Site-specific immobilization of DNA on silicon surfaces by using the thiol–yne reaction

Escorihuela, Jorge; Bañuls, María‐José; Puchades, Rosa; Maquieira, Ángel

doi:10.1039/c4tb01108b

Cited by 34 publications

(31 citation statements)

References 66 publications

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“…Guerrouache et al immobilized Au NPs on a porous monolith surface with alkyne functionality through radical‐mediated thiol–alkyne addition reaction . Similarly, Escorihuela et al used the same approach for site‐specific immobilization of DNA on silicon surfaces . Bhairamadgi et al reported a comparative study of thiol–alkene and thiol–alkyne click chemistry reactions for modification of silicon surfaces .…”

Section: Introductionmentioning

confidence: 99%

Site‐Specific Surface Functionalization via Microchannel Cantilever Spotting (µCS): Comparison between Azide–Alkyne and Thiol–Alkyne Click Chemistry Reactions

Dadfar

Sekula-Neuner

Bog

et al. 2018

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Different types of click chemistry reactions are proposed and used for the functionalization of surfaces and materials, and covalent attachment of organic molecules. In the present work, two different catalyst-free click approaches, namely azide-alkyne and thiol-alkyne click chemistry are studied and compared for the immobilization of microarrays of azide or thiol inks on functionalized glass surfaces. For this purpose, the surface of glass is first functionalized with dibenzocyclooctyne-acid (DBCO-acid), a cyclooctyne with a carboxyl group. Then, the DBCO-terminated surfaces are functionalized via microchannel cantilever spotting with different fluorescent and nonfluorescent azide and thiol inks. Although both routes work reliably for surface functionalization, the protein binding experiments reveal that using a thiol-alkyne route will obtain the highest surface density of molecular immobilization in such spotting approaches. The obtained achievements and results from this work can be used for design and manufacturing of microscale patterns suitable for biomedical and biological applications.

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Section: Introductionmentioning

confidence: 99%

Site‐Specific Surface Functionalization via Microchannel Cantilever Spotting (µCS): Comparison between Azide–Alkyne and Thiol–Alkyne Click Chemistry Reactions

Dadfar

Sekula-Neuner

Bog

et al. 2018

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“…These results corroborated the successful grafting of the silane onto the surface and evidenced the formation of a silane monolayer onto the Si 3 N 4 surface with terminal amine functional groups for further attachment of biomolecules. All electron binding energies carbon peak positions were derived from the literature for other similar systems2122.…”

Section: Resultsmentioning

confidence: 99%

Analysis of alternative splicing events for cancer diagnosis using a multiplexing nanophotonic biosensor

Huertas

Domínguez‐Zotes

Lechuga

2017

Sci Rep

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Personalized medicine is a promising tool not only for prevention, screening and development of more efficient treatment strategies, but also for diminishing the side effects caused by current therapies. Deciphering gene regulation pathways provides a reliable prognostic analysis to elucidate the origin of grave diseases and facilitate the selection of the most adequate treatment for each individual. Alternative splicing of mRNA precursors is one of these gene regulation pathways and enables cells to generate different protein outputs from the same gene depending on their developmental or homeostatic status. Its deregulation is strongly linked to disease onset and progression constituting a relevant and innovative class of biomarker. Herein we report a highly selective and sensitive nanophotonic biosensor based on the direct monitoring of the aberrant alternative splicing of Fas gene. Unlike conventional methods, the nanobiosensor performs a real-time detection of the specific isoforms in the fM-pM range without any cDNA synthesis or PCR amplification requirements. The nanobiosensor has been proven isoform-specific with no crosshybridization, greatly minimizing detection biases. The demonstrated high sensitivity and specificity make our nanobiosensor ideal for examining significant tumor-associated expression shifts of alternatively spliced isoforms for the early and accurate theranostics of cancer.

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“…The reaction efficiency was determined by comparing the atomic ratio determined by XPS with the theoretical value of 9:1 (for F/N) or 9:4 (for F/P), which corresponds to the 100 % surface conversion of the 1,2‐quinone‐functionalized monolayer. This quantitative conversion stands in contrast to surface functionalization with several other popular metal‐free click chemistry reactions (Supporting Information, Table S2), including SPAAC, inverse electron‐demand Diels–Alder, and thiol‐ene and thiol‐yne couplings, in which surface analyses invariably indicate incomplete conversion (typically 15–90 %) of the reactive groups.…”

Section: Figurementioning

confidence: 91%

Rapid and Complete Surface Modification with Strain‐Promoted Oxidation‐Controlled Cyclooctyne‐1,2‐Quinone Cycloaddition (SPOCQ)

et al. 2017

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Strain-promoted oxidation-controlled cyclooctyne-1,2-quinone cycloaddition (SPOCQ) between functionalized bicyclo[6.1.0]non-4-yne (BCN) and surface-bound quinones revealed an unprecedented 100 %c onjugation efficiency.I n addition, monitoring by direct analysis in real time mass spectrometry (DART-MS) revealed the underlying kinetics and activation parameters of this immobilization process in dependence on its microenvironment.Since the term "click" chemistry was coined by Sharpless and co-workers in 2001, [1] this class of transformations has become of crucial importance in organic synthesis and materials science.[2] In the last decade,t his field has focused more on novel click reactions that have an improved kinetic profile without the necessity of toxic metal catalysts like copper.[3] Among the reactions that emerged from this endeavor,t he strain-promoted alkyne-azide cycloaddition (SPAAC) proved aparticularly versatile alternative owing to its bioorthogonality.[4] Recently,v an Delft and co-workers reported the strain-promoted oxidation-controlled cyclooctyne-1,2-quinone cycloaddition (SPOCQ) for selective protein conjugation [5] and hydrogel formation [6] with ar eaction rate around three orders of magnitude higher than those observed for SPAAC. This combination of high yield and high reaction rates prompted us to study the analogous surface reaction, since SPAAConasurface typically stalls at 15-80 % efficiency, [7] thereby limiting its practical applicability as unreacted surface sites cannot be removed by purification as in solution-based chemistry.I mportantly,s olving the issue of variable "clicking" efficiencyo ns urfaces is severely hampered by apoor understanding of the kinetics of the solutionto-surface conjugation reactions.A part from ah andful of cases in which electrochemical methods have been used [8] and the recent measurement of SPAACreactivity [7c] no rigorously measured kinetics on interfacial reactions involving selfassembled monolayers are available.Herein, we report the first example of as urface-bound metal-free click reaction with complete conversion of immobilized groups.W eshow that SPOCQ is afar superior surface click-type reaction that yields fast surface modification with 100 %e fficiency. In particular,w es tudied the application of SPOCQ in the reaction of ab icyclo[6.1.0]non-4-yne (BCN) derivative bearing an MS tag with amonolayer presenting 1,2-quinone groups

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Site-specific immobilization of DNA on silicon surfaces by using the thiol–yne reaction

Cited by 34 publications

References 66 publications

Site‐Specific Surface Functionalization via Microchannel Cantilever Spotting (µCS): Comparison between Azide–Alkyne and Thiol–Alkyne Click Chemistry Reactions

Site‐Specific Surface Functionalization via Microchannel Cantilever Spotting (µCS): Comparison between Azide–Alkyne and Thiol–Alkyne Click Chemistry Reactions

Analysis of alternative splicing events for cancer diagnosis using a multiplexing nanophotonic biosensor

Rapid and Complete Surface Modification with Strain‐Promoted Oxidation‐Controlled Cyclooctyne‐1,2‐Quinone Cycloaddition (SPOCQ)

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