10124-68-2Relevant academic research and scientific papers
Alkane-modified low-molecular-weight polyethylenimine with enhanced gene silencing for siRNA delivery
Guo, Gaoyang,Zhou, Li,Chen, Zhifei,Chi, Weilin,Yang, Xiuqun,Wang, Wei,Zhang, Biliang
, p. 44 - 52 (2013)
Small interfering RNA (siRNA) has tremendous potential as a therapeutic agent for diverse diseases; however, due to its susceptibility to degradation and poor cellular uptake, the low efficiency of administration has been the most important limiting factor for clinical applications of siRNA. Herein, we synthesized alkyl chain modified low-molecular-weight polyethylenimines (LMW PEIs) and found that hydrophobically modified PEIs displayed enhanced efficiency in siRNA-mediated knockdown of target genes. To elucidate the mechanism for increased delivery, we characterized the polymers' physicochemical properties and bioactivity via nuclear magnetic resonance (NMR), gel retardation assay, dynamic laser scattering (DLS) analysis, confocal laser scanning microscopy and flow cytometry. The hydrophobic modification reduced siRNA binding affinity but facilitated the formation of nanoparticles in contrast to the original PEI. The PEIs with eight and thirteen alkyl tails were able to self-assemble into nanoparticles and yielded higher cellular uptake, which leaded to even similar efficiencies of 80-90% knockdown as Lipofectamine 2000 control. These results suggested that the status of polymers in aqueous solution, which depended on the degree of hydrophobic modification, played an important role in the uptake of siRNA. Therefore, we provided new information on the role of hydrophobic content in the enhanced gene silencing activity.
Poly(acrylamide-co-alkylacrylamides) for electrophoretic DNA purification in microchannels
Chiesl, Thomas N.,Shi, Wei,Barron, Annellse E.
, p. 772 - 779 (2005)
We have created a family of water-soluble block copolymers of acrylamide and N-alkylacrylamides that are designed to selectively remove proteins from DNA via microchannel electrophoresis. It was hypothesized that the inclusion of hydrophobic subunits in the polymer chain, in sufficient concentration, could lead to protein adsorption due to hydrophobic interactions. A series of N-alkylacrylamide comonomers with varying alkyl chain lengths (C4, C6, C8) and also an N,N-dialkyl group (C6-C6) were synthesized via reactions between acryloyl chloride and the respective alkylamines. Copolymers were synthesized using an aqueous "micellar" polymerization technique, which involves dissolving acrylamide in the aqueous phase while hydrophobic monomers are solubilized in sodium dodecyl sulfate micelles. Copolymers comprising up to 4 mol % of a hydrophobic subunit (as verified by 1H NMR) were synthesized. Polymer molecular weights were determined by tandem gel permeation chromatography-multiangle laser light scattering, and ranged from 1.5 × 106 to 4.3 × 106. Capillary electrophoresis analysis of bovine serum albumin and β-lactoglobulin migration in these matrixes revealed that the octylacrylamide and dihexylacrylamide copolymers show the most significant extent of protein adsorption while butylacrylamides show no noteworthy adsorption trend. All copolymer matrixes studied allowed the passage of a dsDNA digest, and displayed some DNA sieving ability at 0.5% (w/w) in TTE (50 mM Tris, 50 mM TAPS, 2 mM EDTA, pH 8.4) buffer. These matrixes are demonstrated in on-chip experiments to adsorb protein, in a step toward meeting the front-end processing goals of μ-TAS for genetic analysis applications.
RAFT polymers for protein recognition
Tominey, Alan F.,Liese, Julia,Kraft, Arno,Wei, Sun,Kowski, Klaus,Schrader, Thomas
, (2010)
A new family of linear polymers with pronounced affinity for arginine- and lysine-rich proteins has been created. To this end, N-isopropylacrylamide (NIPAM) was copolymerized in water with a binding monomer and a hydrophobic comonomer using a living radical polymerization (RAFT). The resulting copolymers were water-soluble and displayed narrow polydispersities. They formed tight complexes with basic proteins depending on the nature and amount of the binding monomer as well as on the choice of the added hydrophobic comonomer.
Acylation of alcohols and amines with vinyl acetates catalyzed by Cp*2Sm(thf)2
Ishii, Yasutaka,Takeno, Mitsuhiro,Kawasaki, Yumi,Muromachi, Akifumi,Nishiyama, Yutaka,Sakaguchi, Satoshi
, p. 3088 - 3092 (1996)
Cp*2Sm(thf)2 was found to be an efficient catalyst for the acylation of alcohols and amines with esters under mild conditions. In the present acylation, vinyl and isopropenyl acetates served as good acylating agents. Thus, a variety of alcohols and amines underwent acylation with vinyl and isopropenyl acetates in the presence of Cp*2Sm(thf)2 to give the corresponding esters and amides in good to excellent yields. This catalytic acylation of alcohols and amines offers an additional useful method by the use of various esters, instead of acid anhydrides and acid chlorides, as acylating agents under very mild conditions.
Reactivity of secondary N-alkyl acrylamides in Morita–Baylis–Hillman reactions
Ahmar, Mohammed,Queneau, Yves,Verrier, Charlie,Yue, Xiaoyang
, p. 319 - 330 (2021/10/29)
The Morita–Baylis–Hillman (MBH) reaction of secondary N-alkyl acrylamides, discarded up to now from investigations of the scope of activated alkenes, was studied. Optimization of the reaction conditions revealed that a balance must be found between activation of the MBH coupling reaction and that of the undesired competitive aldehyde Cannizzaro reaction. Using 3-Hydroxyquinuclidine (3-HQD) in a 1:1 water-2-MeTHF mixture provides the appropriate conditions that were applicable to a wide range of diversely substituted secondary N-alkyl acrylamides and aromatic aldehydes, giving rise to novel amide-containing MBH adducts under mild and clean conditions.
