Gálvez A, et al. Effects of 2-methoxyestradiol on apoptosis and HIF-1α and HIF-2α expression in lung cancer cells under normoxia and hypoxia. Oncol Rep. 2016 Jan;35(1):577-83.
  • [3]. Xu L, et al. 2-Methoxyestradiol Alleviates Experimental Autoimmune Uveitis by Inhibiting Lymphocytes Proliferation and T Cell Differentiation. Biomed Res Int. 2016;2016:7948345.
  • [4]. Kang SH, et al. Antitumor effect of 2-methoxyestradiol in a rat orthotopic brain tumor model. Cancer Res. 2006, 66(24),11991-11997.
  • [5]. LaVallee TM, et al. 2-Methoxyestradiol inhibits proliferation and induces apoptosis independently of estrogen receptorsalpha and beta. Cancer Res. 2002 Jul 1;62(13):3691-7.
  • [6]. Chen Y, et al. Oxidative stress induces autophagic cell death independent of apoptosis in transformed and cancer cells. Cell Death Differ. 2008;15(1):171-182.
  • Duber, R., et al. Hypertension 31 , 522-528, (1998) 摘要
  • Klauber, N., et al. Cancer Res

安全信息

GHS Symbol
WGK Germany3
Hazard Codes T,N T
Hazard statements
  • H351 Suspected of causing cancer 怀疑致癌
  • H315 Causes skin irritation 会刺激皮肤
  • H331 Toxic if inhaled 吸入中毒
  • H311 Toxic in contact with skin 皮肤接触中毒
  • H301 Toxic if swallowed 吞食有毒
  • H335 May cause respiratory irritation 可能导致呼吸道刺激
  • H350 May cause cancer 可能致癌
  • H319 Causes serious eye irritation 严重刺激眼睛
  • H360 May damage fertility or the unborn child 可能对生育能力或未出生婴儿造成伤害
  • H372 Causes damage to organs through prolonged or repeated exposure 长期或频繁接触会损伤器官
Personal Protective Equipment Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
RTECSKG7537500
Precautionary statements
  • P273 Avoid release to the environment. 避免释放到环境中。
  • P261 Avoid breathing dust/fume/gas/mist/vapours/spray. 避免吸入粉尘/烟/气体/烟雾/蒸汽/喷雾。
  • P301+P310
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P305+P351+P338
  • P201 Obtain special instructions before use. 使用前获取专门指示。
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
  • P308+P313
  • P405 Store locked up. 上锁保管。
  • P311 Call a POISON CENTER or doctor/physician. 呼叫解毒中心或医生/医师。
  • P281 Use personal protective equipment as required. 使用所需的个人防护装备。
  • P202 Do not handle until all safety precautions have been read and understood. 已阅读并理解所有的安全预防措施之前，切勿操作。
Signal word Danger
Safety Statements
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
  • S22 Do not breathe dust 不要吸入粉尘；
  • S45 In case of accident or if you feel unwell seek medical advice immediately (show the label where possible) 发生事故时或感觉不适时，立即求医（可能时出示标签）；
  • S53 Avoid exposure - obtain special instructions before use 避免接触，使用前获得特别指示说明；
  • S61 Avoid release to the environment. Refer to special instructions/safety data sheet 避免释放到环境中，参考特别指示/安全收据说明书；
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护；
Risk Statements
  • R48 Danger of serious damage to health by prolonged exposure 长期接触有严重损害健康的危险
  • R23/24/25 Toxic by inhalation, in contact with skin and if swallowed 吸入，皮肤接触及吞食都有毒
  • R46 May cause inheritable genetic damage 可能引起遗传基因损害
  • R45 May cause cancer 可能致癌
  • R60 May impair fertility 可能降低生殖能力
  • R61 May cause harm to the unborn child 可能对未出生的婴儿导致伤害
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
  • R51/53
UN Number 3077 UN 3077 9/PG 3
Storage condition -20°C Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). 储存温度-20°C

其他信息

  • 2-Methoxyestradiol
  • 2-Methoxyestradiol (2-MeOE2)使微管解聚，且抑制HIF-1α核积累和HIF转录活性。Phase 2。
  • MOL 文件:362-07-2.mol
  • color:light yellow
  • Sigma Aldrich:362-07-2(sigmaaldrich)

系列性分类

  1. Life Science 生命科学
  2. Cancer Research
  3. Chemopreventive Agents - Cancer Research
  4. Anti-proliferative Agents - Chemopreventive Agents
  1. Analytical & Chromatography 分析化学与色谱
  2. Analytical Standards
  3. Alphabetic - Analytical Standards
  4. M - Alphabetic
  5. META - METH - M
  1. Life Science 生命科学
  2. Cell Biology 细胞生物学
  3. Cell Signaling and Neuroscience - Cell Biology
  4. Cytokines, Growth Factors and Hormones - Cell Signaling and Neuroscience
  5. Hormones - Cytokines, Growth Factors and Hormones
  6. Steroid Hormones - Hormones
  7. Other Steroid Products - Steroid Hormones
  1. Medical Research Areas
  2. Cytosketetal Signaling
  3. Microtubule
  1. Medical Research Areas
  2. PI3K/AKT/mTOR
  3. Caspase
  1. Medical Research Areas
  2. Cytosketetal Signaling
  3. Microtubule/Tubulin  (微管/微管蛋白)
  1. Medical Research Areas
  2. Metabolism
  3. Reactive Oxygen Species  (活性氧)
  1. Medical Research Areas
  2. Metabolism
  3. Endogenous Metabolite  (内源性代谢物)

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