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鹅去氧胆酸； 鹅脱氧胆酸

鹅去氧胆酸； 鹅脱氧胆酸用途

Chenodeoxycholic Acid 是一种疏水初级胆汁酸,能够活化核受体 FXR,该受体与胆固醇代谢有关。
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鹅去氧胆酸； 鹅脱氧胆酸名称

[ CAS 号 ]:
474-25-9

[ 中文名 ]:
鹅去氧胆酸

[ 英文名 ]:
Chenodeoxycholic acid

[中文别名 ]:

[英文别名 ]:

鹅去氧胆酸； 鹅脱氧胆酸生物活性

[ 描述 ]:

Chenodeoxycholic Acid 是一种疏水初级胆汁酸,能够活化核受体 FXR,该受体与胆固醇代谢有关。

[ 相关类别 ]:

信号通路 >> 代谢酶/蛋白酶 >> FXR
天然产物 >> 酸和醛
研究领域 >> 代谢疾病

[ 靶点 ]

Human Endogenous Metabolite


[体外研究]

Chenodeoxycholic acid(CDCA)和Deoxycholic acid(DCA)均抑制11 beta HSD2,IC50值分别为22 mM和38 mM,并引起皮质醇依赖性核转位,并增加盐皮质激素受体(MR)的转录活性[1]。 Chenodeoxycholic acid能够通过激活膜G蛋白偶联受体(TGR5)依赖性途径诱导Cyclin D1蛋白和mRNA表达的显着增加来刺激Ishikawa细胞生长[2]。在培养的人肝母细胞瘤细胞系Hep G2中,Chenodeoxycholic acid(CDCA)诱导LDL受体mRNA水平约4倍,HMG-CoA还原酶和HMG-CoA合酶的mRNA水平增加2倍[3]。布美他尼,BaCl2和囊性纤维化跨膜传导调节因子(CFTR)抑制剂CFTRinh-172对Chenodeoxycholic acid诱导的Isc有抑制作用(≥67％)。腺苷酸环化酶抑制剂MDL12330A使鹅去氧胆酸刺激的Isc降低43％,而鹅去氧胆酸可增加细胞内cAMP浓度[4]。 Chenodeoxycholic acid处理激活C /EBPβ,如其磷酸化,核积累和HepG2细胞中的表达增加所示。 Chenodeoxycholic acid增强含有-1.65-kb GSTA2启动子的构建体的荧光素酶基因转录,该启动子含有C/EBP反应元件(pGL-1651)。 Chenodeoxycholic acid治疗激活AMP激活蛋白激酶(AMPK),导致细胞外信号调节激酶1/2(ERK1/2)激活,使用AMPKα和化学抑制剂的显性阴性突变体的实验结果证明[ 5]。

[激酶实验]

简言之，将转染的HEK-293细胞在炭处理的Dulbecco改良的Eagle培养基中培养24小时，用Hanks溶液洗涤一次，并重悬于含有100mM NaCl，1mM MgCl 2,1mM EDTA，1mM EGTA的缓冲液中， 250mM蔗糖，20mM Tris-HCl，pH7.4。通过在液氮中冷冻来裂解细胞。测定脱氢酶活性，终体积为20μL，含有适当浓度的胆汁酸，30nCi的[3H]皮质醇和未标记的皮质醇，最终浓度为50nM。通过将细胞裂解物与反应混合物混合来开始反应。或者，从转染的HEK-293细胞制备内质网微粒体，并与含有各种浓度的皮质醇和CDCA的反应混合物一起温育。孵育进行20分钟，并且通过薄层色谱（TLC）测定皮质醇向可的松的转化。由于低转化率下TLC方法的不准确性以及转化率高于60-70％时11βHSD2的终产物抑制，因此仅考虑10％至60％的转化率进行计算。使用曲线拟合程序评估抑制常数IC50。结果表示为平均值±SE，并且包括至少四次独立测量。

[细胞实验]

通过将转染的HEK-293细胞和CHO细胞与相应浓度的胆汁酸一起孵育1小时并用台盼蓝染色来分析细胞活力。根据细胞增殖试剂盒I，使用四唑盐MTT（溴化3-（4,5-二甲基噻唑-2-基）-2,5-二苯基四唑鎓）分析胆汁酸的毒性。对照和胆汁酸之间无显着差异在两个测试中获得经处理的细胞。

[参考文献]

[1]. Stauffer AT, et al. Chenodeoxycholic acid and deoxycholic acid inhibit 11 beta-hydroxysteroid dehydrogenase type 2 and cause cortisol-induced transcriptional activation of the mineralocorticoid receptor. J Biol Chem. 2002 Jul 19;277(29):26286-92

[2]. Casaburi I, et al. Chenodeoxycholic acid through a TGR5-dependent CREB signaling activation enhances cyclin D1 expression and promotes human endometrial cancer cell proliferation. Cell Cycle. 2012 Jul 15;11(14):2699-710

[3]. Kawabe Y, et al. The molecular mechanism of the induction of the low density lipoprotein receptor by chenodeoxycholic acid in cultured human cells. Biochem Biophys Res Commun. 1995 Mar 8;208(1):405-11.

[4]. Ao M, et al. Chenodeoxycholic acid stimulates Cl(-) secretion via cAMP signaling and increases cystic fibrosis transmembrane conductance regulator phosphorylation in T84 cells. Am J Physiol Cell Physiol. 2013 Aug 15;305(4):C447-56

[5]. Noh K, et al. Farnesoid X receptor activation by chenodeoxycholic acid induces detoxifying enzymes through AMP-activated protein kinase and extracellular signal-regulated kinase 1/2-mediated phosphorylation of CCAAT/enhancer binding protein β. Drug Metab


[相关活性小分子]

3-甲基腺嘌呤 | 氢化可的松 | 奥贝胆酸 | N-乙酰半胱氨酸 | 维生素A酸； 视黄酸 | 褪黑素 | 地诺前列酮 | 3-(2,6-二氯苯基)-4-(3'-羧基-2-氯二苯乙烯-4-基)氧甲基-5-异丙基异恶唑 | 烟酰胺 | 5'-三磷酸腺苷 | 对乙酰氨基苯酚 | 列腺素 E1 | N-(2,2,2-三氟乙基)-N-[4-[2,2,2-三氟-1-羟基-1-(三氟甲基)乙基]苯基]-苯磺酰胺 | 去氢表雄酮 | 肾上腺酮

鹅去氧胆酸； 鹅脱氧胆酸物理化学性质

[ 密度 ]:
1.1±0.1 g/cm3

[ 沸点 ]:
547.1±25.0 °C at 760 mmHg

[ 熔点 ]:
165-167 °C(lit.)

[ 分子式 ]:
C24H40O4

[ 分子量 ]:
392.572

[ 闪点 ]:
298.8±19.7 °C

[ 精确质量 ]:
392.292664

[ PSA ]:
77.76000

[ LogP ]:
4.66

[ 外观性状 ]:
白色至灰白色结晶粉末

[ 蒸汽压 ]:
0.0±3.3 mmHg at 25°C

[ 折射率 ]:
1.543

[ 储存条件 ]:
库房低温通风干燥

[ 水溶解性 ]:
PRACTICALLY INSOLUBLE

鹅去氧胆酸； 鹅脱氧胆酸MSDS

详细MSDS(安全技术说明书)

鹅去氧胆酸； 鹅脱氧胆酸毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :
FZ1980000
CHEMICAL NAME :
5-beta-Cholan-24-oic acid, 3-alpha,7-alpha-dihydroxy-
CAS REGISTRY NUMBER :
474-25-9
LAST UPDATED :
199806
DATA ITEMS CITED :
30
MOLECULAR FORMULA :
C24-H40-O4
MOLECULAR WEIGHT :
392.64
WISWESSER LINE NOTATION :
L E5 B666TJ A1 E1 FY1&2VQ KQ 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 :
4 gm/kg
TOXIC EFFECTS :
Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - dyspnea Gastrointestinal - hypermotility, diarrhea
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
105 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Gastrointestinal - other changes Skin and Appendages - hair
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>4 gm/kg
TOXIC EFFECTS :
Blood - changes in spleen Skin and Appendages - hair
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
106 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Behavioral - ataxia
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>500 mg/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 :
>2 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 :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
86 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Gastrointestinal - hypermotility, diarrhea Gastrointestinal - other changes
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>4 gm/kg
TOXIC EFFECTS :
Gastrointestinal - ulceration or bleeding from small intestine Skin and Appendages - hair
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
100 mg/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 :
Intramuscular
SPECIES OBSERVED :
Rodent - mouse
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 :
Mammal - dog
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 - hamster
DOSE/DURATION :
500 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 :
3750 mg/kg/30D-C
TOXIC EFFECTS :
Endocrine - changes in adrenal weight Related to Chronic Data - changes in prostate weight Related to Chronic Data - changes in testicular weight
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
45500 mg/kg/26W-C
TOXIC EFFECTS :
Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - phosphatases Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
18200 mg/kg/52W-C
TOXIC EFFECTS :
Liver - other changes Liver - changes in liver weight
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
24 gm/kg/5Y-C
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Liver - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
100 mg/kg
SEX/DURATION :
male 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1785 mg/kg
SEX/DURATION :
female 4-20 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - hepatobiliary system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
550 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Effects on Newborn - physical
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1375 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
3480 mg/kg
SEX/DURATION :
female 15-22 day(s) after conception lactating female 21 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
14820 mg/kg
SEX/DURATION :
female 31 week(s) pre-mating female 1-24 week(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - hepatobiliary system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1500 mg/kg
SEX/DURATION :
female 21-45 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - hepatobiliary system Reproductive - Specific Developmental Abnormalities - endocrine system Reproductive - Specific Developmental Abnormalities - urogenital system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
1500 mg/kg
SEX/DURATION :
female 21-45 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - physical
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
260 mg/kg
SEX/DURATION :
female 6-18 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 - litter size (e.g. # fetuses per litter; measured before birth) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

MUTATION DATA

TYPE OF TEST :
DNA adduct
TEST SYSTEM :
Mammal - species unspecified Lymphocyte
DOSE/DURATION :
10 mg/L
REFERENCE :
CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House, Southfield Road, Eynsham, Oxford OX8 1JJ, UK) V.1- 1980- Volume(issue)/page/year: 15,1911,1994
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鹅去氧胆酸； 鹅脱氧胆酸安全信息

[ 符号 ]:

GHS07

[ 信号词 ]:
Warning

[ 危害声明 ]:
H315-H319

[ 警示性声明 ]:
P305 + P351 + P338

[ 个人防护装备 ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ 危害码 (欧洲) ]:
Xn:Harmful

[ 风险声明 (欧洲) ]:
R63

[ 安全声明 (欧洲) ]:
S22-S24/25-S45-S36/37

[ 危险品运输编码 ]:
NONH for all modes of transport

[ WGK德国 ]:
2

[ RTECS号 ]:
FZ1980000

[ 海关编码 ]:
2918990090

鹅去氧胆酸； 鹅脱氧胆酸上下游产品

鹅去氧胆酸； 鹅脱氧胆酸上游产品

鹅去氧胆酸； 鹅脱氧胆酸下游产品

鹅去氧胆酸； 鹅脱氧胆酸制备

1.取新鲜或冷冻的鸡（或鸭、鹅）胆汁，加入1/10量的工业氢氧化钠，加热煮沸20～24h，并不断补充蒸发的水量，冷却，再用盐酸调pH值为2～3，出现黑色膏状物。静置分层后，取出膏状物，水洗至中性，得总胆汁酸。总胆汁酸中加入2倍量95%乙醇和10%活性炭，加热回流2～3h，趁热过滤。滤液冷却，再加入等体积120号汽油萃取3次脱脂，静置分层，分出下层液体进行减压浓缩，得膏状物。加入大量水到膏状物中，析出沉淀，用水将沉淀洗涤至无色。然后向沉淀物中加入2倍量95%乙醇及5%的氢氧化钠溶液，调节pH=8.5，加热回流2h。再按每升150g的量加入氯化钡，加热回流2h，趁热过滤，滤液浓缩至呈现晶膜或浑浊时，放冷，析出晶体，抽滤，水洗，减压干燥，可得白色鹅去氧胆酸钡盐结晶。再将钡盐用水溶解，并加入含钡盐12%左右的碳酸钠，加热搅拌，过滤，弃去碳酸钡沉淀，滤液再用盐酸调pH=2～3，析出沉淀，过滤，滤饼水洗至中性，干燥，可得鹅去氧胆酸成品。必要时可再用乙酸乙酯重结晶1～2次。

也有采用氯化钙盐提取的方法。
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鹅去氧胆酸； 鹅脱氧胆酸海关

[ 海关编码 ]: 2918990090

[ 中文概述 ]:
2918990090. 其他含其他附加含氧基羧酸（包括酸酐、酰卤化物、过氧化物和过氧酸及该税号的衍生物）. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:30.0%

[ 申报要素 ]: 品名, 成分含量, 用途

[ Summary ]:
2918990090. other carboxylic acids with additional oxygen function and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

鹅去氧胆酸； 鹅脱氧胆酸文献

Transcriptional Regulation of Cytosolic Sulfotransferase 1C2 by Intermediates of the Cholesterol Biosynthetic Pathway in Primary Cultured Rat Hepatocytes.

J. Pharmacol. Exp. Ther. 355 , 429-41, (2015)

Cytosolic sulfotransferase 1C2 (SULT1C2) is expressed in the kidney, stomach, and liver of rats; however, the mechanisms regulating expression of this enzyme are not known. We evaluated transcriptiona...

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...

Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).

J. Sci. Ind. Res. 65(10) , 808, (2006)

Drug-induced liver injury (DILI) is a significant concern in drug development due to the poor concordance between preclinical and clinical findings of liver toxicity. We hypothesized that the DILI typ...


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