Issue 41, 2012

A photocleavable linker for the chemoselective functionalization of biomaterials

Abstract

The functionalization of matrices with “caged” functional groups and their subsequent selective uncaging is a promising approach for generating patterns of bioactive molecules to guide cell growth or recreate in vivo microarchitectures. To date, this has been limited to caged carboxylic acids, amines and thiols, functional groups found within biological systems. We present a bifunctional caged carbonyl linker as an alternative approach for the chemoselective functionalization of biomaterials. This linker was readily coupled to collagen, employed as a model biomaterial, and underwent rapid uncaging in aqueous media upon irradiation with ultraviolet light to yield free carbonyl groups. Modified surfaces proved to be non-adhesive to cells until the chemoselective reintroduction of adhesion following incubation of uncaged carbonyls with gelatin hydrazide, with native gelatin failing to elicit a cellular response.

Graphical abstract: A photocleavable linker for the chemoselective functionalization of biomaterials

Supplementary files

Additions and corrections

Article information

Article type
Paper
Submitted
02 Aug 2012
Accepted
07 Sep 2012
First published
10 Sep 2012

J. Mater. Chem., 2012,22, 21878-21884

A photocleavable linker for the chemoselective functionalization of biomaterials

L. O'Donovan and P. A. De Bank, J. Mater. Chem., 2012, 22, 21878 DOI: 10.1039/C2JM35173K

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