Design, synthesis and pharmacological characterization of coumarin-based fluorescent analogs of excitatory amino acid transporter subtype 1 selective inhibitors, UCPH-101 and UCPH-102

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 23, 2012, Pages 6831-6839

  Huynh, Tri H V ^a   Abrahamsen, Bjarke ^a   Madsen, Karsten K ^a   Gonzalez Franquesa, Alba ^a   Jensen, Anders A ^a   Bunch, Lennart ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

Author keywords

Central nervous system; Coumarin based fluorescent analogs; Excitatory amino acid transporters; Structure activity relationship

Indexed keywords

2 AMINO 4 [4 (7 METHOXY 4 METHYL 2 OXO 2H CHROMEN 3 YL)PHENYL] 5 OXO 7 PHENYL 5,6,7,8 TETRAHYDRO 4H CHROMENE 3 CARBONITRILE; 2' AMINO 7 (DIETHYLAMINO) 4' METHYL 2,5' DIOXO 5',6',7',8' TETRAHYDRO 2H,4'H,4,7 BICHROMENE 3' CARBONITRILE; 2' AMINO 7 (DIETHYLAMINO) 7' (NAPHTHALEN 1 YL) 2,5' DIOXO 5',6',7',8' TETRAHYDRO 2H,4'H,4,4 BICHROMENE 3' CARBONITRILE; 2' AMINO 7 METHOXY 2,5' DIOXO 7' PHENYL 5',6',7',8' TETRAHYDRO 2H,4'H,4,4 BICHROMENE 3' CARBONITRILE; 2' AMINO 7 METHOXY 4' METHYL 2,5' DIOXO 5',6',7',8' TETRAHYDRO 2H,4'H,4,7 BICHROMENE 3' CARBONITRILE; 3 BROMO 7 (DIETHYLAMINO) 4 METHYL 2H CHROMEN 2 ONE; 3 BROMO 7 METHOXY 4 METHYL 2H CHROMEN 2 ONE; 4 (7 METHOXY 4 METHYL 2 OXO 2H CHROMENE 3 YL)BENZALDEHYDE; 4 [7 (DIETHYLAMINO) 4 METHYL 2 OXO 2H CHROMENE 3 YL]BENZALDEHYDE; 5 (7 METHOXY 2 OXO 2H CHROMENE 4 YL)CYCLOHEXANE 1,3 DIONE; 5 [7 (DIETHYLAMINO) 2 OXO 2H CHROMENE 4 YL]CYCLOHEXANE 1,3 DIONE; 5,6,7,8 TETRAHYDRO 4H CHROMENE 3 CARBONITRILE; 7 (DIETHYLAMINO) 2 OXO 2H CHROMENE 4 CARBALDEHYDE; 7 (DIETHYLAMINO) 4 (3 OXOBUT 1 ENYL) 2H CHROMENE 2 ONE; 7 METHOXY 2 OXO 2H CHROMENE 4 CARBALDEHYDE; 7 METHOXY 4 (3 OXOBUT 1 ENYL) 2H CHROMENE 2 ONE; AMINO ACID RECEPTOR STIMULATING AGENT; COUMARIN DERIVATIVE; EXCITATORY AMINO ACID TRANSPORTER 1; EXCITATORY AMINO ACID TRANSPORTER 2; EXCITATORY AMINO ACID TRANSPORTER 3; UCPH 101; UCPH 102; UNCLASSIFIED DRUG;

ARTICLE; CONCENTRATION (PARAMETERS); CONFOCAL LASER MICROSCOPY; DRUG DESIGN; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; FLUORESCENCE ANALYSIS; HUMAN; HUMAN CELL; PH; PROTEIN EXPRESSION; RECEPTOR BINDING; RECEPTOR DOWN REGULATION; STRUCTURE ACTIVITY RELATION;

BENZOPYRANS; COUMARINS; DRUG DESIGN; EXCITATORY AMINO ACID TRANSPORTER 1; FLUORESCENT DYES; HEK293 CELLS; HUMANS; INHIBITORY CONCENTRATION 50; STRUCTURE-ACTIVITY RELATIONSHIP;

MAMMALIA; RODENTIA;

EID: 84869080989     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.09.049     Document Type: Article

References (34)

1. P.M. Beart, and R.D. O'shea Br. J. Pharmacol. 150 2007 5
2. A.C. Foster, and J.A. Kemp Curr. Opin. Pharmacol. 6 2006 7
3. L. Bunch, M.N. Erichsen, and A.A. Jensen Expert Opin. Ther. Targets 13 2009 719
4. S.G. Lee, Z.Z. Su, L. Emdad, P. Gupta, D. Sarkar, A. Borjabad, D.J. Volsky, and P.B. Fisher J. Biol. Chem. 283 2008 13116
5. A.M. Estrada-Sanchez, J. Mejia-Toiber, and L. Massieu Arch. Med. Res. 39 2008 265
6. J.C. Corona, L.B. Tovar-y-Romo, and R. Tapia Expert Opin. Ther. Targets 11 2007 1415
7. K.W. Muir Curr. Opin. Pharmacol. 6 2006 53
8. A.L. Sheldon, and M.B. Robinson Neurochem. Int. 51 2007 333
9. G.M. Alexander, and D.W. Godwin Epilepsy Res. 71 2006 1
10. G. Sanacora, G. Treccani, and M. Popoli Neuropharmacology 2011 1
11. R.M. Karlsson, K. Tanaka, L.M. Saksida, T.J. Bussey, M. Heilig, and A. Holmes Neuropsychopharmacology 34 2009 1578
12. R.M. Karlsson, K. Tanaka, M. Heilig, and A. Holmes Biol. Psychiatry 64 2008 810
13. L.D. Lavis, and R.T. Raines ACS Chem. Biol. 3 2008 142
14. G.A. Reynolds, and K.H. Drexhage Opt. Commun. 13 1975 222
15. J.F. Fisher, and L.A. Trama J. Agric Food Chem. 27 1979 1334
16. W.C. Sun, K.R. Gee, and R.P. Haugland Bioorg. Med. Chem. Lett. 8 1998 3107
17. G. Jones, W.R. Jackson, and C. Choi J. Phys. Chem. 89 1985 294
18. H. Khalfan, R. Abuknesha, M. Randweaver, R.G. Price, and D.J. Robinson J. Histochem. 18 1986 497
19. L. Fan, R.W. Lewis, G.P. Hess, and B. Ganem Bioorg. Med. Chem. Lett. 19 2009 3932
20. J.D. Cohen, S. Thompson, and A.Y. Ting Biochemistry 50 2011 8221
21. M.N. Erichsen, T.H.V. Huynh, B. Abrahamsen, J.F. Bastlund, C. Bundgaard, O. Monrad, A.B. Jensen, C.W. Nielsen, K. Frydenvang, A.A. Jensen, and L. Bunch J. Med. Chem 53 2010 7180
22. A.A. Jensen, M.N. Erichsen, C.W. Nielsen, T.B. Stensbol, J. Kehler, and L. Bunch J. Med. Chem 52 2009 912
23. S. Balalaie, M. Bararjanian, M. Sheikh-Ahmadi, S. Hekmat, and P. Salehi Synth. Commun. 1097 2007 37
24. I. Devi, and P.J. Bhuyan Tetrahedron Lett. 45 2004 8625
25. K. Ito, and J. Maruyama Chem. Pharm. Bull. 31 1983 3014
26. W. Lin, L. Long, J. Feng, B. Wang, and C. Guo Eur. J. Org. Chem. 2007 4301
27. K. Venkateswarlu, K. Suneel, B. Das, K.N. Reddy, and T.S. Reddy Synth. Commun. 39 2009 215
28. H. Guo, and F. Tanaka J. Org. Chem. 74 2009 2417
29. R. Perrone, F. Berardi, N.A. Colabufo, E. Lacivita, M. Leopoldo, and V. Tortorella J. Med. Chem. 46 2003 646
30. E. Rizzi, S. Dallavalle, L. Merlini, G. Pratesi, and F. Zunino Synth. Commun. 36 2006 1117
31. F. Belluti, G. Fontana, N. Carenini, C. Giommarelli, and F. Zunino Bioorg. Med. Chem. 18 2010 3543
32. M. Lang, A. Mühlbauer, C. Gräf, J. Beyer, S. Lang-Fugmann, K. Polborn, and W. Steglich Eur. J. Org. Chem. 2008 816
33. Q. Shi, Y. Lee, H. Song, M. Cheng, S. Jew, H. Park, and B. Jeong Chem. Lett. 37 2008 436
34. A.A. Jensen, and H. Bräuner-Osborne Biochem. Pharmacol. 67 2004 2115