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Uridine diphosphate glucose Sale

(Synonyms: UDP-葡萄糖) 目录号 : GC37866

尿苷二磷酸葡萄糖是动物组织和一些微生物中含葡萄糖的寡糖、多糖、糖蛋白和糖脂的前体。

Uridine diphosphate glucose Chemical Structure

Cas No.:133-89-1

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Sample solution is provided at 25 µL, 10mM.

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实验参考方法

Kinase experiment [1]:

Preparation Method

The reaction mixture for 20S proteasome inhibitory assay contained 0.1 M Tris-acetate, pH 7.0, 20S proteasome, MG-132 and 25 μM substrate dissolved in DMSO in a final volume of 1 ml.

Reaction Conditions

After incubation at 37 ℃ for 15 min, the reaction was stopped by the addition of 0.1 ml of 10% SDS and 0.9 ml of 0.1 M Tris-acetate, pH 9.0.

Applications

After measurement of fluorescence of reaction products, the IC50 of MG-132 against m-calpain and 20S proteasome can be determined. MG-132 inhibits 20S proteasome with IC50 of 100 nM.

Cell experiment [2]:

Cell lines

KIM-2

Preparation Method

MG-132 were diluted in Me2SO. Cells were treated with protease inhibitors or dilutant alone. Supernatant and monolayer cells were harvested by centrifugation and fixed in 70% ethanol in PBS for staining with acridine orange. Equal volumes of cells and acridine orange (5 mg/ml in PBS) were mixed on a microscope slide and examined by fluorescence microscopy.

Reaction Conditions

0, 1.5, 5 μM, 24 h

Applications

MG-132 treatment induces apoptosis in a cell cycle dependent manner.

Animal experiment [2]:

Animal models

C57BL/10ScSn DMD mdx mice

Preparation Method

Localized administration was performed by injection of MG-132 into the gastrocnemius muscles of mdx mice. To visualize the injected muscle, MG-132 (final concentration of 20 μmol/L) was pre-mixed with 1% India ink in phosphate-buffered saline (PBS) for a total volume of 100 μl. Mice were sacrificed 24 hours after injection, and skeletal muscles were quickly isolated for further analysis. To systemically administer MG-132, Alzet Minipumps was subcutaneously implanted in the anterior back region of mdx mice. Experiments were conducted on 6-month-old mdx mice. For 8 days, administration of either different concentrations of MG-132 (delivered at rate of either 1 μg, or 5 μg or 10 μg/kg/24 hours) or the inhibitor-diluent (PBS only) was enforced, as a negative control. Skeletal muscle tissues were collected from untreated (PBS only) and MG-132-treated mdx mice for further analysis.

Dosage form

1 μg, 5 μg, 10 μg/kg, injection into the gastrocnemius muscles or subcutaneously implanted Alzet Minipumps

Applications

MG-132, as a proteasomal inhibitor, effectively rescues the expression levels and plasma membrane localization of dystrophin, β-dystroglycan, α-dystroglycan, and α-sarcoglycan in skeletal muscle fibers from mdx mice. Furthermore, MG-132 reduces muscle membrane damage, as revealed by vital staining of the diaphragm and gastrocnemius muscle isolated from treated mdx mice, and ameliorates the histopathological signs of muscular dystrophy, as judged by hematoxylin and eosin staining of muscle biopsies taken from treated mdx mice.

References:

[1]. Tsubuki, S et al. Differential inhibition of calpain and proteasome activities by peptidyl aldehydes of di-leucine and tri-leucine. Journal of biochemistry vol. 119,3 (1996): 572-6.

[2]. MacLaren, A P et al. p53-dependent apoptosis induced by proteasome inhibition in mammary epithelial cells. Cell death and differentiation vol. 8,3 (2001): 210-8.

[3]. Bonuccelli, Gloria et al. Proteasome inhibitor (MG-132) treatment of mdx mice rescues the expression and membrane localization of dystrophin and dystrophin-associated proteins. The American journal of pathology vol. 163,4 (2003): 1663-75.

产品描述

Uridine diphosphate glucose (uracil-diphosphate glucose, UDPG) is a nucleotide sugar. It is used in nucleotide sugar metabolism as an activated form of glucose, a substrate for enzymes called glucosyltransferases. [1] Uridine diphosphate glucose has been shown to have tissue-specific effects that have proved to be of clinical value in the treatment of some liver ailments. It is also known to have multiple effects on intrahepatic bilirubin metabolism which, in turn, are related to the glycogen synthesis occurring in the liver.[2]

In vitro study demonstrated that the effects of UDPG on cell metabolism do not appear to be limited to enzyme induction. Others have reported that UDPG can have effects under conditions that bar enzyme induction. Results showed that a significant amount of the UDPG, even though it is a highly polar compound, does pass through the membrane unchanged. A large fraction of the UDPG added to incubation media, however, was found in the cell as glucose phosphate, indicating cleavage after penetration of the cell. Eventually. all the UDPG that entered the cells was degraded to glucose phosphate and glucose. The in vitro studies show that G-6-P is not the active form, and several tests show that uridine does not lead to changes like those seen with UDPG. [2]

In vivo study indicated that indicate that the intracellular level of PRPP in animal tissues is greatly affected by extracellular UDPG. The alteration of PRPP level by UDPG is not linearly dose-related. The changes in PRPP that were induced by UDPG were also tissue-specific: mouse liver was more sensitive than was the spleen. This latter specificity may well be related to the therapeutically beneficial effects of UDPG.[2]

References:
[1]. Rademacher T, Pet al. "Glycobiology". Annu Rev Biochem. 1988; 57: 785–838.
[2]. Yip LC, et al. Effects of uridine diphosphoglucose (UDPG) infusion on 5-phosphoribosyl pyrophosphate (PRPP) levels of mouse tissues. Biochem Pharmacol. 1987 Mar 1;36(5):633-7.

尿苷二磷酸葡萄糖(尿嘧啶二磷酸葡萄糖,UDPG)是一种核苷酸糖。它作为葡萄糖的活化形式用于核苷酸糖代谢,葡萄糖是称为葡糖基转移酶的酶的底物。 [1] 尿苷二磷酸葡萄糖已被证明具有组织特异性作用,已证明在某些肝脏疾病的治疗中具有临床价值。还已知它对肝内胆红素代谢有多种影响,而后者又与肝脏中发生的糖原合成有关。[2]

体外研究表明,UDPG 对细胞代谢的影响似乎并不局限于酶诱导。其他人报告说,UDPG 可以在禁止酶诱导的条件下发挥作用。结果表明,大量的 UDPG,即使它是一种高极性化合物,也会通过膜而不会发生变化。然而,在细胞中发现加入孵育培养基的大部分 UDPG 为磷酸葡萄糖,表明在穿透细胞后发生裂解。最终。所有进入细胞的UDPG都被降解为磷酸葡萄糖和葡萄糖。体外研究表明 G-6-P 不是活性形式,多项测试表明尿苷不会导致像 UDPG 那样的变化。 [2]

体内研究表明,动物组织中 PRPP 的细胞内水平受细胞外 UDPG 的影响很大。 UDPG 对 PRPP 水平的改变不是线性剂量相关的。 UDPG 诱导的 PRPP 变化也是组织特异性的:小鼠肝脏比脾脏更敏感。后一种特异性很可能与 UDPG 的治疗有益作用有关。[2]

Chemical Properties

Cas No. 133-89-1 SDF
别名 UDP-葡萄糖
Canonical SMILES OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OP(OP(OC[C@@H]2O[C@@H](N3C=CC(NC3=O)=O)[C@H](O)[C@@H]2O)(O)=O)(O)=O)O)O)O
分子式 C15H24N2O17P2 分子量 566.3
溶解度 Water : ≥ 50 mg/mL 储存条件 Store at -20°C, protect from light, stored under nitrogen
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溶解性数据

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1 mg 5 mg 10 mg
1 mM 1.7658 mL 8.8292 mL 17.6585 mL
5 mM 0.3532 mL 1.7658 mL 3.5317 mL
10 mM 0.1766 mL 0.8829 mL 1.7658 mL
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Research Update

Measurements of Uridine diphosphate glucose and uridine diphosphate galactose--an appraisal

Eur J Pediatr 1995;154(7 Suppl 2):S72-4.PMID:7671969DOI:10.1007/BF02143807.

The recent disproof of a major deficiency of uridine diphosphate galactose in galactosemia should not lead investigators to assume either that enzymatic methods are unreliable for uridine sugar assays or that a defect in galactosylation in galactosemia has been excluded.

31 P-MRS of the healthy human brain at 7 T detects multiple hexose derivatives of Uridine diphosphate glucose

NMR Biomed 2021 Jul;34(7):e4511.PMID:33772915DOI:10.1002/nbm.4511.

Nucleotide sugars are required for the synthesis of glycoproteins and glycolipids, which play crucial roles in many cellular functions such as cell communication and immune responses. Uridine diphosphate-glucose (UDP-Glc) was previously believed to be the only nucleotide sugar detectable in brain by 31 P-MRS. Using spectra of high SNR and high resolution acquired at 7 T, we showed that multiple nucleotide sugars are coexistent in brain and can be measured simultaneously. In addition to UDP-Glc, these also include UDP-galactose (UDP-Gal), -N-acetyl-glucosamine (UDP-GlcNAc) and -N-acetyl-galactosamine (UDP-GalNAc), collectively denoted as UDP(G). Coexistence of these UDP(G) species is evident from a quartet-like multiplet at -9.8 ppm (M-9.8 ), which is a common feature seen across a wide age range (24-64 years). Lineshape fitting of M-9.8 allows an evaluation of all four UDP(G) components, which further aids in analysis of a mixed signal at -8.2 ppm (M-8.2 ) for deconvolution of NAD+ and NADH. For a group of seven young healthy volunteers, the concentrations of UDP(G) species were 0.04 ± 0.01 mM for UDP-Gal, 0.07 ± 0.03 mM for UDP-Glc, 0.06 ± 0.02 mM for UDP-GalNAc and 0.08 ± 0.03 mM for UDP-GlcNA, in reference to ATP (2.8 mM). The combined concentration of all UDP(G) species (average 0.26 ± 0.06 mM) was similar to the pooled concentration of NAD+ and NADH (average 0.27 ± 0.06 mM, with a NAD+ /NADH ratio of 6.7 ± 2.1), but slightly lower than previously found in an older cohort (0.31 mM). The in vivo NMR analysis of UDP-sugar composition is consistent with those from tissue extracts by other modalities in the literature. Given that glycosylation is dependent on the availability of nucleotide sugars, assaying multiple nucleotide sugars may provide valuable insights into potential aberrant glycosylation, which has been implicated in certain diseases such as cancer and Alzheimer's disease.

Efficient biosynthesis of Uridine diphosphate glucose from maltodextrin by multiple enzymes immobilized on magnetic nanoparticles

Carbohydr Res 2010 Jul 19;345(11):1622-6.PMID:20627237DOI:10.1016/j.carres.2010.04.025.

Uridine diphosphate glucose (UDP-Glc) serves as a glucosyl donor in many enzymatic glycosylation processes.This paper describes a multiple enzyme, one-pot, biocatalytic system for the synthesis of UDP-Glc from low cost raw materials: maltodextrin and uridine triphosphate. Three enzymes needed for the synthesis of UDP-Glc (maltodextrin phosphorylase, glucose-1-phosphate thymidylytransferase, and pyrophosphatase)were expressed in Escherichia coli and then immobilized individually on aminofunctionalized magnetic nanoparticles. The conditions for biocatalysis were optimized and the immobilized multiple-enzyme biocatalyst could be easily recovered and reused up to five times in repeated syntheses of UDP-Glc. After a simple purification, approximately 630 mg of crystallized UDP-Glc was obtained from 1 l of reaction mixture, for a moderate yield of around 50% (UTP conversion) at very low cost.

Uridine diphosphate glucose synthase from calf liver: determinants of enzyme activity in vitro

Biochemistry 1975 Dec 16;14(25):5445-50.PMID:172124DOI:10.1021/bi00696a010.

The reaction catalyzed by calf liver Uridine diphosphate glucose synthase (pyrophosphorylase) (EC 2.7.7.9; UTP + glucose 1-phosphate = UDP-glucose + PPi) is an example of an enzymic reaction in which a nucleoside triphosphate other than ATP is the immediate source of metabolic energy. Kinetic properties of the enzyme, acting in the direction of UCP-glucose formation were investigated in vitro. The reaction was inhibited by UDP-glucose (0.072), Pi (11), UDP (1.6), UDP-xylose (0.87), UDP-glucuronate (1.3), and UDP-galacturonate (0.95). The numbers in parentheses indicate the concentration (mM) required for half-maximal inhibition under the conditions used. Other compounds tested, including ATP, ADP, and AMP, had no effect. Over a range of concentrations of UTP (0.04-0.8 MM) and UDP-glucose (0.05-0.03 mM), the reaction rate was more dependent on the concentration ratio [UDP-glucose]/[UTP] than on the absolute concentration of either compound. Comparison of the kinetic properties in vitro with estimates of metabolite levels in vivo suggests that (1) the enzyme operates in a range far from its maximal rate, and (2) the concentrations of glucose 1-phosphate and Pi and the ratio [UDP-glucose]/[UTP] may be the most important determinants of UDP-glucose synthase activity.

Non-enzymatic synthesis of the coenzymes, Uridine diphosphate glucose and cytidine diphosphate choline, and other phosphorylated metabolic intermediates

Orig Life Evol Biosph 1987;17(3-4):307-19.PMID:2819807DOI:10.1007/BF02386470.

The synthesis of Uridine diphosphate glucose (UDPG), cytidine diphosphate choline (CDP-choline), glucose-1-phosphate (G1P) and glucose-6-phosphate (G6P) has been accomplished under simulated prebiotic conditions using urea and cyanamide, two condensing agents considered to have been present on the primitive Earth. The synthesis of UDPG was carried out by reacting G1P and UTP at 70 degrees C for 24 hours in the presence of the condensing agents in an aqueous medium. CDP-choline was obtained under the same conditions by reacting choline phosphate and CTP X G1P and G6P were synthesized from glucose and inorganic phosphate at 70 degrees C for 16 hours. Separation and identification of the reaction products have been performed by paper chromatography, thin layer chromatography, enzymatic analysis and ion pair reverse phase high performance liquid chromatography. These results suggest that metabolic intermediates could have been synthesized on the primitive Earth from simple precursors by means of prebiotic condensing agents.