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

Fumihiro Kawagoe | Zendy; Kaori Yasuda | Zendy; Sayuri Mototani | Zendy; Toru Sugiyama | Zendy; Motonari Uesugi | Zendy; Toshiyuki Sakaki | Zendy; Atsushi Kittaka | Zendy

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

Author(s) -

Fumihiro Kawagoe,

Kaori Yasuda,

Sayuri Mototani,

Toru Sugiyama,

Motonari Uesugi,

Toshiyuki Sakaki,

Atsushi Kittaka

Publication year - 2019

Publication title -

acs omega

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.779

H-Index - 40

ISSN - 2470-1343

DOI - 10.1021/acsomega.9b01500

Subject(s) - chemistry , cyp24a1 , metabolism , vitamin d and neurology , fluoride , stereochemistry , calcitriol receptor , biochemistry , medicine , inorganic chemistry , receptor

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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