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Record W4402892953 · doi:10.1016/j.ejmech.2024.116902

Chemical synthesis and enzymatic late-stage diversification of novel pantothenate analogues with antiplasmodial activity

2024· article· en· W4402892953 on OpenAlexaff
Xiangning Liu, Sian Thistlethwaite, Rohit Kholiya, Jacob Pierscianowski, Kevin J. Saliba, Karine Auclair

Bibliographic record

VenueEuropean Journal of Medicinal Chemistry · 2024
Typearticle
Languageen
FieldNeuroscience
TopicNeurological diseases and metabolism
Canadian institutionsMcGill University
Fundersnot available
KeywordsChemistryEnzymeChemical synthesisStereochemistryBiochemistryDiversification (marketing strategy)In vitro

Abstract

fetched live from OpenAlex

The emergence of resistance to nearly every therapeutic agent directed against malaria-causing Plasmodium parasites emphasises the dire need for new antimalarials. Despite their high potency and low cytotoxicity in vitro, the clinical use of pantothenamides is hindered by pantetheinase-mediated hydrolysis in human serum. We herein report the chemical synthesis and biological activity of a new series of pantothenamide analogues in which the labile amide group is replaced with an isoxazole ring. In addition, we utilised, for the first time, enzymatic late-stage diversification to generate additional isoxazole-containing pantothenamide-mimics. Thirteen novel isoxazole-containing pantothenamide-mimics were generated, several of which display nanomolar antiplasmodial activity against Plasmodium falciparum and are non-toxic to human cells in vitro. Although the derivatives generated via late-stage diversification are less potent than the parent compounds, the most potent still exerted its activity via a mechanism that interferes with the pantothenate-utilising process and appears to be nontoxic to human cells. This increases the appeal of using late-stage diversification to modify pantothenamide-mimics, potentially leading to compounds with improved antiplasmodial and/or pharmacological properties.

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)0.000
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 score0.004
Threshold uncertainty score0.333

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.001
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 head0.037
GPT teacher head0.247
Teacher spread0.211 · 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

Citations3
Published2024
Admission routes1
Has abstractyes

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