Literature DB >> 26367019

Chemical Synthesis and Biological Activities of 20S,24S/R-Dihydroxyvitamin D3 Epimers and Their 1α-Hydroxyl Derivatives.

Zongtao Lin, Srinivasa Reddy Marepally, Dejian Ma, Linda K Myers, Arnold E Postlethwaite1, Robert C Tuckey2, Chloe Y S Cheng2, Tae-Kang Kim3, Junming Yue, Andrzej T Slominski3,4, Duane D Miller, Wei Li.   

Abstract

Bioactive vitamin D3 metabolites 20S,24S-dihydroxyvitamin D3 [20S,24S(OH)2D3] and 20S,24R-dihydroxyvitamin D3 [20S,24R(OH)2D3] were chemically synthesized and confirmed to be identical to their enzymatically generated counterparts. The absolute configurations at C24 and its influence on the kinetics of 1α-hydroxylation by CYP27B1 were determined. Their corresponding 1α-hydroxyl derivatives were subsequently produced. Biological comparisons of these products showed different properties with respect to vitamin D3 receptor activation, anti-inflammatory activity, and antiproliferative activity, with 1α,20S,24R(OH)2D3 being the most potent compound.

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Year:  2015        PMID： 26367019      PMCID： PMC4613797          DOI： 10.1021/acs.jmedchem.5b00881

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


  33 in total

1.  CYP2R1 is a major, but not exclusive, contributor to 25-hydroxyvitamin D production in vivo.

Authors:  Jinge G Zhu; Justin T Ochalek; Martin Kaufmann; Glenville Jones; Hector F Deluca
Journal:  Proc Natl Acad Sci U S A       Date:  2013-09-09       Impact factor: 11.205

Review 2.  25-Hydroxyvitamin D-24-hydroxylase (CYP24A1): its important role in the degradation of vitamin D.

Authors:  Glenville Jones; David E Prosser; Martin Kaufmann
Journal:  Arch Biochem Biophys       Date:  2011-11-12       Impact factor: 4.013

3.  20S-hydroxyvitamin D3, noncalcemic product of CYP11A1 action on vitamin D3, exhibits potent antifibrogenic activity in vivo.

Authors:  Andrzej Slominski; Zorica Janjetovic; Robert C Tuckey; Minh N Nguyen; Keka G Bhattacharya; Jin Wang; Wei Li; Yan Jiao; Weikuan Gu; Monica Brown; Arnold E Postlethwaite
Journal:  J Clin Endocrinol Metab       Date:  2013-01-07       Impact factor: 5.958

4.  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

5.  The noncalcemic vitamin D analogues EB1089 and 22-oxacalcitriol interact with the vitamin D receptor and suppress parathyroid hormone-related peptide gene expression.

Authors:  M Falzon
Journal:  Mol Cell Endocrinol       Date:  1997-03-14       Impact factor: 4.102

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

Authors:  Jianjun Chen; 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
Journal:  Anticancer Res       Date:  2014-05       Impact factor: 2.480

7.  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

8.  A pathway for the metabolism of vitamin D3: unique hydroxylated metabolites formed during catalysis with cytochrome P450scc (CYP11A1).

Authors:  O Guryev; R A Carvalho; S Usanov; A Gilep; R W Estabrook
Journal:  Proc Natl Acad Sci U S A       Date:  2003-12-01       Impact factor: 11.205

9.  Rat CYP24A1 acts on 20-hydroxyvitamin D(3) producing hydroxylated products with increased biological activity.

Authors:  Elaine W Tieu; Edith K Y Tang; Jianjun Chen; Wei Li; Minh N Nguyen; Zorica Janjetovic; Andrzej Slominski; Robert C Tuckey
Journal:  Biochem Pharmacol       Date:  2012-10-05       Impact factor: 5.858

10.  RORα and ROR γ are expressed in human skin and serve as receptors for endogenously produced noncalcemic 20-hydroxy- and 20,23-dihydroxyvitamin D.

Authors:  Andrzej T Slominski; Tae-Kang Kim; Yukimasa Takeda; Zorica Janjetovic; Anna A Brozyna; Cezary Skobowiat; Jin Wang; Arnold Postlethwaite; Wei Li; Robert C Tuckey; Anton M Jetten
Journal:  FASEB J       Date:  2014-03-25       Impact factor: 5.191
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  15 in total

1.  Properties of purified CYP2R1 in a reconstituted membrane environment and its 25-hydroxylation of 20-hydroxyvitamin D3.

Authors:  Chloe Y S Cheng; Tae-Kang Kim; Saowanee Jeayeng; Andrzej T Slominski; Robert C Tuckey
Journal:  J Steroid Biochem Mol Biol       Date:  2017-07-14       Impact factor: 4.292

Review 2.  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 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

5.  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 6.  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 7.  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 8.  Reactions of Allylmagnesium Reagents with Carbonyl Compounds and Compounds with C═N Double Bonds: Their Diastereoselectivities Generally Cannot Be Analyzed Using the Felkin-Anh and Chelation-Control Models.

Authors:  Nicole D Bartolo; Jacquelyne A Read; Elizabeth M Valentín; K A Woerpel
Journal:  Chem Rev       Date:  2020-01-06       Impact factor: 60.622

9.  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

10.  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
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