Modular material system for the microfabrication of biocompatible hydrogels based on thiol-ene-modified poly(vinyl alcohol)

Abstract

Novel modifications of the synthetic polymer poly(vinyl alcohol) (PVA) were developed for application in the field of biomedical engineering. PVA was modified with allyl succinic anhydride, norbornene anhydride as well as with c-thiobutyrolactone to produce macromers with reactive ene and thiol groups, respectively. Cytotoxicity studies have shown that the material exhibits almost no cell-toxicity, when used in concentrations of 1 and 0.1 wt % for 24 h. The obtained macromers were photocrosslinked via thiol-ene chemistry. Storage stability of the macromer mixtures with different concentrations of pyrogallol as stabilizer were investigated. Photorheometry was employed to optimize mixtures concerning reactivity based on their thiol-to-ene ratio, photoinitiator concentration, and macromer content. The crosslinked hydrogels were studied concerning their swellability. To form hydrogels with cellular structure twophoton-polymerization (2PP) was employed. Processing windows for 2PP of selected mixtures were determined.

Near‐Infrared Light‐Sensitive Polyvinyl Alcohol Hydrogel Photoresist for Spatiotemporal Control of Cell‐Instructive 3D Microenvironments

“…First, PVA is a commercial water‐soluble synthetic polymer with excellent cytocompatibility . Second, PVA with hundreds of hydroxyl groups has been modified with a tunable number of norbornene groups for radical thiol–ene photopolymerization . In comparison, existing multiarm PEG macromers can only provide a maximal number of eight groups.…”

3D‐Laser‐Mikro‐Nanodruck: Herausforderungen für die Chemie

“…Leider berichten die meisten Publikationen, die neuartige Photolacke fürb iologische Anwendungen beschreiben, über die Biokompatibilitätd es gedruckten Materials nur in Kurzzeitstudien (1-2 Tage Zellkultivierung). [30][31][32][33][34][35][36][37][38] Jedoch sind einige Wochen Zellkultivierung notwendig,u mz .B.d ie Stammzelldifferenzierung in 3D-Gerüsten zu untersuchen. [37][38][39] Da das Basismaterial eines gedruckten 3D-Mikrogerüsts nicht die charakteristischen Informationen liefert, um spezifische zelluläre Antworten zu erzeugen, ist oft eine Oberflächenbeschichtung mit Biomolekülen notwendig.I m Hinblick auf Biofunktionalisierung sind Peptidsequenzen wie RGD oder IKVAV, [40] Proteine der ECM, Zellmembranproteine wie Cadherine oder Wachstumsfaktoren und Morphogene von Interesse.Eine homogene Funktionalisierung kann meist durch Eintauchen hydrophober Gerüste in eine Proteinlçsung erreicht werden.…”

Conjugated Carbazole‐Based Schiff Bases as Photoinitiators: From Facile Synthesis to Efficient Two‐Photon Polymerization

“…Great efforts have been devoted to development of both materials and methods for 2PP, Among them, two‐photon initiators (2PIs) play key roles in 2PP systems for generating the reactive species, which initiate the polymerization process of multifunctional monomers and oligomers. An efficient 2PP process requires active 2PIs to ensure high writing speeds, low polymerization thresholds, and high‐quality resulting structures.…”