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方案
≥95% (HPLC)
表单
oil
储存条件
desiccated
under inert gas
颜色
colorless to yellow
储存温度
−20°C
SMILES字符串
CCCCCCCCOC(C(CCC(O)=O)=O)=O
InChI
1S/C13H22O5/c1-2-3-4-5-6-7-10-18-13(17)11(14)8-9-12(15)16/h2-10H2,1H3,(H,15,16)
InChI key
QNFIHKFBQFJVKV-UHFFFAOYSA-N
应用
辛基-α-KG研究已用于研究其在细胞活力及补充脑胶质母细胞瘤细胞α-KG水平方面的作用。
生化/生理作用
α-酮戊二酸的膜可渗透前体，其可恢复癌细胞中α-KG依赖性双加氧酶的活性。
辛基α-KG（辛基-2KG）是α-酮戊二酸（α-KG或2KG）的一种膜渗透性前体形式，由于NADP+-依赖的异柠檬酸脱氢酶基因IDH1和IDH2发生突变，因此在肿瘤细胞中经常可以观察到-KG的下调并伴随D-2-羟基戊二酸（D-2HG）的上调，从而导致多种α-KG依赖性双加氧酶的活性降低。通过辛基-α-KG处理（1-5 mM）进行的细胞α-KG的递送可在辛基-2-HG（1-50 mM）处理或IDH1（R132H）突变体表达后恢复细胞脱甲基酶的活性。 在由于琥珀酸脱氢酶（SDH）和/或富马酸盐水合酶（FH）缺乏，而导致三羧酸（TCA）循环失调的细胞中，辛基-α-KG还可以有效地重新激活α-KG依赖的双加氧酶脯氨酰羟化酶（PHD）活性。
储存分类代码
11 - Combustible Solids
WGK
WGK 3
闪点(°F)
Not applicable
闪点(°C)
Not applicable
历史批次信息供参考:
分析证书(COA)
Lot/Batch Number
Shizhong Ke et al.
Hepatology (Baltimore, Md.), 65(1), 134-151 (2016-10-25)
Erythrocytosis is a common paraneoplastic syndrome associated with hepatocellular carcinoma. Although increased erythropoietin (EPO) is found in these patients, the clinical significance and molecular mechanisms underlying this observation are unclear. We demonstrate an inverse relationship between EPO production and overall
Elaine D MacKenzie et al.
Molecular and cellular biology, 27(9), 3282-3289 (2007-02-28)
Succinate dehydrogenase (SDH) and fumarate hydratase (FH) are components of the tricarboxylic acid (TCA) cycle and tumor suppressors. Loss of SDH or FH induces pseudohypoxia, a major tumor-supporting event, which is the activation of hypoxia-inducible factor (HIF) under normoxia. In
Shimin Zhao et al.
Science (New York, N.Y.), 324(5924), 261-265 (2009-04-11)
Heterozygous mutations in the gene encoding isocitrate dehydrogenase-1 (IDH1) occur in certain human brain tumors, but their mechanistic role in tumor development is unknown. We have shown that tumor-derived IDH1 mutations impair the enzyme's affinity for its substrate and dominantly
L Zeng et al.
Oncogene, 34(36), 4758-4766 (2014-12-23)
Cancer cells gain a growth advantage through the so-called Warburg effect by shifting glucose metabolism from oxidative phosphorylation to aerobic glycolysis. Hypoxia-inducible factor 1 (HIF-1) has been suggested to function in metabolic reprogramming; however, the underlying mechanism has not been
Parker L Sulkowski et al.
Science translational medicine, 9(375) (2017-02-06)
2-Hydroxyglutarate (2HG) exists as two enantiomers, (R)-2HG and (S)-2HG, and both are implicated in tumor progression via their inhibitory effects on α-ketoglutarate (αKG)-dependent dioxygenases. The former is an oncometabolite that is induced by the neomorphic activity conferred by isocitrate dehydrogenase
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