Literature DB >> 26433048

Total synthesis of biologically active 20S-hydroxyvitamin D3.

Qinghui Wang1, Zongtao Lin1, Tae-Kang Kim2, Andrzej T Slominski3, Duane D Miller1, Wei Li4.   

Abstract

A total synthetic strategy of 20S-hydroxyvitamin D3 [20S-(OH)D3] involving modified synthesis of key intermediates 7 and 12, Grignard reaction to stereoselectively generate 20S-OH and Wittig-Horner coupling to establish D3 framework, was completed in 16 steps with an overall yield of 0.4%. The synthetic 20S-(OH)D3 activated vitamin D receptor (VDR) and initiated the expression of downstream genes. In addition, 20S-(OH)D3 showed similar inhibitory potency as calcitriol [1,25(OH)2D3] on proliferation of melanoma cells.
Copyright © 2015 Elsevier Inc. All rights reserved.

Entities:  

Keywords:  20S-Hydroxyvitamin D3; PCR; Reporter assay; Thymidine incorporation; Total chemical synthesis; VDR activation

Mesh：

Substances：

Year:  2015        PMID： 26433048      PMCID： PMC4659745          DOI： 10.1016/j.steroids.2015.09.009

Source DB:  PubMed          Journal:  Steroids        ISSN： 0039-128X            Impact factor:   2.668


  37 in total

Review 1.  Pharmacokinetics of vitamin D toxicity.

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Journal:  Am J Clin Nutr       Date:  2008-08       Impact factor: 7.045

Review 2.  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

3.  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

Review 4.  Progesterone synthesis by the human placenta.

Authors:  Robert C Tuckey
Journal:  Placenta       Date:  2005-04       Impact factor: 3.481

5.  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

6.  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

7.  De-orphanization of cytochrome P450 2R1: a microsomal vitamin D 25-hydroxilase.

Authors:  Jeffrey B Cheng; Daniel L Motola; David J Mangelsdorf; David W Russell
Journal:  J Biol Chem       Date:  2003-07-16       Impact factor: 5.157

8.  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

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.  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
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  10 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

Review 3.  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

4.  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

Review 5.  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

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

Authors:  Zongtao Lin; Srinivasa R Marepally; Dejian Ma; Tae-Kang Kim; Allen Sw Oak; Linda K Myers; Robert C Tuckey; Andrzej T Slominski; Duane D Miller; Wei Li
Journal:  J Med Chem       Date:  2016-04-22       Impact factor: 7.446

7.  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

Review 8.  Does Genotype-Phenotype Correlation Exist in Vitamin D-Dependent Rickets Type IA: Report of 13 New Cases and Review of the Literature.

Authors:  Sare Betul Kaygusuz; Ceren Alavanda; Tarik Kirkgoz; Mehmet Eltan; Zehra Yavas Abali; Didem Helvacioglu; Tulay Guran; Pinar Ata; Abdullah Bereket; Serap Turan
Journal:  Calcif Tissue Int       Date:  2021-01-02       Impact factor: 4.333

9.  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

10.  1,25-Dihydroxyvitamin D3 and 20-Hydroxyvitamin D3 Upregulate LAIR-1 and Attenuate Collagen Induced Arthritis.

Authors:  Linda K Myers; Michael Winstead; John D Kee; Jeoungeun J Park; Sicheng Zhang; Wei Li; Ae-Kyung Yi; John M Stuart; Edward F Rosloniec; David D Brand; Robert C Tuckey; Andrzej T Slominski; Arnold E Postlethwaite; Andrew H Kang
Journal:  Int J Mol Sci       Date:  2021-12-12       Impact factor: 5.923
  10 in total

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