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去氧胆酸

去氧胆酸用途

Deoxycholic acid 激活 G 蛋白偶联胆汁酸受体TGR5。

去氧胆酸名称

[ CAS 号 ]:
83-44-3

[ 中文名 ]:
去氧胆酸

[ 英文名 ]:
Deoxycholic acid

[中文别名 ]:

[英文别名 ]:

7-DEOXYCHOLIC ACID
Cholan-24-oic acid, 3,12-dihydroxy-, (3α,5β,12α)-
5b-Deoxycholic acid
Deoxycholatic acid
EINECS 201-478-5
Deoxycholic acid
deoxy-Cholic acid
(3α,5β,12α)-3,12-Dihydroxycholan-24-oic acid
7α-Deoxycholic acid
Kybella

去氧胆酸生物活性

[ 描述 ]:

Deoxycholic acid 激活 G 蛋白偶联胆汁酸受体TGR5。

[ 相关类别 ]:

信号通路 >> G 蛋白偶联受体/G 蛋白 >> GPCR19

天然产物 >> 类固醇

研究领域 >> 代谢疾病

[ 靶点 ]

Human Endogenous Metabolite

[体外研究]

脱氧胆酸(DCA)和chenoDeoxycholic acid(CDCA)作为十二指肠反流的常见成分,在许多生理和病理过程中起协同作用。将细胞在pH 5.5下反复暴露于100μMCDCA和脱氧胆酸至多120分钟。为了模拟体外慢性局部复发疾病,将胃癌细胞系MGC803暴露于含有100μM脱氧胆酸和CDCA的酸化培养基(pH5.5)中。产生未处理的对数生长MGC803细胞系以用作正常pH培养基中的对照。每天暴露于酸化的胆汁酸10分钟,持续60周后,MGC803抗性细胞在暴露120分钟后能够存活并增殖[2]。

[细胞实验]

MGC803细胞在Roswell Park Memorial Institute培养基中培养，所述培养基补充有10％胎牛血清和100U / mL青霉素和100mg / mL链霉素。为了产生MGC803抗性细胞，使用盐酸（A）将MGC803培养基的pH值调节至实验条件。用培养基将胆汁酸GCDA和脱氧胆酸稀释至100μM（B）的最佳工作浓度，并将总pH（A + B）调节至pH5.5，模拟胃环境。最初，MGC803细胞长期暴露于含有胆汁酸（A + B）的酸化培养基中，每24小时一次。在我们的初步实验中优化了实验时间和条件，其显示10分钟足够并且不会导致细胞损伤。重复该过程，MGC803细胞在A + B暴露120分钟后存活并增殖需要60周。对照未处理的细胞在pH7.4的中性RPMI培养基中与抗性细胞平行培养60周。在30和60周时，记录了暴露于酸化胆汁酸（A + B）的MGC803细胞的形态变化[2]。

[参考文献]

[1]. Somm E, et al. β-Klotho deficiency protects against obesity through a crosstalk between liver, microbiota, and brown adipose tissue. JCI Insight. 2017 Apr 20;2(8). pii: 91809.

[2]. Wang X, et al. Acidified bile acids enhance tumor progression and telomerase activity of gastric cancer in micedependent on c-Myc expression. Cancer Med. 2017 Apr;6(4):788-797.

[相关活性小分子]

去氧胆酸物理化学性质

[ 密度 ]:
1.1±0.1 g/cm3

[ 沸点 ]:
547.1±35.0 °C at 760 mmHg

[ 熔点 ]:
171-174 °C(lit.)

[ 分子式 ]:
C₂₄H₄₀O₄

[ 分子量 ]:
392.572

[ 闪点 ]:
298.8±22.4 °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 ]:
室温

[ 水溶解性 ]:
0.24 g/L (15 ºC)

去氧胆酸MSDS

详细MSDS(安全技术说明书)

去氧胆酸毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: FZ2100000

CHEMICAL NAME :: 5-beta-Cholan-24-oic acid, 3-alpha,12-alpha-dihydroxy-

CAS REGISTRY NUMBER :: 83-44-3

BEILSTEIN REFERENCE NO. :: 3219882

LAST UPDATED :: 199701

DATA ITEMS CITED :: 15

MOLECULAR FORMULA :: C24-H40-O4

MOLECULAR WEIGHT :: 392.64

WISWESSER LINE NOTATION :: L E5 B666TJ A1 DQ E1 FY1&2VQ 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 :: 1 gm/kg

TOXIC EFFECTS :: Behavioral - food intake (animal) Nutritional and Gross Metabolic - weight loss or decreased weight gain

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

ROUTE OF EXPOSURE :: Oral

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 :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 130 mg/kg

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

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 2 gm/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 :: Administration onto the skin

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2700 mg/kg/10W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Skin and Appendages - tumors

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1120 mg/kg/22W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Tumorigenic - tumors at site of application

TYPE OF TEST :: TD - Toxic dose (other than lowest)

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1400 mg/kg/22W-I

TOXIC EFFECTS :: Tumorigenic - equivocal tumorigenic agent by RTECS criteria Tumorigenic - tumors at site of application

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 166 mg/kg

SEX/DURATION :: female 12-19 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

MUTATION DATA

TYPE OF TEST :: Morphological transformation

TEST SYSTEM :: Rodent - hamster Embryo

DOSE/DURATION :: 7250 ug/L

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 9,177,1981 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 80398 No. of Facilities: 153 (estimated) No. of Industries: 2 No. of Occupations: 7 No. of Employees: 3527 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 80398 No. of Facilities: 82 (estimated) No. of Industries: 2 No. of Occupations: 5 No. of Employees: 2416 (estimated) No. of Female Employees: 1577 (estimated)

去氧胆酸安全信息

[ 符号 ]:

GHS07

[ 信号词 ]:
Warning

[ 危害声明 ]:
H302

[ 警示性声明 ]:
P301 + P312 + P330

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

[ 危害码 (欧洲) ]:
Xn:Harmful

[ 风险声明 (欧洲) ]:
R22;R36/37/38

[ 安全声明 (欧洲) ]:
S26-S36-S37/39

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

[ WGK德国 ]:
3

[ RTECS号 ]:
FZ2100000

去氧胆酸合成路线

详细合成路线

去氧胆酸上下游产品

去氧胆酸上游产品

去氧胆酸下游产品

去氧胆酸制备

1.牛胆水解液加入氢氧化钠和40%水溶液于80-90℃,搅拌2h，冷却至20℃，过滤后滤液用50%硫酸在10℃调节至ph值1.5，滤集沉淀用水洗至中性。湿滤饼在40℃以乙酸乙酯和苯混合溶液（1∶1）搅拌，趁热滤
去不溶物，冷却，溶液中析出晶体即为成品。

去氧胆酸文献

MicroRNA-99a and 100 mediated upregulation of FOXA1 in bladder cancer.

Oncotarget 5(15) , 6375-86, (2014)

Urothelial cell carcinoma of the bladder (UCC) is a common disease often characterized by FGFR3 dysregulation. Whilst upregulation of this oncogene occurs most frequently in low-grade non-invasive tum...

Involvement of epigenetics and EMT-related miRNA in arsenic-induced neoplastic transformation and their potential clinical use.

Cancer Prev. Res. (Phila.) 8(3) , 208-21, (2015)

Exposure to toxicants leads to cumulative molecular changes that overtime increase a subject's risk of developing urothelial carcinoma. To assess the impact of arsenic exposure at a time progressive m...

MicroRNA expression profiles associated with acquired gefitinib-resistance in human lung adenocarcinoma cells.

Mol. Med. Report. 11(1) , 333-40, (2014)

The aim of the present study was to establish, characterize and elucidate the potential mechanisms of acquired gefitinb resistance, using the A549 human lung cancer cell line. A gefitinib-resistant A5...

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