Synthesis of carbamate-type caged derivatives of a novel glutamate transporter blocker

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 13, 2004, Pages 3687-3694

  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

Caged compound; Carbamate; Excitatory amino acid; Glutamate transporter blocker; Photolysis

Indexed keywords

3 [3 [4 (TRIFLUOROMETHYL)BENZOYLAMINO]BENZYLOXY]ASPARTATE; 3 BENZYLOXY N [[6,7 BIS(CARBOXYMETHOXY)COUMARIN 4 YLMETHOXY]CARBONYL]ASPARTATE; CARBAMIC ACID; GLUTAMATE TRANSPORTER; N [6,7 BIS(CARBOXYMETHOXY)COUMARIN 4 YLMETHOXY]CARBONYL 3 [3 [4 (TRIFLUOROMETHYL)BENZOYL]AMINOBENZYLOXY]ASPARTATE; PROTEIN INHIBITOR; THREO BETA BENZYLOXYASPARTATE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; PHOTOLYSIS; PHOTOREACTIVITY;

AMINATION; AMINO ACID TRANSPORT SYSTEM X-AG; ANIMALS; ASPARTIC ACID; CARBAMATES; CELL LINE; DOGS; FLUORINE; GLUTAMIC ACID; METHYLATION; MOLECULAR STRUCTURE; SPECTRUM ANALYSIS;

STAPHYLOCOCCUS PHAGE 3A;

EID: 2942601813     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.04.011     Document Type: Article

References (32)

1. Marriott G. Methods in Enzymology, 291, Caged Compounds. 1998;Academic, San Diego
2. Shigeri Y., Tatsu Y., Yumoto N. Pharmacol. Therapeu. 91:2001;85-92
3. Hagen V., Frings S., Bending J., Lorenz D., Wiesner B., Kaupp U.B. Angew. Chem., Int. Ed. 41:2002;3625-3628
4. Eckardt T., Hagen V., Schade B., Schmidt R., Schweitzer C., Bendig J. J. Org. Chem. 67:2002;703-710
5. Hagen V., Bendig J., Frings S., Eckardt T., Helm S., Reuter D., Kaupp U.B. Angew. Chem., Int. Ed. 40:2001;1045-1048
6. Hagen V., Bendig J., Frings S., Wiesner B., Schade B., Helm S., Lorenz D., Kaupp U.B. J. Photochem. Photobiol. B: Biol. 53:1999;91-102
7. Sarker A.M., Kaneko Y., Neckers D.C. J. Photochem. Photobiol. A: Chem. 117:1998;67-74
8. Furuta T., Torigai H., Sugimoto M., Iwamura M. J. Org. Chem. 60:1995;3953-3956
9. Furuta T., Wang S.S.-H., Dantzker J.L., Dore T.M., Bybee W.J., Callaway E.M., Denk W., Tsien R.Y. Proc. Natl. Acad. Sci. U.S.A. 96:1999;1193-1200
10. Furuta T., Hirayama Y., Sugimoto M., Iwamura L. Org. Lett. 3:2001;1809-1812
11. Fedoryak O.D., Dore T.M. Org. Lett. 4:2002;3419-3422
12. For review, Danbolt N.C. Prog. Neurobiol. 65:2001;1-105
13. Amara S.G., Fontana A.C.K. Neurochem. Int. 41:2002;313-318
14. Wieboldt R., Gee K.R., Niu L., Ramesh D., Carpenter B.K., Hess G.P. Proc. Natl. Acad. Sci. U.S.A. 91:1994;8752
15. Papageorgiou G., Ogden D.C., Barth A., Corrie J.E.T. J. Am. Chem. Soc. 121:1999;6503-6504
16. Matsuzaki M., Ellis-Davies G.C.R., Nemoto T., Miyashita Y., Iino M., Kasai H. Nat. Neurosci. 4:2001;1086-1092
17. Shimamoto K., Lebrun B., Yasuda-Kamatani Y., Sakaitani M., Shigeri Y., Yumoto N., Nakajima T. Mol. Pharmacol. 53:1998;195-203
18. Shimamoto K., Shigeri Y., Yasuda-Kamatani Y., Lebrun B., Yumoto N., Nakajima T. Bioorg. Med. Chem. Lett. 10:2000;2407-2410
19. Shigeri Y., Shimamoto K., Yasuda-Kamatani Y., Seal R.P., Yumoto N., Nakajima T., Amara S.G. J. Neurochem. 79:2001;297-302
20. Takaoka K., Tatsu Y., Yumoto N., Nakajima T., Shimamoto K. Bioorg. Med. Chem. Lett. 13:2003;965-970
21. Shimamoto K., Sakai R., Takaoka K., Yumoto N., Nakajima T., Amara S.G., Shigeri Y. Mol. Pharmacol. 65:2004;1008-1015
22. Rossi F.M., Margulis M., Tang C.-M., Kao J.P.Y. J. Bio. Chem. 272:1997;32933-32939
23. Kim J.-M., Chang T.-E., Park R.H., Kim D.K., Han D.K., Ahn K.-D. Chem. Lett. 2000;712-713
24. Walker J.W., Reld G.P., McCray J.A., Trenthan D.R. J. Am. Chem. Soc. 110:1988;7170-7177
25. The same reaction using 7b prepared from triphosgen and 6a yielded 12a in only 8%
26. Even if L-TFB-TBOA was irradiated for 60 min in the presence or in the absence of BCMCM-OH, the amount monitored by HPLC did not change, indicating that L-TFB-TBOA does not decompose by UV-irradiation
27. Lu M., Fedoryak O.D., Moister B.R., Dore T.M. Org. Lett. 5:2003;2119-2122
28. The concentration of L-TFB-TBOA in the photolysis samples estimated from the uptake assay was well consistent with that determined from the HPLC analysis. We also confirmed that neither BCMCM-OH nor CMCM-OH affected the glutamate uptake
29. 9 The latter step would be rate-limiting for release of free amino acid (L-TBOA or L-TFB-TBOA) if the photocleavage process of the coumarin-moiety is fast. To estimate the kinetics of 3b and 4, electrophysiological measurements would be needed
30. The chemical yields of the photolysis by repeated irradiation (8 shots) were 5.5 ± 1.5% (3a), 43 ± 1.0% (3b), and 42 ± 1.9% (4), respectively
31. MaCray J.A., Trentham D.R. Annu. Rev. Biophys. Biophys. Chem. 18:1989;239-270
32. 50 would vary according to the condition of using cells