Cationic Copolymerization of 3,3-Bis(hydroxymethyl)oxetane and Glycidol: Biocompatible Hyperbranched Polyether Polyols with High Content of Primary Hydroxyl Groups.
The cationic ring-opening copolymerization of 3,3-bis(hydroxymethyl)oxetane (BHMO) with glycidol using different comonomer ratios (BHMO content from 25 to 90%) and BF3OEt2 as an initiator has been studied. Apparent molecular weights of the resulting hyperbranched polyether copolymers ranged from 1400 to 3300 g mol(-1) (PDI: 1.21-1.48; method: SEC, linear PEG standards). Incorporation of both comonomers is evidenced by MALDI-TOF mass spectroscopy. All hyperbranched polyether polyols with high content of primary hydroxyl groups portray good solubility in water, which correlates with an increasing content of glycerol units. Detailed NMR characterization was employed to elucidate the copolymer microstructures. Kinetic studies via FTIR demonstrated a weak gradient-type character of the copolymers. MTT assays of the copolymers (up to 100 μg mL(-1)) on HEK and fibroblast cell lines (3T3, L929, WEHI) as well as viability tests on the fibroblast cells were carried out to assess the biocompatibility of the materials, confirming excellent biocompatibility. Transfection efficiency characterization by flow cytometry and confocal laser microscopy demonstrated cellular uptake of the copolymers. Antiadhesive properties of the materials on surfaces were assessed by adhesion assays with fibroblast cells.
Institute of Organic Chemistry, Johannes Gutenberg-University Mainz , Duesbergweg 10-14, D-55128 Mainz, Germany.|Graduate School Materials Science in Mainz (MAINZ), Staudingerweg 9, D-55128 Mainz, Germany.
Eva-Maria
EM
Christ
Department of Dermatology, University Medical Center of the Johannes Gutenberg-University , Langenbeckstrasse 1, D-55131 Mainz, Germany.
Dominika
D
Hobernik
Department of Dermatology, University Medical Center of the Johannes Gutenberg-University , Langenbeckstrasse 1, D-55131 Mainz, Germany.
Matthias
M
Bros
Max Planck Institute for Polymer Research , Ackermannweg 10, D-55128 Mainz, Germany.
Manfred
M
Wagner
Institute of Organic Chemistry, Johannes Gutenberg-University Mainz , Duesbergweg 10-14, D-55128 Mainz, Germany.|Graduate School Materials Science in Mainz (MAINZ), Staudingerweg 9, D-55128 Mainz, Germany.
Holger
H
Frey
D001672:Biocompatible Materials / Q000737:chemistry*; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D002412:Cations; D004852:Epoxy Compounds / Q000737:chemistry*; D004988:Ethers, Cyclic / Q000737:chemistry*; D058105:Polymerization; D020005:Propanols / Q000737:chemistry*; D066244:Proton Magnetic Resonance Spectroscopy; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
D001672:Biocompatible Materials; D002412:Cations; D004852:Epoxy Compounds; D004988:Ethers, Cyclic; D020005:Propanols; C479363:3,3-bis(hydroxymethyl)oxetane; C004312:glycidol