Synthesis, photocrosslinking characteristics, and biocompatibility evaluation of N‐vinyl pyrrolidone/polycaprolactone fumarate biomaterials using a new proton scavenger

Abstract

Photocrosslinkable and biodegradable polymeric networks were formulated based on N‐vinyl pyrrolidone‐poly(ε‐caprolactone fumarate) (NVP/PCLF) compositions for hard tissue engineering applications using a new proton scavenger, propylene oxide (PO). The synthesized macromers were obtained as a white clear paste with no colorization. The obtained macromers were thoroughly characterized using spectroscopic (NMR and FT‐IR) and chromatographic (gel permeation chromatography (GPC)) techniques. Photocrosslinking of the PCLF/NVP compositions was achieved using camphorquinone and dimethyl toluidine (DMT) as a photoinitiator system. The cytocompatibility of the macromers and their corresponding networks were evaluated via MTT assay. Characterization of the networks indicated the importance of NVP content on the network properties. Sol fraction studies indicated that more than 90% of the PCLFs were crosslinked over the studied range of PCLF/NVP compositions; however most of the NVP above a stoichiometric ratio of one NVP to fumerate unit remained unreacted. It was also found that in the concentrations more than 10% NVP, the unreacted NVP monomer neither participated in the crosslinking reaction nor homopolymerized to poly(vinyl pyrrolidone) (PVP). The elastic modulus (G′) and estimated molecular weight between crosslinks also confirmed that at the higher NVP content the PCLF photocrosslinking was hindered. Copyright © 2008 John Wiley & Sons, Ltd.

Reformulating polycaprolactone fumarate to eliminate toxic diethylene glycol: Effects of polymeric branching and autoclave sterilization on material properties

“…PCLF has also been used as one component in a wide array of blends for biomaterial scaffolds from injectable in situ cross-linkable scaffolds(4–12), to drug delivery vehicles(13), to electrically conductive nerve conduits composed of PCLF and polypyrrole(14, 15). Previously, PCLF has been synthesized by condensation polymerization of fumaryl chloride with commercially available polycaprolactone diol of molecular weights 530, 1200, or 2000 g mol −1 (16).…”

Potential Application of a Visible Light-Induced Photocured Hydrogel Film as a Wound Dressing Material

“…In line with this, adding NVP in more than double bond quantity, extra NVP formed water soluble homopolymer, that is, PVP [31] (SF: 6.3%), as mentioned above. Hence, sol fraction of cured blends with 10 and 40 wt% NVP is more than that of 20 wt% NVP (SF: 3.1%) while all formulations of photocured blends show the SF less than that of uncured film ( < 0.05) as shown in Figure 2, indicating the photocured films have advantages on the uncured one.…”

“…The result is confirmed with considering the PEGF degree of oligomerization (or C=C fumarate bond quantities) which will be mentioned in the next section. NVP is a monofunctional monomer with low polymerization rate and at higher concentrations the monomer tends to form more linear homopolymer chains rather than cross-linked network resulting in a decrease in final conversion [31]. The formation of the linear water soluble poly-NVP at high NVP concentrations was confirmed by sol fraction test.…”

A thalidomide templated molecularly imprinted polymer that promotes a biologically active chiral entity tagged in colon carcinoma cells and protein-related immune activation

“…The high IC 50 value of the MIPs showed their biocompatibility with the Caco-2 cells that was greatly influenced by the composition of the MIPs [33]. Although, the major ingredients used for polymerization were reported earlier to be biocompatible for the monomer and copolymers such as MAA, EDMA, TRIM and NVP when used alone; the NVP was toxic above 10% but when used in combination with the other monomers/polymer, there was no killing of cancer cells [34].…”