Synthesis of poly(ester-amide) dendrimers based on 2,2-Bis (hydroxymethyl) propanoic acid and glycine

Abstract

Water‐soluble, biodegradable, and biocompatible poly(ester‐amide) dendrimers with hydroxyl functional groups are synthesized from previously prepared AB2 adduct of 2,2‐bis(hydroxymethyl) propanoic acid (bis‐MPA) and glycine as a repeating unit. Two esterification procedures using different coupling reagent/catalyst systems (DCC/DPTS or EDC/DMAP) are studied with respect to efficiency, ease of products purification, and quality of the final products. Both procedures have their own benefits and drawbacks, depending on dendrimer generation. The synthesized poly(ester‐amide) dendrimers as well as commercially available bis‐MPA dendrimers, poly(ester‐amide) hyperbranched polymer, and poly(vinyl alcohol) are used for preparation of solid dispersions of sulfonylurea antidiabetic drug glimepiride to improve its poor water‐solubility. In vitro dissolution studies show in comparison with pure glimepiride in crystalline or amorphous form, to the same extent improved glimepiride solubility for solid dispersions based on dendritic polymers, but not for poly(vinyl alcohol). The amount of glimepiride complexed with both dendrimer types increases with dendrimer generation. © 2014 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2014, 52, 3292–3301

Functional porous membranes from amorphous linear dendritic polyester hybrids

“…To extend the hydrophobic polymers with hydrophilic and functional blocks, bis-MPA based dendrons of generation (G) one (13) and two (8) with a single thiol at the focal point were chosen. 13 Prior to hybridization via UV initiated thiol-ene coupling chemistry (TEC), 11,14,15 P5 and P22 chain-ends were allyl functionalized with 4-pentanoic anhydride (6), Scheme 1 and Table 1.…”

“…Amphiphilic block copolymers which comprise bis-MPA dendritic components are nowadays attractive candidates in fabrication of passive drug delivery systems. 8,9 In the context of generating isoporous membranes, the influence of dendritic components using amphiphilic block copolymers from challenging semi-crystalline polycaprolactone (PCL) was elaborated by Malkoch et al 10,11 By utilizing dendrons as dendritic linkers, a library of amphiphilic block copolymer hybrids was synthesized based on hydrophilic polyethylene glycol (PEG) segments and hydrophobic PCL components. In this study, the addition of dendritic wedges resulted in increased stabilization of water droplets, which leads to formation of more ordered isoporous films.…”

Architecture - behaviour - properties relationship in Star-shaped MPA-PMMA and MPA-PS hyper-branched copolymers

“…One of the most studied hyperbranched systems was bis (Hydroxyl-Methyl) propionic acid polyesters (MPA), which have been used as hyperbranched entities and hyperbranched cores to obtain hyperbranched copolymer macrostructures [2]. These are used in nanomedical applications [19], coatings [20], tumour-targeted molecular imaging probes and therapeutics [21], as biological carriers [22], co-dispersants [23] and more.…”

Hyperbranched polyesters urethane acrylate resin

“…The observed characteristics of this polymer make it desirable for production of coatings. [11][12][13] On the other hand, because of possibility of producing different types of urethane acrylates with desirable properties from isocyanates and polyols and due to high curing rate and lower energy consumption of urethane acrylates, for the past few years the potential uses of urethane acrylates have drawn a lot of attention. [14][15][16] This has also contributed to production of curable hyperbranched polyurethane polymers to be used as coatings with more desirable physical and chemical properties.…”