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Attaching molecules to chlorinated and brominated amorphous carbon substrates via Grignard reactions.

ABSTRACT: Amorphous carbon thin films are an attractive material because they provide a chemically robust surface that has been utilized in biomolecule array, biosensor, and bioelectronic applications. These thin films are particularly versatile because they are deposited at room temperature, making them readily integrated with other materials and devices. Here we present an alternative means of functionalizing carbon substrates based on Grignard chemistry. First, the amorphous carbon substrates are halogenated with a solution-based, radical-initiated halogenation reaction using PX5 (X = Br or Cl). Next, the halogenated surfaces are modified via the formation of a carbon-carbon bond between the surface and the Grignard reagents employed. Alkyl-, perfluoroalkyl-, and poly(ethylene glycol)-Grignard reagents were chosen to show the utility of this reaction scheme in functionalizing carbon surfaces to withstand oxidation and provide a hydrophobic and/or biocompatible substrate.

SUBMITTER: Lockett MR

PROVIDER: S-EPMC2765564 | biostudies-literature | 2009 Apr

REPOSITORIES: biostudies-literature

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Attaching molecules to chlorinated and brominated amorphous carbon substrates via Grignard reactions.

Lockett Matthew R MR Smith Lloyd M LM

Langmuir : the ACS journal of surfaces and colloids 20090401 6

Amorphous carbon thin films are an attractive material because they provide a chemically robust surface that has been utilized in biomolecule array, biosensor, and bioelectronic applications. These thin films are particularly versatile because they are deposited at room temperature, making them readily integrated with other materials and devices. Here we present an alternative means of functionalizing carbon substrates based on Grignard chemistry. First, the amorphous carbon substrates are halog ...[more]

PMID: 19708232

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Project description:Atomic force microscopy (AFM) has been extensively used in studies of biological interactions. Particularly, AFM based force spectroscopy and recognition imaging can sense biomolecules on a single molecule level, having great potential to become a tool for molecular diagnostics in clinics. These techniques, however, require affinity molecules to be attached to AFM tips in order to specifically detect their targets. The attachment chemistry currently used on silicon tips involves multiple steps of reactions and moisture sensitive chemicals, such as (3-aminopropyl)triethoxysilane (APTES) and N-hydroxysuccinimide (NHS) ester, making the process difficult to operate in aqueous solutions. In the present study, we have developed a user-friendly protocol to functionalize the AFM tips with affinity molecules. A key feature of it is that all reactions are carried out in aqueous solutions. In summary, we first synthesized a molecular anchor composed of cyclooctyne and silatrane for introduction of a chemically reactive function to AFM tips and a bifunctional polyethylene glycol linker that harnesses two orthogonal click reactions, copper free alkyne-azide cycloaddition and thiol-vinylsulfone Michael addition, for attaching affinity molecules to AFM tips. The attachment chemistry was then validated by attaching antithrombin DNA aptamers and cyclo-RGD peptides to silicon nitride (SiN) tips, respectively, and measuring forces of unbinding these affinity molecules from their protein cognates human α-thrombin and human α5β1-integrin immobilized on mica surfaces. In turn, we used the same attachment chemistry to functionalize silicon tips with the same affinity molecules for AFM based recognition imaging, showing that the disease-relevant biomarkers such as α-thrombin and α5β1-integrin can be detected with high sensitivity and specificity by the single molecule technique. These studies demonstrate the feasibility of our attachment chemistry for the use in functionalization of AFM tips with affinity molecules.

Dataset Information

Attaching molecules to chlorinated and brominated amorphous carbon substrates via Grignard reactions.

Publications

Attaching molecules to chlorinated and brominated amorphous carbon substrates via Grignard reactions.

Similar Datasets

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