Mass Spectrometry Analysis of DNA and Protein Adducts as Biomarkers in Human Exposure to Cigarette Smoking: Acrolein as an Example

Chen, Hauh‐Jyun Candy

doi:10.1021/acs.chemrestox.2c00354

Cited by 18 publications

(18 citation statements)

References 129 publications

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“…Acrolein can induce oxidative DNA damage due to ROS homeostasis disorders and free radical generation. Moreover, this aldehyde readily reacts with deoxyguanosine (dG), producing two exocyclic DNA adducts, α- and γ-hydroxy-1, N2-propano-2′-deoxyguanosine (a-HOPdG and c-HOPdG), but is also capable of forming adducts of 2′-deoxyadenosine and 2′-deoxycytidine DNA bases and thymidine [ 108 , 160 , 161 ]. The result of the formation of acrolein-DNA adducts is mutations within DNA fragments crucial to the fate of the cell.…”

Section: Acrolein In the Development Of Lung And Oral Cancermentioning

confidence: 99%

The Tobacco Smoke Component, Acrolein, as a Major Culprit in Lung Diseases and Respiratory Cancers: Molecular Mechanisms of Acrolein Cytotoxic Activity

Hikisz

Jacenik

2023

Cells

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Acrolein, a highly reactive unsaturated aldehyde, is a ubiquitous environmental pollutant that seriously threatens human health and life. Due to its high reactivity, cytotoxicity and genotoxicity, acrolein is involved in the development of several diseases, including multiple sclerosis, neurodegenerative diseases such as Alzheimer’s disease, cardiovascular and respiratory diseases, diabetes mellitus and even the development of cancer. Traditional tobacco smokers and e-cigarette users are particularly exposed to the harmful effects of acrolein. High concentrations of acrolein have been found in both mainstream and side-stream tobacco smoke. Acrolein is considered one of cigarette smoke’s most toxic and harmful components. Chronic exposure to acrolein through cigarette smoke has been linked to the development of asthma, acute lung injury, chronic obstructive pulmonary disease (COPD) and even respiratory cancers. This review addresses the current state of knowledge on the pathological molecular mechanisms of acrolein in the induction, course and development of lung diseases and cancers in smokers.

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Section: Acrolein In the Development Of Lung And Oral Cancermentioning

confidence: 99%

The Tobacco Smoke Component, Acrolein, as a Major Culprit in Lung Diseases and Respiratory Cancers: Molecular Mechanisms of Acrolein Cytotoxic Activity

Hikisz

Jacenik

2023

Cells

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“…Acrolein can also form protein adducts, specifically targeting lysine and cysteine. , Cai et al investigated reactions of acrolein with proteins and peptides; they concluded that cysteine was the most reactive amino acid and that the initial products reacted further with protein amino groups . Reaction of acrolein with Cys-34 of albumin by Michael addition was reported by Columbo et al and others; reactions with lysine and histidine were also observed. − Reactions of acrolein with hemoglobin and albumin have recently been reviewed . Protein adducts of acrolein can also be generated during lipid peroxidation .…”

Section: Discussionmentioning

confidence: 99%

Levels of Urinary Mercapturic Acids of Acrolein, Methacrolein, Crotonaldehyde, and Methyl Vinyl Ketone in Relationship to Chronic Obstructive Pulmonary Disease in Cigarette Smokers of the Subpopulations and Intermediate Outcome Measures in COPD Study (SPIROMICS)

Wendt,

Bowler,

Demorest

et al. 2023

Chem. Res. Toxicol.

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Cigarette smoking is an established cause of chronic obstructive pulmonary disease (COPD). Numerous studies implicate acrolein, which occurs in relatively high concentrations in cigarette smoke and reacts readily with proteins, as one causative factor for COPD in smokers. Far less is known about the possible roles in COPD of the related α,β-unsaturated carbonyl compounds of cigarette smoke crotonaldehyde, methacrolein, and methyl vinyl ketone. In the study reported here, we analyzed mercapturic acids of these α,β-unsaturated compounds in the urine of 413 confirmed cigarette smokers in the Subpopulations and Intermediate Outcome Measures in COPD Study (SPIROMICS)�202 with COPD and 211 without COPD. The mercapturic acids analyzed were 3-hydroxypropyl mercapturic acid (3-HPMA) from acrolein, 3-hydroxy-1-methylpropyl mercapturic acid (HMPMA-1) from crotonaldehyde, 3-hydroxy-2-methylpropyl mercapturic acid (HMPMA-2) from methacrolein, and 3-hydroxy-3-methylpropyl mercapturic acid (HMPMA-3) from methyl vinyl ketone. In models adjusting for age, sex, race, pack years of tobacco use, and BMI, all four mercapturic acids were increased in individuals with COPD but not significantly. Stratified by the GOLD status, there were increased levels of the metabolites associated with GOLD 3− 4 compared to that with GOLD 0, with the methacrolein metabolite HMPMA-2 reaching statistical significance (adjusted odds ratio 1.23 [95% CI: 1.00−1.53]). These results highlight the possible role of methacrolein, which has previously received little attention in this regard, as a causative factor in COPD in cigarette smokers.

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“…The effect of acrolein on the key signaling pathways for cell proliferation/death is also significant for the pathogenesis of many diseases [ 9 , 10 ]. Many studies indicate that the mutagenic properties of acrolein result from its significant effectiveness in its direct interaction with DNA and the formation of adducts, primarily with deoxyguanosine [ 11 , 12 ]. In addition, this aldehyde, while interacting with DNA, simultaneously weakens or completely disables repair mechanisms [ 13 ].…”

Section: Introductionmentioning

confidence: 99%

Diet as a Source of Acrolein: Molecular Basis of Aldehyde Biological Activity in Diabetes and Digestive System Diseases

Hikisz

Jacenik

2023

IJMS

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Acrolein, a highly reactive α,β-unsaturated aldehyde, is a compound involved in the pathogenesis of many diseases, including neurodegenerative diseases, cardiovascular and respiratory diseases, diabetes mellitus, and the development of cancers of various origins. In addition to environmental pollution (e.g., from car exhaust fumes) and tobacco smoke, a serious source of acrolein is our daily diet and improper thermal processing of animal and vegetable fats, carbohydrates, and amino acids. Dietary intake is one of the main routes of human exposure to acrolein, which is a major public health concern. This review focuses on the molecular mechanisms of acrolein activity in the context of its involvement in the pathogenesis of diseases related to the digestive system, including diabetes, alcoholic liver disease, and intestinal cancer.

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Mass Spectrometry Analysis of DNA and Protein Adducts as Biomarkers in Human Exposure to Cigarette Smoking: Acrolein as an Example

Cited by 18 publications

References 129 publications

The Tobacco Smoke Component, Acrolein, as a Major Culprit in Lung Diseases and Respiratory Cancers: Molecular Mechanisms of Acrolein Cytotoxic Activity

The Tobacco Smoke Component, Acrolein, as a Major Culprit in Lung Diseases and Respiratory Cancers: Molecular Mechanisms of Acrolein Cytotoxic Activity

Levels of Urinary Mercapturic Acids of Acrolein, Methacrolein, Crotonaldehyde, and Methyl Vinyl Ketone in Relationship to Chronic Obstructive Pulmonary Disease in Cigarette Smokers of the Subpopulations and Intermediate Outcome Measures in COPD Study (SPIROMICS)

Diet as a Source of Acrolein: Molecular Basis of Aldehyde Biological Activity in Diabetes and Digestive System Diseases

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