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

ChemicalBook > CAS DataBase List > Octanoic acid, 6,8-bis[(phenylMethyl)thio]-

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

Product Name: Octanoic acid, 6,8-bis[(phenylMethyl)thio]-
CAS No.: 95809-78-2
Chemical Name: Octanoic acid, 6,8-bis[(phenylMethyl)thio]-
Synonyms: CPI-613;Devimistat;CPI-613, >98%;CPI 613;CPI613;CPI-613(Devimistat);Devimistat (CPI-613);CPI-613;CPI 613;CPI613;6,8-Bis(benzylthio)octanoic acid;alpha-lipoic acid analogue CPI-613;6,8-Bis(benzylsulfanyl)octanoicaci
CBNumber: CB52554078
Molecular Formula: C22H28O2S2
Formula Weight: 388.59
MOL File: 95809-78-2.mol

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

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.

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Safety

Hazard Codes: N
Risk Statements: 50/53
Safety Statements: 60-61
RIDADR: UN 3077 9 / PGIII
WGK Germany: 3
HS Code: 2930.90.2900

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P273Avoid release to the environment.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML0404
Product name: 6,8-Bis(benzylthio)-octanoic acid
Purity: ≥98% (HPLC)
Packaging: 5mg
Price: $64.8
Updated: 2024/03/01

Sigma-Aldrich

Product number: SML0404
Product name: 6,8-Bis(benzylthio)-octanoic acid
Purity: ≥98% (HPLC)
Packaging: 25mg
Price: $429
Updated: 2024/03/01

TCI Chemical

Product number: B5368
Product name: 6,8-Bis(benzylthio)octanoic Acid
Packaging: 5MG
Price: $112
Updated: 2024/03/01

TCI Chemical

Product number: B5368
Product name: 6,8-Bis(benzylthio)octanoic Acid
Packaging: 25MG
Price: $388
Updated: 2024/03/01

Cayman Chemical

Product number: 16981
Product name: CPI-613
Purity: ≥98%
Packaging: 5mg
Price: $39
Updated: 2024/03/01

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

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

Raw materials

Preparation Products

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View Lastest Price from Octanoic acid, 6,8-bis[(phenylMethyl)thio]- manufacturers

Shaanxi Dideu Medichem Co. Ltd

Product: CPI 613 95809-78-2
Price: US $0.00-0.00/KG
Min. Order: 5mg
Purity: 99% HPLC
Supply Ability: 2000tons
Release date: 2019-12-30

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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

CPI 613;CPI613

(+/-)6,8-bis-thiobenzyl octanoic acid

CPI-613(Devimistat)

CPI-613;CPI 613;CPI613

CPI-613, >98%

Devimistat

CPI613; CPI-613; CPI 613; DEVIMISTAT

Octanoic acid, 6,8-bis[(phenylMethyl)thio]- USP/EP/BP

Devimistat (CPI-613)

6,8-Bis(benzylsulfanyl)octanoicaci

95809-78-2

Inhibitor

Inhibitors