Journal
LANGMUIR
Volume 30, Issue 28, Pages 8452-8460Publisher
AMER CHEMICAL SOC
DOI: 10.1021/la500744s
Keywords
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Funding
- NSF Career Award [DMR-1056808]
- Office of Naval Research [N00014-09-01-0258]
- DOE Early Career Award [DE-SC0006398]
- DOE [DE-SC0006398]
- Direct For Mathematical & Physical Scien
- Division Of Materials Research [1313565] Funding Source: National Science Foundation
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The development of strategies to couple biomolecules covalently to surfaces is necessary for constructing sensing arrays for biological and biomedical applications. One attractive conjugation reaction is hydrazone formation the reaction of a hydrazine with an aldehyde or ketone as both hydrazines and aldehydes/ketones are largely bioorthogonal, which makes this particular reaction suitable for conjugating biomolecules to a variety of substrates. We show that the mild reaction conditions afforded by hydrazone conjugation enable the conjugation of DNA and proteins to the substrate surface in significantly higher yields than can be achieved with traditional bioconjugation techniques, such as maleimide chemistry. Next, we designed and synthesized a photocaged aryl ketone that can be conjugated to a surface and photochemically activated to provide a suitable partner for subsequent hydrazone formation between the surface-anchored ketone and DNA- or protein-hydrazines. Finally, we exploit the latent functionality of the photocaged ketone and pattern multiple biomolecules on the same substrate, effectively demonstrating a strategy for designing substrates with well-defined domains of different biomolecules. We expect that this approach can be extended to the production of multiplexed assays by using an appropriate mask with sequential photoexposure and biomolecule conjugation steps.
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