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Record W4296900401 · doi:10.1002/cmdc.202200310

Optimization of <i>N</i> ‐Piperidinyl‐Benzimidazolone Derivatives as Potent and Selective Inhibitors of 8‐Oxo‐Guanine DNA Glycosylase 1

2022· article· en· W4296900401 on OpenAlex
Olov Wallner, Armando Cázares‐Körner, Emma Rose Scaletti, Geoffrey Masuyer, Tove Bekkhus, Torkild Visnes, Kirill Mamonov, Florian Ortis, Thomas Lundbäck, М. И. Волкова, Tobias Koolmeister, Elisée Wiita, Olga Loseva, Monica Pandey, Evert Homan, Carlos Benitéz‐Buelga, Jonathan Davies, Martin Scobie, Ulrika Warpman Berglund, Christina Kalderén, Pål Stenmark, Thomas Helleday, Maurice Michel

Why this work is in the frame

A frame that forgets how it found something cannot be audited. These are the routes that admitted this work.

fundA Canadian funder is recorded on the work.
no affNo Canadian affiliation: this work is invisible to an affiliation-only frame.
No Canadian affiliation. An affiliation-only frame, the usual design, would never have seen this work. It is one of the works that make the case for inverting the frame.

Bibliographic record

VenueChemMedChem · 2022
Typearticle
Languageen
FieldPharmacology, Toxicology and Pharmaceutics
TopicBioactive Compounds and Antitumor Agents
Canadian institutionsnot available
FundersHORIZON EUROPE European Research CouncilInnovative Medicines InitiativeDr Åke Olssons Stiftelse för Haematologisk ForskningVetenskapsrådetCrafoordska StiftelsenUppsala UniversitetCancerfondenEuropean Federation of Pharmaceutical Industries and AssociationsAlfred Österlunds StiftelseEuropean CommissionPain Relief FoundationDiamond Light SourceMcGill UniversityKarolinska InstitutetTorsten Söderbergs Stiftelse
KeywordsGuanineDNA glycosylaseChemistryDNALinkerDNA repairBase excision repairSmall moleculeDNA damageDeoxyguanosineEnzymeBiochemistryStereochemistryGeneNucleotide

Abstract

fetched live from OpenAlex

8-oxo Guanine DNA Glycosylase 1 is the initiating enzyme within base excision repair and removes oxidized guanines from damaged DNA. Since unrepaired 8-oxoG could lead to G : C→T : A transversion, base removal is of utmost importance for cells to ensure genomic integrity. For cells with elevated levels of reactive oxygen species this dependency is further increased. In the past we and others have validated OGG1 as a target for inhibitors to treat cancer and inflammation. Here, we present the optimization campaign that led to the broadly used tool compound TH5487. Based on results from a small molecule screening campaign, we performed hit to lead expansion and arrived at potent and selective substituted N-piperidinyl-benzimidazolones. Using X-ray crystallography data, we describe the surprising binding mode of the most potent member of the class, TH8535. Here, the N-Piperidinyl-linker adopts a chair instead of a boat conformation which was found for weaker analogues. We further demonstrate cellular target engagement and efficacy of TH8535 against a number of cancer cell lines.

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.

Full frame distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: codex-gemma-dda1882f352aValidation 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: Empirical
Teacher disagreement score0.015
Threshold uncertainty score0.844

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
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 head0.061
GPT teacher head0.362
Teacher spread0.301 · 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