Synthesis and photoreactivity of caged blockers for glutamate transporters.
L-TBOA (L-threo-beta-benzyloxyaspartate) is, so far, the most potent non-transportable blocker for glutamate transporters. We synthesized alpha-CMCM-L-TBOA (1a) possessing [7-(carboxymethoxy)coumarin-4-yl]methyl ester as a caging group. alpha-CMCM-L-TBOA (1a) is biologically inactive until UV irradiation and the photolysis of 1a immediately released L-TBOA to show glutamate uptake inhibition. The photoreactivity of the coumarin-type caging group was superior to that of the o-nitrobenzyl-type caging group.
Takaoka
Kiyo
K
Suntory Institute for Bioorganic Research, 1-1-1 Wakayamadai, Shimamoto, Osaka 618-8503, Japan.
Tatsu
Yoshiro
Y
Yumoto
Noboru
N
Nakajima
Terumi
T
Shimamoto
Keiko
K
D027322:Amino Acid Transport System X-AG / Q000037:antagonists & inhibitors*; D000818:Animals; D001224:Aspartic Acid / Q000737:chemistry* / Q000494:pharmacology*; D001692:Biological Transport / Q000187:drug effects; D002460:Cell Line; D003374:Coumarins / Q000737:chemistry / Q000494:pharmacology; D004285:Dogs; D004355:Drug Stability; D018698:Glutamic Acid / Q000378:metabolism; D010782:Photolysis; D013056:Spectrophotometry, Ultraviolet
D027322:Amino Acid Transport System X-AG; D003374:Coumarins; C120673:benzyloxyaspartate; D001224:Aspartic Acid; D018698:Glutamic Acid