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2-脱氧-D-葡萄糖

2-脱氧-D-葡萄糖用途

2-Deoxy-D-glucose 是一种葡萄糖类似物,为葡萄糖代谢抑制剂,通过作用于己糖激酶 (hexokinase) 来抑制糖酵解。

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2-脱氧-D-葡萄糖名称

[ CAS 号 ]:
154-17-6

[ 中文名 ]:
D-2-脱氧葡萄糖

[ 英文名 ]:
2-Deoxy-D-glucose

[中文别名 ]:

[英文别名 ]:

2-DEOXY-D-ARABINOHEXOSE
D-arabino-Hexose, 2-deoxy-
2-Deoxy-D-arabino-hexose
2-Deoxy-D-glucose
2-deoxy-d-arabino-hexos
MFCD00151328
D-Arabino-2-deoxyhexose
EINECS 205-823-0

2-脱氧-D-葡萄糖生物活性

[ 描述 ]:

2-Deoxy-D-glucose 是一种葡萄糖类似物,为葡萄糖代谢抑制剂,通过作用于己糖激酶 (hexokinase) 来抑制糖酵解。

[ 相关类别 ]:

信号通路 >> 代谢酶/蛋白酶 >> 己糖激酶

研究领域 >> 癌症

[体外研究]

2-脱氧-D-葡萄糖(2-DG,4,8或16mM)以剂量和时间依赖性方式显着降低MCF-7细胞中的ATP水平,与2-DG对细胞的作用平行生长。磷酸化Akt的水平显着降低,而磷酸化的AMPK和Sirt-1的水平在暴露于2-脱氧-D-葡萄糖的4-8或16mM的MCF-7细胞中显着增加1,3或5天,以剂量和时间依赖的方式[1]。 2-DG处理增加磷酸戊糖途径(PPP)代谢物的水平并增加葡萄糖-6-磷酸脱氢酶产生NADPH。 NADPH的增加和谷胱甘肽合成酶表达的上调导致NB4细胞中2-DG还原形式的谷胱甘肽增加[3]。

[体内研究]

2-脱氧-D-葡萄糖(0.03％,w/w)导致最终重量减少7％,这在统计学上是显着的,并且延迟了可触知的乳腺癌的出现[1]。 2-脱氧-D-葡萄糖(3 mmol/kg,iv)通过大鼠肌肉中的胰岛素以剂量依赖性方式降低[2]。

[细胞实验]

通过评估贴壁细胞的数量来确定2-DG对细胞生长的影响。简而言之，在培养条件下，将MCF-7细胞以每孔3×10 4个细胞接种在平底96孔板中的100μL培养基中。 24小时后，向细胞中加入含有0,4,8或16mM剂量的2-脱氧-D-葡萄糖的新鲜培养基。在暴露于2-脱氧-D-葡萄糖后的第1,3和5天，将细胞用1％戊二醛固定，用PBS替换，并在4℃下储存。在实验结束时，将所有板用0.02％结晶紫水溶液染色30分钟并用去离子水冲洗。在70％乙醇中重新溶解结合的结晶紫后，使用SPECTRA MAX PLUS微孔板分光光度计系统测定590nm处的吸光度。

[动物实验]

在21日龄时，给大鼠每千克体重（ip）注射50mg 1-甲基-1-亚硝基脲。将大鼠每笼饲养在装有食物杯的固体底聚碳酸酯笼中。注射致癌物质后6天，将所有大鼠随机分成三组中的一组，每组30只大鼠，并随意喂食含有0.0％，0.02％或0.03％（w / w）2-脱氧-D的AIN-93G饮食。 - 葡萄糖（2-DG），持续5周。动物室保持在22±1℃，50％相对湿度和12小时光照/ 12小时黑暗循环。每周称重大鼠三次，并且从致癌后19天开始每周两次触诊以检测乳腺肿瘤。

[参考文献]

[1]. Zhu Z, et al. 2-Deoxyglucose as an energy restriction mimetic agent: effects on mammary carcinogenesis and on mammary tumor cell growth in vitro. Cancer Res. 2005 Aug 1;65(15):7023-30.

[2]. Ueyama A, et al. Nonradioisotope assay of glucose uptake activity in rat skeletal muscle using enzymatic measurement of 2-deoxyglucose 6-phosphate in vitro and in vivo. Biol Signals Recept. 2000 Sep-Oct;9(5):267-74.

[3]. Miwa H, et al. Leukemia cells demonstrate a different metabolic perturbation provoked by 2-deoxyglucose. Oncol Rep. 2013 May;29(5):2053-7.

[相关活性小分子]

3-溴丙酮酸 | 氯尼达明

2-脱氧-D-葡萄糖物理化学性质

[ 密度 ]:
1.4±0.1 g/cm3

[ 沸点 ]:
456.7±45.0 °C at 760 mmHg

[ 熔点 ]:
146-147ºC

[ 分子式 ]:
C₆H₁₂O₅

[ 分子量 ]:
164.156

[ 闪点 ]:
244.1±25.2 °C

[ 精确质量 ]:
164.068466

[ PSA ]:
97.99000

[ LogP ]:
-3.07

[ 外观性状 ]:
白色粉末

[ 蒸汽压 ]:
0.0±2.5 mmHg at 25°C

[ 折射率 ]:
1.534

[ 储存条件 ]:
2~8℃

2-脱氧-D-葡萄糖MSDS

详细MSDS(安全技术说明书)

2-脱氧-D-葡萄糖毒性和生态

CHEMICAL IDENTIFICATION

RTECS NUMBER :: MQ3325000

CHEMICAL NAME :: D-arabino-Hexose, 2-deoxy-

CAS REGISTRY NUMBER :: 154-17-6

BEILSTEIN REFERENCE NO. :: 1723331

LAST UPDATED :: 199701

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C6-H12-O5

MOLECULAR WEIGHT :: 164.18

WISWESSER LINE NOTATION :: VH1YQYQYQ1Q -D-ARABINO

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

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

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 250 mg/kg

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

REFERENCE :: APFRAD Annales Pharmaceutiques Francaises. (SPPIF, B.P.22, F-41353 Vineuil, France) V.1- 1943- Volume(issue)/page/year: 39,327,1981

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

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 2 gm/kg

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

REFERENCE :: JPPMAB Journal of Pharmacy and Pharmacology. (Pharmaceutical Soc. of Great Britain, 1 Lambeth High St., London SEI 7JN, UK) V.1- 1949- Volume(issue)/page/year: 17,814,1965 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2 gm/kg

SEX/DURATION :: female 7-8 day(s) after conception

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

REFERENCE :: 85DJA5 "Malformations Congenitales des Mammiferes," Tuchmann-Duplessis, H., Paris, Masson et Cie, 1971 Volume(issue)/page/year: -,95,1971

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 4 gm/kg

SEX/DURATION :: female 7-14 day(s) after conception

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

REFERENCE :: 85DJA5 "Malformations Congenitales des Mammiferes," Tuchmann-Duplessis, H., Paris, Masson et Cie, 1971 Volume(issue)/page/year: -,95,1971

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 2 gm/kg

SEX/DURATION :: female 7-10 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) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 40,143,1989

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2-脱氧-D-葡萄糖安全信息

[ 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) ]:
R20/21/22

[ 安全声明 (欧洲) ]:
S24/25

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

[ WGK德国 ]:
3

[ RTECS号 ]:
MQ3325000

[ 海关编码 ]:
2912491000

2-脱氧-D-葡萄糖合成路线

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2-脱氧-D-葡萄糖海关

[ 海关编码 ]: 2912491000

[ 中文概述 ]:
2912491000. 醛醇. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:5.5%. 普通关税:30.0%

[ Summary ]:
2912491000. other aldehyde-alcohols. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:5.5%. General tariff:30.0%

2-脱氧-D-葡萄糖文献

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