| Identification | Back Directory | [Name]
Octanoic acid, 6,8-bis[(phenylMethyl)thio]- | [CAS]
95809-78-2 | [Synonyms]
CPI-613
Devimistat
CPI-613, >98%
CPI 613;CPI613
CPI-613(Devimistat)
CPI-613;CPI 613;CPI613
6,8-Bis(benzylthio)octanoic acid
alpha-lipoic acid analogue CPI-613
6,8-Bis(benzylsulfanyl)octanoic acid
CPI613; CPI-613; CPI 613; DEVIMISTAT
(+/-)6,8-bis-thiobenzyl octanoic acid
6,8-Bis[(phenylmethyl)thio]octanoic acid
Octanoic acid, 6,8-bis[(phenylMethyl)thio]-
6,8-Bis[(phenylmethyl)thio]octanoic acid CPI-613
CPI-613; OCTANOIC ACID, 6,8-BIS[(PHENYLMETHYL)THIO]-
Octanoic acid, 6,8-bis[(phenylMethyl)thio]- USP/EP/BP | [EINECS(EC#)]
804-408-7 | [Molecular Formula]
C22H28O2S2 | [MDL Number]
MFCD22420826 | [MOL File]
95809-78-2.mol | [Molecular Weight]
388.587 |
| Chemical Properties | Back Directory | [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. | [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 |
| Hazard Information | Back Directory | [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. | [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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