Premium
Water‐soluble polyamides as potential drug carriers, IV: amine‐functionalized copolyaspartamides
Author(s) -
de L. Machado Maria,
Neuse Eberhard W.,
Perlwitz Axel G.,
Schmitt Siegfried
Publication year - 1990
Publication title -
polymers for advanced technologies
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.61
H-Index - 90
eISSN - 1099-1581
pISSN - 1042-7147
DOI - 10.1002/pat.1990.220010501
Subject(s) - succinimide , nucleophile , amine gas treating , imide , polyamide , diamine , dimethylformamide , polymer chemistry , chemistry , solubility , substituent , macromolecule , organic chemistry , polymer , combinatorial chemistry , biochemistry , solvent , catalysis
Poly‐ D , L ‐succinimide ( 1 ) is converted to copolyaspartamides of the general type 2 by sequential treatment with diamine nucleophiles R′NH 2 and R″NH 2 , in which R′ is a group containing a tertiary amine function providing water solubility, and R″ represents a substituent comprising primary or secondary amino groups capable of interaction with suitably carboxyl‐ or carbonyl‐functionalized drug models. The reactions are performed in dimethylformamide medium under mild, yet carefully controlled conditions conducive to aminolytic imide ring opening in the educt polymer without causing crosslink formation through difunctional interaction of the R″NH 2 co‐nucleophile. The perfectly water‐soluble polymeric products (η inn , 5–30 ml/g), purified and isolated by dialysis (12,000–14,000 molecular mass cut‐off) and freeze‐drying, are of interest as macromolecular carrier species for pharmaceuticals and other biologically active agents. The drug‐binding potential of the target polymers is demonstrated by the coupling, through active ester intermediacy, of phenylacetic acid as a representative drug model to selected copolyamides.