Synthesis of biotinylated photoaffinity probes based on arylsulfonamide gamma-secretase inhibitors

Haruhiko Fuwa; Kenichi Hiromoto; Yasuko Takahashi; Satoshi Yokoshima; Toshiyuki Kan; Tohru Fukuyama; Takeshi Iwatsubo; Taisuke Tomita; Hideaki Natsugari

doi:10.1016/j.bmcl.2006.05.091

Synthesis of biotinylated photoaffinity probes based on arylsulfonamide gamma-secretase inhibitors

Bioorg Med Chem Lett. 2006 Aug 15;16(16):4184-9. doi: 10.1016/j.bmcl.2006.05.091.

Authors

Haruhiko Fuwa¹, Kenichi Hiromoto, Yasuko Takahashi, Satoshi Yokoshima, Toshiyuki Kan, Tohru Fukuyama, Takeshi Iwatsubo, Taisuke Tomita, Hideaki Natsugari

Affiliation

¹ Graduate School of Pharmaceutical Sciences, University of Tokyo, Bunkyo-ku, Japan. hfuwa@bios.tohoku.ac.jp

PMID: 16766183
DOI: 10.1016/j.bmcl.2006.05.091

Abstract

Synthesis and biological evaluation of an arylsulfonamide class of gamma-secretase inhibitors are described. Design, synthesis, and biological evaluation of multifunctional molecular probes harboring a benzophenone photophore as a cross-linking group and a biotin tag are also reported.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amyloid Precursor Protein Secretases
Arylsulfonates / chemistry*
Biotinylation*
Butyrates / pharmacology
Chemistry, Pharmaceutical / methods*
Cross-Linking Reagents / pharmacology
Drug Design
Endopeptidases / chemistry*
Enzyme Inhibitors / pharmacology*
Hydrocarbons, Halogenated / pharmacology
Inhibitory Concentration 50
Light
Models, Chemical
Photoaffinity Labels / chemical synthesis
Photoaffinity Labels / pharmacology*

Substances

4-(2-((1R)-1-(((4-chlorophenyl)sulfonyl)-2,5-difluoroanilino)ethyl)-5-fluorophenyl)butanoic acid
Arylsulfonates
Butyrates
Cross-Linking Reagents
Enzyme Inhibitors
Hydrocarbons, Halogenated
Photoaffinity Labels
Amyloid Precursor Protein Secretases
Endopeptidases