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Display of Amino Groups on Substrate Surfaces by Simple Dip-Coating of Methacrylate-Based Polymers and Its Application to DNA Immobilization
journal contribution
posted on 2013-01-22, 00:00 authored by Ayane Shimomura, Takashi Nishino, Tatsuo MaruyamaThe implementation of a reactive functional group onto
a material
surface is of great importance. Reactive functional groups (e.g.,
an amino group and a hydroxyl group) are usually hydrophilic, which
makes it difficult to display them on a dry polymer surface. We here
propose a novel method for displaying amino groups on the surfaces
of polymeric substrates through dip-coating of a methacrylate-based
copolymer. We synthesized copolymers composed of methyl methacrylate
and 2-aminoethyl methacrylate with different protecting groups or
ion-complexes on their amino groups, then dip-coated the copolymers
onto a poly(methyl methacrylate) (PMMA) substrate. Evaluation using
a cleavable fluorescent compound, which was synthesized in the present
study to quantify a small amount (pmol/cm2) of amino groups
on a solid surface, revealed that the protection of amino groups affected
their surface segregation in the copolymer coating. p-Toluenesulfonate ion-complex and tert-butoxycarbonyl
(Boc) protection of amino groups were found to effectively display
amino groups on the surface (more than 70 pmol/cm2). The
density of amino groups displayed on a surface can be easily controlled
by mixing the copolymer and PMMA before dip-coating. Dip-coating of
the copolymer with Boc protection on various polymeric substrates
also successfully displayed amino groups on their surfaces. Finally,
we demonstrated that the amino groups displayed can be utilized for
the immobilization of a DNA oligonucleotide on a substrate surface.