95809-78-2 Usage
Uses
Used in Cancer Research:
Octanoic acid, 6,8-bis[(phenylMethyl)thio]is used as a pyruvate dehydrogenase (PDH) inhibitor for studying its effects on neurite outgrowth in primary mouse dorsal root ganglia cells. This helps researchers understand the role of PDH in neuronal development and its potential as a therapeutic target for neurological disorders.
Used in Tissue Engineering:
Octanoic acid, 6,8-bis[(phenylMethyl)thio]is used to induce α-smooth muscle actin (αSMA) and pro-collagen I expression in cells, which are important for tissue regeneration and repair. By studying the effects of Octanoic acid, 6,8-bis[(phenylMethyl)thio]on these proteins, researchers can gain insights into the mechanisms of tissue repair and develop new therapeutic strategies for various diseases.
Used in Metabolic Research:
Octanoic acid, 6,8-bis[(phenylMethyl)thio]is used to validate basal respiration in tissue respirometry. This allows researchers to study the metabolic activity of cells and tissues, which can provide valuable information about the energy requirements and metabolic pathways of different cell types.
Used in Drug Development:
As a potent anticancer agent, Octanoic acid, 6,8-bis[(phenylMethyl)thio]is used in the development of new drugs targeting cancer cell mitochondrial metabolism. Its non-genotoxic properties make it a promising candidate for further research and potential clinical applications in cancer treatment.
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.
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
Check Digit Verification of cas no
The CAS Registry Mumber 95809-78-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,5,8,0 and 9 respectively; the second part has 2 digits, 7 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 95809-78:
(7*9)+(6*5)+(5*8)+(4*0)+(3*9)+(2*7)+(1*8)=182
182 % 10 = 2
So 95809-78-2 is a valid CAS Registry Number.
95809-78-2Relevant academic research and scientific papers
Method for synthesizing and preparing anti-tumor innovative drug, namely Devimistat
-
Paragraph 0023; 0026-0037, (2020/07/15)
The invention relates to a method for synthesizing and preparing an anti-tumor innovative drug, namely Devimidat. According to the preparation method for the Devimidat, after a process is improved, metal cobalt polysulfide does not need to be used any more; the process route is simple and convenient; the product, namely the Devimidat can be obtained through two steps which are performed through aone-pot method; and the preparation method has high yield and is applicable to large-scale production.
CPI-613: Antimitochondrial metabolism agent Treatment of hematological malignancies and solid tumors
Moro
, p. 209 - 214 (2017/05/17)
Metabolic changes specifically associated with cancer may constitute an excellent opportunity for the identification of new biomarkers and targets for novel drugs. The coenzyme lipoate is a key player in the control of cell metabolic fluxes and occupies a central position in tumor biology. Previous observations suggested that systemically delivered lipoate analogues might selectively disrupt cancer mitochondrial metabolism, potentially resulting in cancer cell death. CPI-613, the first member of a large set of lipoate analogues, specifically inhibits mitochondrial metabolism in a wide range of tumor cell lines, but not in normal cells, by mechanisms involving pyruvate dehydrogenase and α-ketoglutarate dehydrogenase enzyme complexes. There are 14 ongoing or completed phase I and phase II clinical trials on CPI-613, alone or in combination, showing promising results for several hematological malignancies and solid tumors, particularly for the treatment of acute myeloid leukemia, myelodysplastic syndrome and pancreatic cancer.
An efficient, economical synthesis of the novel anti-tumor agent CPI-613
Gibson, Frank S.,Gupta, Deepak,Shorr, Robert,Rodriguez, Robert
experimental part, p. 855 - 857 (2012/07/14)
An efficient and practical synthesis of the novel anti-tumor compound 6,8-dithiobenzyl octanoic acid, CPI-613 (2), was developed and executed on a practical scale. CPI-613 can be made in a single vessel from (±)-lipoic acid (1) via reductive opening of the disulfide ring followed by benzylation of the sulfhydryls with benzyl bromide. CPI-613 was isolated by simple crystallization in high yield and purity. The process is scaleable and has been demonstrated at up to 100 kg.
