36915-02-3Relevant articles and documents
An efficient, economical synthesis of the novel anti-tumor agent CPI-613
Gibson, Frank S.,Gupta, Deepak,Shorr, Robert,Rodriguez, Robert
, p. 855 - 857 (2011)
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.
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.