Synthesis of biomimetic polyamines

Abstract

Synthesis of methylated oligopropylamines by the stepwise repetition of reactions between methyl acrylate and amine, amidation and reduction of the resulting amide is reported. Longchain oligomers (average 15 nitrogen atoms) were obtained via condensation reactions utilising 1,3-dibromopropane. Three new acrylic monomers were prepared by reaction of oligopropylamines with acryloyl chloride. The synthesized amines and monomers are promising as model compounds for biosilicification reactions, as biologically active substances and as building blocks in organic and polymer chemistry.

Bioinspired thermo- and pH-responsive polymeric amines: Multimolecular aggregates in aqueous media and matrices for silica/polymer nanocomposites

“…2,2 0 -Azobis(isobutyronitrile) (AIBN, Sigma Aldrich) was recrystallized from ethanol. DEAPMA was synthesized according to the literature procedure [19] using the reaction of acryloyl chloride with N 1 ,N 1 -diethyl-N 3 -methyl-1,3-propanediamine. N 1 ,N 3 -dimethyl-N 1 -[3-(methylamino)propyl]-N 3 -(7-nitro-2,1,3-benzoxadiazol-4-yl)propane-1,3-diamine (NBD-N3) was obtained based on a literature method [20] and used as a 0.25 mM DMSO-water (1:4) solution.…”

“…Condensation of silicic acid in the presence of these aggregates resulted in hollow submicrometer spherical particles [12]. The availability of oligopropylamines facilitated the synthesis of more complicated compounds, including acrylate monomers [19,20]. One of these monomers, N-(3-(diethylamino)propyl)-N 0 -methylacrylamide (DEAPMA), gave rise to a thermo-responsive polymer (PDEAPMA, Fig.…”

“…We previously presented a step-wise approach for generating synthetic analogues of methylated oligopropylamines [10,19]. This method facilitated generation of these analogues in adequate quantities, thus allowing the study of their activity in silicification reactions.…”

Design of the Oligonucleotide Carriers: Importance of Polyamine Chain Length

“…Some polymeric amines [22,23] capable of interacting with oligomers of silicic acid and forming stable composite nanoparticles were considered as models of cytoplasmic silicon containing vesicles. We have elaborated [24] a method to synthesize LCPAs as an oligomeric mixture containing polyamines with 6-30 nitrogen atoms.…”

“…N,N-bis [3-(methylamino)propyl]methylamine was prepared following the technique from our earlier work [26]. Oligo(N-methylazetidine) (LCPA, ZS-309 sample) was prepared from 1,3-dibromopropane and N,N-bis [3-(methylamino)propyl]methylamine according to earlier work from our group [24]. AKX-182 polymer was prepared according to the protocol described earlier [13].…”