Thiol-click photochemistry for surface functionalization applied to optical biosensing

Bañuls, María‐José; González-Martı́nez, Miguel Ángel; Sabek, Jad; García-Rupérez, Jaime; Maquieira, Ángel

doi:10.1016/j.aca.2019.01.055

Cited by 15 publications

(9 citation statements)

References 55 publications

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“…Thiolated monolayers allow rapid and simple immobilization of SH-DNA probes by different chemistries without using any crosslinker or other reagent, such as disulphide bond linkage (Sánchez del Rio et al, 2007), or through thiol-ene click photochemistry (Escorihuela et al, 2014a). The latter one can also be also employed by activation of the thiol group at the probe to further reaction with different functional groups at the sensor surface, such as alkenylated and alkynylated surfaces by forming thiol-ene and thiol-yne links, respectively (Bañuls et al, 2019). These approaches can be enhanced by the use of polythiolated probes, generating multiple anchor points at the sensor surface (Bañuls et al, 2017).…”

Section: Nucleic-acid Based Label-free Optical Biosensorsmentioning

confidence: 99%

“…In particular, evanescent-wave biosensors have achieved great progress for NA analyses (Carrascosa et al, 2016). They have been benefited from improvements in biosensor fabrication and production quality (Fernández Gavela et al, 2016; Soler et al, 2019), the availability of new surface chemistry methods (Escorihuela et al, 2015; Escorihuela and Zuilhof, 2017; Bañuls et al, 2019), the availability of highly efficient probes for NA detection (Shi et al, 2015; Nafa et al, 2016; Aviñó et al, 2019a), and new approaches for the enhancement of the detected signal (Guo et al, 2015). Also, the biosensor integration with microfluidics permits the incorporation of different modules, including fluidic transportation, sorting, mixing or separation methods for liquid samples, and the automation of the complete analysis, which pave the way for the full development of the so-called lab-on-a-chip (LoC) platforms (Jung et al, 2015; Szydzik et al, 2015, 2017).…”

Section: Introductionmentioning

confidence: 99%

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Advanced Evanescent-Wave Optical Biosensors for the Detection of Nucleic Acids: An Analytic Perspective

et al. 2019

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Evanescent-wave optical biosensors have become an attractive alternative for the screening of nucleic acids in the clinical context. They possess highly sensitive transducers able to perform detection of a wide range of nucleic acid-based biomarkers without the need of any label or marker. These optical biosensor platforms are very versatile, allowing the incorporation of an almost limitless range of biorecognition probes precisely and robustly adhered to the sensor surface by covalent surface chemistry approaches. In addition, their application can be further enhanced by their combination with different processes, thanks to their integration with complex and automated microfluidic systems, facilitating the development of multiplexed and user-friendly platforms. The objective of this work is to provide a comprehensive synopsis of cutting-edge analytical strategies based on these label-free optical biosensors able to deal with the drawbacks related to DNA and RNA detection, from single point mutations assays and epigenetic alterations, to bacterial infections. Several plasmonic and silicon photonic-based biosensors are described together with their most recent applications in this area. We also identify and analyse the main challenges faced when attempting to harness this technology and how several innovative approaches introduced in the last years manage those issues, including the use of new biorecognition probes, surface functionalization approaches, signal amplification and enhancement strategies, as well as, sophisticated microfluidic solutions.

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Section: Nucleic-acid Based Label-free Optical Biosensorsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Advanced Evanescent-Wave Optical Biosensors for the Detection of Nucleic Acids: An Analytic Perspective

et al. 2019

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“…Polymeric materials obtained from thiol-click reactions should possess certain properties for drug delivery applications including nontoxicity and nonimmunogenicity, the ability to target specific sites, and the ability to remain in the body long enough to achieve the maximum therapeutic effect. All of these characteristics depend on the molecular architecture of the polymer as well as its functionality, which can be carefully controlled through thiol-click reactions. ,− The first example of the thiol Michael addition reaction was reported in the 1960s by Allen et al, and since then, it has become a critical tool for organic syntheses. Several research groups have exploited this reaction in polymer chemistry and material development .…”

Section: Introductionmentioning

confidence: 99%

Degradable Silyl Ether–Containing Networks from Trifunctional Thiols and Acrylates

et al. 2020

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The purpose of this study was the synthesis of novel degradable polymer-based devices capable of releasing an encapsulated agent in a controlled manner with specific interest for use as drug delivery materials. Base-catalyzed thiol Michael additions between trithiols and triacrylates containing silyl ether groups were exploited to prepare a series of degradable cross-linked networks. Disodium fluorescein was loaded as a hydrophilic drug surrogate inside the networks, and the degradation of the networks and the release of dye were monitored. The networks were characterized by Fourier transform infrared spectroscopy, and their thermal and mechanical properties were investigated through thermogravimetric analysis and dynamic mechanical analysis. The effects of the monomer structure on degradation, release behavior, and thermal properties were investigated. The networks prepared from more sterically hindered silyl ether monomers exhibited decreased rates of degradation and correspondingly slower release of encapsulated disodium fluorescein dye. The results suggest that the characteristics of the networks can be fine-tuned by manipulation of the group attached to the Si atom in the silyl ether monomers.

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“…The hydrocarbon chain stabilizes the SAM through van der Waals interactions . The end groups with different properties could cause large changes in physical–chemical properties of the SAMs. ,,, For instance, the hydrophobic end group of −CH 3 makes the SAM surface hydrophobic and highly resistant to adhesion, whereas hydrophilic end groups (e.g., −COOH, −NH 2 , −OH) make the SAM surface hydrophilic and easy to interact with foreign species such as metal ions and biomolecules of proteins from aqueous solutions. ,− Studies on the mechanism of SAMs formation have indicated that the self-assembly process starts with the adsorption of thiols at metal substrates via the formation of Au–S covalent bonds, followed by the ordering and rearrangement of the thiol molecules. ,− It has been reported that introduction of a hydrophilic end group (−COOH, −NH 2 , or −OH) would decrease the orderliness of the formed SAMs as compared to the cases of SAMs with hydrophobic end groups . To date, the mechanism underlying how the properties of end groups affect the adsorption or the ordering and rearrangement processes of the thiol molecules is not particularly clear …”

Section: Introductionmentioning

confidence: 99%

End Group Properties of Thiols Affecting the Self-Assembly Mechanism at Gold Nanoparticles Film As Evidenced by Water Infrared Probe

et al. 2019

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Water infrared probe has been employed for in situ monitoring of the detailed self-assembly processes of four thiol molecules with different end groups (−CH3, −NH2, −COOH, and −OH) on gold nanoparticles (Au NPs) film in aqueous solution. Based on the change of water IR signal, the significant influence of end group properties on the kinetics and thermodynamics of thiols self-assembly can be estimated. It is found that the assembly kinetics of thiols decreases with the increase of the hydrophobicity of the end groups. In addition, the charges carried by the end groups (−COOH and −NH2 terminated thiols) will also slow down the self-assembly kinetics owing to the electrostatic repulsions. However, the isothermal adsorption is only affected by the wettability of the end groups of thiols. The higher hydrophilicity of the end groups results in larger equilibrium constant of the self-assembly process. Results show that water infrared probe offers an additional approach to the monitoring of thiols self-assembly processes with higher sensitivity and more detailed information as compared to traditional molecule fingerprints.

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Thiol-click photochemistry for surface functionalization applied to optical biosensing

Cited by 15 publications

References 55 publications

Advanced Evanescent-Wave Optical Biosensors for the Detection of Nucleic Acids: An Analytic Perspective

Advanced Evanescent-Wave Optical Biosensors for the Detection of Nucleic Acids: An Analytic Perspective

Degradable Silyl Ether–Containing Networks from Trifunctional Thiols and Acrylates

End Group Properties of Thiols Affecting the Self-Assembly Mechanism at Gold Nanoparticles Film As Evidenced by Water Infrared Probe

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