Collect. Czech. Chem. Commun. 2011, 76, 1013-1031
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


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.