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

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

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)673-678
Number of pages6
JournalACS Macro Letters
Volume12
Issue number6
DOIs
Publication statusPublished - 20 Jun 2023

Keywords

  • Humans
  • Amino Acids
  • Tissue Scaffolds/chemistry
  • Biocompatible Materials
  • Tissue Engineering
  • Polyesters
  • Dental Materials
  • Sulfhydryl Compounds/chemistry

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