902768-55-2

Usage

Uses

Used in Pharmaceutical Industry:
N^2'-deacetyl-N^2'-[4-methyl-4-(methyldithio)-1-oxopentyl]-D-maytansine is used as a cytotoxic agent for the development of antibody-drug conjugates. It is specifically used in the potential treatment of cancer, where it can be linked to antibodies that target specific cancer cells, allowing for the delivery of the cytotoxic agent directly to the tumor site.
As an Impurity in Maytansinoid DM4:
N^2'-deacetyl-N^2'-[4-methyl-4-(methyldithio)-1-oxopentyl]-D-maytansine is an impurity found in Maytansinoid DM4, which is a cytotoxic agent used in the development of antibody-drug conjugates. The presence of this impurity may affect the efficacy and safety of the final product, and therefore, it is important to monitor and control its levels during the manufacturing process.

Upstream product

• 796073-57-9 N-methyl-N-[4-methyl-(4-methyldithio)-1-oxopentyl]-L-alanine 
• 57103-68-1 maytansinol 
• 796073-55-7 N-methyl-N-[4-methyl-(4-methyldithio)-1-oxopropyl]-L-alanine 

Relevant academic research and scientific papers

Semisynthetic Maytansine analogues for the targeted treatment of cancer

Maytansine, a highly cytotoxic natural product, failed as an anticancer agent in human clinical trials because of unacceptable systemic toxicity. The potent cell killing ability of maytansine can be used in a targeted delivery approach for the selective destruction of cancer cells. A series of new maytansinoids, bearing a disulfide or thiol substituent were synthesized. The chain length of the ester side chain and the degree of steric hindrance on the carbon atom bearing the thiol substituent were varied. Several of these maytansinoids were found to be even more potent in vitro than maytansine. The targeted delivery of these maytansinoids, using monoclonal antibodies, resulted in a high, specific killing of the targeted cells in vitro and remarkable antitumor activity in vivo.

Method for the preparation of maytansinoid esters

Improved processes for the preparation and purification of maytansinoid esters, especially thiol and disulfide-containing maytansinoids are described. In one aspect the process comprises a process of making a maytansinoid ester comprising forming an anion of maytansinol or a maytansinoid bearing a free C-3 hydroxyl moiety and reacting the anion with an activated carboxyl compound to thereby produce the maytansinoid ester.