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Record W2075417276 · doi:10.1139/v05-121

Ambident reactivity of phenoxyl radicals in DNA adduction

2005· article· en· W2075417276 on OpenAlexfundvenueno aff
Richard A. Manderville

Bibliographic record

VenueCanadian Journal of Chemistry · 2005
Typearticle
Languageen
FieldPharmacology, Toxicology and Pharmaceutics
TopicBioactive Compounds and Antitumor Agents
Canadian institutionsnot available
FundersNational Institutes of HealthUniversity of Guelph
KeywordsChemistryRadicalDeoxyguanosineReactivity (psychology)PhotochemistryAdductPeroxideReactive oxygen speciesPeroxidaseRedoxOrganic chemistryBiochemistryEnzyme

Abstract

fetched live from OpenAlex

Phenols are a class of compounds that can create beneficial effects in vivo owing to their antioxidant properties (through radical scavenging), or they can display hazardous effects owing to their pro-oxidant properties. The mechanism by which phenols act as pro-oxidants stems from their one-electron oxidation into reactive phenoxyl radicals by peroxidase enzymes or redox-active transition metals. In the presence of thiols and molecular oxygen, these reactive phenoxyl radicals stimulate an oxidative stress and cause oxidative damage to biomolecules, which is proposed to contribute to the occurrence of cancer in peroxidase rich tissues. Recent results from our laboratory show that certain phenoxyl radicals can also react directly with the C-8 site of deoxyguanosine to afford oxygen and carbon bonded adducts. This reactivity is consistent with the ambident (oxygen vs. C attachment) electrophilicity of phenoxyl radicals coupled with the susceptibility of the C-8 site of deoxyguanosine to radical attachment. Given that formation of covalent DNA adducts is regarded as the initiation event in the carcinogenic process, C-8 deoxyguanosine adducts of phenolic toxins are expected to contribute greatly to peroxidase driven toxic effects of phenolic xenobiotics. The focus of this review is the role of phenoxyl radicals in direct reactions with DNA and the use of Brown σ+ values to predict their reactivity.Key words: DNA adduction, phenoxyl radicals, chlorophenols, ochratoxin A, deoxyguanosine.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame machine prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: none
Teacher disagreement score0.002
Threshold uncertainty score0.004

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0010.001
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0000.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0010.000

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.077
GPT teacher head0.380
Teacher spread0.302 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one source (direct Gemma or distilled Codex), not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designBench or experimental
Domainnot available
GenreEmpirical

How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".

Quick stats

Citations35
Published2005
Admission routes2
Has abstractyes

Explore more

Same venueCanadian Journal of ChemistrySame topicBioactive Compounds and Antitumor AgentsFrench-language works237,207