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Record W2804911666 · doi:10.1016/j.bmc.2018.05.003

BET bromodomain ligands: Probing the WPF shelf to improve BRD4 bromodomain affinity and metabolic stability

2018· article· en· W2804911666 on OpenAlexfundno aff
Laura E. Jennings, Matthias Schiedel, David S. Hewings, S. Picaud, Corentine M. C. Laurin, Paul A. Bruno, Joseph P. Bluck, Amy R. Scorah, Larissa See, Jessica K. Reynolds, Mustafa Moroglu, Ishna N. Mistry, Amy N. Hicks, Pavel Guzanov, Charles N. G. Evans, Giulia Stazi, Philip C. Biggin, Anna K. Mapp, Ester M. Hammond, P. G. Humphreys, P. Filippakopoulos, Stuart J. Conway

Bibliographic record

VenueBioorganic & Medicinal Chemistry · 2018
Typearticle
Languageen
FieldBiochemistry, Genetics and Molecular Biology
TopicProtein Degradation and Inhibitors
Canadian institutionsnot available
FundersEshelman Institute for Innovation, University of North Carolina at Chapel HillJanssen PharmaceuticalsHorizon 2020Lady Margaret Hall, University of OxfordEngineering and Physical Sciences Research CouncilJanssen BiotechMedical Research CouncilDefence Science and Technology LaboratoryInnovative Medicines InitiativeSyngenta InternationalChinesisch-Deutsche Zentrum für WissenschaftsförderungBiotechnology and Biological Sciences Research CouncilWellcome TrustCancer Research UKCanada Foundation for InnovationMerckOntario Ministry of Economic Development and InnovationGenome CanadaDiamond Light SourceSchool of Public Health, University of California BerkeleyVertex PharmaceuticalsAstraZenecaFundação de Amparo à Pesquisa do Estado de São PauloAbbVieDeutsche ForschungsgemeinschaftGlaxoSmithKlineBayerTakeda Pharmaceuticals U.S.A.PfizerNovartis Pharmaceuticals UK LimitedBoehringer Ingelheim
KeywordsBromodomainChemistryBRD4Ligand (biochemistry)Small moleculeStereochemistryHistoneBiochemistryCombinatorial chemistryReceptorGene

Abstract

fetched live from OpenAlex

Ligands for the bromodomain and extra-terminal domain (BET) family of bromodomains have shown promise as useful therapeutic agents for treating a range of cancers and inflammation. Here we report that our previously developed 3,5-dimethylisoxazole-based BET bromodomain ligand (OXFBD02) inhibits interactions of BRD4(1) with the RelA subunit of NF-κB, in addition to histone H4. This ligand shows a promising profile in a screen of the NCI-60 panel but was rapidly metabolised (t½ = 39.8 min). Structure-guided optimisation of compound properties led to the development of the 3-pyridyl-derived OXFBD04. Molecular dynamics simulations assisted our understanding of the role played by an internal hydrogen bond in altering the affinity of this series of molecules for BRD4(1). OXFBD04 shows improved BRD4(1) affinity (IC50 = 166 nM), optimised physicochemical properties (LE = 0.43; LLE = 5.74; SFI = 5.96), and greater metabolic stability (t½ = 388 min).

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 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)0.001
metaresearch head score (Gemma)0.001
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 score0.019
Threshold uncertainty score0.912

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.001
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)0.0000.000

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 head0.010
GPT teacher head0.233
Teacher spread0.223 · 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 teacher head, 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

Citations26
Published2018
Admission routes1
Has abstractyes

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