Synthesis and photoreactivity of caged blockers for glutamate transporters

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 5, 2003, Pages 965-970

  Takaoka, Kiyo ^a,b   Tatsu, Yoshiro ^c   Yumoto, Noboru ^c   Nakajima, Terumi ^a   Shimamoto, Keiko ^a  

^a SUNTORY INSTITUTE FOR BIOORGANIC RESEARCH   (Japan)

^b JAPAN SOCIETY FOR THE PROMOTION OF SCIENCE   (Japan)

^c NATIONAL INSTITUTE OF ADVANCED INDUSTRIAL SCIENCE AND TECHNOLOGY AIST   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA [7 (CARBOXYMETHOXY)COUMARIN 4 YL]METHYL ESTER THREO BETA BENZYLOXYASPARTATE; BLOCKING AGENT; GLUTAMATE TRANSPORTER; UNCLASSIFIED DRUG;

AMINO ACID TRANSPORT; ARTICLE; DRUG ACTIVITY; DRUG SYNTHESIS; PHOTOLYSIS; PHOTOREACTIVITY; ULTRAVIOLET IRRADIATION;

EID: 0037430546     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(02)01042-9     Document Type: Article

References (33)

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21. em (1 μM): 320 nm/407 nm.
22. 26 -65.7° (c 0.52, DMSO).
23. 2O/TFA=32:68:0.1. Flow rate; 1 mL/min; Detection; 320 nm and 254 nm. As an internal standard for the quantitative analyses, 10 μM of 3′,4′-dimethoxyacetophenone (Rt: 11.1 min) for 1a, 3a and 3b or 40 μM of 2-(3,4-dimethoxyphenyl)ethanol (Rt: 6.7 min) for 2a was included in the sample solution.
24. 2, pH 7.4). A solution (300 μL) of the caged compounds was placed in quartz cuvettes with a path length of 1 mm in a dark box and irradiated at room temperature for 1-240 min.
25. em (1 μM): 320 nm/402 nm.
26. 50 values of L-glutamate for EAAT2 were 63±3.8 and 41±1.9 μM, respectively.
27. MCM-OH (2b) was decomposed 20% for 30 min and 50% for 120 min with UV lamp irradiation (365 nm).
28. A sample [100 μM in PBS(+) solution, 100 μL] placed in a quartz cuvette (path length 1 mm) was irradiated with laser pulse.
29. The chemical yields of the photolysis by repeated irradiation (8 shots) were 38±1.6% (1a), 34±5.6% (1b), and 21±2.9% (3a), respectively.
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33. For the purification of the caged compounds, column of SP-120-5-ODS-AP (Daiso Co. Ltd. Japan), 250 mm × 20 mm I.D. was used and peaks were monitored at only 254 nm to avoid decomposition. Because 1a was hydrolyzed during the lyophilization after HPLC purification, we could not remove a small contamination of L-TBOA from 1a. It may contribute to the activity at the higher concentrations.