Synthesis and self-assembly of pH and ROS dual responsive poly(β-thioester)s was written by Zhao, Wenjing;Qiao, Zengying;Duan, Zhongyu;Wang, Hao. And the article was included in Huaxue Xuebao in 2016.Safety of Diethyleneglycoldiacrylate This article mentions the following:
The Michael addition reaction, which was a mild reaction between activated olefins and nucleophiles, was widely used in synthesis of tailored macromol. architectures. We designed a copolymer nanoparticle to obtain the reactive oxygen species (ROS) and pH dual responsive capability. We synthesized the amphiphilic poly(β-thioester)s copolymers (D-D-P) composed of di(ethylene glycol) diacrylate (DEDA), DL-dithiothreitol (DTT), acryloyl chloride (AC) and hydrophilic mercaptopolyethylene glycol (PEG-SH) with average Mn = 2,000 g·mol-1 via Michael addition reaction. The reactions were facile and controllable, and the structures of acquired copolymers were well characterized. The structures of the polymers were confirmed by 1H NMR, and the number mol. weight and distribution of the copolymer D-D-P were measured by GPC (Mn = 50,400). D-D-P could self-assemble into nanoparticles with core-shell structures by dialysis method due to the composition of hydrophilic side chains and hydrophobic polymer backbones. After the preparation of ROS and pH dual responsive D-D-P nanoparticles in phosphate buffer solution, the morphol. and size of D-D-P nanoparticles were observed by transmission electron microscopy (TEM) and dynamic light scattering (DLS) showed that the number size distribution of nanoparticles was around 280 nm. Nile Red (NR) was a unique neutral hydrophobic mol., which showed very weak fluorescence in aqueous solution and could emit strong fluorescence in the hydrophobic environment. NR absorption and emission spectra were strongly dependent on environment polarity, which made it as a probe mol. that was widely used in the evaluation of microenvironment polarity. The disassembly behaviors of D-D-P nanoparticles were investigated by the change of the nanoparticle size and NR fluorescence spectra. The diameter of nanoparticle decreased under pH 5 and ROS environment conditions, and the NR fluorescence also became weak under pH 5 and ROS environment conditions, which could be attributed to the gradual dissolution of nanoparticles, proving the ROS and pH dual responsive properties of the poly(β-thioester)s. The release behaviors of the DOX encapsulated D-D-P nanoparticles in acidic and oxidative condition were studied by the UV absorption and were further proved in MCF-7 cells. In the experiment, the researchers used many compounds, for example, Diethyleneglycoldiacrylate (cas: 4074-88-8Safety of Diethyleneglycoldiacrylate).
Diethyleneglycoldiacrylate (cas: 4074-88-8) belongs to alcohols. A strong base can deprotonate an alcohol to yield an alkoxide ion (R―O−). For example, sodamide (NaNH2), a very strong base, abstracts the hydrogen atom of an alcohol. Alcohols may be oxidized to give ketones, aldehydes, and carboxylic acids. These functional groups are useful for further reactions. Oxidation of organic compounds generally increases the number of bonds from carbon to oxygen (or another electronegative element, such as a halogen), and it may decrease the number of bonds to hydrogen.Safety of Diethyleneglycoldiacrylate
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts