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Is EQ-5D-5L Better Than EQ-5D-3L? A Head-to-Head Comparison of Descriptive Systems and Value Sets from Seven Countries
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      Synthesis and CYP24A1-Dependent Metabolism of 23-Fluorinated Vitamin D 3 Analogues

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          Abstract

          Two novel 23-fluorinated 25-hydroxyvitamin D 3 analogues were synthesized using Inhoffen–Lythgoe diol as a precursor of the CD-ring, efficiently. Introduction of the C23 fluoro group was achieved by the deoxy-fluorination reaction using N, N-diethylaminosulfur trifluoride or 2-pyridinesulfonyl fluoride (PyFluor). Kinetic studies on the CYP24A1-dependent metabolism of these two analogues revealed that (23 S)-23-fluoro-25-hydroxyvitamin D 3 was more resistant to CYP24A1-dependent metabolism than its 23 R isomer.

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          PyFluor: A Low-Cost, Stable, and Selective Deoxyfluorination Reagent.

          Matthew Nielsen, Christian R Ugaz, Wenping Li … (2015)
          We report an inexpensive, thermally stable deoxyfluorination reagent that fluorinates a broad range of alcohols without substantial formation of elimination side products. This combination of selectivity, safety, and economic viability enables deoxyfluorination on preparatory scale. We employ the [(18)F]-labeled reagent in the first example of a no-carrier-added deoxy-radiofluorination.
          Article 0 comments Cited 58 times – based on 0 reviews     Review now
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            Dual metabolic pathway of 25-hydroxyvitamin D3 catalyzed by human CYP24.

            K Komai, K. Yamamoto, S Shiozawa … (2000)
            Human 25-hydroxyvitamin D3 (25(OH)D3) 24-hydroxylase (CYP24) cDNA was expressed in Escherichia coli, and its enzymatic and spectral properties were revealed. The reconstituted system containing the membrane fraction prepared from recombinant E. coli cells, adrenodoxin and adrenodoxin reductase was examined for the metabolism of 25(OH)D3, 1alpha,25(OH)2D3 and their related compounds. Human CYP24 demonstrated a remarkable metabolism consisting of both C-23 and C-24 hydroxylation pathways towards both 25(OH)D3 and 1alpha,25(OH)2D3, whereas rat CYP24 showed almost no C-23 hydroxylation pathway [Sakaki, T. Sawada, N. Nonaka, Y. Ohyama, Y. & Inouye, K. (1999) Eur. J. Biochem. 262, 43-48]. HPLC analysis and mass spectrometric analysis revealed that human CYP24 catalyzed all the steps of the C-23 hydroxylation pathway from 25(OH)D3 via 23S, 25(OH)2D3, 23S,25,26(OH)3D3 and 25(OH)D3-26,23-lactol to 25(OH)D3-26, 23-lactone in addition to the C-24 hydroxylation pathway from 25(OH)D3 via 24R,25(OH)2D3, 24-oxo-25(OH)D3, 24-oxo-23S,25(OH)2D3 to 24,25,26,27-tetranor-23(OH)D3. On 1alpha,25(OH)2D3 metabolism, similar results were observed. These results strongly suggest that the single enzyme human CYP24 is greatly responsible for the metabolism of both 25(OH)D3 and 1alpha,25(OH)2D3. We also succeeded in the coexpression of CYP24, adrenodoxin and NADPH-adrenodoxin reductase in E. coli. Addition of 25(OH)D3 to the recombinant E. coli cell culture yielded most of the metabolites in both the C-23 and C-24 hydroxylation pathways. Thus, the E. coli expression system for human CYP24 appears quite useful in predicting the metabolism of vitamin D analogs used as drugs.
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              Triply convergent synthesis of 1.alpha.,25-dihydroxy-24(R)-fluorocholecalciferol

              Shian Jan Shiuey, John Partridge, Milan Uskokovic (1988)
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                Author and article information

                Journal
                Journal ID (nlm-ta): ACS Omega
                Journal ID (iso-abbrev): ACS Omega
                Journal ID (publisher-id): ao
                Journal ID (coden): acsodf
                Title: ACS Omega
                Publisher: American Chemical Society
                ISSN (Electronic): 2470-1343
                Publication date (Electronic): 28 June 2019
                Publication date Collection: 30 June 2019
                Volume: 4
                Issue: 6
                Pages: 11332-11337
                Affiliations
                [† ]Faculty of Pharmaceutical Sciences, Teikyo University , 2-11-1 Kaga, Itabashi, Tokyo 173-8605, Japan
                [‡ ]AMED-CREST, The Japan Agency for Medical Research and Development (AMED) , Otemachi, Chiyoda-ku, Tokyo 100-0004, Japan
                [§ ]Faculty of Engineering, Toyama Prefectural University , Imizu, Toyama 939-0398, Japan
                [∥ ]Institute for Chemical Research, Kyoto University , Gokasho, Uji, Kyoto 611-0011, Japan
                Author notes
                [* ]E-mail: akittaka@ 123456pharm.teikyo-u.ac.jp . Tel.: +81-3-3964-8109. Fax: +81-3-3964-8117.
                Article
                DOI: 10.1021/acsomega.9b01500
                PMC ID: 6648426
                SO-VID: f8237f37-02c2-49a0-9817-72011f3fe05d
                Copyright © Copyright © 2019 American Chemical Society
                License:

                This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.

                History
                Date received : 22 May 2019
                Date accepted : 18 June 2019
                Categories
                Subject: Article
                Custom metadata
                document-id-old-9 ao9b01500
                document-id-new-14 ao-2019-01500b
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