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

Bezeichnung:Octanoic acid, 6,8-bis[(phenylMethyl)thio]-

CAS-Nr95809-78-2

Englisch Name:Octanoic acid, 6,8-bis[(phenylMethyl)thio]-

CBNumberCB52554078

SummenformelC22H28O2S2

Molgewicht388.59

MOL-Datei95809-78-2.mol

Octanoic acid, 6,8-bis[(phenylMethyl)thio]- physikalisch-chemischer Eigenschaften

Schmelzpunkt	63-65℃
Siedepunkt	553.0±50.0 °C(Predicted)
Dichte	1.149
storage temp.	2-8°C
Löslichkeit	DMSO: soluble15mg/mL (clear solution)
Aggregatzustand	powder
pka	4.75±0.10(Predicted)
Farbe	white to beige
Stabilität	Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.

Sicherheit

Kennzeichnung gefährlicher	N
R-Sätze:	50/53
S-Sätze:	60-61
RIDADR	UN 3077 9 / PGIII
WGK Germany	3
HS Code	2930.90.2900

Gefahreninformationscode (GHS)

Octanoic acid, 6,8-bis[(phenylMethyl)thio]- Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung
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
Verwenden
CPI 613 is a class of non-redox-active lipoate derivative that disrupts cancer cell mitochondrial metabolism and are potent anticancer agents in vivo.
Verwenden
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.
Lager
Store at +4°C
Einzelnachweise
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]- Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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