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Related Concept Videos

Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

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.
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Glutathione, a tripeptide made up of glutamate, cysteine, and glycine, is a critical player in the detoxification of drugs and xenobiotics via a process known as glutathione conjugation or mercapturic acid formation. This phase II biotransformation reaction involves the covalent binding of glutathione to a drug or its metabolite, enhancing the compound's water solubility and enabling its excretion.
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Related Experiment Video

Updated: May 25, 2026

Synthesis and Bioconjugation of Thiol-Reactive Reagents for the Creation of Site-Selectively Modified Immunoconjugates
08:47

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

Published on: March 6, 2019

Exploiting cell surface thiols to enhance cellular uptake.

Adrian G Torres1, Michael J Gait

  • 1Medical Research Council, Laboratory of Molecular Biology, Hills Road, Cambridge CB2 0QH, UK.

Trends in Biotechnology
|January 21, 2012
PubMed
Summary
This summary is machine-generated.

Researchers propose using cell surface thiol groups to improve the delivery of synthetic biomolecules like oligonucleotides and peptides into cells. This strategy enhances cellular association and internalization for better therapeutic development.

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Last Updated: May 25, 2026

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

  • Biomolecular Chemistry
  • Cell Biology
  • Drug Delivery Systems

Background:

  • Efficient cellular delivery of synthetic biomolecules (oligonucleotides, peptides, nanoparticles) is a major challenge in therapeutic development.
  • The cellular plasma membrane employs specialized, regulated mechanisms for compound internalization.
  • Exploiting natural cellular uptake pathways is a promising strategy for reagent design.

Purpose of the Study:

  • To explore the use of naturally occurring cell surface thiol groups (exofacial thiols) for enhancing cellular delivery.
  • To investigate how thiol-reactive modifications on biomaterials can improve cellular association and internalization.
  • To propose a design strategy for synthetic biomolecules that optimizes cellular delivery.

Main Methods:

  • Discussion of exofacial thiols as natural cell surface targets.
  • Analysis of thiol-reactive groups for conjugation to biomolecules.
  • Review of mechanisms for enhanced cellular association and internalization.

Main Results:

  • Thiol groups on the cell surface can be leveraged to improve the uptake of modified materials.
  • Materials functionalized with thiol-reactive groups demonstrate enhanced cellular association.
  • Internalization of these materials is significantly improved by targeting exofacial thiols.

Conclusions:

  • Targeting exofacial thiols offers a viable strategy for enhancing the cellular delivery of synthetic biomolecules.
  • Thiol modifications should be considered in the rational design of novel therapeutic agents.
  • This approach holds potential for optimizing the delivery of oligonucleotides, peptides, and nanoparticles.