title: Photoactivated bioconjugation between ortho-azidophenols and anilines: a facile approach to biomolecular photopatterning.
abstract: Methods for the surface patterning of small molecules and biomolecules can yield useful platforms for drug screening, synthetic biology applications, diagnostics, and the immobilization of live cells. However, new techniques are needed to achieve the ease, feature sizes, reliability, and patterning speed necessary for widespread adoption. Herein, we report an easily accessible and operationally simple photoinitiated reaction that can achieve patterned bioconjugation in a highly chemoselective manner. The reaction involves the photolysis of 2-azidophenols to generate iminoquinone intermediates that couple rapidly to aniline groups. We demonstrate the broad functional group compatibility of this reaction for the modification of proteins, polymers, oligonucleotides, peptides, and small molecules. As a specific application, the reaction was adapted for the photolithographic patterning of azidophenol DNA on aniline glass substrates. The presence of the DNA was confirmed by the ability of the surface to capture living cells bearing the sequence complement on their cell walls or cytoplasmic membranes. Compared to other light-based DNA patterning methods, this reaction offers higher speed and does not require the use of a photoresist or other blocking material.
authors.affiliation: Department of Chemistry, University of California , Berkeley, California 94720-1460, United States.
authors.forename: Kareem M
authors.initials: KM
authors.lastname: El Muslemany
authors.forename: Amy A
authors.initials: AA
authors.lastname: Twite
authors.forename: Adel M
authors.initials: AM
authors.lastname: ElSohly
authors.forename: Allie C
authors.initials: AC
authors.lastname: Obermeyer
authors.forename: Richard A
authors.initials: RA
authors.lastname: Mathies
authors.forename: Matthew B
authors.initials: MB
authors.lastname: Francis
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry*; D001386:Azides / Q000737:chemistry*; D004277:DNA, Single-Stranded / Q000737:chemistry; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry*; D055668:Photochemical Processes; D011809:Quinones / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000814:Aniline Compounds; D001386:Azides; D004277:DNA, Single-Stranded; D010636:Phenols; D011809:Quinones; C116897:iminoquinone; C023650:aniline