N α-Methylated phenylhistamines exhibit affinity to the hH 4R-a pharmacological and molecular modelling study

Naunyn-Schmiedeberg's Archives of Pharmacology

Volumn 384, Issue 3, 2011, Pages 287-299

  Wittmann, Hans Joachim ^a   Elz, Sigurd ^a   Seifert, Roland ^a   Straßer, Andrea ^a  

^a UNIVERSITY OF REGENSBURG   (Germany)

Author keywords

Gibbs energy; Histamine H 1 receptor; Histamine H 4 receptor; Histaprodifens; Phenylhistamines

Indexed keywords

GUANOSINE TRIPHOSPHATASE; HISTAMINE DERIVATIVE; HISTAMINE H4 RECEPTOR; HISTAPRODIFEN; HYBRID PROTEIN; PHENOPRODIFEN; PHENYLHISTAMINE; TRITIUM; TRYPTOPHAN; UNCLASSIFIED DRUG;

ARTICLE; BINDING COMPETITION; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG SELECTIVITY; DRUG STRUCTURE; ENZYME ASSAY; INSECT CELL; INVERSE AGONISM; LIGAND BINDING; MOLECULAR DYNAMICS; NONHUMAN; PARTIAL AGONISM; PROTEIN EXPRESSION; RECEPTOR AFFINITY; STEADY STATE; STRUCTURAL HOMOLOGY;

BINDING, COMPETITIVE; DOSE-RESPONSE RELATIONSHIP, DRUG; HISTAMINE; HISTAMINE AGONISTS; HUMANS; LIGANDS; MODELS, BIOLOGICAL; MODELS, MOLECULAR; MOLECULAR STRUCTURE; RECEPTORS, G-PROTEIN-COUPLED; RECEPTORS, HISTAMINE; STRUCTURE-ACTIVITY RELATIONSHIP; THERMODYNAMICS;

EID: 80054777013     PISSN: 00281298     EISSN: 14321912     Source Type: Journal    
DOI: 10.1007/s00210-011-0671-5     Document Type: Article

References (37)

1. Ballesteros JA, Shi L, Javitch JA (2001) Structural mimicry in G protein-coupled receptors: implications of the high-resolution structure of rhodopsin for structure-function analysis of rhodopsin-like receptors. Mol Pharmacol 60:1-19 (Pubitemid 32595228)
2. 50) of an enzymatic reaction. Biochem Pharmacol 22:3099-3108
3. Crocker E, Eilers M, Ahuja S, Hornak V, Hirshfeld A, Sheves M, Smith SO (2006) Location of Trp265 in metarhodopsin II: implications for the activation mechanism of the visual receptor rhodopsin. J Mol Biol 357:163-172 (Pubitemid 43339322)
4. 4 receptor as a new therapeutic target for inflammation. TRENDS Pharmacol Sci 26:462-469 (Pubitemid 41207878)
5. 4-receptor. Mol Pharmacol 76:1019-1030
6. 1-receptor agonists. J Med Chem 43:1071-1084 (Pubitemid 30173733)
7. Foord SM, Bonner TI, Neubig RR, Rosser EM, Pin JP, Davenport AP, Spedding M, Harmar AJ (2005) International Union of Pharmacology. XLVI. G protein-coupled receptor list. Pharmacol Rev 57:279-288 (Pubitemid 41043887)
8. 4-receptor agonist: (-)-2-cyano-1-methyl- 3-{(2R,5R)-5-[1H-imidazol-4(5)-yl] tetrahydrofuran-2-yl}methylguanidine. J Med Chem 46:3162-3165
9. G-substituent. J Med Chem 52:2623-2627
10. 4 receptor antagonist. J Med Chem 46:3957-3960 (Pubitemid 37122442)
11. 2-receptor with guanidine-type agonists. Mol Pharmacol 60:1210-1225 (Pubitemid 33144892)
12. 1 receptor agonist activity of a series of 2-phenylhistamines, 2-heteroarylhistamines, and analogues. J Med Chem 38:1287-1294
13. 4 receptor agonist. J Pharm Exp Ther 314:1310-1321 (Pubitemid 41205997)
14. 4 receptors. J Pharmacol Exp Ther 327:88-96
15. 1-receptor agonists. J Med Chem 46:5458-5470 (Pubitemid 37490378)
16. Oostenbrink C, Villa A, Mark AE, van Gunsteren WF (2004) A biomolecular force field based on the free enthalpy of hydration and solvation: the GROMOS force-field parameter sets 53A5 and 53A6. J Comput Chem 25:1656-1676
17. 2 receptor do not affect the species-selective activity of guanidine-type agonists. Naunyn-Schmiedeberg's Arch Pharmacol 376:253-264 (Pubitemid 50002453)
18. Scheerer P, Park JH, Hildebrand PW, Kim YJ, Krauss N, Choe HW, Hofmann KP, Ernst OP (2008) Crystal structure of opsin in its G-protein-interacting conformation. Nature 455:497-503
19. Schneider EH, Schnell D, Papa D, Seifert R (2009) High constitutive activity and a G-protein-independent high-affinity state of the human histamine H4-receptor. Biochemistry 48:1424-1438
20. 4R ligands. J Pharmacol Exp Ther 334:513-521
21. Schuettelkopf AW, van Allten DMF (2004) PRODRG-a tool for high-throughput crystallography of protein-ligand complexes. Acta Cryst D60:1355-1363
22. Seifert R, Wenzel-Seifert K, Bürckstümmer T, Pertz HH, Schunack W, Dove S, Buschauer A, Elz S (2003) Multiple differences in agonist and antagonist pharmacology between human and guinea pig histamine H1-receptor. J Pharmacol Exp Ther 305:1104-1115 (Pubitemid 36617989)
23. 4 receptor inverse agonists using a scaffold hopping approach. J Med Chem 51:7855-7865
24. Smits RA, Leurs R, de Esch IJP (2009) Major advances in the development of histamine H4 receptor ligands. Drug Discovery Today 14:745-753
25. Van der Spoel D, Lindahl E, Hess B, Groenhof G, Mark AE, Berendsen HJC (2005) GROMACS: fast, flexible, and free. J Comput Chem 26:1701-1718 (Pubitemid 43076182)
26. Straßer A, Striegl B, Wittmann H-J, Seifert R (2008) Pharmacological profile of histaprodifens at four recombinant histamine H1 receptor species isoforms. J Pharmacol Exp Ther 324:1-12
27. 1-receptor. Mol Pharmacol 75:1-12
28. 1-receptor species. Mol Inf 29:333-341
29. Straatsma TP, Mc Cammon JA (1991) Multiconfiguration thermodynamic integration. J Chem Phys 95:1175-1188
30. Terzioglu N, van Rijn RM, Bakker RA, De Esch IJP, Leurs R (2004) Synthesis and structure-activity relationships of indole and benzimidazole piperazines as histamine H4 receptor antagonists. Bioorg & Med Chem Lett 14:5251-5256 (Pubitemid 39348908)
31. 4 receptors in allergic inflammation: the search for new antihistamines. Nature Reviews Drug Discovery 7:41-53
32. Thurmond RL, Desai PJ, Dunford PJ, Fung-Leung WP, Hofstra CL, Jiang W, Nguyen S, Riley JP, Sun S, Williams KN, Edwards JP Karlsson L (2004) A potent and selective histamine H4 Receptor antagonist with anti-inflammatory properties. J Pharmacol Exp Ther 309:404-413 (Pubitemid 38393154)
33. Venable JD, Cai H, Chai W, Dvorak CA, Grice CA, Jablonowski JA, Shah CR, Kwok AK, Ly KS, Pio B, Wei J, Desai PJ, Jiang W, Nguyen S, Ling P, Wilson SJ, Dunford PJ
34. 4 antagonists. J Med Chem 48:8289-8298 (Pubitemid 43032536)
35. Villa A, Mark AE (2002) Calculation of the free energy of solvation for natural analogs of amino acid side chains. J Comput Chem 23:548-553 (Pubitemid 34409035)
36. sα has properties of a constitutively active receptor. J Biol Chem 273:5109-5116 (Pubitemid 28108671)
37. q-proteins. Mol Pharmacol 58:954-966