Design, synthesis, and biological evaluation of biotin-labeled (-)-ternatin, a potent fat-accumulation inhibitor against 3T3-L1 adipocytes.
The design, synthesis, and biological activity of biotin-labeled (-)-ternatin are reported. Chemical modification, that is, biotinylation, was conducted using Click chemistry at the 6-position (NMe-D-ProGly moiety), which was a plausible location selected on the basis of our SAR studies. The compound displayed sufficient fat-accumulation inhibitory effect against 3T3-L1 adipocytes for further bio-organic studies.
Shimokawa
Kenichiro
K
Department of Chemistry, Graduate School of Science, Nagoya University, Chikusa, Nagoya, Japan.
Yamada
Kaoru
K
Ohno
Osamu
O
Oba
Yuichi
Y
Uemura
Daisuke
D
D041721:3T3-L1 Cells; D017667:Adipocytes / Q000187:drug effects* / Q000378:metabolism; D000818:Animals; D019440:Anti-Obesity Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D019921:Biotinylation; D015195:Drug Design; D005223:Fats / Q000378:metabolism; D005419:Flavonoids / Q000737:chemistry* / Q000494:pharmacology; D051379:Mice; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D019440:Anti-Obesity Agents; D005223:Fats; D005419:Flavonoids; C051080:ternatin (flavonoid)