4-(3-Aminopropyl)-benzene-1,2-diol: An Improved Material-Independent Surface-Coating Reagent Compared to Dopamine

Dopamine surface chemistry has been of great interest because of its universal coating property and ability to transform nonadhesive molecules into adhesive molecules. Catechol oxidation and intramolecular cyclization underlie the unique property of dopamine (DA) surface chemistry and provide clues for developing new surface modification reagents such as norepinephrine, 5-pyrogallol-2-aminoethane, and perfluorinated DA derivatives. Based on these inspiring properties, a fast and universal surface chemistry technique using 4-(3-aminopropyl)-benzene-1,2-diol (3-catecholpropanamine, CPA) is reported herein. A single carbon insertion in the aliphatic chain of DA gives rise to the significantly accelerated intermolecular assembly and surface coating of CPA. The effect of CPA conjugation on an anticoagulant polysaccharide coating is also investigated. The use of CPA instead of DA to make polysaccharide coating materials improves the coating rate, while maintaining excellent antiplatelet performance on the coated surface.