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Record W2334093877 · doi:10.1021/cg501865h

Molecular Recognition of Steroid Hormones in the Solid State: Stark Differences in Cocrystallization of β-Estradiol and Estrone

2015· article· en· W2334093877 on OpenAlex
Karen J. Ardila‐Fierro, Vânia André, Davin Tan, M. Teresa Duarte, Robert W. Lancaster, P.G. Karamertzanis, Tomislav Friščić

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.

affAt least one author lists a Canadian institution in the pinned OpenAlex snapshot.
fundA Canadian funder is recorded on the work.

Bibliographic record

VenueCrystal Growth & Design · 2015
Typearticle
Languageen
FieldChemistry
TopicCrystallography and molecular interactions
Canadian institutionsMcGill UniversityCentre in Green Chemistry and Catalysis
FundersFonds de recherche du Québec – Nature et technologiesFundação para a Ciência e a TecnologiaNatural Sciences and Engineering Research Council of CanadaCanada Foundation for Innovation
KeywordsSteroidChemistryEstroneSupramolecular chemistryCrystal structureHydrogen bondStereochemistryCrystallographyMoleculeHormoneOrganic chemistryBiochemistry

Abstract

fetched live from OpenAlex

While the understanding of the supramolecular chemistry of steroidal hormones is largely based on receptor binding studies in vitro and in vivo, their solid-state molecular recognition properties remain unexplored. Here, we use mechanochemical cocrystallization and single crystal X-ray structure analysis to gain insight into the solid-state complexation of sex hormones with arenes, by systematic investigation of the ability of two important estrogens ß-estradiol ( bes ) and estrone ( est ) to form cocrystals with 1,2-dimethylnaphthalene, phenanthrene, anthracene, 9,10-anthraquinone, phenanthridine, benzo[h]quinoline, and perfluoronaphthalene. Cocrystallization of bes reveals the formation of a novel hydrogen-bonded lattice host, exhibiting rectangular channels occupied by arene guests. In striking contrast to bes, its 17-keto-analogue est did not yield cocrystals with any of the explored arenes except perfluoronaphthalene, revealing association via arene-perfluorarene π···π stacking. The results reveal previously unknown solid-state complexation behavior of important estrogen hormones, demonstrating how minor changes in the steroid structure, in particular switching from a 17-hydroxyl to a 17-keto group, can result in extraordinary changes to their solid-state self-assembly. In that respect, solid-state chemistry of steroids appears to mirror their important signaling role in biological systems, as very small modifications to the steroid structure lead to large changes in cocrystallization propensity.

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 score0.067
Threshold uncertainty score0.557

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 head0.039
GPT teacher head0.247
Teacher spread0.207 · 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