Synthesis and photochemical transformation of 3β,21-dihydroxypregna-5,7-dien-20-one to novel secosteroids that show anti-melanoma activity
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We have synthesized 3β,21-dihydroxypregna-5,7-dien-20-one (21(OH) 7DHP) and used UVB radiation to induce its photoconversion to analogues of vitamin D (pD), lumisterol (pL) and tachysterol (pT). The number and character of the products and the dynamics of the process were dependent on the UVB dose. The main products: pD and pT compounds were characterized by UV absorption, MS and NMR spectroscopy after RP-HPLC chromatography. In addition, formation of multiple oxidized derivatives of the primary products was detected and one of these derivatives was characterized as oxidized 21-hydroxyisotachysterol compound (21(OH)oxy-piT). These newly synthesized compounds inhibited growth of human melanoma cells in a dose dependent manner, with greater or equal potency to calcitriol. 3β,21-Dihydroxy-9β,10α-pregna-5,7-dien-20-one (21(OH)pL) and 21(OH)oxy-piT had higher potency against pigmented melanoma cells, while the EC(50) for compounds 21(OH)7DHP and (5Z,7E)-3β,21-dihydroxy-9,10-secopregna-5,7,10(19)-trien-20-one (21(OH)pD) were similar in both pigmented and non-pigmented cells. Moreover, 21(OH)7DHP and its derivatives inhibited proliferation of human epidermal HaCaT keratinocytes, albeit at a lower activity compared to melanoma cells. Importantly, 21(OH)7DHP derivatives strongly inhibited the colony formation of human melanoma cells with 21(OH)pD being the most potent. The potential mechanism of action of newly synthesized compounds was similar to that mediated by 1,25(OH)(2)D(3) and involved ligand-induced translocation of vitamin D receptor into the nucleus. In summary, we have characterized for the first time products of UVB-induced conversion of 21(OH)7DHP and documented that these compounds have selective, inhibitory effects on 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 [65]
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 [65]
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 [65]
7DHP can be metabolized by steroidogenic enzymes to several steroidal 5,7-dienes or derivatives.
“7DHP can be metabolized by steroidogenic enzymes to several steroidal 5,7-dienes or their derivatives [188–191].”
From The serum vitamin D metabolome: what we know and what is still to discover (2019) · cites this paper as [191]
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 [191]
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 [191]
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 [167]
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 [167]
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 [167]
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Self-citationNovel vitamin D photoproducts and their precursors in the skin
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Self-citationMalignant Melanoma: An Overview, New Perspectives, and Vitamin D Signaling
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Self-citationEvolutionary formation of melatonin and vitamin D in early life forms: insects take centre stage
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Self-citationKim, T.-K., Wang, J., Janjetovic, Z., Chen, J., Tuckey, R. C., Nguyen, M. N., Tang, E. K. Y., Miller, D., Li, W., & Slominski, A. T. (2012) · Molecular and Cellular Endocrinology · doi:10.1016/j.mce.2012.04.001 · Cited by 67 · see citing works
Self-citationVitamin D in Nature: A Product of Synthesis and/or Degradation of Cell Membrane Components
Göring, H. (2018) · Biochemistry (Moscow) · doi:10.1134/s0006297918110056 · Cited by 61 · see citing works
Chen, J., Wang, J., Kim, T., Tieu, E. W., Tang, E. K. Y., Lin, Z., Kovacic, D., Miller, D. D., Postlethwaite, A. E., Tuckey, R. C., et al. (2014) · PubMed · Cited by 55 · see citing works
Self-citationSlominski, A. T., Brożyna, A. A., Zmijewski, M. A., Janjetović, Z., Kim, T., Slominski, R. M., Tuckey, R. C., Mason, R. S., Jetten, A. M., Guroji, P., et al. (2020) · Advances in experimental medicine and biology · doi:10.1007/978-3-030-46227-7_13 · Cited by 54 · see citing works
Self-citationWasiewicz, T., Szyszka, P., Cichorek, M., Janjetović, Z., Tuckey, R. C., Slominski, A. T., & Zmijewski, M. A. (2015) · International Journal of Molecular Sciences · doi:10.3390/ijms16046645 · Cited by 49 · see citing works
Self-citationVitamin D derivatives enhance cytotoxic effects of H2O2 or cisplatin on human keratinocytes
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Self-citationNew vitamin D analogs as potential therapeutics in melanoma
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Lumisterol is metabolized by CYP11A1: discovery of a new pathway
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Self-citationThe Therapeutic Potential and Molecular Mechanism of Isoflavone Extract against Psoriasis
Li, H., Wu, N., Lee, G., & Hung, C. (2018) · Scientific Reports · doi:10.1038/s41598-018-24726-z · Cited by 28 · see citing works
Novel CYP11A1-Derived Vitamin D and Lumisterol Biometabolites for the Management of COVID-19
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Self-citationBeneficial health effects of ultraviolet radiation: expert review and conference report
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Is Vitamin D Signaling Regulated by and Does It Regulate Circadian Rhythms?
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Domżalski, P., Piotrowska, A., Tuckey, R. C., & Zmijewski, M. A. (2024) · International Journal of Molecular Sciences · doi:10.3390/ijms252010914 · Cited by 8 · see citing works
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Cutaneous Secosteroidal System
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Self-citation
- Authors
- Zmijewski, M. A., Li, W., Chen, J., Kim, T.-K., Zjawiony, J. K., Sweatman, T. W., Miller, D. D., & Slominski, A. T.
- Affiliations
- Gdańsk Medical University (PL)
- University of Tennessee Health Science Center (US)
- University of Mississippi (US)
- Corresponding author
- Slominski, Andrzej T.
- ORCID
- Venue
- Steroids
- Publisher
- Elsevier BV
- Published
- 2011-01
- Volume
- 76
- Issue
- 1-2
- Pages
- 193-203
- ISSN
- 0039-128X (ISSN-L)
- PMC
- PMC3005096
- OpenAlex
- W1966414524
- Cited by
- 51
- References
- 58
- Citations by year
- 2025: 2 · 2024: 7 · 2023: 2 · 2022: 2 · 2021: 2 · 2020: 3 · 2019: 1 · 2018: 5 · 2017: 4 · 2016: 5 · 2015: 3 · 2014: 4 · 2013: 5 · 2012: 6
- FWCI
- 2.38
- Type
- journal article
- Language
- en
- Open access
- green
- www.ncbi.nlm.nih.gov
- Locations
- Steroids (publishedVersion)
- PubMed (publishedVersion)
- Europe PMC (PubMed Central) (acceptedVersion)
- PubMed Central (acceptedVersion)
- Funders
- National Cancer Institute (R15CA125623)
- National Institute of Arthritis and Musculoskeletal and Skin Diseases (AR-052190, R01AR052190)
- National Center for Research Resources (S10RR026377)
- 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
- Physical Sciences › Chemistry › Organic Chemistry › Synthesis and biological activity
- Keywords
- secosteroids, vitamin D analogs, lumisterol, tachysterol, anti-melanoma activity, melanoma cell proliferation, HaCaT keratinocytes, colony formation inhibition, 1,25-dihydroxyvitamin D3
- MeSH terms
- Antineoplastic Agents, Dose-Response Relationship, Drug, Drug Screening Assays, Antitumor, Humans, Melanoma, Molecular Conformation, Photochemistry, Pregnadienediols, Secosteroids, Stereoisomerism, Ultraviolet Rays, Cell Line, Tumor, Cell Proliferation
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