Hydroxylation of CYP11A1-derived products of vitamin D3 metabolism by human and mouse CYP27B1
Open accessAbstract
CYP11A1 can hydroxylate vitamin D3 at carbons 17, 20, 22, and 23, producing a range of secosteroids which are biologically active with respect to their ability to inhibit proliferation and stimulate differentiation of various cell types, including cancer cells. As 1α-hydroxylation of the primary metabolite of CYP11A1 action, 20S-hydroxyvitamin D3 [20(OH)D3], greatly influences its properties, we examined the ability of both human and mouse CYP27B1 to 1α-hydroxylate six secosteroids generated by CYP11A1. Based on their kcat/Km values, all CYP11A1-derived metabolites are poor substrates for CYP27B1 from both species compared with 25-hydroxyvitamin D3. No hydroxylation of metabolites with a 17α-hydroxyl group was observed. 17α,20-Dihydroxyvitamin D3 acted as an inhibitor on human CYP27B1 but not the mouse enzyme. We also tested CYP27B1 activity on 20,24-, 20,25-, and 20,26-dihydroxyvitamin D3, which are products of CYP24A1 or CYP27A1 activity on 20(OH)D3. All three compounds were metabolized with higher catalytic efficiency (kcat/Km) by both mouse and human CYP27B1 than 25-hydroxyvitamin D3. CYP27B1 action on these new dihydroxy derivatives was confirmed to be 1α-hydroxylation by mass spectrometry and nuclear magnetic resonance analyses. Both 1,20,25- and 1,20,26- trihydroxyvitamin D3 were tested for their ability to inhibit melanoma (SKMEL-188) colony formation, and were significantly more active than 20(OH)D3. This study shows that CYP11A1-derived secosteroids are 1α-hydroxylated by both human and mouse CYP27B1 with low catalytic efficiency, and that the presence of a 17α-hydroxyl group completely blocks 1α-hydroxylation. In contrast, the secondary metabolites produced by subsequent hydroxylation of 20(OH)D3 at C24, C25, or C26 are very good substrates for CYP27B1.
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The placenta, adrenal glands, and epidermal keratinocytes metabolize vitamin D3 through a CYP11A1-mediated pathway that is modified by CYP27B1, producing detectable 20(OH)D3, 20,23(OH)2D3, 1,20(OH)2D3, 1,20,23(OH)3D3, and 17,20,23(OH)3D3.
“The placenta, adrenal glands and epidermal keratinocytes have been shown to metabolize vitamin D3 via this CYP11A1-mediated pathway that is modified by the activity of CYP27B1, with 20(OH)D3 (the major metabolite), 20,23(OH)2D3, 1,20(OH)2D3, 1,20,23(OH)3D3 and 17,20,23(OH)3D3 being detected”
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 [53]
20,24(OH)2D3, 20,25(OH)2D3, and 20,26(OH)2D3 can be 1α-hydroxylated by CYP27B1 with catalytic efficiency similar to that for 25(OH)D3 and much higher than for the parent 20(OH)D3.
“20,24(OH)2D3, 20,25(OH)2D3 and 20,26(OH)2D3 can be 1α-hydroxylated by CYP27B1 with a catalytic efficiency similar to that for 1α-hydroxylation of 25(OH)D3 and much higher than for the parent 20(OH)D3”
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 [53]
Several products of the CYP11A1-mediated pathway can be 1α-hydroxylated by purified human CYP27B1, although with lower catalytic efficiency than for 25(OH)D3.
“Several of the products of the CYP11A1-mediated pathway can be 1α-hydroxylated by purified human CYP27B1, although with lower catalytic efficiency than for 25(OH)D3”
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 [53]
CYP11A1-derived products with a 17α-hydroxyl group, such as 17,20(OH)2D3 and 17,20,23(OH)3D3, are not substrates for CYP27B1.
“CYP11A1-derived products with a 17α-hydroxyl group such as 17,20(OH)2D3 and 17,20,23(OH)3D3 are not substrates for CYP27B1”
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 [53]
Addition of a 1α-hydroxyl group to 20,25(OH)2D3 by CYP27B1 further increases anti-melanoma activity, with the opposite effect for 1α-hydroxylation of 20,26(OH)2D3.
“Addition of a 1α-hydroxyl group to 20,25(OH)2D3 by CYP27B1 further increased this anti-melanoma activity with the opposite effect seen for 1α-hydroxylation of 20,26(OH)2D3”
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 [53]
20,24(OH)2D3, 20,25(OH)2D3, and 20,26(OH)2D3 display stronger inhibition of colony formation by SKMEL-188 melanoma cells than the parent 20(OH)D3.
“Initial tests performed on 20,24(OH)2D3, 20,25(OH)2D3 and 20,26(OH)2D3, products of 20(OH)D3 hydroxylation by CYP24A1 [56] and/or CYP27A1 [55] (Fig. 1), revealed that they display stronger inhibition of colony formation by SKMEL-188 melanoma cells than the parent 20(OH)D3”
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 [53]
20(OH)D3 and 20(OH)D2, along with other CYP11A1 pathway products, are poor substrates for CYP27B1.
“the products of the CYP11A1-mediated pathway, including 20(OH)D3 and 20(OH)D2, are poor substrates for CYP27B1 [53,59].”
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 [53]
There is sufficient experimental data to justify further preclinical testing of these novel secosteroids in melanoma.
“In the case of melanoma, there is already sufficient experimental data to justify further preclinical testing of these novel secosteroids [53,56,59,63–65,71,73,77,78,80,81,91,92].”
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 [53]
Human CYP27B1 acts on CYP11A1-derived hydroxyvitamin D products, with catalytic efficiencies from undetectable for 17α-OH substrates to three times higher than 25(OH)D3 1α-hydroxylation for 20S,24R(OH)2D3 and 20S,25(OH)2D3.
“Human CYP27B1 also acted on hydroxyvitamin D products of CYP11A1 action on vitamin D (see Fig. 4) with catalytic efficiencies ranging from undetectable for substrates with a 17α-OH group such as 17α,20S(OH)2D3, to efficiencies three times higher than that for 1α-hydroxylation of 25(OH)D3 for 20S,24R(OH)2D3 and 20S,25(OH)2D3 [103].”
From The serum vitamin D metabolome: what we know and what is still to discover (2019) · cites this paper as [103]
CYP27A1, CYP24A1, CYP2R1 and CYP3A4 can act on 20S(OH)D3 to produce 20,24(OH)2D3 and/or 20,25(OH)2D3 and/or 20,26(OH)2D3, all detected in serum.
“CYP27A1, CYP24A1, CYP2R1 and CYP3A4 can act on 20S(OH)D3 producing 20,24(OH)2D3 and/or 20,25(OH)2D3 and/or 20,26(OH)2D3 and all these products have been detected in serum (Table 3).”
From The serum vitamin D metabolome: what we know and what is still to discover (2019) · cites this paper as [103]
These 20S(OH)D3 products are good substrates for CYP27B1 C1α hydroxylation, and their 1α-hydroxyderivatives are detected in skin.
“In contrast to 20(OH)D3, they are all very good substrates for C1α hydroxylation by CYP27B1 [103] and their 1α-hydroxyderivatives have been detected in skin [152].”
From The serum vitamin D metabolome: what we know and what is still to discover (2019) · cites this paper as [103]
Purified CYP27B1 can 1α-hydroxylate 22(OH)D3, 20S(OH)D3, 20R,22(OH)2D3 and 20S,23S(OH)2D3.
“Purified CYP27B1 can act on 22(OH)D3, 20S(OH)D3, 20R,22(OH)2D3 and 20S,23S(OH)2D3 hydroxylating them at C1α [103].”
From The serum vitamin D metabolome: what we know and what is still to discover (2019) · cites this paper as [103]
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- Authors
- Tang, E. K. Y., Chen, J., Janjetovic, Z., Tieu, E. W., Slominski, A. T., Li, W., & Tuckey, R. C.
- Affiliations
- University of Tennessee Health Science Center (US)
- Venue
- Drug Metabolism and Disposition
- Publisher
- Elsevier BV
- Published
- 2013-05
- Volume
- 41
- Issue
- 5
- Pages
- 1112-1124
- ISSN
- 0090-9556 (ISSN-L)
- PMC
- PMC3629803
- OpenAlex
- W2158555665
- Cited by
- 42
- References
- 51
- Citations by year
- 2026: 1 · 2024: 3 · 2023: 1 · 2022: 7 · 2021: 2 · 2020: 5 · 2019: 1 · 2018: 3 · 2017: 3 · 2016: 5 · 2015: 5 · 2014: 5 · 2013: 1
- FWCI
- 4.25
- Type
- journal article
- Language
- en
- Open access
- bronze
- doi.org
- Locations
- Drug Metabolism and Disposition (publishedVersion)
- Europe PMC (PubMed Central) (publishedVersion)
- PubMed Central (publishedVersion)
- PubMed (publishedVersion)
- UWA Profiles and Research Repository (UWA) (submittedVersion)
- Funders
- National Institutes of Health (1s10od010678-01)
- National Institute of Arthritis and Musculoskeletal and Skin Diseases (R01AR052190)
- National Center for Research Resources (S10RR026377)
- 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
- CYP11A1, CYP27B1, vitamin D3 metabolism, secosteroids, 1α-hydroxylation, 25-hydroxyvitamin D3, melanoma, colony formation inhibition, enzyme inhibition
- MeSH terms
- Animals, Cholecalciferol, Cholesterol Side-Chain Cleavage Enzyme, Enzyme Inhibitors, Humans, Hydroxylation, Magnetic Resonance Spectroscopy, Mass Spectrometry, 25-Hydroxyvitamin D3 1-alpha-Hydroxylase, Mice
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