title: Synthesis and Biological Evaluation of Vitamin D3 Metabolite 20S,23S-Dihydroxyvitamin D3 and Its 23R Epimer.
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.
authors.affiliation: Department of Pharmaceutical Sciences, University of Tennessee Health Science Center , 881 Madison Avenue, Room 561, Memphis, Tennessee 38163, United States.
authors.forename: Zongtao
authors.initials: Z
authors.lastname: Lin
authors.affiliation: Department of Pharmaceutical Sciences, University of Tennessee Health Science Center , 881 Madison Avenue, Room 561, Memphis, Tennessee 38163, United States.
authors.forename: Srinivasa R
authors.initials: SR
authors.lastname: Marepally
authors.affiliation: Department of Pharmaceutical Sciences, University of Tennessee Health Science Center , 881 Madison Avenue, Room 561, Memphis, Tennessee 38163, United States.
authors.forename: Dejian
authors.initials: D
authors.lastname: Ma
authors.affiliation: Department of Dermatology, University of Alabama at Birmingham , Birmingham, Alabama 35294, United States.
authors.forename: Tae-Kang
authors.initials: TK
authors.lastname: Kim
authors.affiliation: Department of Dermatology, University of Alabama at Birmingham , Birmingham, Alabama 35294, United States.
authors.forename: Allen Sw
authors.initials: AS
authors.lastname: Oak
authors.affiliation: Department of Medicine, University of Tennessee Health Science Center , Memphis, Tennessee 38163, United States.
authors.forename: Linda K
authors.initials: LK
authors.lastname: Myers
authors.affiliation: School of Chemistry and Biochemistry, University of Western Australia , Crawley, Western Australia 6009, Australia.
authors.forename: Robert C
authors.initials: RC
authors.lastname: Tuckey
authors.affiliation: Department of Dermatology, University of Alabama at Birmingham , Birmingham, Alabama 35294, United States.|VA Medical Center at Birmingham , Birmingham, Alabama 35294, United States.
authors.forename: Andrzej T
authors.initials: AT
authors.lastname: Slominski
authors.affiliation: Department of Pharmaceutical Sciences, University of Tennessee Health Science Center , 881 Madison Avenue, Room 561, Memphis, Tennessee 38163, United States.
authors.forename: Duane D
authors.initials: DD
authors.lastname: Miller
authors.affiliation: Department of Pharmaceutical Sciences, University of Tennessee Health Science Center , 881 Madison Avenue, Room 561, Memphis, Tennessee 38163, United States.
authors.forename: Wei
authors.initials: W
authors.lastname: Li
mesh_terms: D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D000970:Antineoplastic Agents / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D002762:Cholecalciferol / Q000031:analogs & derivatives / Q000737:chemistry / Q000378:metabolism*; D004100:Dihydroxycholecalciferols / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008958:Models, Molecular; D015394:Molecular Structure; D011971:Receptors, Immunologic / Q000037:antagonists & inhibitors* / Q000276:immunology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
chemical_list: C547379:20,23-dihydroxyvitamin D3; D000894:Anti-Inflammatory Agents, Non-Steroidal; D000970:Antineoplastic Agents; D004100:Dihydroxycholecalciferols; D011971:Receptors, Immunologic; C108073:leukocyte-associated immunoglobulin-like receptor 1; D002762:Cholecalciferol