Role of phosphatidylserine binding in tissue distribution of amine-containing basic compounds

Expert Opinion on Drug Metabolism and Toxicology

Volumn 7, Issue 3, 2011, Pages 353-364

  Murakami, Teruo ^a   Yumoto, Ryoko ^a  

^a HIROSHIMA INTERNATIONAL UNIVERSITY   (Japan)

Author keywords

amine containing basic drugs; interorgan variation; moderately strong basic compounds; phosphatidylserine binding; tissue distribution; very weakly basic compounds

Indexed keywords

ACEBUTOLOL; ALFENTANIL; ALPRAZOLAM; AMINE; BETAXOLOL; BISOPROLOL; BUPIVACAINE; CHLORDIAZEPOXIDE; DESIPRAMINE; DIAZEPAM; DISOPYRAMIDE; FLECAINIDE; FLUNITRAZEPAM; GREPAFLOXACIN; IMIPRAMINE; LIDOCAINE; MEPIVACAINE; METOPROLOL; MEXILETINE; MIDAZOLAM; NORTRIPTYLINE; OXPRENOLOL; PHOSPHATIDYLSERINE; PINDOLOL; PROPRANOLOL; QUINIDINE; TIMOLOL; TRIAZOLAM; UNINDEXED DRUG; VERAPAMIL;

BINDING AFFINITY; BINDING KINETICS; BINDING SITE; CHEMICAL BINDING; CONTINUOUS INFUSION; DRUG BLOOD LEVEL; DRUG DOSE INCREASE; DRUG STRUCTURE; ENANTIOMER; HUMAN; NONHUMAN; PKA; REVIEW; TISSUE DISTRIBUTION;

AMINES; ANIMALS; CELL MEMBRANE; HUMANS; PHARMACEUTICAL PREPARATIONS; PHOSPHATIDYLSERINES; TISSUE DISTRIBUTION;

EID: 79951886926     PISSN: 17425255     EISSN: None     Source Type: Journal    
DOI: 10.1517/17425255.2011.548805     Document Type: Review

References (79)

1. Yanai S, Sugiyama Y, Kim DC, et al. Binding of human epidermal growth factor to tissue homogenates of the rat. (Pubitemid 18034754)
2. Kim DC, Sugiyama Y, Satoh H, et al. Kinetic analysis of in-vivo receptor-dependent binding of human epidermal growth factor by rat tissues. J Pharm Sci 1988;77:200-7
3. Shin HC, Kato Y, Shitara Y, et al. The endothelin receptor is a major determinant for the nonlinear tissue distribution of the endothelin antagonist BQ-123. J Pharmacol Exp Ther 1996;278:607-13 (Pubitemid 27167025)
4. Yamazaki M, Tokui T, Ishigami M, et al. Tissue-selective uptake of pravastatin in rats: contribution of a specific carrier-mediated uptake system. Biopharm Drug Dispos 1996;17:775-89 (Pubitemid 26401289)
5. Kusuhara H, Sugiyama Y. Role of transporters in the tissue-selective distribution and elimination of drugs: transporters in the liver, small intestine, brain and kidney. J Control Release 2002;78:43-54
6. Rowland M, Tozer TN. Clinical pharmacokinetics concepts and applications. 3rd edition. A Wolters Kluwer Company, Lippincott Williams & Wilkins; 1995
7. Ballard P, Leahy DE, Rowland M. Prediction of in vivo tissue distribution from in vitro data 1. Experiments with markers of aqueous spaces. Pharm Res 2000;17:660-3 (Pubitemid 30670629)
8. Terasaki T, Iga T, Sugiyama Y, Hanano M. Pharmacokinetic study on the mechanism of tissue distribution of doxorubicin: interorgan and interspecies variation of tissue-to-plasma partition coefficients in rats, rabbits, and guinea pigs. J Pharm Sci 1984;73:1359-63 (Pubitemid 14021881)
9. Terasaki T, Iga T, Sugiyama Y, Hanano M. Experimental evidence of characteristic tissue distribution of adriamycin. Tissue DNA concentration as a determinant. J Pharm Pharmacol 1982;34:597-600 (Pubitemid 12018063)
10. Terasaki T, Iga T, Sugiyama Y, Hanano M. Interaction of doxorubicin with nuclei isolated from rat liver and kidney. J Pharm Sci 1984;73:524-8 (Pubitemid 14134332)
11. Terasaki T, Iga T, Sugiyama Y, et al. Nuclear binding as a determinant of tissue distribution of adriamycin, daunomycin, adriamycinol, daunorubicinol and actinomycin D. J Pharmacobiodyn 1984;7:269-77 (Pubitemid 14062204)
12. Yata N, Toyoda T, Murakami T, et al. Phosphatidylserine as a determinant for the tissue distribution of weakly basic drugs in rats. Pharm Res 1990;7:1019-25
13. Wierzba K, Sugiyama Y, Okudaira K, et al. Tubulin as a major determinant of tissue distribution of vincristine. J Pharm Sci 1987;76:872-5 (Pubitemid 18006833)
14. Wierzba K, Sugiyama Y, Iga T, Hanano M. Kinetic study on the mechanism of tissue distribution of vinblastine. J Pharmacobiodyn 1988;11:651-61 (Pubitemid 18268038)
15. Harashima H, Mamiya M, Yamazaki M, et al. Significance of binding to Na, K-ATPase in the tissue distribution of ouabain in guinea pigs. Pharm Res 1992;9:474-9
16. Harashima H, Mamiya M, Yamazaki M, et al. Kinetic modeling of ouabain tissue distribution based on slow and saturable binding to Na,K-ATPase. Pharm Res 1992;9:1607-11
17. Houghton JA, Williams LG, Dodge RK, et al. Relationship between binding affinity, retention and sensitivity of human rhabdomyosarcoma xenografts to Vinca alkaloids. Biochem Pharmacol 1987;36:81-8 (Pubitemid 17227216)
18. Nishiura A, Higashi J, Murakami T, et al. A possible contribution of phospholipids in tissue distribution of quinidine in rats. J Pharmacobiodyn 1986;9:819-28 (Pubitemid 17203781)
19. Nishiura A, Murakami T, Higashi Y, Yata N. Role of acidic phospholipids in tissue distribution of quinidine in rats. J Pharmacobiodyn 1987;10:134-41
20. Klein CD, Klingmuller M, Schellinski C, et al. Synthesis, pharmacological and biophysical characterization, and membrane-interaction QSAR analysis of cationic amphiphilic model compounds. J Med Chem 1999;42:3874-88 (Pubitemid 29453468)
21. Fisar Z, Fuksova K, Velenovska M. Binding of imipramine to phospholipid bilayers using radioligand binding assay. Gen Physiol Biophys 2004;23:77-99 (Pubitemid 38735449)
22. Fisar Z. Interactions between tricyclic antidepressants and phospholipid bilayer membranes. Gen Physiol Biophys 2005;24:161-80 (Pubitemid 41195315)
23. Maeda Y, Funakoshi S, Nakamura M, et al. Possible mechanism for pharmacokinetic interaction between lidocaine and mexiletine. Clin Pharmacol Ther 2002;71:389-97 (Pubitemid 34518150)
24. Okeley NM, Gelb MH. A designed probe for acidic phospholipids reveals the unique enriched anionic character of the cytosolic face of the mammalian plasma membrane. J Biol Chem 2004;279:21833-40 (Pubitemid 38679372)
25. Gurtovenko AA, Vattulainen I. Membrane potential and electrostatics of phospholipid bilayers with asymmetric transmembrane distribution of anionic lipids. J Phys Chem B 2008;112:4629-34
26. Boggs JM. Lipid intermolecular hydrogen bonding: influence on structural organization and membrane function. Biochim Biophys Acta 1987;906:353-404 (Pubitemid 17140656)
27. Bauer M, Megret C, Lamure A, et al. Differential scanning calorimetry study of the interaction of antidepressant drugs, noradrenaline, and 5-hydroxytryptamine with a membrane model. J Pharm Sci 1990;79:897-901 (Pubitemid 20362814)
28. Tieleman DP, Marrink SJ, Berendsen HJC. A computer perspective of membranes: molecular dynamics studies of lipid bilayer systems. Biochim Biophys Acta 1997;1331:235-70 (Pubitemid 28015516)
29. Langner M, Kubica K. The electrostatics of lipid surfaces. Chem Phys Lipids 1999;101:3-35 (Pubitemid 29385548)
30. Poulin P, Theil F-P. A priori prediction of tissue:plasma partition coefficients of drugs to facilitate the use of physiologically-based pharmacokinetic models in drug discovery. J Pharm Sci 2000;89:16-35 (Pubitemid 30080151)
31. Rodgers T, Leahy D, Rowland M. Tissue distribution of basic drugs: accounting for enantiomeric, compound and regional differences amongst beta-blocking drugs in rat. J Pharm Sci 2005;94:1237-48 (Pubitemid 40904188)
32. Lombardo F, Obach RS, Shalaeva MY, Gao F. Prediction of volume of distribution values in humans for neutral and basic drugs using physicochemical measurements and plasma protein binding data. J Med Chem 2002;45:2867-76 (Pubitemid 34627657)
33. Adachi Y, Suzuki H, Sugiyama Y. Quantitative evaluation of the function of small intestinal P-glycoprotein: comparative studies between in situ and in vitro. Pharm Res 2003;20:1163-9 (Pubitemid 36951840)
34. Mizuno N, Niwa T, Yotsumoto Y, Sugiyama Y. Impact of drug transporter studies on drug discovery and development. Pharmacol Rev 2003;55:425-61 (Pubitemid 37013212)
35. Yoshida M, Kobunai T, Aoyagi K, et al. Specific distribution of TOP-53 to the lung and lung-localized tumor is determined by its interaction with phospholipids. Clin Cancer Res 2000;6:4396-401
36. Hanada K, Akimoto S, Mitsui K, et al. Enantioselective tissue distribution of the basic drugs disopyramide, flecainide and verapamil in rats: role of plasma protein and tissue phosphatidylserine binding. Pharm Res 1998;15:1250-6 (Pubitemid 28401717)
37. Mori Y, Hanada K, Mori T, et al. Stereoselective pharmacokinetics and pharmacodynamics of verapamil and norverapamil in rabbits. Biol Pharm Bull 2001;24:806-10 (Pubitemid 32633490)
38. Brocks DR. Drug disposition in three dimensions: an update on stereoselectivity in pharmacokinetics. Biopharm Drug Dispos 2006;27:387-406 (Pubitemid 44842300)
39. Suzuki T, Kato Y, Sasabe H, et al. Mechanism for the tissue distribution of grepafloxacin, a fluoroquinolone antibiotic, in rats. Drug Metab Dispos 2002;30:1393-9 (Pubitemid 35397044)
40. Sasabe H, Kato Y, Suzuki T, et al. Differential involvement of multidrug resistance-associated protein 1 and P-glycoprotein in tissue distribution and excretion of grepafloxacin in mice. J Pharmacol Exp Ther 2004;310:648-55 (Pubitemid 38988910)
41. Sasabe H, Kato Y, Suzuki T, et al. Carrier-mediated uptake of grepafloxacin, a fluoroquinolone antibiotic, by the isolated rat lung cells. Drug Metab Pharmacokinet 2005;20:491-5
42. Nishiura A, Murakami T, Higashi Y, Yata N. Role of phosphatidylserine in the cellular and subcellular lung distribution of quinidine in rats. Pharm Res 1988;5:209-13
43. Wojcikowski J, Daniel WA. Distribution interactions between perazine and antidepressant drugs. In vivo studies. Pol J Pharmacol 2000;52:449-57 (Pubitemid 32045908)
44. Wojcikowski J, Daniel WA. Thioridazine-fluoxetine interaction at the level of the distribution process in vivo. Pol J Pharmacol 2002;54:647-54 (Pubitemid 36124515)
45. Post C, Lewis DH. Displacement of nortriptyline and uptake of 14C-lidocaine in the lung after administration of 14C-lidocaine to nortriptyline intoxicated pigs. Acta Pharmacol Toxicol (Copenh) 1979;45:218-24 (Pubitemid 9257289)
46. Post C, Andersson RG. Interactions between lidocaine, norepinephrine and nortriptyline in rat lung slices. Acta Pharmacol Toxicol (Copenh) 1979;45:403-4 (Pubitemid 10165918)
47. Post C, Freedman J, Ramsay CH, Bonnevier A. Redistribution of lidocaine and bupivacaine after intrathecal injection in mice. Anesthesiology 1985;63:410-17 (Pubitemid 16236058)
48. Ohmura S, Yamamoto K, Kobayashi T, Murakami S. Displacement of lidocaine from the lung after bolus injection of bupivacaine. Can J Anaesth 1993;40:676-80 (Pubitemid 24214450)
49. Gueorguieva I, Nestorov IA, Murby S, et al. Development of a whole body physiologically based model to characterise the pharmacokinetics of benzodiazepines. 1: estimation of rat tissue-plasma partition ratios. J Pharmacokinet Pharmacodyn 2004;31:269-98 (Pubitemid 39287337)
50. Rodgers T, Rowland M. Physiologically based pharmacokinetic modelling 2: predicting the tissue distribution of acids, very weak bases, neutrals and zwitterions. J Pharm Sci 2006;95:1238-57 (Pubitemid 43874439)
51. Bjorkman S, Stanski DR, Verotta D, Harashima H. Comparative tissue concentration profiles of fentanyl and alfentanil in humans predicted from tissue/blood partition data obtained in rats. Anesthesiology 1990;72:865-73 (Pubitemid 20149223)
52. Bjorkman S. Prediction of the volume of distribution of a drug: which tissue-plasma partition coefficients are needed? J Pharm Pharmacol 2002;54:1237-45
53. Bjorkman S, Fyge A, Qi Z. Determination of the steady state tissue distribution of midazolam in the rat. J Pharm Sci 1996;85:887-9 (Pubitemid 26269488)
54. Klein CD, Klingmuller M, Schellinski C, et al. Synthesis, pharmacological and biophysical characterization, and membrane-interaction QSAR analysis of cationic amphiphilic model compounds. J Med Chem 1999;42:3874-88 (Pubitemid 29453468)
55. Kaufmann AM, Krise JP. Lysosomal sequestration of amine-containing drugs: analysis and therapeutic implications. J Pharm Sci 2007;96:729-46 (Pubitemid 46657864)
56. Duvvuri M, Konkar S, Funk RS, et al. A chemical strategy to manipulate the intracellular localization of drugs in resistant cancer cells. Biochemistry 2005;44:15743-9 (Pubitemid 41746905)
57. Schmucker DL, Mooney JS, Jones AL. Stereological analysis of hepatic fine structure in the Fischer 344 rat. Influence of sublobular location and animal age. J Cell Biol 1978;78:319-37 (Pubitemid 8403875)
58. Poulin P, Theil FP. Prediction of pharmacokinetics prior to in vivo studies 1. Mechanism-based prediction of volume of distribution. J Pharm Sci 2002;91:129-56 (Pubitemid 34074473)
59. Poulin P, Theil FP. Prediction of pharmacokinetics prior to in vivo studies II. Generic physiologically based pharmacokinetic models of drug disposition. J Pharm Sci 2002;91:1358-70 (Pubitemid 34651198)
60. Yokogawa K, Nakashima E, Ishizaki J, et al. Relationships in the structure-tissue distribution of basic drugs in the rabbits. Pharm Res 1990;7:691-706
61. Yokogawa K, Nakashima E, Ishizaki J, et al. Brain regional pharmacokinetics of biperiden in rats. Biopharm Drug Dispos 1992;13:131-40
62. Ishizaki J, Yokogawa K, Hirano M, et al. Contribution of lysosomes to the subcellular distribution of basic drugs in the rat liver. Pharm Res 1996;13:902-6 (Pubitemid 26227748)
63. Ishizaki J, Yokogawa K, Ichimura F, Ohkuma S. Uptake of imipramine in rat liver lysosomes in vitro and its inhibition by basic drugs. J Pharmacol Exp Ther 2000;294:1088-98 (Pubitemid 30666864)
64. Daniel WA, Bickel MH, Honegger UE. The contribution of lysosomal trapping in the uptake of desipramine and chloroquine by different tissues. Pharmacol Toxicol 1995;77:402-6
65. Daniel WA, Wojcikowski J. Interactions between promazine and antidepressants at the level of cellular distribution. Pharmacol Toxicol 1997;81:259-64 (Pubitemid 27511669)
66. Daniel WA, Wojcikowski J, Palucha A. Intracellular distribution of psychotropic drugs in the grey and white matter of the brain: the role of lysosomal trapping. Br J Pharmacol 2001;134:807-14 (Pubitemid 33016152)
67. Daniel WA. Mechanisms of cellular distribution of psychotropic drugs. Significance for drug action and interactions. Prog Neuropsychopharmacol Biol Psychiatry 2003;27:65-73 (Pubitemid 36126648)
68. Vitovic P, Alakoskela JM, Kinnunen PK. Assessment of drug-lipid complex formation by a high-throughput Langmuir-balance and correlation to phospholipidosis. J Med Chem 2008;51:1842-8 (Pubitemid 351444629)
69. Alakoskela JM, Vitovic P, Kinnunen PK. Screening for the drug-phospholipid interaction: correlation to phospholipidosis. ChemMedChem 2009;4:1224-51
70. Rodgers T, Leahy D, Rowland M. Physiologically based pharmacokinetic modeling 1: predicting the tissue distribution of moderate-to-strong bases. J Pharm Sci 2005;94:1259-76 (Pubitemid 40904190)
71. Poulin P, Theil F-P. Development of a novel method for predicting human volume of distribution at steady-state of basic drugs and comparative assessment with existing methods. J Pharm Sci 2009;98:4941-61
72. Utsugi T, Shibata J, Sugimoto Y, et al. Antitumor activity of a novel podophyllotoxin derivative (TOP-53) against lung cancer and lung metastatic cancer. Cancer Res 1996;56:2809-14 (Pubitemid 26176695)
73. Duca M, Guianvarch D, Meresse P, et al. Synthesis and biological study of a new series of 4-demethylepipodophyllotoxin derivatives. J Med Chem 2005;48:593-603 (Pubitemid 40139801)
74. Hay T, Jones R, Beaumont K, Kemp M. Modulation of the partition coefficient between octanol and buffer at pH 7.4 and pKa to achieve the optimum balance of blood clearance and volume of distribution for a series of tetrahydropyran histamine type 3 receptor antagonists. Drug Metab Dispos 2009;37(9):1864-70
75. de Wolf FA, Demel RA, Bets D, et al. Characterization of the interaction of doxorubicin with (poly)phosphoinositides in model systems. Evidence for specific interaction with phosphatidylinositolmonophosphate and -diphosphate. FEBS Lett 1991;288:237-40
76. de Wolf FA. Binding of doxorubicin to cardiolipin as compared to other anionic phospholipids-an evaluation of electrostatic effects. Biosci Rep 1991;11:275-84
77. de Wolf FA, Nicolay K, de Kruijff B. Effect of doxorubicin on the order of the acyl chains of anionic and zwitterionic phospholipids in liquid-crystalline mixed model membranes: absence of drug-induced segregation of lipids into extended domains. Biochemistry 1992;31:9252-62
78. de Wolf FA, Staffhorst RW, Smits HP, et al. Role of anionic phospholipids in the interaction of doxorubicin and plasma membrane vesicles: drug binding and structural consequences in bacterial systems. Biochemistry 1993;32:6688-95 (Pubitemid 23217139)
79. Speelmans G, Staffhorst RWHM, de Kruijff B. The anionic phospholipid-mediated membrane interaction of the anti-cancer drug doxorubicin is enhanced by phosphatidylethanolamine compared to other zwitterionic phospholipids. Biochemistry 1997;36:8657-62 (Pubitemid 27305151)