The importance of drug-target residence time

Current Opinion in Drug Discovery and Development

Volumn 12, Issue 4, 2009, Pages 488-496

  Zhang, Rumin ^a   Monsma, Frederick ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Binding kinetics; Drug design; Drug target residence time; Enthalpy; Entropy; High performance assay; Koffversus IC50 Ki relation; Slow binding inhibitor; Time dependent inhibition

Indexed keywords

ACETYLSALICYLIC ACID; CANDESARTAN; DARUNAVIR; DESLORATADINE; OMEPRAZOLE; PROTEIN TYROSINE KINASE INHIBITOR;

DECISION MAKING; DRUG DESIGN; DRUG EFFICACY; DRUG SAFETY; DRUG SOLUBILITY; DRUG TARGET RESIDENCE TIME; DRUG TARGETING; HUMAN; IC 50; MEAN RESIDENCE TIME; OUTCOMES RESEARCH; REVIEW;

DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DELIVERY SYSTEMS; DRUG DISCOVERY; MODELS, BIOLOGICAL; PHARMACEUTICAL PREPARATIONS; PHARMACOKINETICS; PROTEIN BINDING; STRUCTURE-ACTIVITY RELATIONSHIP; TIME FACTORS;

EID: 67649973722     PISSN: 13676733     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (55)

1. Kola I, Landis J: Can the pharmaceutical industry reduce attrition rates? Nat Rev Drug Discov (2004) 3(8):711-715.
2. Tummino PJ, Copeland RA: Residence time of receptor-ligand complexes and its effect on biological function. Biochemistry(2008) 47(20):5481-5492. ·· Articulates the arithmetic of model-sensitive residence time and its important roles in the physiology and pharmacology in non-equilibrium open systems such as the human body.
3. Leysen JE, Gommeren W: Drug-receptor dissociation time, new tool for drug research: Receptor binding affinity and drug-receptor dissociation profiles of serotonin-S2, dopamine-D2, histamine-H1 antagonists, and opiates.Drug Dev Res (1986) 8(1-4):119-131. · An early paper supporting the use of slow dissociating inhibitors in drug discovery.
4. Swinney DC: The role of binding kinetics in therapeutically useful drug action. Curr Opin Drug Discovery Dev (2009) 12(1): 31-39. ·· A comprehensive review covering many issues related to drug-binding kinetics.
5. Swinney DC: Applications of binding kinetics to drug discovery: Translation of binding mechanisms to clinically differentiated therapeutic responses. Int J Pharm Med (2008) 22(1):23-34. ·· Highlights binding kinetics and efficient mechanisms for mechanismand non-mechanism-based toxicity.
6. Swinney DC: Can binding kinetics translate to a clinically differentiated drug? From theory to practice. Lett Drug Des Disc (2006) 3(8):569-574.
7. 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(5):461-478.
8. Swinney DC: Biochemical mechanisms of drug action: What does it take for success? Nat Rev Drug Discov (2004) 3(9):801-808. ·· Introduces the concept of biochemical efficiency.
9. Copeland RA, Pompliano DL, Meek TD: Drug-target residence time and its implications for lead optimization. Nat Rev Drug Disc (2006) 5(9):730-739. ·· Introduces the concept of the importance of long dissociative half time for suitable drug efficacy.
10. van Liefde I, Vauquelin G: Sartan-AT1 receptor interactions: In vitro evidence for insurmountable antagonism and inverse agonism. Mol Cell Endocrinol (2009) 302(2):237-243.
11. Vauquelin G, van Liefde I: Slow antagonist dissociation and long-lasting in vivo receptor protection. Trends Pharmacol Sci(2006) 27(7):356-359.
12. Vauquelin G, Fierens F, van Liefde I: Long-lasting angiotensin type 1 receptor binding and protection by candesartan: Comparison with other biphenyl-tetrazole sartans.J Hypertens Suppl (2006) 24(1):S23-S30.
13. Anthes JC, Gilchrest H, Richard C, Eckel S, Hesk D, West RE Jr, Williams SM, Greenfeder S, Billah M, Kreutner W, Egan RE: Biochemical characterization of desloratadine, a potent antagonist of the human histamine H1 receptor. Eur J Pharmacol (2002) 449(3):229-237.
14. Maillard MP, Perregaux C, Centeno C, Stangier J, Wienen W, Brunner HR, Burnier M: In vitro and in vivo characterization of the activity of telmisartan: An insurmountable angiotensin II receptor antagonist. J Pharmacol Exp Ther (2002) 302(3):1089-1095.
15. Dierynck I, De Wit M, Gustin E, Keuleers I, Vandersmissen J, Hallenberger S, Hertogs K: Binding kinetics of darunavir to human immunodeficiency virus type 1 protease explain the potent antiviral activity and high genetic barrier. J Virol(2007) 81(24):13845-13851.
16. Roth GJ, Majerus PW: The mechanism of the effect of aspirin on human platelets. I. Acetylation of a particulate fraction protein. J Clin Invest (1975) 56(3):624-632.
17. Wallmark B, Brändström A, Larsson H: Evidence for acid-induced transformation of omeprazole into an active inhibitor of (H+ + K+)-ATPase within the parietal cell. Biochim Biophys Acta (1984) 778(3):549-558.
18. Kohout TA, Xie Q, Reijmers S, Finn KJ, Guo Z, Zhu YF, Struthers RS: Trapping of a nonpeptide ligand by the extracellular domains of the gonadotropin-releasing hormone receptor results in insurmountable antagonism.Mol Pharmacol (2007) 72(2):238-247.
19. Ehlert FJ: On the analysis of ligand-directed signaling at G protein-coupled receptors. Naunyn Schmiedebergs Arch Pharmacol (2008) 377(4-6):549-577.
20. Michel MC, Alewijnse AE: Ligand-directed signaling: 50 ways to find a lover. Mol Pharmacol (2007) 72(5):1097-1099.
21. Ohlson S: Designing transient binding drugs: A new concept for drug discovery. Drug Disc Today (2008) 13(9-10):433-439. ·· Advocates a radical concept for transient-binding drugs.
22. Lipton SA: Paradigm shift in neuroprotection by NMDA receptor blockade: Memantine and beyond. Nat Rev Drug Discov (2006) 5(2):160-170.
23. Karaman MW, Herrgard S, Treiber DK, Gallant P, Atteridge CE, Campbell BT, Chan KW, Ciceri P, Davis MI, Edeen PT, Faraoni R et al: A quantitative analysis of kinase inhibitor selectivity.Nat Biotechnol (2008) 26(1):127-132.
24. Zhang X, Crespo A, Fernández A: Turning promiscuous kinase inhibitors into safer drugs. Trends Biotechnol (2008) 26(6): 295-301.
25. LoRusso PM, Eder JP: Therapeutic potential of novel selective-spectrum kinase inhibitors in oncology.Expert Opin Invest Drugs (2008) 17(7):1013-1028.
26. Heise CE, Sullivan SK, Crowe PD: Scintillation proximity assay as a high-throughput method to identify slowly dissociating nonpeptide ligand binding to the GnRH receptor.J Biomol Screen (2007) 12(2):235-239.
27. Rich RL, Papalia GA, Flynn PJ, Furneisen J, Quinn J, Klein JS, Katsamba PS, Waddell MB, Scott M, Thompson J, Berlier J et al: A global benchmark study using affinity-based biosensors.Anal Biochem (2009) 386(2):194-216.
28. Shiau AK, Massari ME, Ozbal CC: Back to basics: Label-free technologies for small molecule screening. Comb Chem High Throughput Screen (2008) 11(3):231-237.
29. Rich RL, Myszka DG: Higher-throughput, label-free, real-time molecular interaction analysis. Anal Biochem (2007) 361(1): 1-6.
30. Cheng Y, Prusoff WH: Relationship between the inhibition constant (Ki) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem Pharmacol (1973) 22(23):3099- 3108.
31. Yang J, Copeland RA, Lai Z: Defining balanced conditions for inhibitor screening assays that target bisubstrate enzymes.J Biomol Screen (2009) 14(2):111-120.
32. Murphy DJ: Determination of accurate Ki values for tight-binding enzyme inhibitors: An in silico study of experimental error and assay design. Anal Biochem (2004) 327(1):61-67.
33. Kuzmic? P, Elrod KC, Cregar LM, Sideris S, Rai R, Janc JW: High-throughput screening of enzyme inhibitors: Simultaneous determination of tight-binding inhibition constants and enzyme concentration. Anal Biochem (2000) 286(1):45-50.
34. Grime KH, Bird J, Ferguson D, Riley RJ: Mechanism-based inhibition of cytochrome P450 enzymes: An evaluation of early decision making in vitro approaches and drug-drug interaction prediction methods. Eur J Pharm Sci (2009) 36(2-3):175-191.
35. Fowler S, Zhang H: In vitro evaluation of reversible and irreversible cytochrome P450 inhibition: Current status on methodologies and their utility for predicting drug-drug interactions. AAPS J (2008) 10(2):410-424.
36. Tang W, Stearns RA, Wang RW, Miller RR, Chen Q, Ngui J, Bakshi RK, Nargund RP, Dean DC, Baillie TA: Assessing and minimizing time-dependent inhibition of cytochrome P450 3A in drug discovery: A case study with melanocortin-4 receptor agonists. Xenobiotica (2008) 38(11):1437-1451.
37. Berry LM, Zhao Z: An examination of IC50 and IC50-shift experiments in assessing time-dependent inhibition of CYP3A4, CYP2D6 and CYP2C9 in human liver microsomes.Drug Metab Lett (2008) 2(1):51-59.
38. Peletier LA, Benson N, van der Graaf PH: Impact of plasmaprotein binding on receptor occupancy: An analytical description. J Theor Biol (2009) 256(2):253-262.
39. Cohen C, Samuel G, Fischel O: Computer-assisted drug design, where do we stand? Chimica Oggi (2004) 22(3-4):22-26.
40. Kumar SK, Babu SP: Bioinformatics in drug design and development. Pharma Times (2007) 39(1):26-29.
41. Villaverde MC, González-Louro L, Sussman F: The search for drug leads targeted to the β-secretase: An example of the roles of computer assisted approaches in drug discovery.Curr Top Med Chem (2007) 7(10):980-990.
42. Goldberg DR, Hao MH, Qian KC, Swinamer AD, Gao DA, Xiong Z, Sarko C, Berry A, Lord J, Magolda RL, Fadra T et al: Discovery and optimization of p38 inhibitors via computer-assisted drug design. J Med Chem (2007) 50(17):4016-4026.
43. Gedeck P, Lewis RA: Exploiting QSAR models in lead optimization. Curr Opin Drug Discovery Dev (2008) 11(4): 569-575.
44. Müller W, Crothers DM. Studies of the binding of actinomycin and related compounds to DNA. J Mol Biol (1968) 35(2): 251-290. · An early report on the kinetic differentiation of DNA intercalators caused by slow binding.
45. Kumar P, Han BC, Shi Z, Jia J, Wang YP, Zhang YT, Liang L, Liu QF, Ji ZL, Chen YZ: Kinetic data of bio-molecular interaction database. Nucleic Acids Res (2009) 37:D636-D641.
46. Adebambo KF, Zanoli S, Thomas MG, Cancio R, Howarth NM, Maga G: N2-benzyloxycarbonylguan-9-yl acetic acid derivatives as HIV-1 reverse transcriptase non-nucleoside inhibitors with decreased loss of potency against common drug-resistance mutations. ChemMedChem (2007) 2(10): 1405-1409.
47. Kaplan AP, Bartlett PA: Synthesis and evaluation of an inhibitor of carboxypeptidase A with a ki value in the femtomolar range. Biochem (1991) 30(33):8165-8170.
48. Shaikh SA, Jain T, Sandhu G, Latha N, Jayaram B: From drug target to leads-sketching a physicochemical pathway for lead molecule design in silico. Curr Pharm Des (2007) 13(34): 3454-3470.
49. Chaires JB: Calorimetry and thermodynamics in drug design.Annu Rev Biophys (2008) 37:135-151. · Illustrates with examples the use of thermodynamic insight for drug discovery.
50. Li L, Dantzer JJ, Nowacki J, O'Callaghan BJ, Meroueh SO: PDBcal: A comprehensive dataset for receptor-ligand interactions with three-dimensional structures and binding thermodynamics from isothermal titration calorimetry.Chem Biol Drug Des (2008) 71(6):529-532.
51. Starikov EB, Nordén B: Enthalpy-entropy compensation: A phantom or something useful? J Phys Chem B (2007) 111(51):14431- 14435.
52. Ohtaka H, Muzammil S, Schon A, Velazquez-Campoy A, Vega S, Freire E: Thermodynamic rules for the design of high affinity HIV-1 protease inhibitors with adaptability to mutations and high selectivity towards unwanted targets. Int J Biochem Cell Biol (2004) 36(9):1787-1799. · Introduces the enthalpy funnel hypothesis.
53. Freire E: Do enthalpy and entropy distinguish first in class from best in class? Drug Disc Today (2008) 13(19-20):869-874. · Emphasizes the use of enthalpic-driven binders as starting points for drug design.
54. Papalia GA, Giannetti AM, Arora N, Myszka DG: Thermodynamic characterization of pyrazole and azaindole derivatives binding to p38 mitogen-activated protein kinase using Biacore T100 technology and van't Hoff analysis. Anal Biochem(2008) 383(2):255-264.
55. Gavina JM, Mazhab-Jafari MT, Melacini G, Britz-McKibbin P: Label-free assay for thermodynamic analysis of proteinligand interactions: A multivariate strategy for allosteric ligand screening. Biochemistry (2009) 48(2):223-225.