Literature DB >> 24778017

Novel vitamin D analogs as potential therapeutics: metabolism, toxicity profiling, and antiproliferative activity.

Jianjun Chen1, Jin Wang, Tae-Kang Kim, Elaine W Tieu, Edith K Y Tang, Zongtao Lin, Dianne Kovacic, Duane D Miller, Arnold Postlethwaite, Robert C Tuckey, Andrzej T Slominski, Wei Li.   

Abstract

AIM: To discover novel [20(OH)D3] analogs as antiproliferative therapeutics.
MATERIALS AND METHODS: We studied in vitro liver microsome stability, in vivo toxicity using mice, vitamin D receptor (VDR) translocation, in vitro antiproliferative effect, CYP enzyme metabolism.
RESULTS: 20S- and 20R(OH)D3 had reasonable half-lives of 50 min and 30 min (average) respectively in liver microsomes. They were non-hypercalcemic at a high dose of 60 μg/kg. Three new 20(OH)D3 analogs were designed, synthesized and tested. They showed higher or comparable potency for inhibition of proliferation of normal keratinocytes and in the induction of VDR translocation from cytoplasm to nucleus, compared to 1,25(OH)2D3. These new analogs demonstrated different degrees of metabolism through a range of vitamin D-metabolizing CYP enzymes.
CONCLUSION: Their lack of calcemic toxicity at high doses and their high biological activity suggest that this novel 20(OH)D3 scaffold may represent a promising platform for further development of therapeutically-useful agents.

Entities:  

Keywords:  20(OH)D3 analogs; VDR translocation; hypercalcemic effect; liver microsomal stability

Mesh:

Substances:

Year:  2014        PMID: 24778017      PMCID: PMC4015637     

Source DB:  PubMed          Journal:  Anticancer Res        ISSN: 0250-7005            Impact factor:   2.480


  39 in total

1.  Chemical synthesis of 20S-hydroxyvitamin D3, which shows antiproliferative activity.

Authors:  Wei Li; Jianjun Chen; Zorica Janjetovic; Tae-Kang Kim; Trevor Sweatman; Yan Lu; Jordan Zjawiony; Robert C Tuckey; Duane Miller; Andrzej Slominski
Journal:  Steroids       Date:  2010-06-11       Impact factor: 2.668

2.  Vitamin D analogs 17,20S(OH)2pD and 17,20R(OH)2pD are noncalcemic and exhibit antifibrotic activity.

Authors:  Andrzej T Slominski; Wei Li; Syamal K Bhattacharya; Richard A Smith; Patti L Johnson; Jianjun Chen; Kathleen E Nelson; Robert C Tuckey; Duane Miller; Yan Jiao; Weikuan Gu; Arnold E Postlethwaite
Journal:  J Invest Dermatol       Date:  2011-01-13       Impact factor: 8.551

3.  Correlation between secosteroid-induced vitamin D receptor activity in melanoma cells and computer-modeled receptor binding strength.

Authors:  Tae-Kang Kim; Jin Wang; Zorica Janjetovic; Jianjun Chen; Robert C Tuckey; Minh N Nguyen; Edith K Y Tang; Duane Miller; Wei Li; Andrzej T Slominski
Journal:  Mol Cell Endocrinol       Date:  2012-04-21       Impact factor: 4.102

4.  A novel pathway for sequential transformation of 7-dehydrocholesterol and expression of the P450scc system in mammalian skin.

Authors:  Andrzej Slominski; Jordan Zjawiony; Jacobo Wortsman; Igor Semak; Jeremy Stewart; Alexander Pisarchik; Trevor Sweatman; Josep Marcos; Chuck Dunbar; Robert C Tuckey
Journal:  Eur J Biochem       Date:  2004-11

5.  Hydroxylation of CYP11A1-derived products of vitamin D3 metabolism by human and mouse CYP27B1.

Authors:  Edith K Y Tang; Jianjun Chen; Zorica Janjetovic; Elaine W Tieu; Andrzej T Slominski; Wei Li; Robert C Tuckey
Journal:  Drug Metab Dispos       Date:  2013-03-01       Impact factor: 3.922

6.  Products of vitamin D3 or 7-dehydrocholesterol metabolism by cytochrome P450scc show anti-leukemia effects, having low or absent calcemic activity.

Authors:  Andrzej T Slominski; Zorica Janjetovic; Brian E Fuller; Michal A Zmijewski; Robert C Tuckey; Minh N Nguyen; Trevor Sweatman; Wei Li; Jordan Zjawiony; Duane Miller; Tai C Chen; Gerard Lozanski; Michael F Holick
Journal:  PLoS One       Date:  2010-03-26       Impact factor: 3.240

7.  Pathways and products for the metabolism of vitamin D3 by cytochrome P450scc.

Authors:  Robert C Tuckey; Wei Li; Jordan K Zjawiony; Michal A Zmijewski; Minh N Nguyen; Trevor Sweatman; Duane Miller; Andrzej Slominski
Journal:  FEBS J       Date:  2008-04-10       Impact factor: 5.542

8.  Synthesis and photo-conversion of androsta- and pregna-5,7-dienes to vitamin D3-like derivatives.

Authors:  Michal A Zmijewski; Wei Li; Jordan K Zjawiony; Trevor W Sweatman; Jianjun Chen; Duane D Miller; Andrzej T Slominski
Journal:  Photochem Photobiol Sci       Date:  2008-09-04       Impact factor: 3.982

9.  20-Hydroxycholecalciferol, product of vitamin D3 hydroxylation by P450scc, decreases NF-kappaB activity by increasing IkappaB alpha levels in human keratinocytes.

Authors:  Zorica Janjetovic; Michal A Zmijewski; Robert C Tuckey; Damon A DeLeon; Minh N Nguyen; Lawrence M Pfeffer; Andrzej T Slominski
Journal:  PLoS One       Date:  2009-06-19       Impact factor: 3.240

10.  Sequential metabolism of 7-dehydrocholesterol to steroidal 5,7-dienes in adrenal glands and its biological implication in the skin.

Authors:  Andrzej T Slominski; Michal A Zmijewski; Igor Semak; Trevor Sweatman; Zorica Janjetovic; Wei Li; Jordan K Zjawiony; Robert C Tuckey
Journal:  PLoS One       Date:  2009-02-03       Impact factor: 3.240

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  37 in total

1.  Total synthesis of biologically active 20S-hydroxyvitamin D3.

Authors:  Qinghui Wang; Zongtao Lin; Tae-Kang Kim; Andrzej T Slominski; Duane D Miller; Wei Li
Journal:  Steroids       Date:  2015-10-01       Impact factor: 2.668

2.  Metabolism of 20-hydroxyvitamin D3 and 20,23-dihydroxyvitamin D3 by rat and human CYP24A1.

Authors:  Elaine W Tieu; Wei Li; Jianjun Chen; Tae-Kang Kim; Dejian Ma; Andrzej T Slominski; Robert C Tuckey
Journal:  J Steroid Biochem Mol Biol       Date:  2015-02-26       Impact factor: 4.292

Review 3.  Vitamin D signaling and melanoma: role of vitamin D and its receptors in melanoma progression and management.

Authors:  Andrzej T Slominski; Anna A Brożyna; Michal A Zmijewski; Wojciech Jóźwicki; Anton M Jetten; Rebecca S Mason; Robert C Tuckey; Craig A Elmets
Journal:  Lab Invest       Date:  2017-02-20       Impact factor: 5.662

4.  CYP11A1-derived vitamin D3 products protect against UVB-induced inflammation and promote keratinocytes differentiation.

Authors:  Anyamanee Chaiprasongsuk; Zorica Janjetovic; Tae-Kang Kim; Robert C Tuckey; Wei Li; Chander Raman; Uraiwan Panich; Andrzej T Slominski
Journal:  Free Radic Biol Med       Date:  2020-05-22       Impact factor: 7.376

Review 5.  Photoprotective Properties of Vitamin D and Lumisterol Hydroxyderivatives.

Authors:  Andrzej T Slominski; Anyamanee Chaiprasongsuk; Zorica Janjetovic; Tae-Kang Kim; Joanna Stefan; Radomir M Slominski; Vidya Sagar Hanumanthu; Chander Raman; Shariq Qayyum; Yuwei Song; Yuhua Song; Uraiwan Panich; David K Crossman; Mohammad Athar; Michael F Holick; Anton M Jetten; Michal A Zmijewski; Jaroslaw Zmijewski; Robert C Tuckey
Journal:  Cell Biochem Biophys       Date:  2020-05-22       Impact factor: 2.194

Review 6.  Endogenously produced nonclassical vitamin D hydroxy-metabolites act as "biased" agonists on VDR and inverse agonists on RORα and RORγ.

Authors:  Andrzej T Slominski; Tae-Kang Kim; Judith V Hobrath; Allen S W Oak; Edith K Y Tang; Elaine W Tieu; Wei Li; Robert C Tuckey; Anton M Jetten
Journal:  J Steroid Biochem Mol Biol       Date:  2016-09-28       Impact factor: 4.292

7.  Bioactive forms of vitamin D selectively stimulate the skin analog of the hypothalamus-pituitary-adrenal axis in human epidermal keratinocytes.

Authors:  Justyna M Wierzbicka; Michał A Żmijewski; Anna Piotrowska; Boguslaw Nedoszytko; Magdalena Lange; Robert C Tuckey; Andrzej T Slominski
Journal:  Mol Cell Endocrinol       Date:  2016-08-12       Impact factor: 4.102

8.  Design, Synthesis and Biological Activities of Novel Gemini 20S-Hydroxyvitamin D3 Analogs.

Authors:  Zongtao Lin; Srinivasa R Marepally; Tae-Kang Kim; Zorica Janjetovic; Allen Sw Oak; Arnold E Postlethwaite; Linda K Myers; Robert C Tuckey; Andrzej T Slominski; Duane D Miller; Wei Li
Journal:  Anticancer Res       Date:  2016-03       Impact factor: 2.480

9.  Hydroxylation of 20-hydroxyvitamin D3 by human CYP3A4.

Authors:  Chloe Y S Cheng; Andrzej T Slominski; Robert C Tuckey
Journal:  J Steroid Biochem Mol Biol       Date:  2016-03-09       Impact factor: 4.292

Review 10.  The Role of Classical and Novel Forms of Vitamin D in the Pathogenesis and Progression of Nonmelanoma Skin Cancers.

Authors:  Andrzej T Slominski; Anna A Brożyna; Michal A Zmijewski; Zorica Janjetovic; Tae-Kang Kim; Radomir M Slominski; Robert C Tuckey; Rebecca S Mason; Anton M Jetten; Purushotham Guroji; Jörg Reichrath; Craig Elmets; Mohammad Athar
Journal:  Adv Exp Med Biol       Date:  2020       Impact factor: 2.622

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