Molecular modeling and QSAR-based design of histamine receptor ligands

Bibliography

• Barger G, Dale HH. β-Aminoethylglyoxaline (β-iminazolylethylamine) and the other active principles of ergot. J Chem Soc Transctions 1910;97:2592-5
   Google Scholar
• Parsons ME, Ganellin CR. Histamine and its receptors. Br J Pharmacol 2006;147:S127-35
   PubMed Web of Science ®Google Scholar
• Moguilevsky N, Varsalona F, Noyer M, et al. Stable expression of human H1-histamine-receptor cDNA in Chinese hamster ovary cells. Pharmacological characterisation of the protein, tissue distribution of messenger RNA and chromosomal localisation of the gene. Eur J Biochem 1994;224:489-95
   PubMedGoogle Scholar
• Gantz I, Munzert G, Tashiro T, et al. Molecular cloning of the human histamine H2 receptor. Biochem Biophys Res Commun 1991;178:1386-92
   PubMed Web of Science ®Google Scholar
• Arrang JM, Garbarg M, Schwartz JC. Autoinhibition of brain histamine release mediated by a novel class (H3) of histamine receptors. Nature 1983;302:832-7
   PubMed Web of Science ®Google Scholar
• Lovenberg TW, Roland BL, Wilson SJ, et al. Cloning and functional expression of the human histamine H3 receptor. Mol Pharmacol 1999;55:1101-7
   PubMed Web of Science ®Google Scholar
• Oda T, Morikawa N, Saito Y, et al. Molecular cloning and characterization of a novel type of histamine receptor preferentially expressed in leukocytes. J Biol Chem 2000;275:36781-6
   PubMed Web of Science ®Google Scholar
• Stark H. Histamine receptors. Biotrend Rev 2007;11:1. Available from: www.biotrend.com/reviews [Last accessed 14 July 2009]
   Google Scholar
• Barak N. Betahistine: what's new on the agenda? Expert Opin Invest Drugs 2008;17:795-804
   PubMed Web of Science ®Google Scholar
• Leurs R, Smit MJ, Timmerman H. Molecular pharmacological aspects of histamine receptors. Pharmacol Ther 1995;66:413-63
   PubMed Web of Science ®Google Scholar
• Hill SJ. Distribution, properties and functional characteristics of three classes of histamine receptor. Pharmacol Rev 1990;42:45-83
   PubMed Web of Science ®Google Scholar
• Barbier AJ, Berridge C, Dugovic C, et al. Acute wake-promoting actions of JNJ-5207852, a novel, diamine-based H3 antagonist. Br J Pharmacol 2004;143:649-61
   PubMed Web of Science ®Google Scholar
• Malmlof K, Hohlweg R, Rimvall K. Targeting of the central histaminergic system for treatment of obesity and associated metabolic disorders. Drug Dev Res 2006;67:651-65
   Web of Science ®Google Scholar
• Malmlof K, Zaragoza F, Golozonbova V, et al. Influence of a selective histamine H3 receptor antagonist on hypothalamic neural activity, food intake and body weight. Int J Obes 2005;29:1402-12
   Web of Science ®Google Scholar
• Thurmond RL, Gelfand EW, Dunford PJ. The role of histamine H1 and H4 receptors in allergic inflammation: the search for new antihistamines. Nat Rev Drug Discov 2008;7:41-53
   PubMed Web of Science ®Google Scholar
• de Esch IJP, Thurmond RL, Jongejan A, et al. The histamine H4 receptor as a new therapeutic target for inflammation. Trends Pharm Sci 2005;26:462-9
   PubMed Web of Science ®Google Scholar
• Conelly WM, Shenton FC, Lethbridge N, et al. The histamine H4 receptor is functionally expressed on neurons in the mammalian CNS. Br J Pharmacol 2009;157:55-63
   PubMed Web of Science ®Google Scholar
• Henderson R, Baldwin JM, Ceska TA, et al. Model for the structure of bacteriorhodopsin based on high-resolution electron cryo-microscopy. J Mol Biol 1990;213:899-929
   PubMed Web of Science ®Google Scholar
• Palczewski K, Kumasaka T, Hori T, et al. Crystal structure of rhodopsin: a G protein-coupled receptor. Science 2000;289:739-45
   PubMed Web of Science ®Google Scholar
• Cherezov V, Rosenbaum DM, Hanson MA, et al. High-resolution crystal structure of an engineered human β2-adrenergic G protein-coupled receptor. Science 2007;318:1258-65
   PubMed Web of Science ®Google Scholar
• Rasmussen SGF, Choi HJ, Rosenbaum DM, et al. Crystal structure of the human β2 adrenergic G-protein-coupled receptor. Nature 2007;450:383-7
   PubMed Web of Science ®Google Scholar
• Rosenbaum DM, Cherezov V, Hanson MA, et al. GPCR engineering yields high-resolution structural insights into β2-adrenergic receptor function. Science 2007;318:1266-73
   PubMed Web of Science ®Google Scholar
• Warne T, Serrano-Vega MJ, Baker JG, et al. Structure of a β1-adrenergic G-protein-coupled receptor. Nature 2008;454:486-91
   PubMed Web of Science ®Google Scholar
• Jaakola VP, Griffith MT, Hanson MA, et al. The 2.6 Å crystal structure of a human A2A adenosine receptor bound to an antagonist. Science 2008;322:1211-17
   PubMed Web of Science ®Google Scholar
• Scheerer P, Park JH, Hildebrand PW, et al. Crystal structure of opsin in its G-protein-interacting conformation. Nature 2008;455:497-502
   PubMed Web of Science ®Google Scholar
• Niv MY, Skrabanek L, Filizola M, Weinstein H. Modeling activated states of GPCRs: the rhodopsin template. J Comput Aided Mol Des 2006;20:437-48
   PubMed Web of Science ®Google Scholar
• Straßer A, Wittmann HJ. Analysis of the activation mechanism of the guinea-pig histamine H1-receptor. J Comput Aided Mol Des 2007;21:499-509
   PubMed Web of Science ®Google Scholar
• Jongejan A, Lim HD, Smits RA, et al. Delineation of agonist binding to the human histamine H4 receptor using mutational analysis, homology modeling, and ab initio calculations. J Chem Inf Model 2008;48:1455-63
   PubMed Web of Science ®Google Scholar
• Bakker RA, Jongejan A, Sansuk K, et al. Constitutively active mutants of the histamine H1 receptor suggest a conserved hydrophobic asparagine-cage that constrains the activation of class A G-protein coupled receptors. Mol Pharmacol 2008;73:94-103
   PubMed Web of Science ®Google Scholar
• Lim HD, Jongejan A, Bakker RA, et al. Phenylalanine 169 in the second extracellular loop of the human histamine H4 receptor is responsible for the difference in agonist binding between human and mouse H4 receptors. J Pharmacol Exp Ther 2008;327:88-96
   PubMed Web of Science ®Google Scholar
• Shishoo CJ, Shirsath VS, Rathod IS, Yande VD. Design, synthesis and antihistaminic (H1) activity of some condensed 3-aminopyrimidin-4(3H)-ones. Eur J Med Chem 2000;35:351-8
   PubMed Web of Science ®Google Scholar
• Govoni M, Bakker RA, van de Wetering I, et al. Synthesis and pharmacological identification of neutral histamine H1-receptor antagonists. J Med Chem 2003;46:5812-24
   PubMed Web of Science ®Google Scholar
• Saxena M, Gaur S, Prathipati P, Saxena AK. Synthesis of some substituted pyrazinopyridoindoles and 3D QSAR studies along with related compounds: Piperazines, piperidines, pyrazinoisoquinolines, and diphenhydramine, and its semi-rigid analogs as antihistamines (H1). Bioorg Med Chem 2006;14:8249-58
   PubMed Web of Science ®Google Scholar
• Matsumoto Y, Funahashi J, Mori K, et al. The noncompetititve antagonism of histamine H1 receptors expressed in chinese hamster ovary cells by olopatadine hydrochloride: its potency and molecular mechanism. Pharmacology 2008;81:266-74
   PubMed Web of Science ®Google Scholar
• Bruysters M, Jongejan A, Akdemir A, et al. A Gq/11-coupled mutant histamine H1 receptor F435A activated solely by synthetic ligands (RASSL). J Biol Chem 2005;280:34741-6
   PubMed Web of Science ®Google Scholar
• Jongejan A, Bruysters M, Ballesteros JA, et al. Linking agonist binding to histamine H1 receptor activation. Nat Chem Biol 2005;1:98-103
   PubMed Web of Science ®Google Scholar
• Elz S, Kramer K, Pertz HH, et al. Histaprodifens: synthesis, pharmacological in vitro evaluation, and molecular modeling of a new class of highly active and selective histamine H1-receptor agonists. J Med Chem 2000;43:1071-84
   PubMed Web of Science ®Google Scholar
• Jongejan A, Leurs R. Delineation of receptor-ligand interactions at the human histamine H1 receptor by a combined approach of site-directed mutagenesis and computational techniques – or – how to bind the H1 receptor. Arch Pharm Chem Life Sci 2005;338:248-59
   PubMed Web of Science ®Google Scholar
• Strasser A, Striegl B, Wittmann HJ, Seifert R. Pharmacologcial profile of histaprodifens at four recombinant histamine H1 receptor species isoforms. J Pharm Exp Ther 2008;324:60-71
   PubMed Web of Science ®Google Scholar
• Strasser A, Wittmann HJ, Seifert R. Ligand-specific contribution of the N terminus and E2-loop to pharmacological properties of the histamine H1-receptor. J Pharm Exp Ther 2008;326:783-91
   PubMed Web of Science ®Google Scholar
• Seifert R, Wenzel-Seifert K, Bürckstümmer T, et al. Multiple differences in agonist and antagonist pharmacology between human and guinea pig histamine H1-receptor. J Pharmacol Exp Ther 2003;305:1104-15
   PubMed Web of Science ®Google Scholar
• Bruysters M, Jongejan A, Gillard M, et al. Pharmacological differences between human and guinea pig histamine H1 receptors: Asn84 (2.61) as key residue within an additional binding pocket in the H1 receptor. Mol Pharmacol 2005;67:1045-52
   PubMed Web of Science ®Google Scholar
• Strasser A, Wittmann HJ, Kunze M, et al. Molecular basis for the selective interaction of synthetic agonists with the human histamine H1-receptor compared with the guinea-pig H1-receptor. Mol Pharmacol 2009;75:454-65
   PubMed Web of Science ®Google Scholar
• Wittmann HJ, Seifert R, Strasser A. Contribution of binding enthalpy and entropy to affinity of antagonist and agonist binding at human and guinea-pig histamine H1-receptor. Mol Pharmacol 2009;76:25-37
   PubMed Web of Science ®Google Scholar
• Dove S, Buschauer A. Imidazolylpropylguanidines as histamine H2 receptor agonists: 3D-QSAR of a large series. Pharm Acta Helv 1998;73:145-55
   PubMedGoogle Scholar
• Kelley MT, Bürckstümmer T, Wenzel-Seifert K, et al. Distinct interaction of human and guinea pig histamine H2-receptor with guanidine-type agonists. Mol Pharmacol 2001;60:1210-25
   PubMed Web of Science ®Google Scholar
• Preuss H, Ghorai P, Kraus A, et al. Point mutations in the second extracellular loop of the histamine H2 receptor do not affect the species-selective activity of guanidine-type agonists. Naunyn Schmiedebergs Arch Pharmacol 2007;376:253-64
   PubMed Web of Science ®Google Scholar
• Lorenzi S, Mor M, Bordi F, et al. Validation of a histamine H3 receptor model through structure-activity relationships for classical H3 antagonists. Bioorg Med Chem 2005;13:5647-57
   PubMed Web of Science ®Google Scholar
• Ghorai P, Kraus A, Keller M, et al. Acylguanidines as bioisosteres of guanidines: NG-acylated imidazolylpropylguanidines, a new class of histamine H2 receptor agonists. J Med Chem 2008;51:7193-204
   PubMed Web of Science ®Google Scholar
• Kraus A, Ghorai P, Birnkammer T, et al. NG-acylated aminothiazolylpropylguanidines as potent and selective histamine H2 receptor agonists. ChemMedChem 2009;4:232-40
   PubMed Web of Science ®Google Scholar
• Watanabe M, Kazuta J, Hayashi H, et al. Stereochemical diversity-oriented conformational restriction strategy. Development of potent histamine H3 and/or H4 receptor antagonists with imidazolylcyclopropane structure. J Med Chem 2006;49:5587-96
   PubMed Web of Science ®Google Scholar
• Sasse A, Sadek B, Ligneau X, et al. New histamine H3-receptor ligands of the proxifan series: imoproxifan and other selective antagonists with high oral in vivo potency. J Med Chem 2000;43:3335-43
   PubMed Web of Science ®Google Scholar
• Stark H, Ligneau X, Sadek B, et al. Analogues and derivatives of ciproxifan, a novel prototype for generating potent histamine H3-receptor antagonists. Bioorg Med Chem Lett 2000;10:2379-80
   PubMed Web of Science ®Google Scholar
• Vacondio F, Mor M, Silva C, et al. Imidazole H3-antagonists: relationship between structure and ex vivo binding to rat brain H3-receptors. Eur J Pharm Sci 2004;23:89-98
   PubMed Web of Science ®Google Scholar
• de Esch IJP, Timmerman H, Menge WMPB, et al. A qualitative model for the histamine H3-receptor explaining agonistic and antagonistic activity simultaneously. Arch Pharm Pharm Med Chem 2000;333:254-60
   PubMed Web of Science ®Google Scholar
• Windhorst AD, Timmerman H, Worthington EA, et al. Characterization of the binding site of the histamine H receptor. 2. Synthesis, in vitro pharmacology, and QSAR of a series of monosubstituted benzyl analogues of thioperamide. J Med Chem 2000;43:1754-61
   PubMed Web of Science ®Google Scholar
• Stark H, Sippl W, Ligneau X, et al. Different antagonist binding properties of human and rat histamine H3 receptors. Bioorg Med Chem Lett 2001;11:951-4
   PubMed Web of Science ®Google Scholar
• Yao BB, Hutchins CW, Carr TL, et al. Molecular modelling and pharmacological analysis of species-related histamine H3 receptor heterogeneity. Neuropharmacology 2003;44:773-86
   PubMed Web of Science ®Google Scholar
• Uveges AJ, Kowal D, Zhang Y, et al. The role of transmembrane helix 5 in agonist binding to the human H3 receptor. J Pharmacol Exp Ther 2002;301:451-8
   PubMed Web of Science ®Google Scholar
• Chen HF. Computational study of histamine H3-receptor antagonist with support vector machines and three dimension quantitative structure activity relationship methods. Anal Chim Acta 2008;624:203-9
   PubMed Web of Science ®Google Scholar
• Schlegel B, Laggner C, Meier R, et al. Generation of a homology model of the human histamine H3 receptor for ligand docking and pharmacophore-based screening. J Comput Aided Mol Des 2007;21:437-53
   PubMed Web of Science ®Google Scholar
• Roche O, Rodriguez Sarmiento MR. A new class of histamine H3 receptor antagonists derived from ligand based design. Bioorg Med Chem Lett 2007;17:3670-5
   PubMed Web of Science ®Google Scholar
• Roche O, Nettekoven M, Vifian W, Rodriguez Sarmiento MR. Refinement of histamine H3 ligands pharmacophore model leads to a new class of potent and selective naphthalene inverse agonists. Bioorg Med Chem Lett 2008;18:4377-9
   PubMed Web of Science ®Google Scholar
• Rodriguez Sarmiento MR, Nettekoven MH, Taylor S, et al. Selective naphthalene H3 receptor inverse agonists with reduced potential to induce phospholipidosis and their quinoline analogs. Bioorg Med Chem Lett 2009;15:4495-500
   Google Scholar
• Pierson PD, Fettes A, Freichel C, et al. 5-Hydroxyindole-2-carboxylic acid amides: novel histamine-3 receptor inverse agonists for the treatment of obesity. J Med Chem 2009;52:3855-68
   PubMed Web of Science ®Google Scholar
• Axe FU, Bembenek SD, Szalma S. Three-dimensional models of histamine H3 receptor antagonist complexes and their pharmacophore. J Mol Graph Model 2006;24:456-64
   PubMed Web of Science ®Google Scholar
• Dastmalchi S, Hamzeh-Mivehroud M, Ghafourian T, Hamzely H. Molecular modelling of histamine H3 receptor and QSAR studies on arylbenzofuran derived H3 antagonists. J Mol Graph Model 2008;26:834-44
   PubMed Web of Science ®Google Scholar
• Lim HD, Istyastono EP, van de Stolpe A, et al. Clobenpropit analogs as dual activity ligands for the histamine H3 and H4 receptors: synthesis, pharmacological evaluation, and cross-target QSAR studies. Bioorg Med Chem 2009;17:3987-94
   PubMed Web of Science ®Google Scholar
• Wijtmans M, Celanire S, Snip E, et al. 4-Benzyl-1H-imidazoles with oxazoline termini as histamine H3 receptor agonists. J Med Chem 2008;51:2944-53
   PubMed Web of Science ®Google Scholar
• Liu H, Altenbach RJ, Carr TL, et al. cis-4-(Piperazin-1-yl)-5,6,7a,8,9,10,11, 11a-octahydrobenzofurol[2,3-h]quinazolin-2-amine (A-987306), a new histamine H4R antagonist, that blocks pain responses against carrageenan-induced hyperalgesia. J Med Chem 2008;51:7094-8
   PubMed Web of Science ®Google Scholar
• Igel P, Schneider E, Schnell D, et al. NG-acylated imidazolylpropylguanidines as potent histamine H4 receptor agonists: selectivity by variation of the NG-substituent. J Med Chem 2009;52:2623-7
   PubMed Web of Science ®Google Scholar
• Hashimoto T, Harusawa S, Araki L, et al. A selective human H4-receptor agonist: (-)-2-cyano-1-methyl-3-{(2R,5R)-5-[1H-imidazol-4(5)-yl] tetrahydrofuran-2-yl}methylguanidine. J Med Chem 2003;46:3162-5
   PubMed Web of Science ®Google Scholar
• Terzioglu N, van Rijn RM, Bakker RA, et al. Synthesis and structure-activity relationships of indole and benzimidazole piperazines as histamine H4 receptor antagonists. Bioorg Med Chem Lett 2004;14:5251-6
   PubMed Web of Science ®Google Scholar
• Lim HD, Smits RA, Bakker RA, et al. Discovery of S-(2-Guanidylethyl)-isothiourea (VUF8430) as a potent nonimidazole histamine H4 receptor agonists. J Med Chem 2006;49:6650-1
   PubMed Web of Science ®Google Scholar
• Cowart MD, Altenbach RJ, Liu H, et al. Rotationally constrained 2,4-diamino5,6-substituted pyrimidines: a new class of histamine H4 receptor antagonists with improved druglikeness and in vivo efficacy in pain and inflammation models. J Med Chem 2008;51:6547-57
   PubMed Web of Science ®Google Scholar
• Smits RA, Lim HD, Stegink B, et al. Characterization of the histamine H4 receptor binding site. Part 1. Synthesis and pharmacological evaluation dibenzodiazepine derivatives. J Med Chem 2006;49:4512-16
   PubMed Web of Science ®Google Scholar
• Smits RA, Lim HD, Hanzer A, et al. Fragment based design of new H4 receptor ligands with anti-inflammatory properties in vivo. J Med Chem 2008;51:2457-67
   PubMed Web of Science ®Google Scholar
• Smits RA, de Esch IJP, Zuiderveld OB, et al. Discovery of quinazolines as histamine H4 receptor inverse agonists using a scaffold hopping approach. J Med Chem 2008;51:7855-65
   PubMed Web of Science ®Google Scholar
• Shin N, Coates E, Murgolo NJ, et al. Molecular modeling and site-specific mutagenesis of the histamine-binding site of the histamine H4 receptor. Mol Pharmacol 2002;62:38-47
   PubMed Web of Science ®Google Scholar
• Jojart B, Kiss R, Viskolcz B, Keseru G. Activation mechanism of the human histamine H4 receptor – an explicit membrane molecular dynamics simulation study. J Chem Inf Model 2008;48:1199-210
   PubMed Web of Science ®Google Scholar
• Kiss R, Kiss B, Konczol A, et al. Discovery of novel human histamine H4 receptor ligands by large-scale structure-based virtual screening. J Med Chem 2008;51:3145-53
   PubMed Web of Science ®Google Scholar
• Lim HD, van Rijn RM, Ling P, et al. Evaluation of histamine H1-, H2-, and H3-receptor ligands at the human histamine H4 receptor: Identification of 4-methylhistamine as the first potent and selective H4 receptor agonist. J Pharmacol Exp Ther 2005;314:1310-21
   PubMed Web of Science ®Google Scholar
• Lim HD, Smits RA, Bakker RA, et al. Discovery of S-(2-Guanidylethyl)-isothiourea (VUF8430) as a potent nonimidazole histamine H4 receptor agonist. J Med Chem 2006;49:6650-1
   PubMed Web of Science ®Google Scholar
• Ballesteros JA, Shi L, Javitch JA. Structural mimikry in G protein-coupled receptors: implications of the high resolution structure of rhodopsin for structure-function analysis of rhodopsin-like receptors. Mol Pharmacol 2001;60:1-19
   PubMed Web of Science ®Google Scholar