2. Academic Validation
  3. Synthesis of Norgestomet and its 17β-isomer and evaluation of their agonistic activities against progesterone receptor

Synthesis of Norgestomet and its 17β-isomer and evaluation of their agonistic activities against progesterone receptor

  • Bioorg Med Chem. 2021 Nov 1:49:116425. doi: 10.1016/j.bmc.2021.116425.
Takashi Kurohara 1,  Takahito Ito 1,  Genichiro Tsuji 2,  Takashi Misawa 3,  Hidetomo Yokoo 4,  Yuta Yanase 5,  Takuji Shoda 1,  Takatoshi Sakai 1,  Junko Hosoe 1,  Nahoko Uchiyama 1,  Hiroshi Akiyama 6,  Yosuke Demizu 5
Affiliations

Affiliations

  • 1 National Institute of Health Sciences, 3-25-26, Tonomachi, Kawasaki, Kanagawa 210-9501, Japan.
  • 2 National Institute of Health Sciences, 3-25-26, Tonomachi, Kawasaki, Kanagawa 210-9501, Japan. Electronic address: gtsuji@nihs.go.jp.
  • 3 National Institute of Health Sciences, 3-25-26, Tonomachi, Kawasaki, Kanagawa 210-9501, Japan. Electronic address: misawa@nihs.go.jp.
  • 4 National Institute of Health Sciences, 3-25-26, Tonomachi, Kawasaki, Kanagawa 210-9501, Japan; Graduate School of Medicine, Kyoto Prefectural University of Medicine, 465, Kajii-cho, Sakyo-ku, Kyoto-shi, Kyoto 606-0823, Japan.
  • 5 National Institute of Health Sciences, 3-25-26, Tonomachi, Kawasaki, Kanagawa 210-9501, Japan; Graduate School of Medical Life Science, Yokohama City University, 1-7-29, Yokohama, Kanagawa 230-0045, Japan.
  • 6 National Institute of Health Sciences, 3-25-26, Tonomachi, Kawasaki, Kanagawa 210-9501, Japan; School of Pharmaceutical Sciences, Hoshi University, 2-4-41, Ebara, Shinagawa-ku, Tokyo 142-8501, Japan.
PMID: 34607200 DOI: 10.1016/j.bmc.2021.116425
Abstract

Norgestomet is a synthetic progesterone derivative applied in veterinary medicine to control estrus and ovulation in cattle. Norgestomet has been widely used in the livestock industry to promote the synchronization of estrus in cattle and increase pregnancy rates. However, highly reproducible synthetic methods for Norgestomet have been rarely reported. Here, we described a method for the synthesis of Norgestomet and performed quantitative NMR analysis to determine the purity of the products. Moreover, the agonistic activity of the synthesized compounds against progesterone receptors (PRs) was evaluated using an Alkaline Phosphatase assay. We synthesized Norgestomet with 97.9% purity that exhibited agonistic activity against PR with EC50 values of 4.5 nM. We also synthesized the 17β-isomer of Norgestomet with 92.7% purity that did not exhibit any PR agonistic activity. The proposed synthetic route of Norgestomet can facilitate the assessment of residual Norgestomet in foods.

Keywords

Agonist; Hormone-like activity; Norgestomet; Progesterone receptor; Residual drugs in food.

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