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Synthesis and CYP24A1-Dependent Metabolism of 23-Fluorinated Vitamin D₃ Analogues.

ABSTRACT: Two novel 23-fluorinated 25-hydroxyvitamin D₃ 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 D₃ was more resistant to CYP24A1-dependent metabolism than its 23R isomer.

SUBMITTER: Kawagoe F

PROVIDER: S-EPMC6648426 | biostudies-literature | 2019 Jun

REPOSITORIES: biostudies-literature

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Synthesis and CYP24A1-Dependent Metabolism of 23-Fluorinated Vitamin D3 Analogues.

Kawagoe Fumihiro F Yasuda Kaori K Mototani Sayuri S Sugiyama Toru T Uesugi Motonari M Sakaki Toshiyuki T Kittaka Atsushi A

ACS omega 20190628 6

Two novel 23-fluorinated 25-hydroxyvitamin D3 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 D3 was more resistant ...[more]

PMID: 31460236

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