3-Methoxylphenylpropyl amides as novel receptor subtype-selective melatoninergic ligands: Characterization of physicochemical and pharmacokinetic properties

Xenobiotica

Volumn 41, Issue 1, 2011, Pages 35-45

  Zhu, Jing ^a   Hu, Yueqing ^a   Ho, Maurice K C ^a   Wong, Yung H ^a,b  

^a Biotechnology Research Institute   (Hong Kong)

^b HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

Melatonin receptor; Metabolic stability; Metabolite profiling; MT2 selective agonist; Permeability

Indexed keywords

3 METHOXYLPHENYLPROPYL AMIDE; CYTOCHROME P450; DRUG METABOLITE; MELATONIN; MELATONIN 2 RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; BINDING AFFINITY; BLOOD BRAIN BARRIER; CANCER CELL; CANCER CELL CULTURE; CELL MEMBRANE PERMEABILITY; CENTRAL NERVOUS SYSTEM; CLINICAL EVALUATION; COLORECTAL CARCINOMA; DRUG ABSORPTION; DRUG BINDING; DRUG DEGRADATION; DRUG DISTRIBUTION; DRUG HALF LIFE; DRUG METABOLISM; DRUG PENETRATION; DRUG PROTEIN BINDING; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG TRANSFORMATION; DRUG TRANSPORT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; IN VITRO STUDY; INTESTINE EPITHELIUM; LIPOPHILICITY; LIVER METABOLISM; NONHUMAN; PHYSICAL CHEMISTRY; PLASMA PROTEIN BINDING;

AMIDES; ANIMALS; BLOOD PROTEINS; CACO-2 CELLS; CELL MEMBRANE PERMEABILITY; CHROMATOGRAPHY, LIQUID; DOGS; DRUG STABILITY; HUMANS; LIGANDS; MASS SPECTROMETRY; MELATONIN; METABOLIC NETWORKS AND PATHWAYS; MICROSOMES, LIVER; P-GLYCOPROTEIN; PROTEIN BINDING; RATS; RECEPTORS, MELATONIN; SUBSTRATE SPECIFICITY; TIME FACTORS;

RATTUS;

EID: 78650220835     PISSN: 00498254     EISSN: 13665928     Source Type: Journal    
DOI: 10.3109/00498254.2010.524264     Document Type: Article

References (47)

1. Artursson P, Karlsson J. (1991). Correlation between oral drug absorption in humans and apparent drug permeability coefficients in human intestinal epithelial (Caco-2) cells. Biochem Biophys Res Commun 175:880-885.
2. Artursson P, Palm K, Luthman K. (2001). Caco-2 monolayers in experimental and theoretical predictions of drug transport. Adv Drug Deliv Rev 46:27-43.
3. Blask DE. (2009). Melatonin, sleep disturbance and cancer risk. Sleep Med Rev 13:257-264.
4. Beaulieu E, Demeule M, Ghitescu L, Béliveau R. (1997). P-glycoprotein is strongly expressed in the luminal membranes of the endothelium of blood vessels in the brain. Biochem J 326(Pt 2):539-544.
5. Beedham C, Smith JA, Steele DL, Wright PA. (1987). Chlorpromazine inhibition of melatonin metabolism by normal and induced rat liver microsomes. Eur J Drug Metab Pharmacokinet 12:299-302.
6. Buscemi N, Vandermeer B, Hooton N, Pandya R, Tjosvold L, Hartling L, Vohra S, Klassen TP, Baker G. (2006). Efficacy and safety of exogenous melatonin for secondary sleep disorders and sleep disorders accompanying sleep restriction: Meta-analysis. BMJ 332:385-393.
7. Cogburn JN, DonoVan MG, Schasteen CS. (1991). A model of human small intestinal absorptive cells. 1. Transport barrier. Pharm Res 8:210-216.
8. Chan AS, Lai FP, Lo RK, Voyno-Yasenetskaya TA, Stanbridge EJ, Wong YH. (2002). Melatonin mt1 and MT2 receptors stimulate c-Jun N-terminal kinase via pertussis toxin-sensitive and -insensitive G proteins. Cell Signal 14:249-257.
9. Davies B, Morris T. (1993). Physiological parameters in laboratory animals and humans. Pharm Res 10:1093-1095.
10. Dennis AS, Mark JA, Barry CJ. (1997). Properties of cytochrome P450 isoenzymes and their substrates Part 1: Active site characteristics. Drug Discov Today, 2:406-114.
11. Dolder CR, Nelson M, Snider M. (2008). Agomelatine treatment of major depressive disorder. Ann Pharmacother 42:1822-1831.
12. Ebisawa T, Karne S, Lerner MR, Reppert SM. (1994). Expression cloning of a high-affinity melatonin receptor from Xenopus dermal melanophores. Proc Natl Acad Sci USA 91:6133-6137.
13. Ganes DA, Hindmarsh KW, Midha KK. (1986). Doxylamine metabolism in rat and monkey. Xenobiotica 16:781-794.
14. Garberg P, Ball M, Borg N, Cecchelli R, Fenart L, Hurst RD, Lindmark T, Mabondzo A, Nilsson JE, Raub TJ, Stanimirovic D, Terasaki T, Oberg JO, Osterberg T. (2005). In vitro models for the blood-brain barrier. Toxicol In Vitro 19:299-334.
15. Gumbleton M, Audus KL. (2001). Progress and limitations in the use of in vitro cell cultures to serve as a permeability screen for the blood-brain barrier. J Pharm Sci 90:1681-1698.
16. Houston JB. (1994). Utility of in vitro drug metabolism data in predicting in vivo metabolic clearance. Biochem Pharmacol 47:1469-1479.
17. Hu Y, Ho MK, Chan KH, New DC, Wong YH. (2010). Synthesis of substituted N-[3-(3-methoxyphenyl)propyl] amides as highly potent MT(2)-selective melatonin ligands. Bioorg Med Chem Lett 20:2582-2585.
18. Iwatsubo T, Hirota N, Ooie T, Suzuki H, Shimada N, Chiba K, Ishizaki T, Green CE, Tyson CA, Sugiyama Y. (1997). Prediction of in vivo drug metabolism in the human liver from in vitro metabolism data. Pharmacol Ther 73:147-171.
19. Jusko WJ, Gretch M. (1976). Plasma and tissue protein binding of drugs in pharmacokinetics. Drug Metab Rev 5:43-140.
20. Kratochwil NA, Huber W, Müller F, Kansy M, Gerber PR. (2002). Predicting plasma protein binding of drugs: A new approach. Biochem Pharmacol 64:1355-1374.
21. Köppel C, Tenczer J, Arndt I, Ibe K. (1987). Urinary metabolism of chlorphenoxamine in man. Arzneimittelforschung 37:1062-1064.
22. Lai FP, Mody SM, Yung LY, Kam JY, Pang CS, Pang SF, Wong YH. (2002). Molecular determinants for the differential coupling of Galpha(16) to the melatonin MT1, MT2 and Xenopus Mel1c receptors. J Neurochem 80:736-745.
23. Lau YY, Krishna G, Yumibe NP, Grotz DE, Sapidou E, Norton L, Chu I, Chen C, Soares AD, Lin CC. (2002). The use of in vitro metabolic stability for rapid selection of compounds in early discovery based on their expected hepatic extraction ratios. Pharm Res 19:1606-1610.
24. Leo A, Hansch C, Elkins D. (1971) Partition coefficients and their uses. Chem Rev 71:525-616.
25. Liu C, Weaver DR, Jin X, Shearman LP, Pieschl RL, Gribkoff VK, Reppert SM. (1997). Molecular dissection of two distinct actions of melatonin on the suprachiasmatic circadian clock. Neuron 19:91-102.
26. Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. (1997). Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Delivery Rev 23:4-25.
27. Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW. (2002). Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther 303:1029-1037.
28. Mody SM, Hu Y, Ho MK, Wong YH. (2007). In search of novel and therapeutically significant melatoninergic ligands. Recent Pat CNS Drug Discov 2:241-245.
29. Nassar AE, Kamel AM, Clarimont C. (2004). Improving the decisionmaking process in the structural modification of drug candidates: Enhancing metabolic stability. Drug Discov Today 9:1020-1028.
30. New DC, Tsim ST, Wong YH. (2003). G protein-linked effector and second messenger systems involved in melatonin signal transduction. Neurosignals 12:59-70.
31. Pandi-Perumal SR, Srinivasan V, Poeggeler B, Hardeland R, Cardinali DP. (2007). Drug Insight: The use of melatonergic agonists for the treatment of insomnia-focus on ramelteon. Nat Clin Pract Neurol 3:221-228.
32. Reiter RJ, Tan DX, Fuentes-Broto L. (2010). Melatonin: A multitasking molecule. Prog Brain Res 181:127-151.
33. Reppert SM, Weaver DR, Ebisawa T. (1994). Cloning and characterization of a mammalian melatonin receptor that mediates reproductive and circadian responses. Neuron 13:1177-1185.
34. Reppert SM, Godson C, Mahle CD, Weaver DR, Slaugenhaupt SA, Gusella JF. (1995). Molecular characterization of a second melatonin receptor expressed in human retina and brain: The Mel1b melatonin receptor. Proc Natl Acad Sci USA 92: 8734-8738.
35. Rivara S, Vacondio F, Fioni A, Silva C, Carmi C, Mor M, Lucini V, Pannacci M, Caronno A, Scaglione F, Gobbi G, Spadoni G, Bedini A, Orlando P, Lucarini S, Tarzia G. (2009). N-(Anilinoethyl) amides:D esign and synthesis of metabolically stable, selective melatonin receptor ligands. ChemMedChem 4: 1746-1755.
36. Semak I, Korik E, Antonova M, Wortsman J, Slominski A. (2008). Metabolism of melatonin by cytochrome P450s in rat liver mitochondria and microsomes. J Pineal Res 45:515-523.
37. Slominski A, Tobin DJ, Zmijewski MA, Wortsman J, Paus R. (2008). Melatonin in the skin: Synthesis, metabolism and functions. Trends Endocrinol Metab 19:17-24.
38. SugDen D, Pickering H, Teh MT, Garratt PJ. (1997). Melatonin receptor pharmacology: Toward subtype specificity. Biol Cell 89: 531-537.
39. Tozer TN, Gambertoglio JG, Furst DE, Avery DS, Holford NH. (1983). Volume shifts and protein binding estimates using equilibrium dialysis: Application to prednisolone binding in humans. J Pharm Sci 72:1442-1446.
40. Uchikawa O, Fukatsu K, Tokunoh R, Kawada M, Matsumoto K, Imai Y, Hinuma S, Kato K, Nishikawa H, Hirai K, Miyamoto M, Ohkawa S. (2002). Synthesis of a novel series of tricyclic indan derivatives as melatonin receptor agonists. J Med Chem 45:4222-4239.
41. Van Den Heuvel CJ, Ferguson SA, Macchi MM, Dawson D. (2005). Melatonin as a hypnotic: Con. Sleep Med Rev 9:71-80.
42. Vanholder R, Van Landschoot N, De Smet R, Schoots A, Ringoir S. (1988) Drug protein binding in chronic renal failure: Evaluation of nine drugs. Kidney Int 33:996-1004.
43. Von Gall C, Stehle JH, Weaver DR. (2002). Mammalian melatonin receptors: Molecular biology and signal transduction. Cell Tissue Res 309:151-162.
44. Wallez V, Durieux-Poissonnier S, Chavatte P, Boutin JA, Audinot V, Nicolas JP, Bennejean C, Delagrange P, Renard P, Lesieur D. (2002). Synthesis and structure-affinity-activity relationships of novel benzofuran derivatives as MT(2) melatonin receptor selective ligands. J Med Chem 45:2788-2800.
45. Wang Q, Rager JD, Weinstein K, Kardos PS, Dobson GL, Li J, Hidalgo IJ. (2005). Evaluation of the MDR-MDCK cell line as a permeability screen for the blood-brain barrier. Int J Pharm 288: 349-359.
46. Yeleswaram K, McLaughlin LG, Knipe JO, Schabdach D. (1997). Pharmacokinetics and oral bioavailability of exogenous melatonin in preclinical animal models and clinical implications. J Pineal Res 22:45-51.
47. Zhu J, Lee S, Ho MKC, Hu Y, Pang H, Ip FCF, Chin AC, Harley CB, Ip NC, Wong YH. (2010). In vitro intestinal absorption and first-pass intestinal and hepatic metabolism of cycloastragenol, a potent small molecule telomerase activator. Drug Metabol Pharmacokin 25:478-487.