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Synthesis and in vitro Property Study of Polyaspartamides
Author(s) -
YAN GuoPing,
WANG XiaoYan,
WANG XuLi,
HUANG ShiWen,
ZHUO RenXi
Publication year - 2007
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200790323
Subject(s) - chemistry , cationic polymerization , lysine , cytotoxicity , amine gas treating , dna , solubility , polymer chemistry , stereochemistry , nuclear chemistry , in vitro , organic chemistry , amino acid , biochemistry
Cationic polyaspartamides including poly‐ α , β ‐[ N′ ‐(2‐aminoethy1)‐ L ‐aspartamide] (PAEA), poly‐ α , β ‐[ N′ ‐(4‐aminobutyl)‐ L ‐aspartamide] (PABA), poly‐ α , β ‐[ N′ ‐(6‐aminohexyl)‐ L ‐aspartamide] (PAHA), poly‐ α , β ‐[ N′ ‐(5‐amino‐3‐azapentyl)‐ L ‐aspartamide] (PAAPA) and poly‐ α , β ‐[ N′ ‐(8‐amino‐3,6‐diazaoctyl)‐ L ‐aspartamide] (PADAOA) were synthesized from polysuccinimide. Their properties were evaluated by 1 H NMR, IR, GPC, fluorescence measurement and in vitro cytotoxicity assays. The molecular weights per primary amine charge group of PAEA(1) ( M n =2229), PAAPA and PADAOA are 212, 279, and 226. Polyaspartamides including PAEA(1), PAAPA, PADAOA and low molecular weight PAHA are markedly less toxic than poly(ethyleneimine) and poly( L ‐lysine), however, PABA and higher molecular weight PAHA are slightly less toxic than poly( L ‐lysine). Cell cytotoxicity of PAHA was seen to decrease with increasing molecular weight of PAHA, due to water solubility reduction. The negatively charged plasmid DNA has been found to be completely neutralized and complexed by the cationic polyaspartamides at an N/P ratio of 5:1 to 10:1, forming self‐assembled polyplexes via ionic interactions. These polyaspartamide/DNA complexes possess stable zeta potentials and mean particle diameters of about 180 nm for PAEA (1)/DNA and PAAPA/DNA complexes and 280 nm for PADAOA/DNA complexes.