title: Design, synthesis, and biological action of 20R-hydroxyvitamin D3.
abstract: The non-naturally occurring 20R epimer of 20-hydroxyvitamin D3 is synthesized based on chemical design and hypothesis. The 20R isomer is separated by semipreparative HPLC, and its structure is characterized. A comparison of 20R isomer to its 20S counterpart in biological evaluation demonstrates that they have different behaviors in antiproliferative and metabolic studies.
authors.affiliation: Department of Pharmaceutical Sciences, University of Tennessee Health Science Center, Memphis, Tennessee 38163, USA.
authors.forename: Yan
authors.initials: Y
authors.lastname: Lu
authors.forename: Jianjun
authors.initials: J
authors.lastname: Chen
authors.forename: Zorica
authors.initials: Z
authors.lastname: Janjetovic
authors.forename: Phillip
authors.initials: P
authors.lastname: Michaels
authors.forename: Edith K Y
authors.initials: EK
authors.lastname: Tang
authors.forename: Jin
authors.initials: J
authors.lastname: Wang
authors.forename: Robert C
authors.initials: RC
authors.lastname: Tuckey
authors.forename: Andrzej T
authors.initials: AT
authors.lastname: Slominski
authors.forename: Wei
authors.initials: W
authors.lastname: Li
authors.forename: Duane D
authors.initials: DD
authors.lastname: Miller
mesh_terms: D015090:25-Hydroxyvitamin D3 1-alpha-Hydroxylase / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002112:Calcifediol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002454:Cell Differentiation / Q000187:drug effects; D049109:Cell Proliferation / Q000187:drug effects; D002478:Cells, Cultured; D002786:Cholesterol Side-Chain Cleavage Enzyme / Q000737:chemistry; D015195:Drug Design; D006801:Humans; D015603:Keratinocytes / Q000166:cytology / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: C480634:20-hydroxyvitamin D3; D000970:Antineoplastic Agents; D015090:25-Hydroxyvitamin D3 1-alpha-Hydroxylase; D002786:Cholesterol Side-Chain Cleavage Enzyme; D002112:Calcifediol