ArticleJournal of medicinal chemistry2012
Neurosteroid analogues. 17. Inverted binding orientations of androsterone enantiomers at the steroid potentiation site on γ-aminobutyric acid type A receptors.
Article in Journal of medicinal chemistry, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 25 citations in OpenAlex.
- New directions in neurosteroid therapeutics in neuropsychiatry.Neuroscience and biobehavioral reviews · 2025Review
- Synthesis and Evaluation of a Novel Zuranolone Analog with High GABAMolecules (Basel, Switzerland) · 2025Article
- Structural insights into opposing actions of neurosteroids on GABANature communications · 2023Article
- Neurosteroid enantiomers as potentially novel neurotherapeutics.Neuroscience and biobehavioral reviews · 2023Review
- Synthetic studies on the indane SHIP1 agonist AQX-1125.Organic & biomolecular chemistry · 2022Article
- Rational approaches for the design of various GABA modulators and their clinical progression.Molecular diversity · 2021Review
- Neurosteroids as novel antidepressants and anxiolytics: GABA-A receptors and beyond.Neurobiology of stress · 2019Article
- Inhibitable photolabeling by neurosteroid diazirine analog in the β3-Subunit of human hetereopentameric type A GABA receptors.European journal of medicinal chemistry · 2019Article
- Hexafluoroisopropanol-Mediated Domino Reaction for the Synthesis of Thiazolo-androstenones: Potent Anticancer Agents.ACS omega · 2018Article
- Synthesis and pharmacological evaluation of neurosteroid photoaffinity ligands.European journal of medicinal chemistry · 2017Article
- Comparison of Steroid Modulation of Spontaneous Inhibitory Postsynaptic Currents in Cultured Hippocampal Neurons and Steady-State Single-Channel Currents from Heterologously Expressed α1β2γ2L GABA(A) Receptors.Molecular pharmacology · 2016Article
- Anticonvulsant potencies of the enantiomers of the neurosteroids androsterone and etiocholanolone exceed those of the natural forms.Psychopharmacology · 2014Article
- Structural requirements of steroidal agonists of transient receptor potential melastatin 3 (TRPM3) cation channels.British journal of pharmacology · 2014Article
- Neurosteroid analogues. 18. Structure-activity studies of ent-steroid potentiators of γ-aminobutyric acid type A receptors and comparison of their activities with those of alphaxalone and allopregnanolone.Journal of medicinal chemistry · 2014Article
- Neurosteroids, stress and depression: potential therapeutic opportunities.Neuroscience and biobehavioral reviews · 2013Review
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Authors and funding
10 authors at 2 institutions in 1 country.
Funding
Abstract
The enantiomer pair androsterone and ent-androsterone are positive allosteric modulators of γ-aminobutyric acid (GABA) type A receptors. Each enantiomer was shown to bind at the same receptor site. Binding orientations of the enantiomers at this site were deduced using enantiomer pairs containing OBn substituents at either C-7 or C-11. 11β-OBn-substituted steroids and 7α-OBn-substituted ent-steroids potently displace [(35)S]-tert-butylbicyclophosphorothionate, augment GABA currents, and anesthetize tadpoles. In contrast, 7β-OBn-substituted steroids and 11α-OBn-substituted ent-steroids have diminished actions. The results suggest that the binding orientations of the active analogues are inverted relative to each other with the 7α- and 11β-substituents similarly located on the edges of the molecules not in contact with the receptor surface. Analogue potentiation of the GABA current was abrogated by an α(1) subunit Q241L mutation, indicating that the active analogues act at the same sites in α(1)β(2)γ(2L) receptors previously associated with positive neurosteroid modulation.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.