ArticlePloS one2011
1α,25(OH)2-3-epi-vitamin D3, a natural physiological metabolite of vitamin D3: its synthesis, biological activity and crystal structure with its receptor.
Article in PloS one, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 27 papers.
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Who cites it
27 citing papers in PubMed, 85 citations in OpenAlex.
- Vitamin D: A key player in COVID-19 immunity and lessons from the pandemic to combat immune-evasive variants.Inflammopharmacology · 2024Review
- 4-Hydroxy-1α,25-Dihydroxyvitamin DBiomolecules · 2024Article
- Dietary 25 Hydroxyvitamin D3 Improved Serum Concentration Level and Alkaline Phosphatase Activity during Lactation but Had Meager Impact on Post-Farrowing Reproductive Performance in Sows.Animals : an open access journal from MDPI · 2024Article
- Vitamin D and Its Metabolites Status before and during Chemotherapy in Caucasian Breast Cancer Patients.Metabolites · 2023Article
- A Mathematical Model for Determining the Body's Fluctuating Need for and Synthesis of Active Vitamin D.Biomedicines · 2023Article
- The Centennial Collection of VDR Ligands: Metabolites, Analogs, Hybrids and Non-Secosteroidal Ligands.Nutrients · 2022Review
- Inflammatory Markers in Non-Obese Women with Polycystic Ovary Syndrome Are Not Elevated and Show No Correlation with Vitamin D Metabolites.Nutrients · 2022Article
- Recommendations on the measurement and the clinical use of vitamin D metabolites and vitamin D binding protein - A position paper from the IFCC Committee on bone metabolism.Clinica chimica acta; international journal of clinical chemistry · 2021Review
- A Non-Invasive Hair Test to Determine Vitamin DMolecules (Basel, Switzerland) · 2021Article
- Review
- Vitamin D Status in Children With Short Stature: Accurate Determination of Serum Vitamin D Components Using High-Performance Liquid Chromatography-Tandem Mass Spectrometry.Frontiers in endocrinology · 2021Article
- Epimers of Vitamin D: A Review.International journal of molecular sciences · 2020Review
- Association of Differing Qatari Genotypes with Vitamin D Metabolites.International journal of endocrinology · 2020Article
- Association of vitamin DTherapeutic advances in chronic disease · 2020Article
- Vitamin D Metabolism Revised: Fall of Dogmas.Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research · 2019Review
- Vitamin D and Its Synthetic Analogs.Journal of medicinal chemistry · 2019Review
- Association of Vitamin D Metabolites With Embryo Development and Fertilization in Women With and Without PCOS Undergoing Subfertility Treatment.Frontiers in endocrinology · 2019Article
- Endogenously produced nonclassical vitamin D hydroxy-metabolites act as "biased" agonists on VDR and inverse agonists on RORα and RORγ.The Journal of steroid biochemistry and molecular biology · 2017Review
- The Road Not So Travelled: Should Measurement of Vitamin D Epimers during Pregnancy Affect Our Clinical Decisions?Nutrients · 2017Article
- 25OHD analogues and vacuum blood collection tubes dramatically affect the accuracy of automated immunoassays.Scientific reports · 2015Article
Corrections and comments
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Authors and funding
11 authors at 6 institutions in 4 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
backgroundThe 1α,25-dihydroxy-3-epi-vitamin-D3 (1α,25(OH)2-3-epi-D3), a natural metabolite of the seco-steroid vitamin D3, exerts its biological activity through binding to its cognate vitamin D nuclear receptor (VDR), a ligand dependent transcription regulator. In vivo action of 1α,25(OH)2-3-epi-D3 is tissue-specific and exhibits lowest calcemic effect compared to that induced by 1α,25(OH)2D3. To further unveil the structural mechanism and structure-activity relationships of 1α,25(OH)2-3-epi-D3 and its receptor complex, we characterized some of its in vitro biological properties and solved its crystal structure complexed with human VDR ligand-binding domain (LBD). METHODOLOGY/PRINCIPAL
findingsIn the present study, we report the more effective synthesis with fewer steps that provides higher yield of the 3-epimer of the 1α,25(OH)2D3. We solved the crystal structure of its complex with the human VDR-LBD and found that this natural metabolite displays specific adaptation of the ligand-binding pocket, as the 3-epimer maintains the number of hydrogen bonds by an alternative water-mediated interaction to compensate the abolished interaction with Ser278. In addition, the biological activity of the 1α,25(OH)2-3-epi-D3 in primary human keratinocytes and biochemical properties are comparable to 1α,25(OH)2D3. CONCLUSIONS/SIGNIFICANCE: The physiological role of this pathway as the specific biological action of the 3-epimer remains unclear. However, its high metabolic stability together with its significant biologic activity makes this natural metabolite an interesting ligand for clinical applications. Our new findings contribute to a better understanding at molecular level how natural metabolites of 1α,25(OH)2D3 lead to significant activity in biological systems and we conclude that the C3-epimerization pathway produces an active metabolite with similar biochemical and biological properties to those of the 1α,25(OH)2D3.
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