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去氢表雄酮

去氢表雄酮用途

DHEA是最丰富的类固醇激素之一。 DHEA通过多种信号传导途径介导其作用,并通过转化成雄激素和雌激素衍生物(例如,雄激素,雌激素,7α和7β DHEA,以及7α和7β表雄甾酮衍生物)通过其特异性受体起作用。

去氢表雄酮名称

[ CAS 号 ]:
53-43-0

[ 中文名 ]:
去氢表雄酮

[ 英文名 ]:
Dehydroepiandrosterone

[中文别名 ]:

[英文别名 ]:

3β-Hydroxy-androst-5-ene-17-one
DHEA
17-Hormoforin
3-β-hydroxyandrost-5-en-17-one
3b-hydroxy-Androst-5-en-17-one
(3b)-3-Hydroxyandrost-5-en-17-one
3β-hydroxy-androst-5-en-17-one
(3β)-3-hydroxy-Androst-5-en-17-one
D5-Androsten-3b-ol-17-one
(3β)-3-Hydroxyandrost-5-en-17-one

去氢表雄酮生物活性

[ 描述 ]:

[ 相关类别 ]:

信号通路 >> 其他 >> 雄激素受体

天然产物 >> 类固醇

研究领域 >> 内分泌

[ 靶点 ]

Human Endogenous Metabolite

[体外研究]

DHEA是一种有效的抗细胞凋亡因子,可逆转前列腺癌细胞(DU145和LNCaP细胞系)以及结肠癌细胞(Caco2细胞系)中血清剥夺诱导的细胞凋亡。 DHEA显着降低所有3种癌细胞类型中血清剥夺诱导的细胞凋亡,用APOPercentage测定法定量(分别用DHEA或NGF处理12小时后细胞凋亡从0.587±0.053降至0.142±0.0016或0.059±0.002; n = 3,P <0.01),并通过流式细胞术分析(FACS)检测DU145细胞。 DHEA的抗细胞凋亡作用是剂量依赖性的,纳摩尔浓度下的EC50(分别在DU145和Caco2细胞中EC50：11.2±3.6nM和12.4±2.2nM)[1]。 DHEA是人类的主要性类固醇前体,可以直接转化为雄激素。如通过胸苷掺入测定所评估的,DHEA(≥1μM)引起Chub-S7增殖的剂量依赖性抑制。 DHEA处理以剂量依赖性方式抑制关键的糖皮质激素调节基因H6PDH(≥100nM)和HSD11B1(≥1μM)在分化前脂肪细胞中的表达。与此结果一致,DHEA处理(≥1μM)导致11β-HSD1氧化还原酶活性(≥1μM)显着降低,并且在分化的脂肪细胞中使用的最高DHEA剂量(25μMDHEA)下脱氢酶活性同时增加[2]。

[体内研究]

与喂食对照AIN-76A饮食的小鼠相比,处理8周的雄性B6小鼠(5只小鼠组)的饮食中的DHEA(0.45％w/w)导致体温显着降低。类似的比较表明对照和配对喂养的小鼠也有显着差异。喂食DHEA的动物的温度显着低于喂食对照饮食的小鼠26/29次测试;饲喂DHEA饮食的小鼠对受影响较小,8/29值显着低于随意喂食AIN-76A的小鼠。喂食DHEA或喂食DHEA的小鼠的温度在测试中显着不同21/29倍。喂食对照饮食的小鼠的体重显着高于喂食DHEA或喂给DHEA的小鼠的体重。除第9周(n = 3)外,每周平均摄取来自笼子的食物摄入量(克/天)(n = 7)。喂食DHEA的小鼠的食物摄入量显着减少。通过设计,喂给DHEA的小鼠配对吃了大约相同的量。因此,似乎DHEA通过食物限制和单独的机制降低体温[3]。

[激酶实验]

将Chub-S7细胞在含有冷DHEA（20nM）和氚化DHEA（0.2μCi/孔）的DMEM中孵育48小时。温育后，使用二氯甲烷萃取类固醇，使用正己烷/ 1-己醇（75:25）作为流动相系统，通过薄层色谱法分离。通过与未标记的参考类固醇的迁移来鉴定代谢物，所述类固醇通过暴露于Lieberman-Burchard试剂（乙醇 - 乙酸酐 - 硫酸）可视化。使用LabLogic AR-200扫描仪量化类固醇转化。使用比色96孔板测定法测量蛋白质浓度并用于标准化转化。活动表示为转化百分比[2]。

[细胞实验]

将Chub-S7前脂肪细胞和人原代前脂肪细胞分别以密度1×105和2.5×105接种到24孔板中。过夜培养后，培养基补充有DHEA，雄烯二醇或DHEAS（0-100μM）。孵育24,48或72小时后，通过与放射性标记的胸苷（0.2μCi/孔）一起温育培养最后6小时来评估细胞增殖。用TCA沉淀蛋白质，并在NaOH中刮擦细胞。通过闪烁计数分析所得裂解物中放射性标记的核材料的相应含量。数据表示为对照的百分比[2]。

[动物实验]

小鼠[3]给小鼠喂食Purina Lab Chow直到实验开始（第0天）。然后在0900和1000小时之间喂食5只小鼠的组，其中含有无添加剂或DHEA（0.45％w / w）的沉淀的AIN-76A饮食。饮食在4°C下储存不超过六个月，以保持最佳活动。除了对用DHEA处理的小鼠配对喂养的小鼠外，小鼠随意给予饮食。饲喂配对喂养的小鼠的AIN-76A饮食量由每天喂食DHEA的小鼠消耗的食物重量决定。从第1天开始到第59天结束的不同时间点测量体重（克）。通过称重每只5只小鼠的食物消耗来确定每日食物摄入量（克/天）。计算第1周至第8周的平均值±SEM值（n = 7）;第9周只有3天。

[参考文献]

[1]. Anagnostopoulou V, et al. Differential effects of dehydroepiandrosterone and testosterone in prostate and colon cancer cell apoptosis: the role of nerve growth factor (NGF) receptors. Endocrinology. 2013 Jul;154(7):2446-56.

[2]. McNelis JC, et al. Dehydroepiandrosterone exerts anti-glucocorticoid action on human preadipocyte proliferation, differentiation and glucose uptake. Am J Physiol Endocrinol Metab. 2013 Nov 1;305(9):E1134-44.

[3]. Catalina F, et al. Decrease of core body temperature in mice by dehydroepiandrosterone. Exp Biol Med (Maywood). 2002 Jun;227(6):382-8.

[相关活性小分子]

去氢表雄酮物理化学性质

[ 密度 ]:
1.1±0.1 g/cm3

[ 沸点 ]:
426.7±45.0 °C at 760 mmHg

[ 熔点 ]:
146-151ºC

[ 分子式 ]:
C₁₉H₂₈O₂

[ 分子量 ]:
288.424

[ 闪点 ]:
182.1±21.3 °C

[ 精确质量 ]:
288.208923

[ PSA ]:
37.30000

[ LogP ]:
3.42

[ 外观性状 ]:
白色细结晶粉末

[ 蒸汽压 ]:
0.0±2.3 mmHg at 25°C

[ 折射率 ]:
1.560

[ 储存条件 ]:
库房通风低温干燥

去氢表雄酮MSDS

详细MSDS(安全技术说明书)

去氢表雄酮毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: BV8396000

CHEMICAL NAME :: Androst-5-en-17-one, 3-beta-hydroxy-

CAS REGISTRY NUMBER :: 53-43-0

BEILSTEIN REFERENCE NO. :: 2058110

LAST UPDATED :: 199707

DATA ITEMS CITED :: 18

MOLECULAR FORMULA :: C19-H28-O2

MOLECULAR WEIGHT :: 288.47

WISWESSER LINE NOTATION :: L E5 B666 FV LUTJ A1 E1 OQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >10 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >10 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 900 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 159 gm/kg/84W-C

TOXIC EFFECTS :: Tumorigenic - Carcinogenic by RTECS criteria Liver - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 25 gm/kg/52D-C

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Reproductive - Tumorigenic effects - ovarian tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Implant

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 400 mg/kg/50D-C

TOXIC EFFECTS :: Tumorigenic - neoplastic by RTECS criteria Reproductive - Tumorigenic effects - ovarian tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1800 mg/kg

SEX/DURATION :: female 2-19 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - abortion

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 300 mg/kg

SEX/DURATION :: female 15-20 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 357 mg/kg

SEX/DURATION :: male 10 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - prostate, seminal vesicle, Cowper's gland, accessory glands

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 300 mg/kg

SEX/DURATION :: female 20 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Maternal Effects - menstrual cycle changes or disorders

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 600 mg/kg

SEX/DURATION :: female 10 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - other effects Endocrine - changes in luteinizing hormone Endocrine - estrogenic

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 240 mg/kg

SEX/DURATION :: female 13-20 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - endocrine system Reproductive - Specific Developmental Abnormalities - urogenital system

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 240 mg/kg

SEX/DURATION :: female 13-20 day(s) after conception

TOXIC EFFECTS :: Reproductive - Maternal Effects - ovaries, fallopian tubes

TYPE OF TEST :: Unscheduled DNA synthesis

MUTATION DATA

TEST SYSTEM :: Rodent - rat

DOSE/DURATION :: 3780 mg/kg/14D (Continuous)

REFERENCE :: CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 52,2977,1992 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 81794 No. of Facilities: 28 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 700 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 81794 No. of Facilities: 39 (estimated) No. of Industries: 1 No. of Occupations: 3 No. of Employees: 2085 (estimated) No. of Female Employees: 1457 (estimated)

去氢表雄酮安全信息

[ 符号 ]:

GHS02, GHS06, GHS08

[ 信号词 ]:
Danger

[ 危害声明 ]:
H225-H301 + H311 + H331-H370

[ 警示性声明 ]:
P210-P260-P280-P301 + P310-P311

[ 个人防护装备 ]:
dust mask type N95 (US);Eyeshields;Gloves

[ 危害码 (欧洲) ]:
Xi: Irritant;

[ 风险声明 (欧洲) ]:
R36/37/38

[ 安全声明 (欧洲) ]:
S24/25

[ 危险品运输编码 ]:
UN1230 - class 3 - PG 2 - Methanol, solution

[ WGK德国 ]:
2

[ RTECS号 ]:
BV8396000

[ 海关编码 ]:
2937290090

去氢表雄酮合成路线

详细合成路线

去氢表雄酮上下游产品

去氢表雄酮上游产品

去氢表雄酮下游产品

去氢表雄酮制备

3β-羟基-5-雄烯-17-酮，亦称脱氢表雄酮，缩写DHA或DHEA。具有较弱的雄性激素作用，可以从尿中检测出来，经常以硫酸酯形态排出。

去氢表雄酮海关

[ 海关编码 ]: 2937290014

[ 中文概述 ]:
HS:2937290014 达那唑;脱氢氯甲基睾酮〔包括雄-1-烯-3,17-二酮;(Δ)雄烯二醇;普拉睾酮;去氧甲基睾酮〕增值税率:17.0% 退税率:9.0% 监管条件:L 最低关税:4.0% 普通关税:30.0%

[ 申报要素 ]: 品名, 成分含量, 用途, 包装

[ 监管条件 ]: L.药品进出口准许证

[ Summary ]:
HS:2937290014 (3s,8r,9s,10r,13s,14s)-3-hydroxy-10,13-dimethyl-3,4,7,8,9,10,11,12,13,14,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17(2h)-one VAT:17.0% Tax rebate rate:9.0% Supervision conditions:l MFN tariff:4.0% General tariff:30.0%

去氢表雄酮文献

Assessment of the potential of polyphenols as a CYP17 inhibitor free of adverse corticosteroid elevation.

Biochem. Pharmacol. 90(3) , 288-96, (2014)

Inhibition of 17α-hydroxylase/17,20-lyase (CYP17), which dictates the proceeding of androgen biosynthesis, is recommended as an effective treatment for androgen-dependent diseases. However, androgen d...

Mechanistic Scrutiny Identifies a Kinetic Role for Cytochrome b5 Regulation of Human Cytochrome P450c17 (CYP17A1, P450 17A1).

PLoS ONE 10 , e0141252, (2015)

Cytochrome P450c17 (P450 17A1, CYP17A1) is a critical enzyme in the synthesis of androgens and is now a target enzyme for the treatment of prostate cancer. Cytochrome P450c17 can exhibit either one or...

Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.

Chem. Res. Toxicol. 23 , 171-83, (2010)

Drug-induced liver injury is one of the main causes of drug attrition. The ability to predict the liver effects of drug candidates from their chemical structures is critical to help guide experimental...

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