Octanoic acid, 6,8-bis[(phenylMethyl)thio]- Chemical Properties

Melting point:

63-65℃

Boiling point:

553.0±50.0 °C(Predicted)

Density 

1.149

storage temp. 

2-8°C

solubility 

DMSO: soluble15mg/mL (clear solution)

form 

powder

pka

4.75±0.10(Predicted)

color 

white to beige

Stability:

Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.

Safety Information

Hazard Codes 

N

Risk Statements 

50/53

Safety Statements 

60-61

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

HS Code 

2930.90.2900

Octanoic acid, 6,8-bis[(phenylMethyl)thio]- Usage And Synthesis

Description

CPI-613 (95809-78-2) is a lipoic acid analog which potently disrupts mitochondrial metabolism with selectivity for tumor cells in vitro and shows strong antitumor activity in vivo.1?? Inhibits alpha-ketoglutarate dehydrogenase (KGDH) by a redox mechanisms selectively in tumor cells.2 Inhibits pyruvate dehydrogenase (PDH) as a mechanistically distinct, non-redox, effect.1,2 A novel anticancer agent with a mitochondria-targeted mode of action with non-genotoxic properties.3. Has been used (along with PS48) to induce a Warburg-like metabolic state in fibroblasts.4 Combination treatment of CPI-613 and chloroquine inhibits the progression of clear cell sarcoma in a mouse model.5

Uses

CPI 613 is a class of non-redox-active lipoate derivative that disrupts cancer cell mitochondrial metabolism and are potent anticancer agents in vivo.

Uses

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.

storage

Store at +4°C

References

1) Zachar et al. (2011), Non-redox-active Lipoate Derivates Disrupt Cancer Cell Mitochondrial Metabolism and Are Potent Anticancer Agents in Vivo; J. Mol. Med. (Berl), 89 1137 2) Stuart et al. (2014), A Strategically designed Small Molecule Attacks Alpha-ketoglutarate Dehydrogenase in Tumor Cells Through a Redox Process; Cancer Metab., 2 4 3) Dorsam and Fahrer (2016), The Disulfide Compound α-lipoic Acid and Its Derivatives: A Novel Class of Anticancer Agents Targeting Mitochondria; Cancer Lett., 371(1) 12 4) Mordhorst et al. (2018), Pharmacologic Reprogramming Designed to Induce a Warburg Effect in Porcine Fetal Fibroblasts Alters Gene Expression and Quantities of Metabolites From Conditioned Media Without Increased Cell Proliferation; Cell Reprogram., 20 38 5) Egawa et al. (2018), Therapeutic Potential of CPI-613 for Targeting Tumorous Mitochondrial Energy Metabolism and Inhibiting Autophagy in Clear Cell Sarcoma; PLoS One, 13(6) e0198940

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