Issue 16, 2021

Synthesis of a zwitterionic N-Ser–Ser-C dimethacrylate cross-linker and evaluation in polyampholyte hydrogels

Abstract

Polyampholyte hydrogels are attractive materials for tissue engineering scaffolds as they offer a wide variety of features including nonfouling, selective protein delivery, and tunable physical characteristics. However, to improve the potential performance of these materials for in vivo applications, there is a need for a higher diversity of zwitterionic cross-linker species to replace commonly used ethylene glycol (EG) based chemistries. Towards this end, the synthesis of a dipeptide based zwitterionic cross-linker, N-Ser–Ser-C dimethacrylate (S–S) from N-Boc-L-serine is presented. The strategy utilized a convergent coupling of methacrylated serine partners followed by careful global deprotection to yield the zwitterionic cross-linker with good overall yields. This novel cross-linker was incorporated into a polyampholyte hydrogel and its physical properties and biocompatibility were compared against a polyampholyte hydrogel synthesized with an EG-based cross-linker. The S–S cross-linked hydrogel demonstrated excellent nonfouling performance, while promoting enhanced cellular adhesion to fibrinogen delivered from the hydrogel. Therefore, the results suggest that the S–S cross-linker will demonstrate superior future performance for in vivo applications.

Graphical abstract: Synthesis of a zwitterionic N-Ser–Ser-C dimethacrylate cross-linker and evaluation in polyampholyte hydrogels

Supplementary files

Article information

Article type
Paper
Submitted
17 Apr 2021
Accepted
03 Jul 2021
First published
05 Jul 2021

Biomater. Sci., 2021,9, 5508-5518

Synthesis of a zwitterionic N-Ser–Ser-C dimethacrylate cross-linker and evaluation in polyampholyte hydrogels

M. Chakraborty, S. L. Haag, M. T. Bernards and K. V. Waynant, Biomater. Sci., 2021, 9, 5508 DOI: 10.1039/D1BM00603G

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