TY - JOUR
T1 - Optically active iodohelicene derivatives exhibit histamine N-methyl transferase inhibitory activity
AU - Ichinose, Wataru
AU - Sawato, Tsukasa
AU - Kitano, Haruna
AU - Shinozaki, Yasuhiro
AU - Arisawa, Mieko
AU - Saito, Nozomi
AU - Yoshikawa, Takeo
AU - Yamaguchi, Masahiko
N1 - Funding Information:
Acknowledgements This work was financially supported by Grants-in-Aid for Scientific Research (nos. 17H03050 and 17H08203) from the Japan Society for the Promotion of Science (JSPS), and Platform Project for Supporting Drug Discovery and Life Science Research from AMED under Grant Number JP18am0101100. TS thanks JSPS for a Research Fellowship for Young Scientists (no. 17J02496).
Publisher Copyright:
© 2018, The Author(s) under exclusive licence to the Japan Antibiotics Research Association.
PY - 2019/6/1
Y1 - 2019/6/1
N2 - Optically active helicene derivatives inhibit the activity on histamine N-methyl transferase (HNMT). Specifically, methyl (P)-1,12-dimethylbenzo[c]phenanthrene-8-carboxylate with 6-iodo and 5-trifluoromethanesulfonyloxy groups inhibits HNMT activity on the μM order of IC 50 . Chirality is important, and (M)-isomers exhibits substantially reduced activity. The 6-iodo group is also essential, which suggests the involvement of halogen bonds in protein binding. Substituents on the sulfonate moiety also affect the inhibitory activity.
AB - Optically active helicene derivatives inhibit the activity on histamine N-methyl transferase (HNMT). Specifically, methyl (P)-1,12-dimethylbenzo[c]phenanthrene-8-carboxylate with 6-iodo and 5-trifluoromethanesulfonyloxy groups inhibits HNMT activity on the μM order of IC 50 . Chirality is important, and (M)-isomers exhibits substantially reduced activity. The 6-iodo group is also essential, which suggests the involvement of halogen bonds in protein binding. Substituents on the sulfonate moiety also affect the inhibitory activity.
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U2 - 10.1038/s41429-018-0118-z
DO - 10.1038/s41429-018-0118-z
M3 - Article
C2 - 30459457
AN - SCOPUS:85057004279
SN - 0021-8820
VL - 72
SP - 476
EP - 481
JO - Journal of Antibiotics
JF - Journal of Antibiotics
IS - 6
ER -