Development of Benzophenone-Alkyne Bifunctional Sigma Receptor Ligands

ChemBioChem

Volumn 13, Issue 15, 2012, Pages 2277-2289

  Guo, Lian Wang ^a   Hajipour, Abdol R ^a,b   Karaoglu, Kerim ^a,c   Mavlyutov, Timur A ^a   Ruoho, Arnold E ^a  

^a UNIVERSITY OF WISCONSIN SCHOOL OF MEDICINE AND PUBLIC HEALTH   (United States)

^b ISFAHAN UNIVERSITY OF TECHNOLOGY   (Iran)

^c ISTANBUL UNIVERSITY   (Turkey)

Author keywords

Alkynes; Benzophenone; Click chemistry; Sigma 2 receptor ligand; Sigma2 18k

Indexed keywords

(4 NITROPHENYL)[4 [(PROP 2 YNYLAMINO)METHYL]PHENYL]METHANONE; 3 (4 (4 FLUOROPHENYL)PIPERAZIN 1 YL)PROPAN 1 AMINE; 3 (4 CYCLOHEXYLPIPERAZIN 1 YL)PROPAN 1 AMINE; 3 (6,7 DIMETHOXY 3,4 DIHYDROISOQUINOLIN 2(1H)YL)PROPAN 1 AMINE; 4 (3 BROMOPROPYL)PHENYL)(4 TOLYL)METHANONE; 4 (BROMOMETHYL) 4' NITROBENZOPHENONE; 4 (BROMOMETHYL)BENZOPHENONE; 4 METHYL 4' NITROBENZOPHENONE; 4 METHYLBENZOPHENONE; [4 [[3 (4 CYCLOHEXYLPIPERAZIN 1 YL)PROPYL](PROP 2 YNYL)AMINO]METHYL]PHENYL](4 NITROPHENYL)METHANONE; [4 [[3 (4 CYCLOHEXYLPIPERAZIN 1 YL)PROPYLAMINO]METHYL]PHENYL](4 NITROPHENYL)METHANONE; [4 [[3 [4 (4 FLUOROPHENYL)PIPERAZIN 1 YL]PROPYLAMINO]METHYL]PHENYL](4 NITROPHENYL)METHANONE; ALKYNE; BENZOPHENONE; PROGESTERONE RECEPTOR; SIGMA RECEPTOR LIGAND; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ANIMAL TISSUE; ARTICLE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; NONHUMAN; PHOTOAFFINITY LABELING; PRIORITY JOURNAL; RAT;

ALKYNES; BENZOPHENONES; CELL LINE; CLICK CHEMISTRY; CROSS-LINKING REAGENTS; HUMANS; LIGANDS; PHOTOCHEMICAL PROCESSES; RECEPTORS, SIGMA;

EID: 84867205113     PISSN: 14394227     EISSN: 14397633     Source Type: Journal    
DOI: 10.1002/cbic.201200427     Document Type: Article

References (36)

1. T. P. Su, T. Hayashi, T. Maurice, S. Buch, A. E. Ruoho, Trends Pharmacol. Sci. 2010, 31, 557-566.
2. R. Quirion, W. D. Bowen, Y. Itzhak, J. L. Junien, J. M. Musacchio, R. B. Rothman, T. P. Su, S. W. Tam, D. P. Taylor, Trends Pharmacol. Sci. 1992, 13, 85-86.
3. M. Hanner, F. F. Moebius, A. Flandorfer, H. G. Knaus, J. Striessnig, E. Kempner, H. Glossmann, Proc. Natl. Acad. Sci. USA 1996, 93, 8072-8077.
4. T. Hayashi, T. P. Su, Cell 2007, 131, 596-610.
5. T. P. Su, E. D. London, J. H. Jaffe, Science 1988, 240, 219-221.
6. D. Fontanilla, M. Johannessen, A. R. Hajipour, N. V. Cozzi, M. B. Jackson, A. E. Ruoho, Science 2009, 323, 934-937.
7. S. Ramachandran, U. B. Chu, T. A. Mavlyutov, A. Pal, S. Pyne, A. E. Ruoho, Eur. J. Pharmacol. 2009, 609, 19-26.
8. E. J. Cobos, J. M. Entrena, F. R. Nieto, C. M. Cendan, E. Del Pozo, Curr. Neuropharmacol. 2008, 6, 344-366.
9. T. Maurice, T. P. Su, Pharmacol. Ther. 2009, 124, 195-206.
10. S. Narayanan, C. Mesangeau, J. H. Poupaert, C. R. McCurdy, Curr. Top. Med. Chem. 2011, 11, 1128-1150.
11. J. A. Fishback, M. J. Robson, Y. T. Xu, R. R. Matsumoto, Pharmacol. Ther. 2010, 127, 271-282.
12. T. A. Mavlyutov, R. W. Nickells, L. W. Guo, Mol. Vision 2011, 17, 1034-1043.
13. B. J. Vilner, C. S. John, W. D. Bowen, Cancer Res. 1995, 55, 408-413.
14. R. H. Mach, C. R. Smith, I. Al-Nabulsi, B. R. Whirrett, S. R. Childers, K. T. Wheeler, Cancer Res. 1997, 57, 156-161.
15. K. W. Crawford, W. D. Bowen, Cancer Res. 2002, 62, 313-322.
16. K. W. Crawford, A. Coop, W. D. Bowen, Eur. J. Pharmacol. 2002, 443, 207-209.
17. A. Azzariti, N. A. Colabufo, F. Berardi, L. Porcelli, M. Niso, G. M. Simone, R. Perrone, A. Paradiso, Mol. Cancer Ther. 2006, 5, 1807-1816.
18. M. S. Ostenfeld, N. Fehrenbacher, M. Hoyer-Hansen, C. Thomsen, T. Farkas, M. Jaattela, Cancer Res. 2005, 65, 8975-8983.
19. C. Zeng, S. Vangveravong, J. Xu, K. C. Chang, R. S. Hotchkiss, K. T. Wheeler, D. Shen, Z. P. Zhuang, H. F. Kung, R. H. Mach, Cancer Res. 2007, 67, 6708-6716.
20. R. H. Mach, K. T. Wheeler, Cent. Nerv. Syst. Agents Med. Chem. 2009, 9, 230-245.
21. J. Xu, C. Zeng, W. Chu, F. Pan, J. M. Rothfuss, F. Zhang, Z. Tu, D. Zhou, D. Zeng, S. Vangveravong, F. Johnston, D. Spitzer, K. C. Chang, R. S. Hotchkiss, W. G. Hawkins, K. T. Wheeler, R. H. Mach, Nat. Commun. 2011, 2, 380.
22. S. B. Hellewell, W. D. Bowen, Brain Res. 1990, 527, 244-253.
23. S. B. Hellewell, A. Bruce, G. Feinstein, J. Orringer, W. Williams, W. D. Bowen, Eur. J. Pharmacol. 1994, 268, 9-18.
24. A. Pal, A. R. Hajipour, D. Fontanilla, S. Ramachandran, U. B. Chu, T. Mavlyutov, A. E. Ruoho, Mol. Pharmacol. 2007, 72, 921-933.
25. A. R. Hajipour, L. W. Guo, A. Pal, T. Mavlyutov, A. E. Ruoho, Bioorg. Med. Chem. 2011, 19, 7435-7440.
26. L. W. Guo, A. R. Hajipour, M. L. Gavala, M. Arbabian, K. A. Martemyanov, V. Y. Arshavsky, A. E. Ruoho, Bioconjugate Chem. 2005, 16, 685-693.
27. J. Gubbens, E. Ruijter, L. E. de Fays, J. M. Damen, B. de Kruijff, M. Slijper, D. T. Rijkers, R. M. Liskamp, A. I. de Kroon, Chem. Biol. 2009, 16, 3-14.
28. Z. Tu, J. Xu, L. A. Jones, S. Li, C. Dumstorff, S. Vangveravong, D. L. Chen, K. T. Wheeler, M. J. Welch, R. H. Mach, J. Med. Chem. 2007, 50, 3194-3204.
29. F. Berardi, S. Ferorelli, C. Abate, N. A. Colabufo, M. Contino, R. Perrone, V. Tortorella, J. Med. Chem. 2004, 47, 2308-2317.
30. C. Mésangeau, S. Narayanan, A. M. Green, J. Shaikh, N. Kaushal, E. Viard, Y. T. Xu, J. A. Fishback, J. H. Poupaert, R. R. Matsumoto, C. R. McCurdy, J. Med. Chem. 2008, 51, 1482-1486.
31. A. R. Hajipour, D. Fontanilla, U. B. Chu, M. Arbabian, A. E. Ruoho, Bioorg. Med. Chem. 2010, 18, 4397-4404.
32. S. Ramachandran, H. Lu, U. Prabhu, A. E. Ruoho, Protein Expression Purif. 2007, 51, 283-292.
33. D. Schepmann, K. Lehmkuhl, S. Brune, B. Wunsch, J. Pharm. Biomed. Anal. 2011, 55, 1136-1141.
34. R. R. Matsumoto, W. D. Bowen, M. A. Tom, V. N. Vo, D. D. Truong, B. R. De Costa, Eur. J. Pharmacol. 1995, 280, 301-310.
35. Y. Cheng, W. H. Prusoff, Biochem. Pharmacol. 1973, 22, 3099-3108.
36. L. W. Guo, H. Muradov, A. R. Hajipour, M. K. Sievert, N. O. Artemyev, A. E. Ruoho, J. Biol. Chem. 2006, 281, 15412-15422.