Photo-conversion of two epimers (20R and 20S) of pregna-5,7-diene-3β, 17α, 20-triol and their bioactivity in melanoma cells
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Pregna-5,7-dienes and their hydroxylated derivatives can be formed in vivo when there is a deficiency in 7-dehydrocholesterol (7-DHC) Delta-reductase function, e.g., Smith-Lemli-Opitz syndrome (SLOS). Ultraviolet B (UVB) radiation induces photoconversion of 7-DHC to vitamin D3, lumisterol3 and tachysterol3. Two epimers (20R and 20S) of pregna-5,7-diene-3beta,17alpha,20-triol (4R and 4S, respectively) were synthesized and their UVB photo-conversion products identified as corresponding 9,10-secosteroids with vitamin D-like and tachysterol-like structures, and 5,7-dienes with inverted configuration at C-9 and C-10 (lumisterol-like). The number and character of the products and the dynamics of the process were dependent on the UVB dose. At high UVB doses, the formation of multiple oxidized derivatives of the primary products, and the formation of 5,7,9(11)-triene, were observed. The production of vitamin D-like, tachysterol-like and lumisterol-like derivatives was also observed in human skin treated with 4R and 4S, and subjected to UV irradiation, as shown by RP-HPLC. Newly synthesized compounds inhibited melanoma growth in dose dependent manner, and some of them showed equal or higher potency than 1,25(OH)2D3. In summary, we have characterized for the first time the products of UV induced conversion of pregna-5,7-diene-3beta,17alpha,20-triols and documented that the newly synthesized compounds have antiproliferative properties against melanoma cells.
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Δ7-steroids and their hydroxy-derivatives, as well as their pregna/androsta-calciferol, lumisterol-like, and tachysterol-like photoderivatives, have anti-melanoma activity including inhibition of soft agar growth.
“Tests performed with Δ7-steroids and their hydroxy-derivatives, as well as with their pregna or androsta-calciferol (pD and aD), lumisterol-like (pL and aL) and tachysterol-like (pT and aT) photoderivatives, reveal that they have anti-melanoma activity including inhibition of growth in soft agar”
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 [64]
Stimulation of melanogenesis increases the antiproliferative effect of some short side chain secosteroids, in contrast to 20(OH)D3 where the effect is opposite.
“The stimulation of melanogenesis appeared to increase the antiproliferative effect of some of the secosteroids with a short side chain [64,65], which is in contrast to 20(OH)D3 where the effect was opposite”
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 [64]
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 [64]
These steroidal 5,7-dienes are predicted to undergo UVB phototransformation to secosteroids with short or no side chain that could enter the bloodstream.
“It is predicted [188] that these steroidal 5,7-dienes will undergo phototransformation to the corresponding secosteroids after exposure to UVB in the skin, producing vitamin D derivatives with a short (pregnenolone-like) or no (androgenlike) side chain, which could potentially enter the bloodstream [59, 65, 191–193].”
From The serum vitamin D metabolome: what we know and what is still to discover (2019) · cites this paper as [192]
They show in vitro anti-proliferative effects against melanoma cells, melanocytes, keratinocytes and fibroblasts and anti-fibrotic activities.
“they show in vitro anti-proliferative effects against melanoma cells, melanocytes, keratinocytes and fibroblasts as well as anti-fibrotic activities [189, 191, 192, 194, 196, 197]”
From The serum vitamin D metabolome: what we know and what is still to discover (2019) · cites this paper as [192]
Pregna-5,7-diene-3β,17α,20-triol can be converted by UVR into pregna-5,7,9(11)-triene-3β,17α,20S-triol.
“Interestingly, we have recently shown that another 5,7-diene, pregna-5,7-diene-3β,17α,20-triol, when subjected to UVR may also be converted to a triene, namely pregna-5,7,9(11)-triene-3β,17α,20S-triol [166].”
From Steroidogenesis in the skin: Implications for local immune functions (2013) · cites this paper as [166]
Accumulation of atypical steroidal 5,7-dienes in UV-irradiated skin may produce new classes of secosteroids with altered side chains.
“The accumulation of unusual steroidal 5,7-dienes in skin subjected to UV irradiation may generate new classes of secosteroids with modified side-chains [166, 167].”
From Steroidogenesis in the skin: Implications for local immune functions (2013) · cites this paper as [166]
Photoconversion of 5-7-dienes has been shown in vitro and ex vivo in human skin.
“This photoconversion of 5–7-dienes was demonstrated not only in vitro [164, 166, 167] but also ex vivo in human skin [166].”
From Steroidogenesis in the skin: Implications for local immune functions (2013) · cites this paper as [166]
Photoconversion of 5-7-dienes yields not only vitamin D analogues but also tachysterol- and lumisterol-like derivatives.
“It has to be stressed that such reactions lead not only to formation of vitamin D analogues, but also to other tachysterol- and lumisterol-like derivatives.”
From Steroidogenesis in the skin: Implications for local immune functions (2013) · cites this paper as [166]
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Self-citation
- Authors
- Zmijewski, M. A., Li, W., Zjawiony, J. K., Sweatman, T. W., Chen, J., Miller, D. D., & Slominski, A. T.
- Affiliations
- University of Tennessee Health Science Center (US)
- University of Mississippi (US)
- Corresponding author
- Slominski, Andrzej T.
- Venue
- Steroids
- Publisher
- Elsevier BV
- Published
- 2009-02
- Volume
- 74
- Issue
- 2
- Pages
- 218-228
- ISSN
- 0039-128X (ISSN-L)
- PMC
- PMC2631623
- OpenAlex
- W2027278752
- Cited by
- 62
- References
- 37
- Citations by year
- 2025: 2 · 2024: 4 · 2023: 2 · 2022: 3 · 2021: 5 · 2020: 4 · 2019: 1 · 2018: 2 · 2017: 3 · 2016: 2 · 2015: 3 · 2014: 6 · 2013: 5 · 2012: 7
- FWCI
- 3.32
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Locations
- Steroids (publishedVersion)
- PubMed (publishedVersion)
- PubMed Central (acceptedVersion)
- Funders
- National Cancer Institute (R15CA125623)
- National Institute of Arthritis and Musculoskeletal and Skin Diseases (AR-052190, R01AR052190)
- Topics
- Health Sciences › Medicine › Pathology and Forensic Medicine › Vitamin D Research Studies
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Steroid Chemistry and Biochemistry
- Health Sciences › Medicine › Pulmonary and Respiratory Medicine › Photodynamic Therapy Research Studies
- Keywords
- epimers, photoconversion, UV-B radiation, Smith-Lemli-Opitz syndrome, tachysterol, lumisterol, antiproliferative activity, melanoma cells, 1,25-dihydroxyvitamin D3
- MeSH terms
- Acetylation, Humans, Melanoma, Magnetic Resonance Spectroscopy, Photolysis, Pregnadienes, Pregnadienetriols, Secosteroids, Skin, Mass Spectrometry, Stereoisomerism, Ultraviolet Rays, Cell Line, Tumor, Cell Proliferation
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