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Related Concept Videos

Electrophiles02:28

Electrophiles

This lesson explains the definition, classification, and characteristic features of an electrophile that are key features of nucleophilic substitution reactions. An analysis of their charge and orbital picture helps understand their reactivity for seeking electrons. Electrophiles can be classified into positive and neutral species. Other classes include free radicals and polar functional groups.
While a positive electrophile, like a proton, reacts due to its vacant, low-energy 1s orbital, the...
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a low‐energy SOMO, which interacts...
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For instance, consider...
Bioactivation and Tissue Toxicity01:25

Bioactivation and Tissue Toxicity

Bioactivation is a metabolic process that transforms less reactive substances into highly reactive metabolites, initiating tissue toxicity. This transformation can lead to various toxic effects, including carcinogenesis and teratogenesis. Reactive metabolites are classified into two main types: electrophiles and free radicals.Electrophiles are electron-deficient species and are produced primarily by the enzyme cytochrome P-450 during the metabolism of compounds containing carbon, nitrogen, or...
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired molecule. These three...
Toxic Reactions: Overview01:26

Toxic Reactions: Overview

When toxic substances penetrate the human body, they disseminate to various tissues, undergoing metabolic changes. This process yields reactive metabolites that may covalently bind with specific target molecules, resulting in toxicity.
Toxicity falls into two primary categories: local and systemic.
Local toxicity appears at the exposure site, such as protein denaturation caused by caustic substances.
In contrast, systemic toxicity requires the toxic agent's absorption and distribution,...

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Monitoring On-Target Signaling Responses in Larval Zebrafish - Z-REX Unmasks Precise Mechanisms of Electrophilic Drugs and Metabolites
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Monitoring On-Target Signaling Responses in Larval Zebrafish - Z-REX Unmasks Precise Mechanisms of Electrophilic Drugs and Metabolites

Published on: June 2, 2023

Adductomics: characterizing exposures to reactive electrophiles.

Stephen M Rappaport1, He Li, Hasmik Grigoryan

  • 1Center for Exposure Biology, School of Public Health and College of Chemistry, University of California, Berkeley, CA 94720-7356, USA. srappaport@berkeley.edu

Toxicology Letters
|April 20, 2011
PubMed
Summary
This summary is machine-generated.

Characterizing the human exposome requires unbiased methods to identify toxicants. Adductomics, particularly focusing on human serum albumin (HSA), offers a promising approach to understanding environmental exposures and their health impacts.

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Quantification of three DNA Lesions by Mass Spectrometry and Assessment of Their Levels in Tissues of Mice Exposed to Ambient Fine Particulate Matter
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Quantification of three DNA Lesions by Mass Spectrometry and Assessment of Their Levels in Tissues of Mice Exposed to Ambient Fine Particulate Matter
12:15

Quantification of three DNA Lesions by Mass Spectrometry and Assessment of Their Levels in Tissues of Mice Exposed to Ambient Fine Particulate Matter

Published on: May 29, 2019

Area of Science:

  • Environmental Health Sciences
  • Biochemistry
  • Analytical Chemistry

Background:

  • The human exposome encompasses all toxicants from exogenous and endogenous sources, crucial for understanding environmental disease causes.
  • Reactive electrophiles are key exposome components, modifying DNA and proteins.
  • Measuring adducts formed between electrophiles and blood nucleophiles is vital for exposome characterization.

Purpose of the Study:

  • To review the potential of adductomics for elucidating the human exposome.
  • To highlight the significance of the human serum albumin (HSA) Cys(34) subadductome in this context.

Main Methods:

  • Adductomics defines the totality of adducts with a specific nucleophilic target.
  • Hemoglobin (Hb) and HSA adducts are preferred for exposome characterization due to abundance and residence time.
  • Fixed-step selected reaction monitoring (FS-SRM) mass spectrometry enables unbiased profiling of HSA-Cys(34) adducts.

Main Results:

  • The HSA-Cys(34) hotspot offers unique advantages for adductomic analysis.
  • A novel FS-SRM method allows for unbiased visualization of the HSA-Cys(34) subadductome.
  • Previous methods primarily focused on targeted adducts of HSA-Cys(34).

Conclusions:

  • Adductomics, especially focusing on HSA-Cys(34), holds significant potential for partially characterizing the human exposome.
  • This approach can advance our understanding of environmental exposures and their links to disease.