Abstract
Novel bioengineering functional organoboron polymers were synthesized by 1) amidolysis of poly(acrcylic acid) (PAA) with 2-aminoethyldiphenyl borinate (2-AEPB), 2) esterification of organoboron PAA polymer (PAA-B) with a-hydroxy-methoxypoly(ethylene oxide) (PEO) as a compatibilizer and 3) conjugation of organoboron PEO branches (PAA-B-PEO) with folic acid (FA) as a targeting agent. Structure and composition of the synthesized polymers were characterized by FTIR-ATR and 1H (13C) NMR spectroscopy, chemical and physical analysis methods. Anti-tumor activity of organoboron functional polymer and its complex with FA (PAA-B-PEO-F) against cancer and normal cells were evaluated by using different biochemical methods such as cytotoxicity, statistical, apoptotic and necrotic cell indexes, double staining and caspase-3 immune staining, light and fluorescence inverted microscope analyses. It was found that citotoxicity and apoptotic/necrotic effects of polymers significantly depend on the structure and composition of studied polymers, and increase the following raw: PAA << PAA-B < PAA-B-PEO < PAA-B-PEO-F. Among them, PAA-B-PEO-F complex at 400 mg mL–1 concentration as a therapeutic drug exhibits minimal toxicity toward the nor-mal cells, but influential for HeLa cancer cells.
Highlights
Many natural polymers such as polylysine, polyarginine, dextran derivatives, heparin and chitosan, and synthetic bioengineering polymers such as poly(acrylic acid) (PAA), copolymers of maleic anhydride, have been reported to have direct or indirect antitumor activity via stimulation of the immune system [1,2,3]
Comparative analysis of FTIR-ATR spectra (Figure 1) of 2-aminoethyldiphenyl borinate (2-AEPB), PAA and its organoboron derivative indicates that the characteristic bands of acid C=O groups disappearance in the spectra of PAA and its organoboron amide (PAA-B)-1 polymer prepared from 1:1 molar feed ratio of PAA: 2-AEPB
It was observed that antitumor activity significantly depends on the structure, amount of ionizable free carboxylic groups, organoboron linkages and complexed fragments in the functionalized polymers, and changes in the following row: PAA
Summary
Many natural polymers such as polylysine, polyarginine, dextran derivatives, heparin and chitosan, and synthetic bioengineering polymers such as poly(acrylic acid) (PAA), copolymers of maleic anhydride, have been reported to have direct or indirect antitumor activity via stimulation of the immune system [1,2,3]. The PAA and its copolymers have been often used as carriers in drug release systems, because of their multifunctional nature, unique properties and good biocompatibility [4,5]. Dimitrov et al [5] studied the biopharmaceutical characterization of hydrogels based on crosslinked. PAA and showed that this studied systems provide retarded drug release and appear to be potential candidates for use in the pharmaceutical practice. PAA is grafted to the poly(ethylene glycol) hydro-gel by photo-induced graft polymerization. Due to carboxyl functionality of PAA, collagen and cell adhesion protein, they could be covalently immobilized on to the poly(ethylene glycol) hydrogel [6]. Most of the hydrogels utilized as adhesives for dermatological patches were composed using PAA and its salts as matrix polymers. The ionic interactions between the carboxyl groups of the polymer and polyvalent cations such as calcium, copper, and aluminum cause the formation of the chemical crosslinking used to increase their mechanical strengths [7]
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