Amino Acid-Based Polyphosphorodiamidates with Hydrolytically Labile Bonds for Degradation-Tuned Photopolymers
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in: ACS Macro Letters, Jahrgang 12.2023, Nr. 6, 09.05.2023, S. 673-678.
Publikationen: Beitrag in Fachzeitschrift › Artikel › Forschung › (peer-reviewed)
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TY - JOUR
T1 - Amino Acid-Based Polyphosphorodiamidates with Hydrolytically Labile Bonds for Degradation-Tuned Photopolymers
AU - Haudum, Stephan
AU - Lenhart, Stefan
AU - Müller, Stefanie Monika
AU - Tupe, Disha
AU - Naderer, Christoph
AU - Dehne, Tilo
AU - Sittinger, Michael
AU - Major, Zoltan
AU - Grießer, Thomas
AU - Brüggemann, Oliver
AU - Jacak, Jaroslaw
AU - Teasdale, Ian
N1 - Publisher Copyright: © 2023 The Authors. Published by American Chemical Society
PY - 2023/5/9
Y1 - 2023/5/9
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=85159576935&partnerID=8YFLogxK
U2 - 10.1021/acsmacrolett.3c00173
DO - 10.1021/acsmacrolett.3c00173
M3 - Article
C2 - 37158040
AN - SCOPUS:85159576935
VL - 12.2023
SP - 673
EP - 678
JO - ACS Macro Letters
JF - ACS Macro Letters
SN - 2161-1653
IS - 6
ER -