SML0404
6,8-Bis(benzylthio)-octanoic acid
≥98% (HPLC), E1α pyruvate dehydrogenase modulator, powder
Synonym(s):
6,8-Bis[(phenylmethyl)thio-octanoic acid, CPI-613
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About This Item
Empirical Formula (Hill Notation):
C22H28O2S2
CAS Number:
Molecular Weight:
388.59
UNSPSC Code:
12352106
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
6,8-Bis(benzylthio)-octanoic acid, ≥98% (HPLC)
Quality Level
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 15 mg/mL (clear solution)
storage temp.
2-8°C
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
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.
signalword
Warning
hcodes
pcodes
Hazard Classifications
Aquatic Acute 1 - Aquatic Chronic 1
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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
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
Global Trade Item Number
| SKU | GTIN |
|---|---|
| SML0404-25MG | 04061832925677 |
| SML0404-5MG | 04061832925684 |