Thiol-based michael-type addition. A systematic evaluation of its controlling factors

Gennari, Arianna; Wedgwood, Jennifer; Lallana, Enrique; Francini, Nora; Tirelli, Nicola

doi:10.1016/j.tet.2020.131637

Cited by 24 publications

(29 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Yet there is a possibility of a side reaction between the NH-end of the peptide and the maleimide group. Although it was shown [ 32 ] that the thiol conversion in Michael addition is higher when the pH is strongly basic, to hinder the possible conjugation via the terminal amino group of the peptide [ 31 ] the buffer with acidic pH should be used. This may lead to the low effectivity of the reaction in used here MES buffer, which reflects obtained data.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Direct and Indirect Biomimetic Peptide Modification of Alginate: Efficiency, Side Reactions, and Cell Response

Golunova

Velychkivska

Mikšovská

et al. 2021

IJMS

View full text Add to dashboard Cite

In the fast-developing field of tissue engineering there is a constant demand for new materials as scaffolds for cell seeding, which can better mimic a natural extracellular matrix as well as control cell behavior. Among other materials, polysaccharides are widely used for this purpose. One of the main candidates for scaffold fabrication is alginate. However, it lacks sites for cell adhesion. That is why one of the steps toward the development of suitable scaffolds for cells is the introduction of the biofunctionality to the alginate structure. In this work we focused on bone-sialoprotein derived peptide (TYRAY) conjugation to the molecule of alginate. Here the comparison study on four different approaches of peptide conjugation was performed including traditional and novel modification methods, based on 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide/N-hydroxy succinimide (EDC/NHS), 4-(4,6-dimethoxy-1,3,5-triazine-2-yl)-4-methylmorpholinium chloride (DMTMM), thiol-Michael addition and Cu-catalyzed azide–alkyne cycloaddition reactions. It was shown that the combination of the alginate amidation with the use of and subsequent Cu-catalyzed azide–alkyne cycloaddition led to efficient peptide conjugation, which was proven with both NMR and XPS methods. Moreover, the cell culture experiment proved the positive effect of peptide presence on the adhesion of human embryonic stem cells.

show abstract

Section: Resultsmentioning

confidence: 99%

“…The coupling yield was similar to that reported elsewhere [ 9 ]. The observed low maleimide group consumption can be also connected to the spontaneous formation of disulfides between two cysteine residues of peptides [ 32 ]. Thereby it lowers the concentration of the active thiol groups available for the Michael addition.…”

Section: Resultsmentioning

confidence: 99%

Direct and Indirect Biomimetic Peptide Modification of Alginate: Efficiency, Side Reactions, and Cell Response

Golunova

Velychkivska

Mikšovská

et al. 2021

IJMS

View full text Add to dashboard Cite

show abstract

“…For example, gelatin molecules were grafted on the surface of PDA-modified carbon nanotube via Michael addition reaction between the amino groups of gelatin and the quinone units of PDA [ 26 ]. More interestingly, the “thiol-Michael” click reaction is also a widely used mild method to prepare various functional materials [ 27 , 28 , 29 ]. Thus, due to the high activity of the quinone units of PDA, many other functional molecules may be attached to the surface of PDA-coated materials via the “thiol-Michael” click reaction.…”

Section: Introductionmentioning

confidence: 99%

Combination of Mussel Inspired Method and “Thiol-Michael” Click Reaction for Biocompatible Alginate-Modified Carbon Nanotubes

et al. 2021

View full text Add to dashboard Cite

Carbon nanotubes (CNTs) have attracted great interest in biomedical fields. However, the potential toxicity and poor dispersion of CNTs have greatly limited its application. In this work, a mussel-inspired method combined with the “thiol-Michael” click reaction was used to modify the surface of CNT and improve its properties. Firstly, a CNT was treated with dopamine, and then alginate grafted with L-cysteine was anchored onto the surface of CNT via click reaction, which realized the long-time dispersion of CNT in water. Furthermore, the in vitro test also demonstrated that the alginate may improve the biocompatibility of CNT, and thus may broaden the application of CNT in the biomedical field.

show abstract

“…The attachment of DB-TPP to Qβ forms a covalent twocarbon "bridge" between the free thiol groups in reduced Qβ (Figure 1B). 35,36 First, Qβ is reduced using tris(2-carboxyethyl) phosphine (TCEP), which is confirmed by electrophoretic mobility in nonreducing sodium dodecyl sulfate polyacrylamide gel electrophoresis (SDS-PAGE). The starting Qβ pentameric and hexametric subunit bands are shown in Figure 1C, which are converted almost exclusively into monomer bands following reduction.…”

Section: Resultsmentioning

confidence: 97%

“…The dibromomaleimide moiety reacts with thiol groups in a two-step reaction, 34 each step having a half-life of seconds. 28,35 Qβ contains 180 disulfide bonds, each of which can be a potential site for functionalization via this approach. The attachment of DB-TPP to Qβ forms a covalent twocarbon "bridge" between the free thiol groups in reduced Qβ (Figure 1B).…”

Section: Resultsmentioning

confidence: 99%

Intracellular Delivery of Virus-Like Particles Using a Sheddable Linker

Shahrivarkevishahi

Hagge

Chen

et al. 2021

Preprint

View full text Add to dashboard Cite

Intracellular targeting is an important aspect of the efficient delivery of drugs and nanotherapeutics. Cytosolic transport of nanomaterials is often an essential requirement for therapeutic delivery into cells but remains a challenge owing to the endosomal trap and eventual lysosomal degradation of cargo. To address this, we designed a functional carrier that escapes the endosome and delivers biological materials into the cell's cytoplasm. For this purpose, we synthesized a glutathione-sensitive linker that connects the well-known mitochondria targeting lipophilic triphenylphosphonium cation (TPP) to the surface of a proteinaceous nanoparticle based on the engineered virus-like particle (VLP) Qβ. Once in the cytosol, the thiol sensitive linker severs the TPP from the nanoparticle, halting its trafficking to the mitochondria, and marooning it in the cytosol. We demonstrate the successful in vitro cytosolic delivery of a VLP loaded with Green Fluorescent Protein, where evenly distributed fluorescence is observed in A549 lung cancer cells after four hours. We further demonstrate successful cytosolic delivery by showing that encapsulating siRNA inside the VLP promotes luminescence silencing in luciferase expressing HeLa cells more efficiently than VLPs that lack our sheddable TPP linker.

show abstract

Thiol-based michael-type addition. A systematic evaluation of its controlling factors

Cited by 24 publications

References 17 publications

Direct and Indirect Biomimetic Peptide Modification of Alginate: Efficiency, Side Reactions, and Cell Response

Direct and Indirect Biomimetic Peptide Modification of Alginate: Efficiency, Side Reactions, and Cell Response

Combination of Mussel Inspired Method and “Thiol-Michael” Click Reaction for Biocompatible Alginate-Modified Carbon Nanotubes

Intracellular Delivery of Virus-Like Particles Using a Sheddable Linker

Contact Info

Product

Resources

About