Photolithography of dithiocarbamate-anchored monolayers and polymers on gold

Leonov, Alexei P.; Wei, Alexander

doi:10.1039/c0jm04153j

Cited by 14 publications

(10 citation statements)

References 48 publications

(61 reference statements)

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“…The method shows compelling potential for ligand immobilization in immunosensors employing gold surface as the substrate. Although there are some reported studies using this methodology, they are mostly focused on small molecules; 25,28−33 for example, dopamine, epinephrine, different kinds of amino acid (e.g., tryptophan), and very few larger molecules, such as polyethyleneimine (22 kDa) 34 and biocompounds, namely, oligonucleotide 35 and glucose oxidase, 28 have been immobilized on gold by this new method. To our knowledge, this is the first study reporting the use of in situ DTC formation to prepare an immunosensing surface and clearly show its feasibility toward ligand detection and prevention of nonspecific adsorption.…”

Section: Introductionmentioning

confidence: 99%

Antibody Oriented Immobilization on Gold using the Reaction between Carbon Disulfide and Amine Groups and Its Application in Immunosensing

et al. 2012

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Carbon disulfide (CS 2 ) can spontaneously react with amine groups to form dithiocarbamates on gold surface, providing the possibility to immobilize some compounds with primary or secondary amine groups in one step. Using this principle, an immunosensor interface prepared for immunoglobulin G (IgG) sensing surface toward anti-IgG has been fabricated for the first time by simply immersing gold slides into a mixed aqueous solution of CS 2 and protein A, followed by incubation in immunoglobulin G solution. The reaction between CS 2 and protein A has been followed by UV−vis spectroscopy, whereas cyclic voltammetry has been employed in the characterization of the modified gold surface with CS 2 and protein A, both methods indicating that protein A immobilization is implemented by CS 2 . Conventional ellipsometry, atomic force microscopy (AFM), as well as surface plasmon resonance (SPR) have been used to evaluate the specific binding of protein A with IgG and IgG with anti-IgG, revealing that IgG is specifically captured to form the biosensing interface, maintaining its bioactivity. Compared to direct adsorption of IgG on the gold surface, the IgG sensing surface constructed of CS 2 and protein A is far more sensitive to capture anti-IgG as its target molecule. In addition, the modified surface is proven to have good capability to inhibit nonspecific adsorption, as supported by control experiments using lysozyme and BSA. To conclude, antibody immobilization using this one-step method has potential as a simple and convenient surface modification approach for immunosensor development.

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Section: Introductionmentioning

confidence: 99%

Antibody Oriented Immobilization on Gold using the Reaction between Carbon Disulfide and Amine Groups and Its Application in Immunosensing

et al. 2012

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“…Such applications require both the high durability of bioreceptor-Au transducer coupling and possibly high surface density of DNA probes (Keighley et al, 2008 ). The thoughtful choice of linkage chemistry is particularly important due to the need to ensure the compatibility with the methods of multispotting, typically used for fabrication of sensing platforms for high-throughput screening (Brockmann et al, 1999 ; Leonov and Wei, 2011 ; Simon et al, 2015 ). Among methods of gold biofunctionalization, these based on monolayers of compounds capable of chemisorption via terminal, sulfur-containing groups, mainly thiol derivatives, and more rarely other such as disulfides, sulfides, thioesters, isothiocyanates, or dithiocarbamates (DTCs) (Ulman, 1996 ; Mandler and Kraus-Ophir, 2011 ).…”

Section: Introductionmentioning

confidence: 99%

SPRi-Based Biosensing Platforms for Detection of Specific DNA Sequences Using Thiolate and Dithiocarbamate Assemblies

2018

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The framework of presented study covers the development and examination of the analytical performance of surface plasmon resonance-based (SPR) DNA biosensors dedicated for a detection of model target oligonucleotide sequence. For this aim, various strategies of immobilization of DNA probes on gold transducers were tested. Besides the typical approaches: chemisorption of thiolated ssDNA (DNA-thiol) and physisorption of non-functionalized oligonucleotides, relatively new method based on chemisorption of dithiocarbamate-functionalized ssDNA (DNA-DTC) was applied for the first time for preparation of DNA-based SPR biosensor. The special emphasis was put on the correlation between the method of DNA immobilization and the composition of obtained receptor layer. The carried out studies focused on the examination of the capability of developed receptors layers to interact with both target DNA and DNA-functionalized AuNPs. It was found, that the detection limit of target DNA sequence (27 nb length) depends on the strategy of probe immobilization and backfilling method, and in the best case it amounted to 0.66 nM. Moreover, the application of ssDNA-functionalized gold nanoparticles (AuNPs) as plasmonic labels for secondary enhancement of SPR response is presented. The influence of spatial organization and surface density of a receptor layer on the ability to interact with DNA-functionalized AuNPs is discussed. Due to the best compatibility of receptors immobilized via DTC chemisorption: 1.47 ± 0.4 · 1012 molecules · cm−2 (with the calculated area occupied by single nanoparticle label of ~132.7 nm2), DNA chemisorption based on DTCs is pointed as especially promising for DNA biosensors utilizing indirect detection in competitive assays.

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“…It has been argued that DTCs can form more robust monolayers than alkylthiols on gold, aided by the favorable epitaxy between the bidentate carbodithioate unit and the Au(111) surface. [6] DTCs have been used to anchor a variety of functional molecules and polymers [7,8] onto metal surfaces, such as peptides, [6] carbohydrates, [9] DNA, [10] and cancer-targeting ligands. [11] …”

Section: Introductionmentioning

confidence: 99%

Practical Synthesis of Aromatic Dithiocarbamates

Padungros

Wei

2014

Synthetic Communications

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GRAPHICAL ABSTRACT Oxidation-sensitive N,N-diaryl dithiocarbamates (DTCs) are synthesized in good yields by the generation of metal amide salts from N-benzoyl precursors, followed by addition of CS2. para-Substituted diphenylamines are prepared by electrophilic aromatic substitution of diphenylbenzamide and saponification. Deacylation of electron-rich species such as bis(p-dimethylaminophenyl)benzamide is challenging because of the oxidative sensitivity of the anionic intermediate but could be achieved in good yield by using n-BuLi to generate a hemiaminal adduct, prior to acidification. The N,N-diaryl DTCs are stable as alkali salts and can be used to produce densely packed monolayers on gold surfaces.

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Photolithography of dithiocarbamate-anchored monolayers and polymers on gold

Cited by 14 publications

References 48 publications

Antibody Oriented Immobilization on Gold using the Reaction between Carbon Disulfide and Amine Groups and Its Application in Immunosensing

Antibody Oriented Immobilization on Gold using the Reaction between Carbon Disulfide and Amine Groups and Its Application in Immunosensing

SPRi-Based Biosensing Platforms for Detection of Specific DNA Sequences Using Thiolate and Dithiocarbamate Assemblies

Practical Synthesis of Aromatic Dithiocarbamates

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