Guanidine-acylguanidine bioisosteric approach in the design of radioligands: Synthesis of a tritium-labeled NG-propionylargininamide ([3H]-UR-MK114) as a highly potent and selective neuropeptide Y Y1 receptor antagonist

Journal of Medicinal Chemistry

Volumn 51, Issue 24, 2008, Pages 8168-8172

  Keller, Max ^a   Pop, Nathalie ^a   Hutzler, Christoph ^a   Beck Sickinger, Annette G ^b   Bernhardt, Günther ^a   Buschauer, Armin ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

^b UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ARGININE DERIVATIVE; GUANIDINE; GUANIDINE DERIVATIVE; N ALPHA (2,2 DIPHENYLACETYL) N (4 HYDROXYBENZYL) N OMEGA PROPANOYLARGININAMIDE H 3; NALPHA (DIPHENYLACETYL) N (4 HYDROXYBENZYL) DEXTRO ARGININAMIDE; NEUROPEPTIDE Y1 RECEPTOR; RADIOLIGAND; TRITIUM; UNCLASSIFIED DRUG; UR MK 114;

ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG BINDING SITE; DRUG DESIGN; DRUG POTENCY; DRUG RECEPTOR BINDING; HUMAN; HUMAN CELL; ISOTOPE LABELING; LIGAND BINDING;

ANIMALS; ARGININE; BINDING SITES; CELL LINE, TUMOR; CHEMISTRY, PHARMACEUTICAL; CHO CELLS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CRICETINAE; CRICETULUS; DRUG DESIGN; GUANIDINE; HUMANS; KINETICS; RECEPTORS, NEUROPEPTIDE Y; TRITIUM;

EID: 58149100622     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm801018u     Document Type: Article

References (27)

1. Reubi, J. C.; Gugger, M.; Waser, B.; Schaer, J. C. Y(1)-mediated effect of neuropeptide Y in cancer: breast carcinomas as targets. Cancer Res. 2001, 61, 4636-4641.
2. Magni, P.; Motta, M. Expression of neuropeptide Y receptors in human prostate cancer cells. Ann. Oncol. 2001, 12 (2), S27-S29.
3. Körner, M.; Waser, B.; Reubi, J. C. High expression of neuropeptide y receptors in tumors of the human adrenal gland and extra-adrenal paraganglia. Clin. Cancer Res. 2004, 10, 8426-8433.
4. Körner, M.; Reubi, J. C. NPY receptors in human cancer: a review of current knowledge. Peptides 2007, 28, 419-425.
5. 1 receptor antagonist: BIBP3226. Eur. J. Pharmacol. 1994, 271, R11-R13.
6. 1 receptor. Mol. Pharmacol. 1996, 50, 285-292.
7. Hutzler, C. Synthese und pharmakologische Aktivität neuer Neuropeptid Y Rezeptorliganden: Von N,N-disubstituierten Alkanamiden zu hochpotenten Y1-Antagonisten der Argininamid-Reihe . Doctoral Thesis. University of Regensburg, Regensburg, Germany, 2001.
8. Brennauer, A.; Dove, S.; Buschauer, A. Structure-Activity Relationships of Nonpeptide Neuropeptide Y Receptor Antagonists. Handb. Exp. Pharm. 2004, 162, 506-537.
9. Gers, T.; Kunce, D.; Markowski, P.; Izdebski, J. Reagents for efficient conversion of amines to protected guanidines. Synthesis 2004, 37-42.
10. Bernatowicz, M. S.; Wu, Y.; Matsueda, G. R. Urethane protected derivatives of 1-guanyl-pyrazole for the mild and efficient preparation of guanidines. Tetrahedron Lett. 1993, 34, 3389-3392.
11. Drake, B.; Patek, M.; Lebl, M. A convenient preparation of monosubstituted N,N′-di(BOC)-protected guanidines. Synthesis 1994, 579-582.
12. Feichtinger, K.; Zapf, C.; Sings, H. L.; Goodman, M. Diprotected Triflylguanidines: A New Class of Guanidinylation Reagents. J. Org. Chem. 1998, 63, 3804-3805.
13. Feichtinger, K.; Sings, H. L.; Baker, T. J.; Matthews, K.; Goodman, M. Triurethane-Protected Guanidines and Triflyldiurethane-Protected Guanidines: New Reagents for Guanidinylation Reactions. J. Org. Chem. 1998, 63, 8432-8439.
14. Brennauer, A. Acylguanidines as bioisosteric groups in argininamidetype neuropeptide Y Y1 and Y2 receptor antagonists: synthesis, stability and pharmacological activity. Doctoral Thesis. University of Regensburg, Regensburg, Germany, 2006.
15. 1 receptor antagonist. ChemBioChem 2007, 8, 1981-1988.
16. Schneider, E.; Mayer, M.; Ziemek, R.; Li, L.; Hutzler, C.; Bernhardt, G.; Buschauer, A. A simple and powerful flow cytometric method for the simultaneous determination of multiple parameters at G protein-coupled receptor subtypes. ChemBioChem 2006, 7, 1400-1409.
17. 2 receptor ligands. Eur. J. Pharmacol. 2006, 551, 10-18.
18. 1 receptor antagonistic activity of N,N-disubstituted ω-guanidino- and ω- aminoalkanoic acid amides. Arch. Pharm. (Weinheim) 1997, 330, 333-342.
19. Kenakin, T. P. A Pharmacology Primer: Theory, Applications, and Methods, 2nd ed.; Academic Press: New York, 2007.
20. 1 receptor. J. Recept. Signal Transduct. Res. 1998, 18, 363-385.
21. 3H]BIBP3226. Eur. J. Pharmacol. 1995, 278, 239-242.
22. 1 receptor expression in a human breast cancer cell line. Cancer Res. 2006, 66, 3706-3714.
23. Michel, M. C.; Beck-Sickinger, A.; Cox, H.; Doods, H. N.; Herzog, H.; Larhammar, D.; Quirion, R.; Schwartz, T.; Westfall, T. XVI. International Union of Pharmacology recommendations for the nomenclature of neuropeptide Y, peptide YY, and pancreatic polypeptide receptors. Pharmacol. Rev. 1998, 50, 143-150.
24. 2 receptors in rat and guinea-pig brains. Neuroscience 1997, 76, 215-224.
25. 3H]BIBP3226. Neuroreport 1996, 7, 901-904.
26. 2 receptor agonists J. Med. Chem. 10.1021/jm800841w.
27. Cheng, Y.; Prusoff, W. H. Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.