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)

pka

4.75±0.10(Predicted)

form 

powder

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.

InChI

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)

InChIKey

ZYRLHJIMTROTBO-UHFFFAOYSA-N

SMILES

C(O)(=O)CCCCC(SCC1=CC=CC=C1)CCSCC1=CC=CC=C1

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] ZUZANA ZACHAR. Non-redox-active lipoate derivates disrupt cancer cell mitochondrial metabolism and are potent anticancer agents in vivo.[J]. Journal of Molecular Medicine-Jmm, 2011, 89 11: 1137-1148. DOI:10.1007/s00109-011-0785-8
[2] SHAWN D STUART. A strategically designed small molecule attacks alpha-ketoglutarate dehydrogenase in tumor cells through a redox process.[J]. Cancer & Metabolism, 2014: 4. DOI:10.1186/2049-3002-2-4
[3] BASTIAN DÖRSAM  Jörg F. The disulfide compound α-lipoic acid and its derivatives: A novel class of anticancer agents targeting mitochondria[J]. Cancer letters, 2016, 371 1: Pages 12-19. DOI:10.1016/j.canlet.2015.11.019
[4] BETHANY R MORDHORST. 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.[J]. Cellular reprogramming, 2018, 20 1: 38-48. DOI:10.1089/cell.2017.0040
[5] YUKI EGAWA. Therapeutic potential of CPI-613 for targeting tumorous mitochondrial energy metabolism and inhibiting autophagy in clear cell sarcoma.[J]. PLoS ONE, 2018: e0198940. DOI:10.1371/journal.pone.0198940

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