Microscale Tattooing of Hydrogels and Cells: Benzoxaborole‐Driven Microcontact Printing (µCP) on Glycosylated Surfaces

Abstract

Abstract Microcontact printing (µCP) is a widely used technique for microscale surface patterning. In this study, we present a polymer‐supported µCP method for the patterning of (bioactive) glycosylated surfaces under hydrated conditions. Patterning is achieved by direct contact with a grooved polydimethylsiloxane (PDMS) stamp, whose surface was grafted with a dopamine‐containing polymer. The polymer brushes offer an anchor for the boronic acid derivative 6‐aminobenzo[c][1,2]oxaborol‐1(3H)‐ol (ABOB), used as an ink for surface functionalization, to introduce patterns to three different surfaces as substrates: (1) monosaccharide‐modified hydrogel surfaces possessing aldose (glucose, fucose, galactose) or ketose (fructose, sorbose) functions; (2) glycosylated surfaces of polymeric microspheres; and (3) the membranes of mammalian cells, such as human primary gastric cells and others. During µCP, ABOB patterns transferred to the target surface through the formation of carbohydrate‐ABOB complexes at fully hydrated, neutral pH conditions. Fluorescence microscopy confirmed the successful transfer of ABOB patterns to glycosylated surfaces, with clear “tattoo‐like” signatures observed on hydrogels, glycosylated particle surfaces and cellular interfaces.