Facilitating Myers-Saito cyclization through acid-triggered tautomerization for the development of maleimide-based antitumor agents was written by Lu, Haotian;Ma, Hailong;Li, Baojun;Zhang, Mengsi;Chen, Huimin;Wang, Yue;Li, Xinxin;Ding, Yun;Hu, Aiguo. And the article was included in Journal of Materials Chemistry B in 2020.Application of 6413-10-1 The following contents are mentioned in the article:
Enyne-allene compounds undergo Myers-Saito cyclization at physiol. temperature to generate diradical intermediates that are capable of inducing DNA damage and cell death. The high reactivity of enyne-allene however limits their promising prospect as anticancer agents due to the spontaneous cyclization during storage and delivery. Regulating the cyclization process by taking advantage of the characteristics of a tumor cellular microenvironment, such as employing a low pH value to activate the cyclization process, is thus of essential importance. In this work, a novel enediyne (EDY) system with locked carbonyl groups was specifically designed and synthesized. Unlocking the protected carbonyl groups in the presence of acid would facilitate the rearrangement of propargyl moieties into an allene group, enabling the formation of an enyne-allene structure and occurrence of Myers-Saito cyclization. The pH-dependent diradical generation and DNA-cleavage ability of the designed EDY system were confirmed by ESR anal. and DNA gel electrophoresis. A promising cytotoxicity against HeLa cells with half inhibition concentrations (IC50) as low as 1.40μM was obtained, which was comparable to those of many com. applied anticancer drugs. Further in vitro experiments revealed that this EDY system induced intracellular DNA damage and subsequently resulted in S-phase arrest and cytotoxicity through programmed apoptosis. This study involved multiple reactions and reactants, such as Ethyl 2-(2-methyl-1,3-dioxolan-2-yl)acetate (cas: 6413-10-1Application of 6413-10-1).
Ethyl 2-(2-methyl-1,3-dioxolan-2-yl)acetate (cas: 6413-10-1) belongs to dioxole derivatives. Dioxoles, particularly fluorinated dioxoles, are used as co-monomers to make polymers that find use in forming protective coatings for chemical resistance. 1,3-Benzodioxole can be synthesized from catechol with disubstituted halomethanes.Application of 6413-10-1
Referemce:
1,3-Benzodioxole – Wikipedia,
Dioxole | C3H4O2 – PubChem