Literature DB >> 27070779

Synthesis and Biological Evaluation of Vitamin D3 Metabolite 20S,23S-Dihydroxyvitamin D3 and Its 23R Epimer.

Zongtao Lin1, Srinivasa R Marepally1, Dejian Ma1, Tae-Kang Kim2, Allen Sw Oak2, Linda K Myers3, Robert C Tuckey4, Andrzej T Slominski2,5, Duane D Miller1, Wei Li1.   

Abstract

The vitamin D3 metabolite, 20S,23S-dihydroxyvitamin D3, was chemically synthesized for the first time and identified to be the same as the enzymatically produced metabolite. The C23 absolute configurations of both 20S,23S/R-dihydroxyvitamin D3 epimers were unambiguously assigned by NMR and Mosher ester analysis. Their kinetics of CYP27B1 metabolism were investigated during the production of their 1α-hydroxylated derivatives. Bioactivities of these products were compared in terms of vitamin D3 receptor activation, anti-inflammatory, and antiproliferative activities.

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Year:  2016        PMID： 27070779      PMCID： PMC5330258          DOI： 10.1021/acs.jmedchem.6b00182

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  32 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.  6β-hydroxytestosterone, a cytochrome P450 1B1 metabolite of testosterone, contributes to angiotensin II-induced hypertension and its pathogenesis in male mice.

Authors:  Ajeeth K Pingili; Mehmet Kara; Nayaab S Khan; Anne M Estes; Zongtao Lin; Wei Li; Frank J Gonzalez; Kafait U Malik
Journal:  Hypertension       Date:  2015-04-13       Impact factor: 10.190

Review 3.  The role of CYP11A1 in the production of vitamin D metabolites and their role in the regulation of epidermal functions.

Authors:  Andrzej T Slominski; Tae-Kang Kim; Wei Li; Ae-Kyung Yi; Arnold Postlethwaite; Robert C Tuckey
Journal:  J Steroid Biochem Mol Biol       Date:  2013-10-28       Impact factor: 4.292

4.  The cytochrome P450scc system opens an alternate pathway of vitamin D3 metabolism.

Authors:  Andrzej Slominski; Igor Semak; Jordan Zjawiony; Jacobo Wortsman; Wei Li; Andre Szczesniewski; Robert C Tuckey
Journal:  FEBS J       Date:  2005-08       Impact factor: 5.542

5.  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

6.  In vivo evidence for a novel pathway of vitamin D₃ metabolism initiated by P450scc and modified by CYP27B1.

Authors:  Andrzej T Slominski; Tae-Kang Kim; Haleem Z Shehabi; Igor Semak; Edith K Y Tang; Minh N Nguyen; Heather A E Benson; Elena Korik; Zorica Janjetovic; Jianjun Chen; Charles R Yates; Arnold Postlethwaite; Wei Li; Robert C Tuckey
Journal:  FASEB J       Date:  2012-06-08       Impact factor: 5.191

7.  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

8.  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

9.  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

10.  Detection of novel CYP11A1-derived secosteroids in the human epidermis and serum and pig adrenal gland.

Authors:  Andrzej T Slominski; Tae-Kang Kim; Wei Li; Arnold Postlethwaite; Elaine W Tieu; Edith K Y Tang; Robert C Tuckey
Journal:  Sci Rep       Date:  2015-10-08       Impact factor: 4.379
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  13 in total

Review 1.  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

2.  Chemical synthesis, biological activities and action on nuclear receptors of 20S(OH)D3, 20S,25(OH)2D3, 20S,23S(OH)2D3 and 20S,23R(OH)2D3.

Authors:  Pawel Brzeminski; Adrian Fabisiak; Radomir M Slominski; Tae-Kang Kim; Zorica Janjetovic; Ewa Podgorska; Yuwei Song; Mohammad Saleem; Sivani B Reddy; Shariq Qayyum; Yuhua Song; Robert C Tuckey; Venkatram Atigadda; Anton M Jetten; Rafal R Sicinski; Chander Raman; Andrzej T Slominski
Journal:  Bioorg Chem       Date:  2022-02-08       Impact factor: 5.275

3.  CYP11A1‑derived vitamin D hydroxyderivatives as candidates for therapy of basal and squamous cell carcinomas.

Authors:  Andrzej T Slominski; Anna A Brożyna; Tae-Kang Kim; Mahmoud M Elsayed; Zorica Janjetovic; Shariq Qayyum; Radomir M Slominski; Allen S W Oak; Changzhao Li; Ewa Podgorska; Wei Li; Anton M Jetten; Robert C Tuckey; Edith K Y Tang; Craig Elmets; Mohammad Athar
Journal:  Int J Oncol       Date:  2022-07-01       Impact factor: 5.884

Review 4.  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

Review 5.  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

Review 6.  On the role of classical and novel forms of vitamin D in melanoma progression and management.

Authors:  Andrzej T Slominski; Anna A Brożyna; Cezary Skobowiat; Michal A Zmijewski; Tae-Kang Kim; Zorica Janjetovic; Allen S Oak; Wojciech Jozwicki; Anton M Jetten; Rebecca S Mason; Craig Elmets; We Li; Robert M Hoffman; Robert C Tuckey
Journal:  J Steroid Biochem Mol Biol       Date:  2017-07-01       Impact factor: 4.292

Review 7.  The serum vitamin D metabolome: What we know and what is still to discover.

Authors:  Robert C Tuckey; Chloe Y S Cheng; Andrzej T Slominski
Journal:  J Steroid Biochem Mol Biol       Date:  2018-09-08       Impact factor: 4.292

8.  Investigation of 20S-hydroxyvitamin D3 analogs and their 1α-OH derivatives as potent vitamin D receptor agonists with anti-inflammatory activities.

Authors:  Zongtao Lin; Srinivasa R Marepally; Emily S Y Goh; Chloe Y S Cheng; Zorica Janjetovic; Tae-Kang Kim; Duane D Miller; Arnold E Postlethwaite; Andrzej T Slominski; Robert C Tuckey; Carole Peluso-Iltis; Natacha Rochel; Wei Li
Journal:  Sci Rep       Date:  2018-01-24       Impact factor: 4.379

9.  Detection of 7-Dehydrocholesterol and Vitamin D3 Derivatives in Honey.

Authors:  Tae-Kang Kim; Venkatram Atigadda; Pawel Brzeminski; Adrian Fabisiak; Edith K Y Tang; Robert C Tuckey; Andrzej T Slominski
Journal:  Molecules       Date:  2020-06-02       Impact factor: 4.411

10.  1α,20S-Dihydroxyvitamin D3 Interacts with Vitamin D Receptor: Crystal Structure and Route of Chemical Synthesis.

Authors:  Zongtao Lin; Hao Chen; Anna Y Belorusova; John C Bollinger; Edith K Y Tang; Zorica Janjetovic; Tae-Kang Kim; Zhongzhi Wu; Duane D Miller; Andrzej T Slominski; Arnold E Postlethwaite; Robert C Tuckey; Natacha Rochel; Wei Li
Journal:  Sci Rep       Date:  2017-08-31       Impact factor: 4.379
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