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

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.