Collect. Czech. Chem. Commun. 2011, 76, 1013-1031
https://doi.org/10.1135/cccc2010080
Published online 2011-07-18 08:28:39

Bioengineering functional copolymers. XV. Synthesis of organoboron amide-ester branched derivatives of oligo(maleic anhydride) and their interaction with HeLa and L929 fibroblast cells

Gülten Kahramana, Mustafa Türkb, Zakir M. O. Rzayevc,*, M. Elif Unsald and Ernur Söylemezc

a Turkish Atomic Energy Authority (TAEK), Sarayköy Nuclear Research & Training Center, 06983 Ankara, Turkey
b Kirikkale University, Department of Biology, Faculty of Arts and Sciences, Yahşihan, 71450 Kirikkale, Turkey
c Institute of Science & Engineering, Division of Nanotechnology and Nanomedicine, Hacettepe University, Beytepe, 06800 Ankara, Turkey
d Middle East Technical University, R & D Training and Measure Center, 06531 Ankara, Turkey

This article is part of serial Bioengineering functional copolymers.

Abstract

Novel bioengineering functional organoboron oligomers were synthesized by (i) amidolysis of oligo(maleic anhydride) (OMA) with 2-aminoethyldiphenylborinate (2-AEPB), (ii) esterification of organoboron oligomer (OMA-B) with α-hydroxy-ω-methoxypoly(ethylene oxide) (PEO) as a compatibilizer and (iii) conjugation of organoboron PEO branches (OMA-B-PEO) with folic acid as a taggering agent. Structure and composition of the synthesized oligomers were characterized by FTIR-ART and 1H (13C) NMR spectroscopy, chemical and physical analysis methods. Interaction of functional oligomers and oligomer···FA complex (OMA-B-PEO-F) with HeLa and L929 fibroblast cells were investigated by using different biochemical methods such as cytotoxicity, statistical, apoptotic and necrotic cell indexes, double staining and caspase-3 immunostaining, light and fluorescence inverted microscope analyses. It was found that citotoxisity and apoptotic/necrotic effects of oligomers significantly depend on the structure and composition of studied oligomers, and increase the following raw: OMA << OMA-B < OMA-B-PEO < OMA-B-PEO-F. A folic acid complex (MA-PEG-B-F) at 400 μg ml–1 (2.36 μmol ml–1) concentration as a therapeutic drug exhibits minimal toxcisity toward the fibroblast cells, but influential for HeLa cells.

Keywords: Synthesis; Amidolysis; Organoboron oligomers; Conjugation; Cytotoxicity; Apoptotic and necrotic effects.

References: 33 live references.