Synthesis and CYP24A1-Dependent Metabolism of 23-Fluorinated Vitamin D(3) Analogues

[Image: see text] 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-pyri...

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Autores principales: Kawagoe, Fumihiro, Yasuda, Kaori, Mototani, Sayuri, Sugiyama, Toru, Uesugi, Motonari, Sakaki, Toshiyuki, Kittaka, Atsushi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648426/
https://www.ncbi.nlm.nih.gov/pubmed/31460236
http://dx.doi.org/10.1021/acsomega.9b01500
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author Kawagoe, Fumihiro
Yasuda, Kaori
Mototani, Sayuri
Sugiyama, Toru
Uesugi, Motonari
Sakaki, Toshiyuki
Kittaka, Atsushi
author_facet Kawagoe, Fumihiro
Yasuda, Kaori
Mototani, Sayuri
Sugiyama, Toru
Uesugi, Motonari
Sakaki, Toshiyuki
Kittaka, Atsushi
author_sort Kawagoe, Fumihiro
collection PubMed
description [Image: see text] 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 (23S)-23-fluoro-25-hydroxyvitamin D(3) was more resistant to CYP24A1-dependent metabolism than its 23R isomer.
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spelling pubmed-66484262019-08-27 Synthesis and CYP24A1-Dependent Metabolism of 23-Fluorinated Vitamin D(3) Analogues Kawagoe, Fumihiro Yasuda, Kaori Mototani, Sayuri Sugiyama, Toru Uesugi, Motonari Sakaki, Toshiyuki Kittaka, Atsushi ACS Omega [Image: see text] 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 (23S)-23-fluoro-25-hydroxyvitamin D(3) was more resistant to CYP24A1-dependent metabolism than its 23R isomer. American Chemical Society 2019-06-28 /pmc/articles/PMC6648426/ /pubmed/31460236 http://dx.doi.org/10.1021/acsomega.9b01500 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Kawagoe, Fumihiro
Yasuda, Kaori
Mototani, Sayuri
Sugiyama, Toru
Uesugi, Motonari
Sakaki, Toshiyuki
Kittaka, Atsushi
Synthesis and CYP24A1-Dependent Metabolism of 23-Fluorinated Vitamin D(3) Analogues
title Synthesis and CYP24A1-Dependent Metabolism of 23-Fluorinated Vitamin D(3) Analogues
title_full Synthesis and CYP24A1-Dependent Metabolism of 23-Fluorinated Vitamin D(3) Analogues
title_fullStr Synthesis and CYP24A1-Dependent Metabolism of 23-Fluorinated Vitamin D(3) Analogues
title_full_unstemmed Synthesis and CYP24A1-Dependent Metabolism of 23-Fluorinated Vitamin D(3) Analogues
title_short Synthesis and CYP24A1-Dependent Metabolism of 23-Fluorinated Vitamin D(3) Analogues
title_sort synthesis and cyp24a1-dependent metabolism of 23-fluorinated vitamin d(3) analogues
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648426/
https://www.ncbi.nlm.nih.gov/pubmed/31460236
http://dx.doi.org/10.1021/acsomega.9b01500
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