Inhibition of the cellular function of perforin by 1-amino-2,4- dicyanopyrido[1,2-a]benzimidazoles

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 13, 2011, Pages 4091-4100

  Lyons, Dani M ^a   Huttunen, Kristiina M ^a,b   Browne, Kylie A ^c   Ciccone, Annette ^c   Trapani, Joseph A ^c   Denny, William A ^a   Spicer, Julie A ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b UNIVERSITY OF EASTERN FINLAND   (Finland)

^c PETER MACCALLUM CANCER CENTRE   (Australia)

Author keywords

Dicyanopyrido 1,2 a benzimidazole; Perforin; Perforin inhibitor

Indexed keywords

1 AMINO 3 [4 (2 HYDROXYETHOXY)PHENYL]PYRIDO[1,2 A]BENZIMIDAZOL 2,4 DICARBONITRILE; 2 [4 (1 AMINO 2,4 DICYANO 6 METHYLBENZO[4,5]IMIDAZO[1,2 A]PYRIDIN 3 YL)PHENOXY]ACETAMIDE; 2 [4 (1 AMINO 2,4 DICYANO 6 METHYLPYRIDO[1,2 A]BENZIMIDAZOL 3 YL)PHENOXY]ACETAMIDE; 2 [4 (1 AMINO 2,4 DICYANOPYRIDO[1,2 A]BENZIMIDAZOL 3 YL)PHENOXY] N (2 HYDROXYETHYL)ACETAMIDE; 2 [4 (1 AMINO 2,4 DICYANOPYRIDO[1,2 A]BENZIMIDAZOL 3 YL)PHENOXY] N (2 HYDROXYPROPYL)ACETAMIDE; 2 [4 (1 AMINO 2,4 DICYANOPYRIDO[1,2 A]BENZIMIDAZOL 3 YL)PHENOXY] N (2 PYRIDIN 4 YLETHYL)ACETAMIDE; 2 [4 (1 AMINO 2,4 DICYANOPYRIDO[1,2 A]BENZIMIDAZOL 3 YL)PHENOXY] N (2,3 DIHYDROXYPROPYL)ACETAMIDE; 2 [4 (1 AMINO 2,4 DICYANOPYRIDO[1,2 A]BENZIMIDAZOL 3 YL)PHENOXY] N ETHYLACETAMIDE; 2 [4 (1 AMINO 2,4 DICYANOPYRIDO[1,2 A]BENZIMIDAZOL 3 YL)PHENOXY] N ISOPROPYLACETAMIDE; 2 [4 (1 AMINO 2,4 DICYANOPYRIDO[1,2 A]BENZIMIDAZOL 3 YL)PHENOXY] N METHYLACETAMIDE; 2 [4 (1 AMINO 2,4 DICYANOPYRIDO[1,2 A]BENZIMIDAZOL 3 YL)PHENOXY] N PROPYLACETAMIDE; 2 [4 (1 AMINO 2,4 DICYANOPYRIDO[1,2 A]BENZIMIDAZOL 3 YL)PHENOXY] N,N DIMETHYLACETAMIDE; 2 [4 (1 AMINO 6 CHLORO 2,4 DICYANOBENZO[4,5]IMIDAZO[1,2 A]PYRIDIN 3 YL)PHENOXY]ACETAMIDE; 2 [4 [2 (1H BENZO[D]IMIDAZOL 2 YL) 2 CYANOVINYL]PHENOXY]ACETAMIDE; 2 [4 [2 CYANO 2 (4 METHYL 1H BENZO[D]IMIDAZOL 2YL)VINYL]PHENOXY]ACETAMIDE; 3 [4 (1 AMINO 2,4 DICYANOPYRIDO[1,2 A]BENZIMIDAZOL 3 YL)PHENYL] N METHYLPROPANAMIDE; 4 (1 AMINO 2,4 DICYANOPYRIDO[1,2 A]BENZIMIDAZOL 3 YL) N (2,3 DIHYDROXYPROPYL)BENZAMIDE; 4 (9 AMINO 6,8 DICYANOPYRIDO[1,2 A]BENZIMIDAZOL 7 YL) N (2 HYDROXYETHYL)BENZAMIDE; 4 (9 AMINO 6,8 DICYANOPYRIDO[1,2 A]BENZIMIDAZOL 7 YL) N (2 HYDROXYPROPYL)BENZAMIDE; 4 (9 AMINO 6,8 DICYANOPYRIDO[1,2 A]BENZIMIDAZOL 7 YL) N (2 MORPHOLIN 4 YLETHYL)BENZAMIDE; 4 (9 AMINO 6,8 DICYANOPYRIDO[1,2 A]BENZIMIDAZOL 7 YL) N (2 PYRIDIN 4 YLETHYL)BENZAMIDE; 4 (9 AMINO 6,8 DICYANOPYRIDO[1,2 A]BENZIMIDAZOL 7 YL) N (3 HYDROXYPROPYL)BENZAMIDE; 4 (9 AMINO 6,8 DICYANOPYRIDO[1,2 A]BENZIMIDAZOL 7 YL) N [2(DIMETHYLAMINO)ETHYL]BENZAMIDE; 4 (9 AMINO 6,8 DICYANOPYRIDO[1,2 A]BENZIMIDAZOL 7 YL) N ETHYLBENZAMIDE; 4 (9 AMINO 6,8 DICYANOPYRIDO[1,2 A]BENZIMIDAZOL 7 YL) N METHYLBENZAMIDE; 4 (9 AMINO 6,8 DICYANOPYRIDO[1,2 A]BENZIMIDAZOL 7 YL) N,N DIMETHYLBENZAMIDE; 4 (9 AMINO 6,8 DICYANOPYRIDO[1,2 A]BENZIMIDAZOL 7 YL)BENZAMIDE; BENZIMIDAZOLE DERIVATIVE; PERFORIN; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; CELL FUNCTION; CHANNEL GATING; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; CYTOLYSIS; CYTOTOXICITY; DRUG STRUCTURE; HIGH THROUGHPUT SCREENING; HUMAN; HUMAN CELL; INHIBITION KINETICS; LEUKEMIA CELL LINE; NATURAL KILLER CELL; STRUCTURE ACTIVITY RELATION;

BENZIMIDAZOLES; CELL LINE; HUMANS; KILLER CELLS, NATURAL; PERFORIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79959530773     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.05.013     Document Type: Article

References (17)

1. M.G. Lichtenheld, K.J. Olsen, P. Lu, D.M. Lowrey, A. Hameed, H. Hengartner, and E.R. Podack Nature 335 1988 448
2. P.J. Peters, J. Borst, V. Oorschot, M. Fukuda, O. Kraehenbuehl, J. Tschopp, J.W. Slot, and J. G Hans J. Exp. Med. 173 1991 1099
3. C.J. Rosado, A.M. Buckle, R.H.P. Law, R.E. Butcher, W.-T. Kan, C.H. Bird, K. Ung, K.A. Browne, K. Baran, T.A. Bashtannyk-Puhalovich, N.G. Faux, W. Wong, C.J. Porter, R.N. Pike, A.M. Ellisdon, M.C. Pearce, S.P. Bottomley, J. Emsley, A.I. Smith, J. Rossjohn, E.L. Hartland, I. Voskoboinik, J.A. Trapani, P.I. Bird, M.A. Dunstone, and J.C. Whisstock Science 317 2007 1548
4. D. Kagi, B. Ledermann, K. Burki, P. Seiler, B. Odermatt, K.J. Olsen, E.J. Podack, R.M. Zinkernagel, and H. Hengartner Nature 369 1994 31
5. I. Voskoboinik, M.-C. Thia, J. Fletcher, A. Ciccone, K. Browne, M.J. Smyth, and J.A. Trapani J. Biol. Chem. 280 2005 8426
6. K. Baran, M. Dunstone, J. Chia, A. Ciccone, K.A. Browne, C.J.P. Clarke, N. Lukoyanova, H. Saibil, J.C. Whisstock, I. Voskoboinik, and J.A. Trapani Immunity 30 2009 684
7. R.H.P. Law, N. Lukoyanova, I. Voskoboinik, T.T. Caradoc-Davies, K. Baran, M.A. Dunstone, M.E. D'Angelo, E.V. Orlova, F. Coulibaly, S. Verschoor, K.A. Browne, A. Ciccone, M.J. Kuiper, P.B. Bird, J.A. Trapani, H.R. Saibil, and J.C. Whisstock Nature 468 2010 447
8. J.C. Choy Cell Death Differ. 17 2010 567
9. J.C. Choy, A. Kerjner, B.W. Wong, B.M. McManus, and D.J. Granville Am. J. Pathol. 165 2004 127
10. G. Lena, J.A. Trapani, V.R. Sutton, A. Ciccone, K.A. Browne, M.J. Smyth, W.A. Denny, and J.A. Spicer J. Med. Chem. 51 2008 7614
11. H. Ogbomo, T. Biru, M. Michaelis, N. Loeschmann, H.W. Doerr, and J. Cinatl Biochem. Pharmacol. 81 2011 251
12. Trapani, J. A.; Smyth, M. J. WO 2005083098 A1.
13. K. Bogdanowicz-Szwed, and A. Czarny J. Prakt. Chem. 335 1993 279
14. M.H. Elnagdi, K.U. Sadek, M.A. El-Maghraby, M.A. Selim, A.K. Khalafallah, and M.A. Reaslan Phosphorus, Sulfur Silicon Relat. Elem. 105 1995 51
15. G.Y. Chao, Q.F. Wang, X.K. Song, and J. Sun J. Org. Chem. 74 2009 710
16. Alekshun, M. N.; Amoo, V.; Kim, O. K.; Verma, A. K. WO 2006076009 A2.
17. N. Hoettecke, M. Liebeck, K. Baumann, R. Schubenel, E. Winkler, H. Steiner, and B. Schmidt Bioorg. Med. Chem. Lett. 20 2010 2958