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Record W3045872953 · doi:10.1002/ardp.202000156

Probing simple structural modification of α‐mangostin on its cholinesterase inhibition and cytotoxicity

2020· article· en· W3045872953 on OpenAlexaff
Kooi Yeong Khaw, Pravin Kumar, Siti R. Yusof, Surash Ramanathan, Vikneswaran Murugaiyah

Bibliographic record

VenueArchiv der Pharmazie · 2020
Typearticle
Languageen
FieldAgricultural and Biological Sciences
TopicNatural Compound Pharmacology Studies
Canadian institutionsCentre for Drug Research and Development
Fundersnot available
KeywordsButyrylcholinesteraseAcetylcholinesteraseChemistryCholinesteraseCytotoxicityAchéToxicityStereochemistryEnzymeInhibitory postsynaptic potentialBiochemistryPharmacologyIn vitroOrganic chemistryBiology

Abstract

fetched live from OpenAlex

Abstract α‐Mangostin has been reported to possess a broad range of pharmacological effects including potent cholinesterase inhibition, but the development of α‐mangostin as a potential lead compound is impeded by its toxicity. The present study investigated the impact of simple structural modification of α‐mangostin on its cholinesterase inhibitory activities and toxicity toward neuroblastoma and liver cancer cells. The dialkylated derivatives retained good acetylcholinesterase (AChE) inhibitory activities with IC 50 values between 4.15 and 6.73 µM, but not butyrylcholinesterase (BChE) inhibitory activities, compared with α‐mangostin, a dual inhibitor (IC 50 : AChE, 2.48 µM; BChE, 5.87 µM). Dialkylation of α‐mangostin produced AChE selective inhibitors that formed hydrophobic interactions at the active site of AChE. Interestingly, all four dialkylated derivatives of α‐mangostin showed much lower cytotoxicity, being 6.4‐ to 9.0‐fold and 3.8‐ to 5.5‐fold less toxic than their parent compound on neuroblastoma and liver cancer cells, respectively. Likewise, their selectivity index was higher by 1.9‐ to 4.4‐fold; in particular, A2 and A4 showed improved selectivity index compared with α‐mangostin. Taken together, modification of the hydroxyl groups of α‐mangostin at positions C‐3 and C‐6 greatly influenced its BChE inhibitory and cytotoxic but not its AChE inhibitory activities. These dialkylated derivatives are viable candidates for further structural modification and refinement, worthy in the search of new AChE inhibitors with higher safety margins.

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)0.000
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 score0.259
Threshold uncertainty score0.212

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)0.0000.000

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 head0.092
GPT teacher head0.312
Teacher spread0.220 · 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

Citations14
Published2020
Admission routes1
Has abstractyes

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