Thiol-reactive Particles

Thiol-reactive particles are engineered particles bearing chemical groups that selectively react with thiols, sulfur-containing groups found in molecules such as cysteine, making them useful tools for controlling particle-biomolecule interactions in medicine. Their reactive surfaces typically form covalent bonds when thiolate sulfur attacks an electrophilic site, a process influenced by pH, accessibility, and the local chemical environment. By tuning particle composition, size, and surface chemistry, researchers can attach peptides or other thiol-containing biomolecules, regulate protein adsorption, and study cellular uptake. These particles support research in drug delivery, diagnostic biosensors, and biomaterials, while careful control of reactivity helps limit unintended modification of biological proteins.

Thiol-reactive Particles - Related Videos

Research

JoVE Journal - Chemistry

Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates

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Cited by 8 •

2019

In this protocol, we will describe the synthesis of PODS, a phenyoxadiazolyl methyl sulfone-based reagent for the site-selective attachment of cargos to the thiols of biomolecules, particularly antibodies. In addition, we will describe the synthesis and characterization of a PODS-bearing bifunctional chelator and its conjugation to a model antibody.

Fluorescent Functionalization of Virus-Like Particles via Disulfide Re-bridging

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2026

Source: Chen, Z., et al. Making Conjugation-induced Fluorescent PEGylated Virus-like Particles by Dibromomaleimide-disulfide Chemistry. J. Vis. Exp. (2018)This video demonstrates the fluorescent functionalization of virus-like particles by re-bridging reduced disulfides with a polyethylene glycol (PEG) linker, producing stable, trackable conjugates suitable for cellular imaging and targeted delivery in biomedical applications.

Education

JoVE Core - Organic Chemistry

Preparation and Reactions of Thiols

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2023

Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol. This reaction fails because the thiol product can undergo a second nucleophilic substitution reaction in the presence of an excess alkyl halide to generate a sulfide as a by-product. This limitation can be overcome by using thiourea as the nucleophile. The reaction first produces an alkyl...

Research

JoVE Journal - Biology
Free Sample

Profiling Thiol Redox Proteome Using Isotope Tagging Mass Spectrometry

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Cited by 50 •

2012

Reactive oxygen species level is elevated when cells encounter stress conditions. Here we show the example of 3'-3' diaminobenzidine staining as well as cysTMT labeling and mass spectrometry to profile the redox proteome in Pseudomonas syringae treated tomato leaves.

Research

JoVE Journal - Chemistry
Free Sample

Synthesis of Programmable Main-chain Liquid-crystalline Elastomers Using a Two-stage Thiol-acrylate Reaction

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Cited by 107 •

2016

A novel methodology is presented to synthesize and program main-chain liquid-crystalline elastomers using commercially available starting monomers. A wide range of thermomechanical properties was tailored by adjusting the amount of crosslinker, while the actuation performance was dependent on the amount of applied strain during programming.

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