110-72-5Relevant articles and documents
Rigorous control of vesicle-forming lipid pKa by fluorine-conjugated bioisosteres for gene-silencing with siRNA
Okamoto, Ayaka,Koide, Hiroyuki,Morita, Naoki,Hirai, Yusuke,Kawato, Yuji,Egami, Hiromichi,Hamashima, Yoshitaka,Asai, Tomohiro,Dewa, Takehisa,Oku, Naoto
, p. 87 - 92 (2019)
While the influence of pKa provided by amine-containing materials in siRNA delivery vectors for use in gene-silencing has been widely studied, there are little reports in which amine pKa is controlled rigorously by using bioisosteres and its effect on gene-silencing. Here, we report that amine pKa could be rigorously controlled by replacement of hydrogen atom(s) with fluorine atom(s). A series of mono- and di-amine lipids with a different number of fluorine atoms were synthesized. The pKa of the polyamine lipids was shifted to a lower value with an increase in the number of fluorine atoms. The optimal pKa for high gene-silencing efficiency varied according to the number of amine residues in the polyamine lipid. Whereas the endosomal escape ability of mono-amine lipid-containing lipid vesicles (LVs) depended on the pKa, that of all tested di-amine lipid-containing LVs showed equal membrane-destabilizing activity. LVs showing moderately weak interactions with siRNA facilitated cytoplasmic release of siRNA, resulting in strong gene-silencing. These findings indicate that appropriate amine pKa engineering depending on the number of amines is important for the induction of effective RNA interference.
The synthesis of asymmetric ethylenediamine derivatives catalyzed by ion-exchange resins
Wang, Wenwen,Wei, Ruisong,Yin, Guohui,Tian, Jun,Duan, Yifan,Chen, Ligong,Li, Yang
, p. 4511 - 4522 (2015/06/30)
The ring-opening reaction of aziridine with alkylamines over a series of ion-exchange resins was investigated. Among these catalysts, D001-CC exhibited excellent catalytic performance. The catalysts were characterized by SEM and N2 adsorption-desorption. The results indicated that the selectivity of N,N-diethylethylenediamine mainly depended on the acidity and S BET of the resins. Strong Br?nsted acid sites played an important role on the conversion of aziridine, and the distribution of acid sites on catalyst had a significant effect on the selectivity of N,N-diethylethylenediamine. The reaction parameters, such as reaction time, molar ratio, reaction temperature, and catalyst loading, were also optimized and N,N-diethylethylenediamine was obtained in an excellent yield of 97 %. Furthermore, D001-CC was efficiently recycled five times by simple treatment with large amounts of deionized water and mineral acid. Finally, a series of asymmetric ethylenediamine derivatives were successfully synthesized with this method. Therefore, a simple and versatile process for the synthesis of asymmetric ethylenediamine derivatives has been established over ion-exchange resins.
N-alkylation of ethylenediamine with alcohols catalyzed by CuO-NiO/γ-Al2O3
Huang, Jia-Min,Xu, Lu-Feng,Qian, Chao,Chen, Xin-Zhi
experimental part, p. 304 - 307 (2012/08/28)
A simple method for N-alkylation of 1, 2-diaminoethane with different alcohols in a fixed-bed reactor using cheap CuO-NiO/γ-Al2O 3 as the catalyst has been developed. The present catalytic system was applicable in the N-alkylation of 1, 2-diaminoethane with both primary and secondary alcohols. Mono-N-alkylation of 1, 2-diaminoethane with low-carbon alcohols resulted in high yields; the yields of tetra-N-alkylation of 1, 2-diaminoethane with low-carbon alcohols declined markedly with the increase of the molecular volume of alcohols.