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Record W2343608145 · doi:10.1021/acs.jmedchem.6b00012

Identification of a Chemical Probe for Family VIII Bromodomains through Optimization of a Fragment Hit

2016· article· en· W2343608145 on OpenAlexfundno aff
Brian S. Gerstenberger, John D. Trzupek, C. Tallant, Oleg Fedorov, P. Filippakopoulos, Paul E. Brennan, Vita Fedele, Sarah Martin, S. Picaud, Catherine Rogers, Mihir D. Parikh, Alexandria P. Taylor, Brian Samas, Alison O’Mahony, Ellen L. Berg, Gabriel Pallares, Adam D. Torrey, Daniel K. Treiber, I. Samardjiev, Brian T. Nasipak, Teresita Padilla‐Benavides, Qiong Wu, Anthony N. Imbalzano, Jeffrey A. Nickerson, Mark E. Bunnage, Susanne Müller, Stefan Knapp, Dafydd R. Owen

Bibliographic record

VenueJournal of Medicinal Chemistry · 2016
Typearticle
Languageen
FieldBiochemistry, Genetics and Molecular Biology
TopicProtein Degradation and Inhibitors
Canadian institutionsnot available
FundersStructural Genomics ConsortiumCanadian Institutes of Health ResearchNational Cancer InstituteNational Institutes of HealthMinistero dello Sviluppo EconomicoWellcome TrustNational Institute of General Medical SciencesWellcome
KeywordsBromodomainChemistryBRD4LysineHistoneChromatinAcetylationBiochemistryStructure–activity relationshipPhenotypic screeningIn vitroSmall moleculeComputational biologyStereochemistryPhenotypeAmino acidGeneBiology

Abstract

fetched live from OpenAlex

The acetyl post-translational modification of chromatin at selected histone lysine residues is interpreted by an acetyl-lysine specific interaction with bromodomain reader modules. Here we report the discovery of the potent, acetyl-lysine-competitive, and cell active inhibitor PFI-3 that binds to certain family VIII bromodomains while displaying significant, broader bromodomain family selectivity. The high specificity of PFI-3 for family VIII was achieved through a novel bromodomain binding mode of a phenolic headgroup that led to the unusual displacement of water molecules that are generally retained by most other bromodomain inhibitors reported to date. The medicinal chemistry program that led to PFI-3 from an initial fragment screening hit is described in detail, and additional analogues with differing family VIII bromodomain selectivity profiles are also reported. We also describe the full pharmacological characterization of PFI-3 as a chemical probe, along with phenotypic data on adipocyte and myoblast cell differentiation assays.

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: Empirical
Teacher disagreement score0.002
Threshold uncertainty score0.005

Distilled classifier scores by category (both heads)

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 integrity0.0000.001
Insufficient payload (model declined to judge)0.0020.000

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 head0.011
GPT teacher head0.259
Teacher spread0.248 · 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

Citations110
Published2016
Admission routes1
Has abstractyes

Explore more

Same venueJournal of Medicinal ChemistrySame topicProtein Degradation and InhibitorsFrench-language works237,207