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Merck
CN

SML0404

6,8-Bis(benzylthio)-octanoic acid

≥98% (HPLC), E1α pyruvate dehydrogenase modulator, powder

别名:

6,8-Bis[(phenylmethyl)thio-octanoic acid, CPI-613

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关于此项目

经验公式(希尔记法):
C22H28O2S2
化学文摘社编号:
分子量:
388.59
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.77
MDL number:
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产品名称

6,8-Bis(benzylthio)-octanoic acid, ≥98% (HPLC)

SMILES string

OC(=O)CCCCC(CCSCc1ccccc1)SCc2ccccc2

InChI

1S/C22H28O2S2/c23-22(24)14-8-7-13-21(26-18-20-11-5-2-6-12-20)15-16-25-17-19-9-3-1-4-10-19/h1-6,9-12,21H,7-8,13-18H2,(H,23,24)

InChI key

ZYRLHJIMTROTBO-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 15 mg/mL (clear solution)

storage temp.

2-8°C

Quality Level

Application

6,8-Bis(benzylthio)-octanoic acid has been used as pyruvate dehydrogenase (PDH) inhibitor:
  • to study its effects on neurite outgrowth in primary mouse dorsal root ganglia cells
  • to induce α-smooth muscle actin (αSMA) and pro-collagen I expression and to assess PDH enzyme activity in whole-cell lysates
  • to validate basal respiration in tissue respirometry

Biochem/physiol Actions

6,8-Bis(benzylthio)-octanoic acid (CPI-613) is a lipoate analog. It acts as a mitochondrial disrupter by blocking the mitochondrial enzymes pyruvate dehydrogenase and α-ketoglutarate dehydrogenase.
6,8-Bis(benzylthio)-octanoic acid is an E1α pyruvate dehydrogenase (PDH) modulator that prevents cancer cells from metabolizing glucose for energy. 6,8-Bis(benzylthio)-octanoic acid has been granted orphan drug status by the US FDA for pancreatic cancer.
6,8-Bis(benzylthio)-octanoic acid is an E1α pyruvate dehydrogenase (PDH) modulator.

pictograms

Environment

signalword

Warning

hcodes

Hazard Classifications

Aquatic Acute 1 - Aquatic Chronic 1

存储类别

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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Alexander Strom et al.
Molecular metabolism, 43, 101114-101114 (2020-11-10)
The lack of effective treatments against diabetic sensorimotor polyneuropathy demands the search for new strategies to combat or prevent the condition. Because reduced magnesium and increased methylglyoxal levels have been implicated in the development of both type 2 diabetes and
Bethany R Mordhorst et al.
Scientific reports, 9(1), 9417-9417 (2019-07-03)
A metabolic phenomenon known as the Warburg effect has been characterized in certain cancerous cells, embryonic stem cells, and other rapidly proliferative cell types. Previously, our attempts to induce a Warburg-like state pharmaceutically via CPI-613 and PS48 treatment did augment
Edward R Smith et al.
Scientific reports, 10(1), 17914-17914 (2020-10-23)
TGF-β1 reprograms metabolism in renal fibroblasts, inducing a switch from oxidative phosphorylation to aerobic glycolysis. However, molecular events underpinning this are unknown. Here we identify that TGF-β1 downregulates acetyl-CoA biosynthesis via regulation of the pyruvate dehydrogenase complex (PDC). Flow cytometry
Dmitry D Zhdanov et al.
Biochimie, 174, 34-43 (2020-04-22)
The nuclease activity of deoxyribonuclease 1 (DNase I) is regulated by alternative splicing (AS) of its mRNA. The aim of this study was to define the ability of a splice-switching oligonucleotide (SSO) that base-paired with DNase I pre-mRNA to induce
Mattia Quattrocelli et al.
JCI insight, 4(24) (2019-12-20)
In humans, chronic glucocorticoid use is associated with side effects like muscle wasting, obesity, and metabolic syndrome. Intermittent steroid dosing has been proposed in Duchenne Muscular Dystrophy patients to mitigate the side effects seen with daily steroid intake. We evaluated

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