PN-II-RU-TE-2014-4-0654

Unprecedented polyesters as coating for solid surfaces with application in medicine and nanotechnology

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Results for Objective 3

O3. Synthesis and characterization of functionalized PAHCA II on supports by coupling of PAHCA I with applicatory functions

 

           The main activities of objective 3 were focused on the synthesis of materials based on the functionalized polymers poly(benzofurane-co-arylacetic acid), poly(tartronic-co-glycolic acid), polytartronic acid and poly(2-hydroxy-pentandioic acid 5-allyl ester). Nanostructures consisting of these polmers were used as platforms for further functionalization.

           In the case of nanostructures based on poly(benzofurane-co-arylacetic acid) we used all three reactive groups (phenol, carboxyl, lactone ring) existing in the polymer structure to decorate the nanostructures with interesting applicatory function such as: glucose, McMillan catalyst, proline derivatives, dopamine, N,N’-bis(carboxymethyl)-L-lysine, the fluorescent marker 7-amino-4-methylqinoline-2(1H)-on, hystamine, arginine and 1-(3-aminopropyl)imidazole. To functionalize this nanostructure at the phenol moieties bromo-substituted compounds with useful applicatory entities were applied. In order to exploit the lactone ring as linking point we used just amines without a catalyst and for the carboxyl group the linkage was achieved by interaction with amines using EDC (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide) coupling method or with alcohols using Steglich esterification method.

           Poly(tartronic-co-glycolic acid)-based nanostructures were linked to glucosamine and N,N’-bis(carboxymethyl)-L-lysine while the polytartronic acid coated nanostructures were functionalized with glucosamine and guanine. This functionalization was brought about by the EDC coupling method in the presence of hydroxybenzotriazole (HOBt) and diisopropylethylamine (DIPEA).

           Nanostructure coated with poly(2-hydroxy-pentandioic acid 5-allyl ester) were linked with cysteine by the thiol-ene reaction where 2,2′-azobis(2-methylpropionitrile) (AIBN) acted as mediator.

           All the functionalized nanostructures where meticulously investigated in terms of structure, morphology and properties.