Metabolism of 1α-hydroxyvitamin D3 by cytochrome P450scc to biologically active 1α,20-dihydroxyvitamin D3
Open accessAbstract
Cytochrome P450scc (CYP11A1) metabolizes vitamin D3 to 20-hydroxyvitamin D3 as the major product, with subsequent production of dihydroxy and trihydroxy derivatives. The aim of this study was to determine whether cytochrome P450scc could metabolize 1alpha-hydroxyvitamin D3 and whether products were biologically active. The major product of 1alpha-hydroxyvitamin D3 metabolism by P450scc was identified by mass spectrometry and NMR as 1alpha,20-dihydroxyvitamin D3. Mass spectrometry of minor metabolites revealed the production of another dihydroxyvitamin D3 derivative, two trihydroxy-metabolites made via 1alpha,20-dihydroxyvitamin D3 and a tetrahydroxyvitamin D3 derivative. The Km for 1alpha-hydroxyvitamin D3 determined for P450scc incorporated into phospholipid vesicles was 1.4 mol substrate/mol phospholipid, half that observed for vitamin D3. The kcat was 3.0 mol/min/mol P450scc, 6-fold lower than that for vitamin D3. 1alpha,20-Dihydroxyvitamin D3 inhibited DNA synthesis by human epidermal HaCaT keratinocytes propagated in culture, in a time- and dose-dependent fashion, with a potency similar to that of 1alpha,25-dihydroxyvitamin D3. 1alpha,20-Dihydroxyvitamin D3 (10 microM) enhanced CYP24 mRNA levels in HaCaT keratinocytes but the potency was much lower than that reported for 1alpha,25-dihydroxyvitamin D3. We conclude that the presence of the 1-hydroxyl group in vitamin D3 does not alter the major site of hydroxylation by P450scc which, as for vitamin D3, is at C20. The major product, 1alpha,20-dihydroxyvitamin D3, displays biological activity on keratinocytes and therefore might be useful pharmacologically.
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The Km for conversion of vitamin D3 to 20(OH)D3 by CYP11A1 is higher than for cholesterol metabolism.
“The Km for the conversion of vitamin D3 to 20(OH)D3 by CYP11A1 is higher than that for the metabolism of cholesterol”
From The role of CYP11A1 in the production of vitamin D metabolites and their role in the regulation of epidermal functions (2014) · cites this paper as [50]
CYP11A1 can hydroxylate the prodrug 1(OH)D3 to the biologically active product 1,20(OH)2D3, providing an alternative route to 25-hydroxylation for activation.
“However, CYP11A1 can hydroxylate the prodrug 1(OH)D3 to the biologically active product, 1,20(OH)2D3, providing an alternative route to 25-hydroxylation for activation of this compound”
From The role of CYP11A1 in the production of vitamin D metabolites and their role in the regulation of epidermal functions (2014) · cites this paper as [50]
1α-hydroxylated products 1,20(OH)2D3, 1,20(OH)2D2, and 1,20,23(OH)3D3 show similar inhibition of keratinocyte proliferation and stimulation of differentiation and VDR expression to their precursors, but greater stimulation of CYP24A1 expression.
“These products show similar inhibition of keratinocyte proliferation and stimulation of differentiation and VDR expression to those of their precursors, but display greater stimulation of CYP24A1 expression”
From The role of CYP11A1 in the production of vitamin D metabolites and their role in the regulation of epidermal functions (2014) · cites this paper as [50]
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- Authors
- Tuckey, R. C., Janjetovic, Z., Li, W., Nguyen, M. N., Zmijewski, M. A., Zjawiony, J., & Slominski, A.
- Affiliations
- The University of Western Australia (AU)
- University of Tennessee Health Science Center (US)
- University of Mississippi (US)
- Corresponding author
- Tuckey, Robert C.
- Venue
- The Journal of Steroid Biochemistry and Molecular Biology
- Publisher
- Elsevier BV
- Published
- 2008-12
- Volume
- 112
- Issue
- 4-5
- Pages
- 213-219
- ISSN
- 0960-0760 (ISSN-L)
- PMC
- PMC2605774
- OpenAlex
- W1977233186
- Cited by
- 48
- References
- 32
- Citations by year
- 2024: 2 · 2023: 2 · 2022: 1 · 2021: 2 · 2020: 4 · 2019: 4 · 2018: 2 · 2017: 2 · 2016: 1 · 2015: 6 · 2014: 3 · 2013: 2 · 2012: 5
- FWCI
- 2.84
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Locations
- The Journal of Steroid Biochemistry and Molecular Biology (publishedVersion)
- PubMed (publishedVersion)
- Europe PMC (PubMed Central) (acceptedVersion)
- PubMed Central (acceptedVersion)
- UWA Profiles and Research Repository (UWA) (submittedVersion)
- Funders
- National Institutes of Health
- National Institute of Arthritis and Musculoskeletal and Skin Diseases (R01AR052190)
- Topics
- Health Sciences › Medicine › Pathology and Forensic Medicine › Vitamin D Research Studies
- Life Sciences › Pharmacology, Toxicology and Pharmaceutics › Pharmacology › Pharmacogenetics and Drug Metabolism
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Steroid Chemistry and Biochemistry
- Keywords
- 1α-hydroxyvitamin D3, cytochrome P450scc, CYP11A1, vitamin D3 metabolism, keratinocytes, DNA synthesis inhibition, 1,25-dihydroxyvitamin D3, phospholipid vesicles
- MeSH terms
- Animals, Cattle, Cholesterol Side-Chain Cleavage Enzyme, Humans, Hydroxycholecalciferols, Kinetics, Steroid Hydroxylases, Keratinocytes, Gene Expression, Nuclear Magnetic Resonance, Biomolecular, Cell Proliferation, Vitamin D3 24-Hydroxylase
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
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