- Rigorous control of vesicle-forming lipid pKa by fluorine-conjugated bioisosteres for gene-silencing with siRNA
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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.
- Okamoto, Ayaka,Koide, Hiroyuki,Morita, Naoki,Hirai, Yusuke,Kawato, Yuji,Egami, Hiromichi,Hamashima, Yoshitaka,Asai, Tomohiro,Dewa, Takehisa,Oku, Naoto
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Read Online
- The synthesis of asymmetric ethylenediamine derivatives catalyzed by ion-exchange resins
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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.
- Wang, Wenwen,Wei, Ruisong,Yin, Guohui,Tian, Jun,Duan, Yifan,Chen, Ligong,Li, Yang
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p. 4511 - 4522
(2015/06/30)
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- HIV INTEGRASE INHIBITORS
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The present invention features compounds that are HIV integrase inhibitors and therefore are useful in the inhibition of HIV replication, the prevention and/or treatment of infection by HIV, and in the treatment of AIDS and/or ARC.
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- N-alkylation of ethylenediamine with alcohols catalyzed by CuO-NiO/γ-Al2O3
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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.
- Huang, Jia-Min,Xu, Lu-Feng,Qian, Chao,Chen, Xin-Zhi
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experimental part
p. 304 - 307
(2012/08/28)
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- N-alkylation of ethylenediamine with alcohols catalyzed by CuO-NiO/?3-Al2O3
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A simple method for N-alkylation of 1,2-diaminoethane with different alcohols in a fixed-bed reactor using cheap CuO-NiO/?3-Al2O3 as the catalyst has been developed. The present catalytic system was applicable in the N-alkylation of
- Huang, Jia-Min,Xu, Lu-Feng,Qian, Chao,Chen, Xin-Zhi
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p. 304 - 307
(2015/03/03)
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- METHOD FOR PRODUCING N-MONOALKYL-SUBSTITUTED ALKYLENE AMINE
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PROBLEM TO BE SOLVED: To provide a method for producing an N-monoalkyl-substituted alkylene amine especially useful for uses such as medicine intermediates, agrochemical intermediates, urethane resin-foaming catalysts, surfactants and the like among alkyl-substituted alkylene amine compounds from an alcohol and an alkylene amine as raw materials. SOLUTION: This method for producing the N-monoalkyl-substituted alkylene amine is characterized by reacting the alkylene amine with a ≥2C alkyl alcohol in the presence of a copper-containing oxide catalyst system. The N-monoalkyl-substituted alkylenamine is produced in high conversion and in N-monoalkylation selectivity.
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Page/Page column 6; 8
(2010/02/11)
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- Bleach and oxidation catalyst
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A bleach and oxidation catalyst is provided comprising a catalytically active iron, manganese or copper complex including a specified pentadentate nitrogen-containing ligand. The metal complex can activate hydrogen peroxide or peroxyacids and provides favourable stain removal properties. In addition, a considerably improved stability of these metal complex compounds in alkaline aqueous environment has been obtained, in particular at the peroxy compound concentrations generally present in the fabric washing liquor.
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- Method and apparatus for sunless tanning
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Apparatus for simulating skin tanning comprises a receptacle containing a fluid comprising dihydroxyacetone, a receptacle containing a fluid comprising a secondary polyamine, and dispensing means for simultaneously or sequentially providing desired amounts of dihydroxyacetone and polyamine.
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- Process for preparing N-alkylethylenediamines
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This disclosure describes a novel process for preparing N-alkylethylenediamines which are useful as intermediates for purifying penicillins. N-alkylethylenediamines are also useful for preparing penicillins and cephalosporins. Specifically, N-ethylethylenediamine is useful for manufacturing piperacillin which is useful as an antibiotic. More particularly, the invention relates to a process for the efficient reaction of an alkyl halide and ethylenediamine and the recovery of anhydrous, ethylenediamine-free N-alkylethylenediamines therefrom.
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