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2-Deoxy-D-glucose Sale

(Synonyms: 2-脱氧-D-葡萄糖; 2-DG; 2-Deoxy-D-arabino-hexose; D-Arabino-2-deoxyhexose) 目录号 : GC17430

2-Deoxy-D-glucose (2DG),是一种葡萄糖类似物,作为竞争性糖酵解抑制剂。

2-Deoxy-D-glucose Chemical Structure

Cas No.:154-17-6

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10mM (in 1mL DMSO)
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1g
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5g
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Sample solution is provided at 25 µL, 10mM.

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实验参考方法

Cell experiment [1]:

Cell lines

Cell lines SkBr3, MCF-7, BT474, and MDA/MB468,

Preparation Method

Cells were plated at 4000 cells well-1 in a 96-well plate, allowed 24 h to attach and subsequently exposed for 4 days to 2-Deoxy-D-glucose.

Reaction Conditions

4-12 mM for 0-4 days

Applications

Growth of MDA/MB468 cells was completely inhibited by treatment with 8 mM 2-Deoxy-D-glucose. Treatment with 4 mM 2-Deoxy-D-glucose resulted in approximately 30% inhibition of cell growth. Of the breast cancer cell lines tested, SkBr3 was the most sensitive to the growth inhibitory effects of 2-Deoxy-D-glucose. Cell growth was completely inhibited at 4 mM 2-Deoxy-D-glucose.

Animal experiment [2]:

Animal models

male Sprague-Dawley (SD) rats

Preparation Method

Animals were handled routinely in order to reduce stress associated with injection. 2-deoxy-d-glucose (400 mg/kg), or saline, was administered intraperitoneally.

Dosage form

Intraperitoneal injection , 400 mg/kg

Applications

Ad concentrations increased from 2.73 ng/ml to 7.2 ng/ml while NAd concentrations increased from 1.8 ng/ml to 3.14 ng/ml after injected 2-deoxy-d-glucose.

References:

[1]: Aft R L, Zhang F W, Gius D. Evaluation of 2-deoxy-D-glucose as a chemotherapeutic agent: mechanism of cell death[J]. British journal of cancer, 2002, 87(7): 805-812.
[2]: Bobrovskaya L, Damanhuri H A, Ong L K, et al. Signal transduction pathways and tyrosine hydroxylase regulation in the adrenal medulla following glucoprivation: an in vivo analysis[J]. Neurochemistry international, 2010, 57(2): 162-167.

产品描述

2-Deoxy-D-glucose (2DG), is a glucose analogue, act as competitive glycolytic inhibitor [1].

2-Deoxy-d-glucose (2DG) has been demonstrated to be a powerful agent for blocking and probing increased sugar metabolism in cancer cells [2]. Because of its similarity to glucose, 2-Deoxy-D-glucose inhibits glycolysis, but as chemically it is also 2-deoxymannose it is able to compete with mannose in the growing lipid-linked oligosaccharide chain during the initial steps of N-linked glycosylation. This mannose-like property of 2-Deoxy-D-glucose results in misfolded proteins leading to endoplasmic reticulum (ER) stress [3].

2-Deoxy-D-glucose delivered in the diet produces cardiac toxicity in rats at doses ranging from 0.02 to 0.3 g/kg (0.04-0.6% 2-Deoxy-D-glucose by weight in the diet) and hastens mortality at doses above 0.2 g/kg (0.4% in the diet) [4]. 2-Deoxy-D-glucose evoked increases in plasma adrenaline and glucose at 20 and 60 min [5].

References:
[1]. Mühlenberg T, Grunewald S, Treckmann J, et al. Inhibition of KIT-glycosylation by 2-deoxyglucose abrogates KIT-signaling and combination with ABT-263 synergistically induces apoptosis in gastrointestinal stromal tumor[J]. PloS one, 2015, 10(3): e0120531.
[2]. El Mjiyad N, Caro-Maldonado A, Ramirez-Peinado S, Munoz-Pinedo C. Sugar-free approaches to cancer cell killing. Oncogene. 2011 Jan;30(3):253-64.
[3]. Kurtoglu, Metin, Johnathan C. Maher, and Theodore J. Lampidis. "Differential toxic mechanisms of 2-deoxy-D-glucose versus 2-fluorodeoxy-D-glucose in hypoxic and normoxic tumor cells." Antioxidants & redox signaling 9.9 (2007): 1383-1390.
[4]. Minor R K, Smith Jr D L, Sossong A M, et al. Chronic ingestion of 2-deoxy-D-glucose induces cardiac vacuolization and increases mortality in rats[J]. Toxicology and applied pharmacology, 2010, 243(3): 332-339.
[5]. Bobrovskaya L, Damanhuri H A, Ong L K, et al. Signal transduction pathways and tyrosine hydroxylase regulation in the adrenal medulla following glucoprivation: an in vivo analysis[J]. Neurochemistry international, 2010, 57(2): 162-167.

2-Deoxy-D-glucose (2DG),是一种葡萄糖类似物,作为竞争性糖酵解抑制剂[1]

2-脱氧-d-葡萄糖 (2DG) 已被证明是一种强大的药物,可阻断和探测癌细胞中增加的糖代谢[2]。由于其与葡萄糖的相似性,2-脱氧-D-葡萄糖抑制糖酵解,但在化学上它也是 2-脱氧甘露糖,它能够在 N-连接糖基化的初始步骤中与生长的脂质连接的寡糖链中的甘露糖竞争. 2-脱氧-D-葡萄糖的这种类似甘露糖的特性导致错误折叠的蛋白质导致内质网 (ER) 应激 [3]

饮食中提供的 2-脱氧-D-葡萄糖在 0.02 至 0.3 g/kg 的剂量范围内(饮食中 0.04-0.6% 2-脱氧-D-葡萄糖按重量计)对大鼠产生心脏毒性并加速死亡率剂量超过 0.2 g/kg(饮食中的 0.4%)[4]。 2-脱氧-D-葡萄糖在 20 分钟和 60 分钟时引起血浆肾上腺素和葡萄糖的增加[5]

Chemical Properties

Cas No. 154-17-6 SDF
别名 2-脱氧-D-葡萄糖; 2-DG; 2-Deoxy-D-arabino-hexose; D-Arabino-2-deoxyhexose
化学名 (4R,5S,6R)-6-(hydroxymethyl)tetrahydro-2H-pyran-2,4,5-triol
Canonical SMILES [H][C@]([C@](C1([H])[H])([H])O[H])([C@](C([H])([H])O[H])([H])OC1([H])O[H])O[H]
分子式 C6H12O5 分子量 164.16
溶解度 DMF: 10 mg/ml,DMSO: 20 mg/ml,PBS (pH 7.2): 10 mg/ml 储存条件 Store at -20°C
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1 mM 6.0916 mL 30.4581 mL 60.9162 mL
5 mM 1.2183 mL 6.0916 mL 12.1832 mL
10 mM 0.6092 mL 3.0458 mL 6.0916 mL
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Research Update

2-Deoxy-d-Glucose and Its Analogs: From Diagnostic to Therapeutic Agents

The ability of 2-deoxy-d-glucose (2-DG) to interfere with d-glucose metabolism demonstrates that nutrient and energy deprivation is an efficient tool to suppress cancer cell growth and survival. Acting as a d-glucose mimic, 2-DG inhibits glycolysis due to formation and intracellular accumulation of 2-deoxy-d-glucose-6-phosphate (2-DG6P), inhibiting the function of hexokinase and glucose-6-phosphate isomerase, and inducing cell death. In addition to glycolysis inhibition, other molecular processes are also affected by 2-DG. Attempts to improve 2-DG's drug-like properties, its role as a potential adjuvant for other chemotherapeutics, and novel 2-DG analogs as promising new anticancer agents are discussed in this review.

2-Deoxy-D-glucose targeting of glucose metabolism in cancer cells as a potential therapy

Cancer cells are characterized by altered glucose metabolism known as the Warburg effect in which aerobic glycolysis is increased. Glucose is converted to lactate even under sufficient oxygen tension. Interfering with this process may be a potential effective strategy to cause cancer cell death because these cells rely heavily on glucose metabolism for survival and proliferation. 2-Deoxy-D-glucose (2DG), a glucose analog, targets glucose metabolism to deplete cancer cells of energy. In addition, 2DG increases oxidative stress, inhibits N-linked glycosylation, and induces autophagy. It can efficiently slow cell growth and potently facilitate apoptosis in specific cancer cells. Although 2DG itself has limited therapeutic effect in many types of cancers, it may be combined with other therapeutic agents or radiotherapy to exhibit a synergistic anticancer effect. In this review, we describe the Warburg effect and discuss 2DG and its underlying mechanisms and potential application for cancer treatment.

2-NBDG as a fluorescent indicator for direct glucose uptake measurement

Evaluation of glucose uptake ability in cells plays a fundamental role in diabetes mellitus research. In this study, we describe a sensitive and non-radioactive assay for direct and rapid measuring glucose uptake in single, living cells. The assay is based on direct incubation of mammalian cells with a fluorescent d-glucose analog 2-[N-(7-nitrobenz-2-oxa-1,3-diazol-4-yl) amino]-2-deoxy-D-glucose (2-NBDG) followed by flow cytometric detection of fluorescence produced by the cells. A series of experiments were conducted to define optimal conditions for this assay. By this technique, it was found that insulin lost its physiological effects on cells in vitro meanwhile some other anti-diabetic drugs facilitated the cell glucose uptake rates with mechanisms which likely to be different from those of insulin or those that were generally accepted of each drug. Our findings show that this technology has potential for applications in both medicine and research.

2-Deoxy-D-glucose: is this the final cure for COVID-19: or yet another mirage?

2-Deoxy-D-glucose and combined 2-Deoxy-D-glucose/albendazole exhibit therapeutic efficacy against Echinococcus granulosus protoscoleces and experimental alveolar echinococcosis

2-Deoxy-D-glucose (2-DG) is a glucose analog used as a promising anticancer agent. It exerts its effects by inhibiting the glycolytic energy metabolism to deplete cells of energy. The larval stage of Echinococcus relies on glycolysis for energy production. Therefore, in this study, we investigated the in vitro and in vivo efficacy of 2-DG against the larval stage of Echinococcus granulosus and E. multilocularis. 2-DG exhibited significant time- and dose-dependent effects against in vitro cultured E. granulosus protoscoleces and E. multilocularis metacestodes. A daily oral administration of 500 mg/kg 2-DG in E. multilocularis-infected mice effectively reduced the weight of metacestodes. Notably, the combination treatment, either 2-DG (500 mg/kg/day) + albendazole (ABZ) (200 mg/kg/day) or 2-DG (500 mg/kg/day) + half-dose of ABZ (100 mg/kg/day), exhibited a potent therapeutic effect against E. multilocularis, significantly promoting the reduction of metacestodes weight compared with the administration of 2-DG or ABZ alone. Furthermore, the combination significantly promoted apoptosis of the cells of metacestodes and inhibited glycolysis in metacestodes, compared with the administration of 2-DG or ABZ alone. In conclusion, 2-DG exerts an effective activity against the larval stage of Echinococcus. Thus, it may be a promising anti-Echinococcus drug, and its combination with ABZ may provide a new strategy for the treatment of echinococcosis in humans.