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SML2200

Sigma-Aldrich

辛-(R)-2HG

≥98% (HPLC), film, α-KG-dependent dioxygenases prolyl hydroxylases inhibitor

同義詞:

(2R)-2-羟基戊二酸辛酯, (2R)-辛基-α-羟基戊二酸, 1-辛基-D-2-羟基戊二酸盐, 1-辛基酯, R-2HG 辛基酯, 羟基戊二酸, 辛-D-2HG, 辛基-2HG

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About This Item

經驗公式(希爾表示法):
C13H24O5
CAS號碼:
分子量::
260.33
MDL號碼:
分類程式碼代碼:
12352200
NACRES:
NA.77
暫時無法取得訂價和供貨情況

產品名稱

辛-(R)-2HG, ≥98% (HPLC)

化驗

≥98% (HPLC)

形狀

film

儲存條件

desiccated

顏色

colorless

溶解度

DMSO: 2 mg/mL, clear

儲存溫度

−20°C

SMILES 字串

O[C@H](CCC(=O)O)C(=O)OCCCCCCCC

InChI 密鑰

UJZOKTKSGUOCCM-LLVKDONJSA-N

應用

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。[1]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。[2]

生化/生理作用

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。

準備報告

The density is not reported for this compound. The molecular weight is 260.33. The solubility is tested at 2mg/mL in DMSO, however other sources suggest that it is soluble in DMSO up to 10mg/mL.

儲存類別代碼

11 - Combustible Solids

水污染物質分類(WGK)

WGK 3

閃點(°F)

Not applicable

閃點(°C)

Not applicable


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Zachary J Reitman et al.
The Journal of biological chemistry, 289(34), 23318-23328 (2014-07-06)
Mutations in the cytosolic NADP(+)-dependent isocitrate dehydrogenase (IDH1) occur in several types of cancer, and altered cellular metabolism associated with IDH1 mutations presents unique therapeutic opportunities. By altering IDH1, these mutations target a critical step in reductive glutamine metabolism, the
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)
IDH1R132H Causes Resistance to HDAC Inhibitors by Increasing NANOG in Glioblastoma Cells
Kim G H, et al.
International Journal of Molecular Sciences, 20(11), 2679-2679 (2019)
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
Jing-Yi Chen et al.
Scientific reports, 6, 32428-32428 (2016-09-01)
Mutations of isocitrate dehydrogenase 1 (IDH1) and IDH2 in acute myeloid leukemia (AML) cells produce the oncometabolite R-2-hydroxyglutarate (R-2HG) to induce epigenetic alteration and block hematopoietic differentiation. However, the effect of R-2HG released by IDH-mutated AML cells on the bone

Questions

  1. What is the density of this product? I can´t find it and I want to have a 100mM stock.

    1 answer
    1. The density is not reported for this compound. The molecular weight is 260.33. The solubility is tested at 2mg/mL in DMSO, however other sources suggest that it is soluble in DMSO up to 10mg/mL. This rate has not been validated.

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