6,8-Bis(benzylthio)octanoic acid

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Description: PDH and KGDH inhibitor
Chemical Name: 6,8-Bis[(phenylmethyl)thio]octanoic acid
Purity: ≥99% (HPLC)
Datasheet
Citations (1)
Reviews
Literature (2)

Biological Activity for 6,8-Bis(benzylthio)octanoic acid

6,8-Bis(benzylthio)octanoic acid is a pyruvate dehydrogenase (PDH) and α-ketoglutarate dehydrogenase (KGDH) inhibitor. Disrupts tumor cell mitochondrial metabolism, and increases mitochondrial reactive oxygen species (ROS) production in H460 lung carcinoma cells. Has no effect on KGDH activity in normal bronchial epithelial cells. Induces cell death of multiple tumor cell lines selectively over normal cells in vitro. Inhibits tumor growth of H460 and BxPC-3 tumor cell xenografts in mice.

Technical Data for 6,8-Bis(benzylthio)octanoic acid

M. Wt 388.59
Formula C22H28O2S2
Storage Store at +4°C
Purity ≥99% (HPLC)
CAS Number 95809-78-2
PubChem ID 24770514
InChI Key ZYRLHJIMTROTBO-UHFFFAOYSA-N
Smiles OC(CCCCC(SCC2=CC=CC=C2)CCSCC1=CC=CC=C1)=O

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

Tocris products are intended for laboratory research use only, unless stated otherwise.

Solubility Data for 6,8-Bis(benzylthio)octanoic acid

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 38.86 100
ethanol 38.86 100

Preparing Stock Solutions for 6,8-Bis(benzylthio)octanoic acid

The following data is based on the product molecular weight 388.59. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.57 mL 12.87 mL 25.73 mL
5 mM 0.51 mL 2.57 mL 5.15 mL
10 mM 0.26 mL 1.29 mL 2.57 mL
50 mM 0.05 mL 0.26 mL 0.51 mL

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Product Datasheets for 6,8-Bis(benzylthio)octanoic acid

References for 6,8-Bis(benzylthio)octanoic acid

References are publications that support the biological activity of the product.

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 PMID: 21769686

Stuart et al (2014) A strategically designed small molecule attacks alpha-ketoglutarate dehydrogenase in tumor cells through a redox process. Cancer Metab. 2 4 PMID: 24612826

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 e0198940 PMID: 29879220


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1 Citation for 6,8-Bis(benzylthio)octanoic acid

Citations are publications that use Tocris products. Selected citations for 6,8-Bis(benzylthio)octanoic acid include:

Norbert et al (2020) Mitochondrial Ca2+ Signaling Is an Electrometabolic Switch to Fuel Phagosome Killing. Cell Rep 33 108411 PMID: 33238121


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Literature in this Area

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This poster summarizes the main metabolic pathways in cancer cells and highlights potential targets for cancer therapeutics. Genetic changes and epigenetic modifications in cancer cells alter the regulation of cellular metabolic pathways providing potential cancer therapeutic targets.