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| | Octanoic acid, 6,8-bis[(phenylMethyl)thio]- Basic information |
| Product Name: | Octanoic acid, 6,8-bis[(phenylMethyl)thio]- | | Synonyms: | alpha-lipoic acid analogue CPI-613;CPI-613;CPI-613; OCTANOIC ACID, 6,8-BIS[(PHENYLMETHYL)THIO]-;Octanoic acid, 6,8-bis[(phenylMethyl)thio]-;6,8-Bis(benzylthio)octanoic acid;6,8-Bis[(phenylmethyl)thio]octanoic acid;6,8-Bis[(phenylmethyl)thio]octanoic acid CPI-613;6,8-Bis(benzylsulfanyl)octanoic acid | | CAS: | 95809-78-2 | | MF: | C22H28O2S2 | | MW: | 388.59 | | EINECS: | 804-408-7 | | Product Categories: | Inhibitor;Inhibitors | | Mol File: | 95809-78-2.mol | ![Octanoic acid, 6,8-bis[(phenylMethyl)thio]- Structure](CAS/GIF/95809-78-2.gif) |
| | 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. |
| 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 |
| | Octanoic acid, 6,8-bis[(phenylMethyl)thio]- Preparation Products And Raw materials |
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