Rebinding: or why drugs may act longer in vivo than expected from their in vitro target residence time

Bibliography

• Shimada S, Nakajima Y, Yamamoto K, Comparative pharmacodynamics of eight calcium channel blocking agents in Japanese essential hypertensive patients. Biol Pharm Bull 1996;19:430-7
   PubMed Web of Science ®Google Scholar
• Mager DE, Wyska E, Jusko WJ. Diversity of mechanism-based pharmacodynamic models. Drug Metab Dispos 2003;31:510-19
   PubMed Web of Science ®Google Scholar
• Ploeger BA, van der Graaf PH, Danhof M. Incorporating receptor theory in mechanism-based pharmacokinetic-pharmacodynamic (PK-PD) modeling. Drug Metab Pharmacokinet 2009;24:3-15
   PubMed Web of Science ®Google Scholar
• Swinney DC. Biochemical mechanisms of drug action: what does it take for success? Nat Rev Drug Discov 2004;3:801-8
   PubMed Web of Science ®Google Scholar
• Swinney DC. Biochemical mechanisms of new molecular entities (NMEs) approved by United States FDA during 2001-2004: mechanisms leading to optimal efficacy and safety. Curr Top Med Chem 2006;6:461-78
   PubMed Web of Science ®Google Scholar
• Swinney DC. Can binding kinetics translate to a clinically differentiated drug? From theory to practice. Lett Drug Des Discov 2006;3:569-74
   Web of Science ®Google Scholar
• Swinney DC. Applications of binding kinetics to drug discovery: Translation of binding mechanisms to clinically differentiated therapeutic responses. Int J Pharm Med 2008;22:23-34
   Google Scholar
• Swinney DC. The role of binding kinetics in therapeutically useful drug action. Curr Opin Drug Discov Devel 2009;12:31-9
   PubMed Web of Science ®Google Scholar
• Copeland RA, Pompliano DL, Meek TD. Drug-target residence time and its implications for lead optimization. Nat Rev Drug Discov 2006;5:730-9
   PubMed Web of Science ®Google Scholar
• Tummino PJ, Copeland RA. Residence time of receptor-ligand complexes and its effect on biological function. Biochemistry 2008;47:5481-92
   PubMed Web of Science ®Google Scholar
• Copeland RA. The dynamics of drug-target interactions: drug-target residence time and its impact on efficacy and safety Expert Opin Drug Discov 2010;5:305-10
   PubMed Web of Science ®Google Scholar
• Zhang R, Monsma F. The importance of drug-target residence time. Curr Opin Drug Discov Devel 2009;12:488-96
   PubMed Web of Science ®Google Scholar
• Vauquelin G, Van Liefde I. Slow antagonist dissociation and long-lasting in vivo receptor protection. Trends Pharmacol Sci 2006;27:356-9
   PubMed Web of Science ®Google Scholar
• Vauquelin G, Fierens F, Van Liefde I. Long-lasting AT1 receptor binding and protection by Candesartan: comparison to other biphenyl-tetrazole sartans. J Hypertens 2006;24:S23-30
   Web of Science ®Google Scholar
• Kapur S, Seeman P. Antipsychotic agents differ in how fast they come off the dopamine D2 receptors. Implications for atypical antipsychotic action. J Psychiatry Neurosci 2000;25:161-6
   PubMed Web of Science ®Google Scholar
• Kapur S, Seeman P. Does fast dissociation from the dopamine d(2) receptor explain the action of atypical antipsychotics?: a new hypothesis. Am J Psychiatry 2001;158:360-9
   PubMed Web of Science ®Google Scholar
• Perry DC, Mullis KB, Oie S, Sadee W. Opiate antagonist receptor binding in vivo: evidence for a new receptor binding model. Brain Res 1980;199:49-61
   PubMed Web of Science ®Google Scholar
• Motulsky HJ, Mahan LC. The kinetics of competitive radioligand binding predicted by the law of mass action. Mol Pharmacol 1984;25:1-9
   PubMed Web of Science ®Google Scholar
• Dowling MR, Charlton SJ. Quantifying the association and dissociation rates of unlabelled antagonists at the muscarinic M3 receptor. Br J Pharmacol 2006;148:927-37
   PubMed Web of Science ®Google Scholar
• Hara M, Kiyama R, Nakajima S, Kinetic studies on the interaction of nonlabelled antagonists with the angiotensin II receptor. Eur J Pharmacol 1995;289:267-73
   PubMed Web of Science ®Google Scholar
• Vanderheyden PML, Fierens FLP, De Backer J-P, Vauquelin G. Reversible and syntopic interaction between angiotensin II AT1 receptor antagonists and human AT1 receptors expressed in CHO-K1 cells. Biochem Pharmacol 2000;59:927-35
   PubMed Web of Science ®Google Scholar
• Heise CE, Sullivan S, Crowe PD. Scintillation proximity assay as high-throughput method to identify slowly dissociating nonpeptide ligand binding to the GnRH receptor. J Biomol Screen 2007;12:235-9
   PubMed Web of Science ®Google Scholar
• Malany S, Hernandez LM, Smith WF, Analytical method for simultaneously measuring ex vivo drug receptor occupancy and dissociation rate: application to (R)-dimethindene occupancy of central histamine H1 receptors. J Recept Signal Transduct Res 2009;29:84-93
   PubMed Web of Science ®Google Scholar
• Packeu A, Wennerberg M, Ballendran A, Vauquelin G. Estimation of the dissociation rate of unlabelled ligand-receptor complexes by a ‘two-step’ competition binding approach. Br J Pharmacol 2010; In press
   PubMed Web of Science ®Google Scholar
• Vauquelin G, Szczuka A. Kinetic versus allosteric mechanisms to explain insurmountable antagonism and delayed ligand dissociation. Neurochem Int 2007;51:254-60
   PubMed Web of Science ®Google Scholar
• Fierens FLP, Vanderheyden PML, De Backer J-P, Vauquelin G. Binding of the antagonist [3H]candesartan to angiotensin II AT1 receptor-transfected Chinese hamster ovary cells. Eur J Pharmacol 1999;367:413-22
   PubMed Web of Science ®Google Scholar
• Limbird LE. Cell surface receptors: a short course in theory and methods. Limbird LE, editor. Kluwer Academic Publishers, Boston; 1996. p. 61-122
   Google Scholar
• Silhavy TJ, Szmelcman S, Boos W, Schwartz M. On the significance of the retention of ligand by protein. Proc Natl Acad Sci USA 1975;72:2120-4
   PubMed Web of Science ®Google Scholar
• De Meyts P. Cooperative properties of hormone receptors in cell membranes. J Supramol Struct 1976;4:241-58
   PubMedGoogle Scholar
• Le MT, Pugsley M, Vauquelin G, Van Liefde I. Angiotensin II AT1 antagonism and insurmountability: comparison of olmesartan and telmisartan. Br J Pharmacol 2007;151:952-62
   PubMed Web of Science ®Google Scholar
• Packeu A, De Backer J-P, Van Liefde I, Antagonist-dopamine D2L-receptor interactions in intact cells. Biochem Pharmacol 2008;75:2192-203
   PubMedGoogle Scholar
• Wennerberg M, Cheng L, Hjorth S, Binding properties of antagonists to CB1 cannabinoid receptors in intact cells. Fundam Clin Pharmacol 2010; In press
   PubMed Web of Science ®Google Scholar
• Vauquelin G, Charlton S. Long-lasting target binding and rebinding as mechanisms to prolong in vivo drug action. Br J Pharmacol 2010; In press
   Web of Science ®Google Scholar
• Christopoulos A, Kenakin T. G protein-coupled receptor allosterism and complexing. Pharmacol Rev 2003;54:323-74
   Web of Science ®Google Scholar
• Goldstein B, Posner RG, Torney DC, Competition between solution and cell surface receptors for ligand. Dissociation of hapten bound to surface antibody in the presence of solution antibody. Biophys J 1989;56:955-66
   PubMed Web of Science ®Google Scholar
• Ojima M, Inada Y, Shibouta Y, Candesartan (CV-11974) dissociates slowly from the angiotensin ATl receptor. Eur J Pharmacol 1997;319:137-46
   PubMed Web of Science ®Google Scholar
• Morsing P, Adler G, Brandt-Eliasson U, Mechanistic differences of various AT1-receptor blockers in isolated vessels of different origin. Hypertension 1999;33:1406-13
   PubMed Web of Science ®Google Scholar
• Robertson MJ, Barnes JC, Drew GM, Clark KL, Pharmacological profile of GR 117289 in vitro: a novel potent and specific non-peptide angiotensin ATl receptor antagonist. Br J Pharmacol 1992;107:1173-80
   PubMed Web of Science ®Google Scholar
• Sadee W, Perry DC, Rosenbaum JS, Herz A. [3H]-diprenorphine receptor binding in vivo and in vitro. Eur J Pharmacol 1982;81:431-40
   PubMed Web of Science ®Google Scholar
• Gifford AN, Gatley J, Volkow ND. Evaluation of the importance of rebinding to receptors in slowing the approach to equilibrium of high-affinity PET and SPECT radiotracers. Synapse 1998;28:167-75
   PubMed Web of Science ®Google Scholar
• Delacretaz E, Nussberger J, Biollaz J, Characterization of the angiotensin II receptor antagonist TCV-116 in healthy volunteers. Hypertension 1995;25:14-21
   PubMed Web of Science ®Google Scholar
• Israili ZH. Clinical pharmacokinetics of angiotensin II (AT1) receptor blockers in hypertension. J Hum Hypertens. 2000;14(Suppl 1):S73-86
   PubMedGoogle Scholar
• Sutter A, Riopelle RG, Harris-Warrick RM, Shooter EM. Nerve growth factor receptors. Characterization of two distinct classes of binding sites on chick embryo sensory ganglia cells. J Biol Chem 1979;254:5972-82
   PubMed Web of Science ®Google Scholar
• Frost JJ, Wagner HR Jr. Kinetics of binding to opiate receptors in vivo predicted from in vitro parameters. Brain Res 1984;305:1-11
   PubMed Web of Science ®Google Scholar
• Kopelman R. Fractal reaction kinetics. Science 1988;241:1620-6
   PubMed Web of Science ®Google Scholar
• Schnell S, Turner TE. Reaction kinetics in intracellular environments with macromolecular crowding: simulations and rate laws. Prog Biophys Mol Biol 2004;85:235-60
   PubMed Web of Science ®Google Scholar
• Posner RG, Le BJ, Conrad DH, Aggregation of IgE-receptor complexes on rat basophilic leukemia cells does not change the intrinsic affinity but can alter the kinetics of the ligand-IgE interaction. Biochemistry 1992;31:5350-6
   PubMed Web of Science ®Google Scholar
• Goldstein B, Dembo M. Approximating the effects of diffusion on reversible reactions at the cell surface: ligand-receptor kinetics. Biophys J 1995;68:1222-30
   PubMed Web of Science ®Google Scholar
• Coombs D, Goldstein B. Effects of geometry of the immunological synapse on the delivery of effector molecules. Biophys J 2004;87:2215-20
   PubMed Web of Science ®Google Scholar
• DeLisi C. The effect of cell size and receptor density on ligand - receptor reaction rate constants. Mol Immunol 1981;18:507-11
   PubMed Web of Science ®Google Scholar
• DeLisi C, Wiegel FW. Effect of nonspecific forces and finite receptor number on rate constants of ligand - cell bound-receptor interactions. Proc Natl Acad Sci USA 1981;78:5569-72
   PubMed Web of Science ®Google Scholar
• Berg HC, Purcell EM. Physics of chemoreception. Biophys J 1977;20:193-219
   PubMed Web of Science ®Google Scholar
• Lovich MA, Creel C, Hong K, Carrier proteins determine local pharmacokinetics and arterial distribution of paclitaxel. J Pharm Sci 2001;90:1324-35
   PubMed Web of Science ®Google Scholar
• Hrabctova S, Nicholson C. Contribution of dead-space microdomains to tortuosity of brain extracellular space. Neurochem Int 2004;45:467-77
   PubMed Web of Science ®Google Scholar
• Dokoumetzidis A, Karalis V, Iliadis A, Macheras P. The heterogeneous course of drug transit through the body. Trends Pharmacol Sci 2004;25:140-6
   PubMed Web of Science ®Google Scholar
• Dityatev A, Schacher M. The extracellular matrix and synapses. Cell Tissue Res 2006;326:647-54
   PubMed Web of Science ®Google Scholar
• Pang KS, Weiss M, Macheras P. Advanced pharmacokinetic models based on clearance circulatory and fractal concepts. AAPS J 2007;9:E268-83
   PubMed Web of Science ®Google Scholar
• Vargova L, Sykova E. Extracellular space diffusion and extrasynaptic transmission. Physiol Res 2008;57:S89-99
   PubMed Web of Science ®Google Scholar
• Kane BE, Grant MKO, El-Fakahany EE, Ferguson DSM. Synthesis and evaluation of xanomeline analogs – probing the wash-resistant phenomenon at the M1 muscarinic acetylcholine receptor. Bioorg Med Chem 2008;16:1376-92
   PubMed Web of Science ®Google Scholar
• Sargent DF, Bean JW, Schwyzer R. Conformation and orientation of regulatory peptides on lipid membranes. Key to the molecular mechanism of receptor selection. Biophys Chem 1988;31:183-93
   PubMed Web of Science ®Google Scholar
• Herbette LG, Trumbore M, Chester DW, Katz AM. Possible molecular basis for the pharmacokinetics and pharmacodynamics of three membrane-active drugs: propranolol nimodipine and amiodarone. J Mol Cell Cardiol 1988;20:373-8
   PubMed Web of Science ®Google Scholar
• Vauquelin G, Packeu A. Ligands their receptors and plasma membranes. Mol Cell Endocrinol 2009;311:1-10
   PubMed Web of Science ®Google Scholar
• Adam G, Delbruck M. Reduction of dimensionality in biological diffusion processes. In: Rich A, Davidson N, editors, Structural chemistry and molecular biology. Freeman, Co., San Francisco; 1968. p. 198-215
   Google Scholar
• Schwyzer R. 100 Years lock-and-key concept: are peptide keys shaped and guided to their receptors by the target cell membrane? Biopolymers 1995;37:5-16
   PubMed Web of Science ®Google Scholar
• Sargent DF, Schwyzer R. Membrane lipid phase as catalyst for peptide-receptor interactions. Proc Natl Acad Sci USA 1986;83:5774-8
   PubMed Web of Science ®Google Scholar
• Rhodes DG, Newton R, Butler R, Herbette L. Equilibrium and kinetic studies of the interactions of salmeterol with membrane bilayers. Mol Pharmacol 1992;42:596-602
   PubMed Web of Science ®Google Scholar
• Szczuka A, Packeu A, Wennerberg M, Vauquelin G. Molecular mechanism of the persistent bronchodilatory effect of the partial beta2-adrenoceptor agonist salmeterol. Br J Pharmacol 2009;158:183-94
   PubMed Web of Science ®Google Scholar
• Anderson GP. Formoterol: pharmacology molecular basis of agonism and mechanism of long duration of a highly potent and selective beta2-adrenoceptor agonist bronchodilator. Life Sci 1993;52:2145-60
   PubMed Web of Science ®Google Scholar
• Coleman RA, Johnson M, Nials AT, Vardey CJ. Exosites: their current status and their relevance to the duration of action of long-acting beta2-adrenoceptor agonists. Trends Pharmacol Sci 1996;17:324-30
   PubMed Web of Science ®Google Scholar
• Christopoulos A, Pierce TL, Sorman JL, El-Fakahany EE. On the unique binding and activating properties of xanomeline at the M1 muscarinic acetylcholine receptor. Mol Pharmacol 1998;53:1120-30
   PubMed Web of Science ®Google Scholar
• Coleman RA. On the mechanism of the persistent action of salmeterol: what is the current position? Br J Pharmacol 2009;158:180-2
   PubMed Web of Science ®Google Scholar
• Nieba L, Krebber A, Pluckthun A. Competition BIAcore for measuring true affinities: large differences from values determined from binding kinetics. Anal Biochem 1996;234:155-65
   PubMed Web of Science ®Google Scholar
• Schuck P, Minton AP. Analysis of mass transport-limited binding kinetics in evanescent wave biosensors. Anal Biochem 1996;240:262-72
   PubMed Web of Science ®Google Scholar
• Myszka DG, He X, Dembo M, Extending the range of rate constants available from BIACORE: interpreting mass transport-influenced binding data. Biophys J 1998;75:583-94
   PubMed Web of Science ®Google Scholar
• Christensen LLH. Theoretical analysis of protein concentration determination using biosensor technology under conditions of partial mass transport limitation. Anal Biochem 1997;249:153-64
   PubMed Web of Science ®Google Scholar
• Vauquelin G, Morsing P, Fierens FLP, A two-state receptor model for the interaction between angiotensin II AT1 receptors and their non-peptide antagonists. Biochem Pharmacol 2001;61:277-84
   PubMed Web of Science ®Google Scholar
• Charlton S, Vauquelin G. Elusive equilibrium: the challenge of interpreting receptor pharmacology using calcium assays. Br J Pharmacol 2010; In press
   Web of Science ®Google Scholar
• Verheijen I, Fierens FLP, De Backer J-P, Interaction between the partially insurmountable antagonist valsartan and human recombinant angiotensin II type 1 receptors. Fundam Clin Pharmacol 2000;14:577-85
   PubMed Web of Science ®Google Scholar
• Spivak CE, Oz M, Beglan CL, Shrager RI. Diffusion delays and unstirred layer effects at monolayer cultures of Chinese hamster ovary cells: radioligand binding confocal microscopy and mathematical simulations. Cell Biochem Biophys 2006;45:43-58
   PubMed Web of Science ®Google Scholar
• Innis RB, Cunningham VJ, Delforge J, Consensus nomenclature for in vivo imaging of reversibly binding radioligands. J Cereb Blood Flow Metab 2007;27:1533-39
   PubMed Web of Science ®Google Scholar
• Fierens F, Vanderheyden PML, Roggeman C, Distinct binding properties of the AT1 receptor antagonist [3H]candesartan to intact cells and membrane preparations. Biochem Pharmacol 2002;63:1273-9
   PubMed Web of Science ®Google Scholar
• Hara M, Tozawa F, Itazaki K, Endothelin ET(B) receptors show different binding profiles in intact cells and cell membrane preparations. Eur J Pharmacol 1998;345:339-42
   PubMed Web of Science ®Google Scholar
• Verheijen I, Tourlousse D, Vanderheyden PML, Effect of saponin and filipin on antagonist binding to AT1 receptors in intact cells. Biochem Pharmacol 2004;67:601-6
   PubMedGoogle Scholar
• Grießner M, Broker P, Lehmann A, Detection of angiotensin II type 1 receptor ligands by a cell-based assay. Anal Bioanal Chem 2009;395:1937-40
   PubMed Web of Science ®Google Scholar
• Cunningham VJ, Hume SP, Price GR, Compartmental analysis of diprenorphine binding to opiate receptors in the rat in vivo and its comparison with equilibrium data in vitro. J Cereb Blood Flow Metab 1991;11:1-9
   PubMed Web of Science ®Google Scholar
• Frost JJ. PET Imaging of the opioid receptor: the early years. Med Mol Biol 2001;28:509-13
   Web of Science ®Google Scholar
• Votaw JR, Kessler RM, de Paulis T. Failure of the three compartment model to describe the pharmacokinetics in brain of a high affinity substituted benzamide. Synapse 1993;15:177-90
   PubMed Web of Science ®Google Scholar
• Moerlein SM, Perlmutter JS, Markham J, Welch MJ. In vivo kinetics of [18F](N-methyl)benperidol: a novel PET tracer for assessment of dopaminergic D2-like receptor binding. J Cereb Blood Flow Metab 1997;17:833-45
   PubMed Web of Science ®Google Scholar
• Syrota A, Paillotin G, Davy JM, Aumont MC. Kinetics of in vivo binding of antagonist to muscarinic cholinergic receptor in the human heart studied by positron emission tomography. Life Sci 1984;27:937-45
   Google Scholar
• Syrota A, Comar D, Paillotin G, Muscarinic cholinergic receptor in the human heart evidenced under physiological conditions by positron emission tomography. Proc Natl Acad Sci USA 1985;82:584-8
   PubMed Web of Science ®Google Scholar
• Delforge J, Le Guludec D, Syrota A, Bendriem B. Quantification of myocardial muscarinic receptors with PET in humans. J Nucl Med 1993;34:981-91
   PubMed Web of Science ®Google Scholar
• Visser TJ, van Waarde A, van der Mark TW, Detection of muscarinic receptors in the human lung using PET. J Nucl Med 1999;40:1270-6
   PubMed Web of Science ®Google Scholar
• Delforge J, Syrota A, Lançon J-P, Cardiac beta-adrenergic receptor density measured in vivo using PET, CGP 12177, and a new graphical mehod. J Nucl Med 1991;32:739-48
   PubMed Web of Science ®Google Scholar
• Li Z-B, Niu G, Wang H, Imaging of urokinase-type plasminogen activator receptor expression using a 64Cu-labeled linear peptide antagonist by microPET. Clin Cancer Res 2008;14:4758-66
   PubMed Web of Science ®Google Scholar
• Mansi R, Wang X, Forrer F, Evaluation of a 1,4,7, 10-tetraazacyclododecane-1,4, 7,10-tetraacetic acid-conjugated bombesin-based radio-antagonist for the labeling with single-photon emission computed tomography, positron emission tomography, and therapeutic radionuclides. Clin Cancer Res 2009;15:5240-9
   PubMed Web of Science ®Google Scholar
• Dijkgraaf I, Rijnders AY, Soede A, Synthesis of DOTA-conjugated multivalent cyclic-RGD peptide dendrimers via 1,3-dipolar cycloaddition and their biological evaluation: implications for tumor targeting and tumor imaging purposes. Org Biomol Chem 2007;5:935-44
   PubMed Web of Science ®Google Scholar
• Schottelius M, Wester HJ. Molecular imaging targeting peptide receptors. Methods 2009;48:161-77
   PubMed Web of Science ®Google Scholar
• Fujita M, Imaizumi M, Zoghbi SS, Kinetic analysis in healthy humans of a novel positron emission tomography radioligand to image the peripheral benzodiazepine receptor, a potential biomarker for inflammation. Neuroimage 2008;40:43-52
   PubMed Web of Science ®Google Scholar
• Terry GE, Liow JS, Zoghbi SS, Quantitation of cannabinoid CB1 receptors in healthy human brain using positron emission tomography and an inverse agonist radioligand. Neuroimage 2009;48:362-70
   PubMed Web of Science ®Google Scholar
• Seneca N, Caia L, Liowa J-S, Brain and whole-body imaging in nonhuman primates with [11C]MeS-IMPY, a candidate radioligand for beta-amyloid plaques. Nucl Med Biol 2007;34:681-9
   PubMed Web of Science ®Google Scholar