Solid phase synthesis of functionalised SAM-forming alkanethiol–oligoethyleneglycols

Murray, James; Nowak, D.; Pukenas, Laurynas; Azhar, Rizuan; Guillorit, Mathieu; Wälti, Christoph; Critchley, Kevin; Johnson, Steven; Bon, Robin S.

doi:10.1039/c4tb00573b

Cited by 10 publications

(9 citation statements)

References 27 publications

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“…Syntheses of linkers and TEOTA ligand The linker compounds 2-azidoethanol (mEG-N3) 1 34 36 and 1azido-23-hydroxy-3,6,9,12,15,18,21-heptaoxatricosane (oEG-N3) 4 37 , as well as the copperchelating ligand TEOTA 38 were synthesized according to published protocols.…”

Section: 4mentioning

confidence: 99%

Phage capsid nanoparticles with defined ligand arrangement block influenza virus entry

et al. 2020

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Section: 4mentioning

confidence: 99%

Phage capsid nanoparticles with defined ligand arrangement block influenza virus entry

et al. 2020

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“…Although there are literature reports of the synthesis of oligo(ethylene glycol)-terminated alkanethiols, ,,, few studies have reported on prefunctionalization of these tethers with biologically active small molecules. − To the best of our knowledge, prefunctionalization with neurotransmitters or their precursors has not been reported.…”

Section: Resultsmentioning

confidence: 99%

Small-Molecule Patterning via Prefunctionalized Alkanethiols

et al. 2018

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Interactions between small molecules and biomolecules are important physiologically and for biosensing, diagnostic, and therapeutic applications. To investigate these interactions, small molecules can be tethered to substrates through standard coupling chemistries. While convenient, these approaches co-opt one or more of the few small-molecule functional groups needed for biorecognition. Moreover, for multiplexing, individual probes require different surface functionalization chemistries, conditions, and/or protection/deprotection strategies. Thus, when placing multiple small-molecules on surfaces, orthogonal chemistries are needed that preserve all functional groups and are sequentially compatible. Here, we approach high-fidelity small-molecule patterning by coupling small-molecule neurotransmitter precursors, as examples, to monodisperse asymmetric oligo(ethylene glycol)alkanethiols during synthesis and prior to self-assembly on Au substrates. We use chemical lift-off lithography to singly and doubly pattern substrates. Selective antibody recognition of pre-functionalized thiols was comparable to or better than recognition of small molecules functionalized to alkanethiols after surface assembly. These findings demonstrate that synthesis and patterning approaches that circumvent sequential surface conjugation chemistries enable biomolecule recognition and afford gateways to multiplexed small-molecule functionalized substrates.

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“…To explore the dual sensing capabilities of our device, we used the electrophotonic technology to monitor and quantify electrochemical reactions occurring at the silicon surface. Using established silane chemistry 14 (see Supplementary Method 1 for details), the surface of the photonic electrode was modified to render it thiol-reactive, enabling conjugation of a redox-active methylene blue (MB) analogue labelled with a thiol linker 15 16 . Figure 1f demonstrates the spectral shift in photonic resonance that results after exposure of the functionalized surface to the thiolated MB.…”

Section: Resultsmentioning

confidence: 99%

The electrophotonic silicon biosensor

et al. 2016

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The emergence of personalized and stratified medicine requires label-free, low-cost diagnostic technology capable of monitoring multiple disease biomarkers in parallel. Silicon photonic biosensors combine high-sensitivity analysis with scalable, low-cost manufacturing, but they tend to measure only a single biomarker and provide no information about their (bio)chemical activity. Here we introduce an electrochemical silicon photonic sensor capable of highly sensitive and multiparameter profiling of biomarkers. Our electrophotonic technology consists of microring resonators optimally n-doped to support high Q resonances alongside electrochemical processes in situ. The inclusion of electrochemical control enables site-selective immobilization of different biomolecules on individual microrings within a sensor array. The combination of photonic and electrochemical characterization also provides additional quantitative information and unique insight into chemical reactivity that is unavailable with photonic detection alone. By exploiting both the photonic and the electrical properties of silicon, the sensor opens new modalities for sensing on the microscale.

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Solid phase synthesis of functionalised SAM-forming alkanethiol–oligoethyleneglycols

Cited by 10 publications

References 27 publications

Phage capsid nanoparticles with defined ligand arrangement block influenza virus entry

Phage capsid nanoparticles with defined ligand arrangement block influenza virus entry

Small-Molecule Patterning via Prefunctionalized Alkanethiols

The electrophotonic silicon biosensor

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