Red-fluorescent argininamide-type NPY Y1 receptor antagonists as pharmacological tools

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 9, 2011, Pages 2859-2878

  Keller, Max ^a   Erdmann, Daniela ^a   Pop, Nathalie ^a   Pluym, Nikola ^a   Teng, Shangjun ^a   Bernhardt, Günther ^a   Buschauer, Armin ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

Argininamide derivatives; Confocal microscopy; Flow cytometry; Fluorescent ligands; NPY Y1 receptor; Y1R antagonism; Y1R binding

Indexed keywords

12 (BENZYLOXYCARBONYLAMINO) 4,7,10 TRIOXODODECANOIC ACID; 4 (2 TERT BUTOXYCARBONYLAMINOETHYL)AMINOCARBONYLBUTANOIC ACID; 4 (3 TERT BUTOXYCARBONYLAMINOPROPYL)AMINOCARBONYLBUTANOIC ACID; 4 (8 TERT BUTOXYCARBONYLAMINO 3,6 DIOXAOCTYL)AMINOCARBONYLBUTANOIC ACID; 5 (8 TERT BUTOXYCARBONYLAMINO 3,6 DIOXAOCTYL)AMINOCARBONYLPENTANOIC ACID; 6 (TERT BUTOXYCARBONYLAMINO)HEXANOIC ACID; CYANINE DYE 5; FLUORESCENT DYE; N (4 AMINOMETHYLBENZYL)UREA; N ALPHA (2,2 DIPHENYLACETYL) N (4 UREIDOMETHYLBENZYL)ARGININAMIDE; N ALPHA (2,2 DIPHENYLACETYL) N (4 UREIDOMETHYLBENZYL)ORNITHINAMIDE; N DELTA BENZYLOXYCARBONYL N (4 UREIDOMETHYLBENZYL)ORNITHINE; N DELTA BENZYLOXYCARBONYL N ALPHA (2,2 DIPHENYLACETYL) N (4 UREIDOMETHYLBENZYL)ORNITHINAMIDE; N DELTA BENZYLOXYCARBONYL N ALPHA(TERT BUTOXYCARBONYL)ORNITHINE; N OMEGA (12 AMINO 4,7,10 TRIOXADODECANOYL) N ALPHA (2,2 DIPHENYLACETYL) N (4 HYDROXYBENZYL)ARGININAMIDE BIS(HYDROTRIFLUOROACETATE); N OMEGA (6 AMINOHEXANOYL) N ALPHA (2,2 DIPHENYLACETYL) N (4 HYDROXYBENZYL)ARGININAMIDE BIS(HYDROTRIFLUOROACETATE); N OMEGA (6 AMINOHEXANOYL) N ALPHA (2,2 DIPHENYLACETYL) N (4 UREIDOMETHYLBENZYL)ARGININAMIDE BIS(HYDROTRIFLUOROACETATE); N OMEGA (8 AMINO 3,6 DIOXAOCTANOYL) N ALPHA (2,2 DIPHENYLACETYL) N (4 HYDROXYBENZYL)ARGININAMIDE BIS(HYDROTRIFLUOROACETATE); N OMEGA [4 (2 AMINOETHYL)AMINOCARBONYLBUTANOYL] N ALPHA (2,2 DIPHENYLACETYL) N (4 HYDROXYBENZYL)ARGININAMIDE BIS(HYDROTRIFLUOROACETATE); N OMEGA [4 (3 AMINOPROPYL)AMINOCARBONYLBUTANOYL] N ALPHA (2,2 DIPHENYLACETYL) N (4 HYDROXYBENZYL)ARGININAMIDE BIS(HYDROTRIFLUOROACETATE); N OMEGA [5 (8 AMINO 3,6 DIOXAOCTYL)AMINOCARBONYLPENTANOYL] N ALPHA (2,2 DIPHENYLACETYL) N (4 HYDROXYBENZYL)ARGININAMIDE BIS(HYDROTRIFLUOROACETATE); N OMEGA TERT BUTOXYCARBONYL N ALPHA (2,2 DIPHENYLACETYL) N (4 UREIDOMETHYL BENZYL)ARGININAMIDE HYDROACETATE; N OMEGA TERT BUTOXYCARBONYL N ALPHA (2,2 DIPHENYLACETYL) N (4 UREIDOMETHYL BENZYL)ARGININAMIDE HYDROTRIFLUOROACETATE; N TERT BUTOXYCARBONYL N' [N (4 TERTBUTOXYCARBONYLAMINOBUTYL)AMINOCARBONYL]METHYLISOTHIOUREA; N2 DIPHENYLACETYL N (4 UREIDOMETHYLBENZYL)ARGININAMIDE; NALPHA (DIPHENYLACETYL) N (4 HYDROXYBENZYL) DEXTRO ARGININAMIDE; NEUROPEPTIDE Y RECEPTOR ANTAGONIST; TERT BUTYL 2 AMINOETHYLCARBAMIC ACID; TERT BUTYL 4 (AMINOMETHYL)BENZYLCARBAMATE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CHEMICAL REACTION; CONFOCAL MICROSCOPY; DRUG STRUCTURE; DRUG SYNTHESIS; FLOW CYTOMETRY; HUMAN; HYDROPHOBICITY; LIGAND BINDING; NEAR INFRARED SPECTROSCOPY; QUANTUM YIELD; RADIOASSAY; SIGNAL NOISE RATIO; STEREOCHEMISTRY;

ARGININE; BENZOTHIAZOLES; CARBOCYANINES; CELL LINE, TUMOR; FLOW CYTOMETRY; FLUORESCENT DYES; HUMANS; PROTEIN BINDING; RECEPTORS, NEUROPEPTIDE Y;

EID: 79955482584     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.03.045     Document Type: Article

References (55)

1. I. Böhme, and A.G. Beck-Sickinger Cell Commun. Signal. 7 2009 16
2. E. Schneider, M. Mayer, R. Ziemek, L. Li, C. Hutzler, G. Bernhardt, and A. Buschauer Chembiochem 7 2006 1400
3. Y. Dumont, P. Gaudreau, M. Mazzuferi, D. Langlois, J.G. Chabot, A. Fournier, M. Simonato, and R. Quirion Br. J. Pharmacol. 146 2005 1069
4. N. Ingenhoven, and A.G. Beck-Sickinger J. Recept. Signal Transduct. Res. 17 1997 407
5. E. Schneider, M. Keller, A. Brennauer, B.K. Hoefelschweiger, D. Gross, O.S. Wolfbeis, G. Bernhardt, and A. Buschauer Chembiochem 8 2007 1981
6. M. Keller, N. Pop, C. Hutzler, A.G. Beck-Sickinger, G. Bernhardt, and A. Buschauer J. Med. Chem. 51 2008 8168
7. P. Igel, D. Schnell, G. Bernhardt, R. Seifert, and A. Buschauer ChemMedChem 4 2009 225
8. M. Keller, S. Teng, G. Bernhardt, and A. Buschauer ChemMedChem 4 2009 1733
9. S. Weiss, M. Keller, G. Bernhardt, A. Buschauer, and B. König Bioorg. Med. Chem. 16 2008 9858
10. C. Hutzler, J. Kracht, M. Mayer, F. Graichen, B. Bauer, E. Schreiber, S. Bollwein, G. Bernhardt, S. Dove, G. Fricker, and A. Buschauer Arch. Pharm. (Weinheim, Ger.) 334 2001 17
11. J.C. Reubi, M. Gugger, B. Waser, and J.C. Schaer Cancer Res. 61 2001 4636
12. P. Magni, and M. Motta Ann. Oncol. 12 2001 S27
13. M. Körner, B. Waser, and J.C. Reubi Clin. Cancer Res. 10 2004 8426
14. M. Körner, B. Waser, and J.C. Reubi Lab. Invest. 84 2004 71
15. M. Körner, B. Waser, and J.C. Reubi Int. J. Cancer 115 2005 734
16. M. Körner, and J.C. Reubi J. Neuropathol. Exp. Neurol. 67 2008 741
17. M. Körner, and J.C. Reubi Peptides 28 2007 419
18. I.U. Khan, D. Zwanziger, I. Bohme, M. Javed, H. Naseer, S.W. Hyder, and A.G. Beck-Sickinger Angew. Chem., Int. Ed. 49 2010 1155
19. B. Guerin, V. Dumulon-Perreault, M.C. Tremblay, S. Ait-Mohand, P. Fournier, C. Dubuc, S. Authier, and F. Benard Bioorg. Med. Chem. Lett. 20 2010 950
20. K. Rudolf, W. Eberlein, W. Engel, H.A. Wieland, K.D. Willim, M. Entzeroth, W. Wienen, A.G. Beck-Sickinger, and H.N. Doods Eur. J. Pharmacol. 271 1994 R11
21. H.A. Wieland, W. Engel, W. Eberlein, K. Rudolf, and H.N. Doods Br. J. Pharmacol. 125 1998 549
22. B.K. Wetzl, S.M. Yarmoluk, D.B. Craig, and O.S. Wolfbeis Angew. Chem., Int. Ed. 43 2004 5400
23. D.B. Craig, B.K. Wetzl, A. Duerkop, and O.S. Wolfbeis Electrophoresis 26 2005 2208
24. R. Buffa, P. Zahradnik, and P. Foltinova Heterocycl. Commun. 7 2001 331
25. Engel, W.; Eberlein, W.; Rudolf, K.; Doods, H.; Wieland, H.-A.; Willim, K.-D.; Entzeroth, M.; Wienen, W. German Patent DE 19544687, 1997; Chem. Abstr. 1997, 127, 81788.
26. J.F. Callahan, D. Ashton-Shue, H.G. Bryan, W.M. Bryan, G.D. Heckman, L.B. Kinter, J.E. McDonald, M.L. Moore, and D.B. Schmidt J. Med. Chem. 32 1989 391
27. R. Duschinsky, and L.A. Dolan J. Am. Chem. Soc. 68 1946 2350
28. J. Marx, and L. Marx-Moll Chem. Ber. 87 1954 1499
29. W. Kirmse, and M. Buschhoff Chem. Ber. 100 1967 1491
30. A. Eschalier, G. Dureng, P. Duchene-Marullaz, J. Berecoechea, and J. Anatol Eur. J. Med. Chem. 18 1983 139
31. Fegley, G.; Bell, S. C.; Costenza, S.; Duke, J.; Reddy, E. P.; Reddy, M. V. R. WO Patent 2008033475, 2008; Chem. Abstr. 148, 379331.
32. A. Brennauer, M. Keller, M. Freund, G. Bernhardt, and A. Buschauer Tetrahedron Lett. 48 2007 6996
33. P. Majer, and R.S. Randad J. Org. Chem. 59 1994 1937
34. B. Caro, F. Le Guen-Robin, M. Salmain, and G. Jaouen Tetrahedron 56 1999 257
35. M. Müller, S. Knieps, K. Gessele, S. Dove, G. Bernhardt, and A. Buschauer Arch. Pharm. (Weinheim) 330 1997 333
36. Brennauer, A.; Dove, S.; Buschauer, A. In Handbook of Experimental Pharmacology, Michel, M. C., Ed.; Springer: Heidelberg, 2004; Vol. 162, p 506.
37. P.M. Vanderheyden, I. Van Liefde, J.P. de Backer, and G. Vauquelin J. Recept. Signal Transduct. 18 1998 363
38. R. Ziemek, A. Brennauer, E. Schneider, C. Cabrele, A.G. Beck-Sickinger, G. Bernhardt, and A. Buschauer Eur. J. Pharmacol. 551 2006 10
39. R. Ziemek, E. Schneider, A. Kraus, C. Cabrele, A.G. Beck-Sickinger, G. Bernhardt, and A. Buschauer J. Recept. Signal Transduct. 27 2007 217
40. S. Weiss, M. Keller, G. Bernhardt, A. Buschauer, and B. König Bioorg. Med. Chem. 18 2010 6292
41. J.C. Reubi, and B. Waser Eur. J. Nucl. Med. Mol. Imaging 30 2003 781
42. H. Amlal, S. Faroqui, A. Balasubramaniam, and S. Sheriff Cancer Res. 66 2006 3706
43. T.P. Kenakin A Pharmacology Primer: Theory, Applications, and Methods 2007 Academic Press
44. H.A. Wieland, K.D. Willim, M. Entzeroth, W. Wienen, K. Rudolf, W. Eberlein, W. Engel, and H.N. Doods J. Pharmacol. Exp. Ther. 275 1995 143
45. A. Kraus, P. Ghorai, T. Birnkammer, D. Schnell, S. Elz, R. Seifert, S. Dove, G. Bernhardt, and A. Buschauer ChemMedChem 2008
46. Bauer, J.; Martin, R. O.; Rodriguez, S. U.S. Patent 2005-113443, 2005; Chem. Abstr. 143, 267243.
47. J.P. Henichart, R. Houssin, J.L. Bernier, and J.P. Catteau J. Chem. Soc., Chem. Commun. 1982 1295
48. D. Donati, C. Morelli, A. Porcheddu, and M. Taddei J. Org. Chem. 69 2004 9316
49. GB Patent 945536, 1964; Chem. Abstr. 1964, 60, 60474.
50. D. Magde, J.H. Brannon, T.L. Cremers, and J. Olmsted III J. Phys. Chem. 83 1979 696
51. I. Aiglstorfer, A. Uffrecht, K. Gessele, C. Moser, A. Schuster, S. Merz, B. Malawska, G. Bernhardt, S. Dove, and A. Buschauer Regul. Pept. 75-76 1998 9
52. J.L. Biedler, L. Helson, and B.A. Spengler Cancer Res. 33 1973 2643
53. C. Moser, G. Bernhardt, J. Michel, H. Schwarz, and A. Buschauer Can. J. Physiol. Pharmacol. 78 2000 134
54. S.W. Burchiel, B.S. Edwards, F.W. Kuckuck, F.T. Lauer, E.R. Prossnitz, J.T. Ransom, and L.A. Sklar Methods 21 2000 221
55. Y. Cheng, and W.H. Prusoff Biochem. Pharmacol. 22 1973 3099