Amino Acid-Based Polyphosphorodiamidates with Hydrolytically Labile Bonds for Degradation-Tuned Photopolymers

Stephan Haudum, Stefan Lenhart, Stefanie Monika Müller, Disha Tupe, Christoph Naderer, Tilo Dehne, Michael Sittinger, Zoltan Major, Thomas Grießer, Oliver Brüggemann, Jaroslaw Jacak, Ian Teasdale

Publikation: Beitrag in FachzeitschriftArtikelForschungBegutachtung


Photochemical additive manufacturing technologies can produce complex geometries in short production times and thus have considerable potential as a tool to fabricate medical devices such as individualized patient-specific implants, prosthetics and tissue engineering scaffolds. However, most photopolymer resins degrade only slowly under the mild conditions required for many biomedical applications. Herein we report a novel platform consisting of amino acid-based polyphosphorodiamidate (APdA) monomers with hydrolytically cleavable bonds. The substituent on the α-amino acid can be used as a handle for facile control of hydrolysis rates of the monomers into their endogenous components, namely phosphate and the corresponding amino acid. Furthermore, monomer hydrolysis is considerably accelerated at lower pH values. The monomers underwent thiol-yne photopolymerization and could be 3D structured via multiphoton lithography. Copolymerization with commonly used hydrophobic thiols demonstrates not only their ability to regulate the ambient degradation rate of thiol-yne polyester photopolymer resins, but also desirable surface erosion behavior. Such degradation profiles, in the appropriate time frames, in suitably mild conditions, combined with their low cytotoxicity and 3D printability, render these novel photomonomers of significant interest for a wide range of biomaterial applications.
Seiten (von - bis)673-678
FachzeitschriftACS Macro Letters
PublikationsstatusVeröffentlicht - 9 Mai 2023

Bibliographische Notiz

Funding Information:
The project has received funding from the European Union’s Horizon 2020 research and innovation programme under Grant Agreement No. 953134 “Inkplant”. We thank Dmitry Sivun for proofreading the manuscript.

Publisher Copyright:
© 2023 The Authors. Published by American Chemical Society

Dieses zitieren