95809-78-2 Usage
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
Different sources of media describe the Uses of 95809-78-2 differently. You can refer to the following data:
1. CPI 613 is a class of non-redox-active lipoate derivative that disrupts cancer cell mitochondrial metabolism and are potent anticancer agents in vivo.
2. 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 cellsto induce α-smooth muscle actin (αSMA) and pro-collagen I expression and to assess PDH enzyme activity in whole-cell lysatesto 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.
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 articles and documents
Method for synthesizing and preparing anti-tumor innovative drug, namely Devimistat
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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.
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.
