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关于此项目
经验公式(希尔记法):
C13H24O5
化学文摘社编号:
分子量:
260.33
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
Assay:
≥98% (HPLC)
Form:
film
Storage condition:
desiccated
产品名称
辛-(R)-2HG, ≥98% (HPLC)
assay
≥98% (HPLC)
form
film
storage condition
desiccated
color
colorless
solubility
DMSO: 2 mg/mL, clear
storage temp.
−20°C
SMILES string
O[C@H](CCC(=O)O)C(=O)OCCCCCCCC
InChI key
UJZOKTKSGUOCCM-LLVKDONJSA-N
Application
辛基-(R)-2羟基戊二酸酯(HG)已被用作胶质母细胞瘤细胞中的膜渗透性致癌代谢物(oncometabolite),用于测试其对NANOG转录因子表达的影响。它还被用作酮戊二酸酯(α-KG)依赖性脱氧酶α的竞争性抑制剂。
Biochem/physiol Actions
抑制 α-酮戊二酸/α-KG 依赖性双加氧酶类的肿瘤代谢产物 D-2-羟基戊二酸的膜渗透前体形式。
辛基-(R)-2HG (Octyl-D-2HG) 是肿瘤细胞因 NADP + 依赖性异柠檬酸脱氢酶基因 IDH1 和 IDH2 突变而产生的肿瘤代谢产物 D-2-羟基戊二酸盐 (D-2HG) 的膜渗透前体形式。D-2HG 通过与 α-KG 结合竞争抑制多种 α-酮戊二酸/α-KG-依赖性双加氧酶。通过 Octyl-(R)-2HG 处理 (1-50 mM) 的细胞 D-2HG 传递显示出抑制脱甲基酶活性(~148%H3K9me2 和 ~310%H3K79me2 上调;U-87 mg 中 50 mm)以及因为分别抑制 α-KG-依赖性双加氧酶脯氨酰羟化酶 (PHD) 和胶原脯氨酰-4-羟化酶 (C-P4H)而增加 HIF-1α通过, 降低内皮抑素水平。
Preparation Note
该化合物未报告密度。分子量为260.33。DMSO中的溶解性经测试为2 mg/mL,然而其他数据来源表明其在DMSO中的溶解度可高达10 mg/mL。
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Steven M Chan et al.
Nature medicine, 21(2), 178-184 (2015-01-20)
Mutant isocitrate dehydrogenase (IDH) 1 and 2 proteins alter the epigenetic landscape in acute myeloid leukemia (AML) cells through production of the oncometabolite (R)-2-hydroxyglutarate (2-HG). Here we performed a large-scale RNA interference (RNAi) screen to identify genes that are synthetic
Javier A Menendez et al.
Stem cell reports, 6(3), 273-283 (2016-02-16)
By impairing histone demethylation and locking cells into a reprogramming-prone state, oncometabolites can partially mimic the process of induced pluripotent stem cell generation. Using a systems biology approach, combining mathematical modeling, computation, and proof-of-concept studies with live cells, we found
alpha-Ketoglutarate-Activated NF-$\kappa$B Signaling Promotes Compensatory Glucose Uptake and Brain Tumor Development
Wang X, et al.
Molecular Cell, 76(1), 148-162 (2019)
全球贸易项目编号
| 货号 | GTIN |
|---|---|
| SML2200-25MG | 04061835345120 |
| SML2200-5MG | 04061835345137 |