Biopolym. Cell. 2018; 34(3):207-217.
Bioorganic Chemistry
Fluorine-containing polyamphiphiles of block structure constructed of synthetic and biopolymer blocks
1Paiuk O. L., 1Mitina N. Ye., 2Myagkota O. S., 3Volianiuk K. A., 4Musat N., 4Stryganyuk G. Z., 2Reshetnyak O. V., 1Kinash N. I., 1Hevus O. I., 4Shermolovich Yu. G., 1Zaichenko A. S.
- Lviv Polytechnic National University
12, S. Bandery Str., Lviv, Ukraine, 79013 - Ivan Franko National University of Lviv
1, Universytetska Str., Lviv, Ukraine, 79000 - Helmholtz Centre for Environmental Research - UFZ,
15, Permoserstraße Str., Leipzig, Germany, 04318 - Institute of organic chemistry NAS of Ukraine
5, Murmanska Str., Kyiv, Ukraine, 02660
Abstract
Aim. Purposeful preparation of polymeric surfactants combining hydrophobic fluorine-containing and hydrophilic synthetic and natural blocks via radical and non-radical reactions using peroxide, epoxide and/or amino- terminal groups of the polymeric elementary blocks. Methods. Radical and non-radical condensation reactions, polymerization, spectral (NMR- and luminescence spectroscopy), gel-permeation chromatography and other analytical techniques`. Results. Primary oligomers poly(F-MA)-MP were synthesized via radical polymerization of fluorine-alkyl methacrylate (F-MA) in the presence of peroxide-containing telogen (MP). That provides controlling the oligomer chain length and architectures as well as entering a terminal peroxide group in the macromolecules. Radical polymerization of vinyl pyrrolidone (NVP) initiated by poly(F-MA)-MP as macroinitiator in the presence of epoxide-containing derivative of cumene (CGE) was used for obtaining water soluble poly(F-MA)-block-poly(NVP)-CGE. Finally oligonucleotide (ONC) was attached via condensation reaction of ONC primary amino group with terminal epoxide group of poly(F-MA)-block-poly(NVP)-CGE. Conclusions. A series of novel block/comb-like copolymers with synthetic and natural parts was synthesized. Obtained tri-block copolymers can be used as markers for labeling bacteria and pathological items including cancer cells.
Keywords: fluorinated polyamphiphiles, oligonucleotide, radical and coupling reactions, hybrid block-copolymer, bacteria labeling.
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