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

Bibliography

• Yanai S, Sugiyama Y, Kim DC, Binding of human epidermal growth factor to tissue homogenates of the rat. Chem Pharm Bull (Tokyo) 1987;35:4891-7
   PubMed Web of Science ®Google Scholar
• Kim DC, Sugiyama Y, Satoh H, Kinetic analysis of in-vivo receptor-dependent binding of human epidermal growth factor by rat tissues. J Pharm Sci 1988;77:200-7
   PubMed Web of Science ®Google Scholar
• Shin HC, Kato Y, Shitara Y, 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
   PubMed Web of Science ®Google Scholar
• Yamazaki M, Tokui T, Ishigami M, Tissue-selective uptake of pravastatin in rats: contribution of a specific carrier-mediated uptake system. Biopharm Drug Dispos 1996;17:775-89
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Rowland M, Tozer TN. Clinical pharmacokinetics concepts and applications. 3rd edition. A Wolters Kluwer Company, Lippincott Williams & Wilkins; 1995
   Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Terasaki T, Iga T, Sugiyama Y, Nuclear binding as a determinant of tissue distribution of adriamycin, daunomycin, adriamycinol, daunorubicinol and actinomycin D. J Pharmacobiodyn 1984;7:269-77
   PubMedGoogle Scholar
• Yata N, Toyoda T, Murakami T, Phosphatidylserine as a determinant for the tissue distribution of weakly basic drugs in rats. Pharm Res 1990;7:1019-25
   PubMed Web of Science ®Google Scholar
• Wierzba K, Sugiyama Y, Okudaira K, Tubulin as a major determinant of tissue distribution of vincristine. J Pharm Sci 1987;76:872-5
   PubMed Web of Science ®Google Scholar
• Wierzba K, Sugiyama Y, Iga T, Hanano M. Kinetic study on the mechanism of tissue distribution of vinblastine. J Pharmacobiodyn 1988;11:651-61
   PubMedGoogle Scholar
• Harashima H, Mamiya M, Yamazaki M, Significance of binding to Na,K-ATPase in the tissue distribution of ouabain in guinea pigs. Pharm Res 1992;9:474-9
   PubMed Web of Science ®Google Scholar
• Harashima H, Mamiya M, Yamazaki M, Kinetic modeling of ouabain tissue distribution based on slow and saturable binding to Na,K-ATPase. Pharm Res 1992;9:1607-11
   PubMed Web of Science ®Google Scholar
• Houghton JA, Williams LG, Dodge RK, Relationship between binding affinity, retention and sensitivity of human rhabdomyosarcoma xenografts to Vinca alkaloids. Biochem Pharmacol 1987;36:81-8
   PubMed Web of Science ®Google Scholar
• Nishiura A, Higashi J, Murakami T, A possible contribution of phospholipids in tissue distribution of quinidine in rats. J Pharmacobiodyn 1986;9:819-28
   PubMedGoogle Scholar
• 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
   PubMedGoogle Scholar
• Klein CD, Klingmuller M, Schellinski C, Synthesis, pharmacological and biophysical characterization, and membrane-interaction QSAR analysis of cationic amphiphilic model compounds. J Med Chem 1999;42:3874-88
   PubMed Web of Science ®Google Scholar
• Fisar Z, Fuksova K, Velenovska M. Binding of imipramine to phospholipid bilayers using radioligand binding assay. Gen Physiol Biophys 2004;23:77-99
   PubMed Web of Science ®Google Scholar
• Fisar Z. Interactions between tricyclic antidepressants and phospholipid bilayer membranes. Gen Physiol Biophys 2005;24:161-80
   PubMed Web of Science ®Google Scholar
• Maeda Y, Funakoshi S, Nakamura M, Possible mechanism for pharmacokinetic interaction between lidocaine and mexiletine. Clin Pharmacol Ther 2002;71:389-97
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Boggs JM. Lipid intermolecular hydrogen bonding: influence on structural organization and membrane function. Biochim Biophys Acta 1987;906:353-404
   PubMed Web of Science ®Google Scholar
• Bauer M, Megret C, Lamure A, 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Langner M, Kubica K. The electrostatics of lipid surfaces. Chem Phys Lipids 1999;101:3-35
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Mizuno N, Niwa T, Yotsumoto Y, Sugiyama Y. Impact of drug transporter studies on drug discovery and development. Pharmacol Rev 2003;55:425-61
   PubMed Web of Science ®Google Scholar
• Yoshida M, Kobunai T, Aoyagi K, 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
   PubMed Web of Science ®Google Scholar
• Hanada K, Akimoto S, Mitsui K, 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
   PubMed Web of Science ®Google Scholar
• Mori Y, Hanada K, Mori T, Stereoselective pharmacokinetics and pharmacodynamics of verapamil and norverapamil in rabbits. Biol Pharm Bull 2001;24:806-10
   PubMed Web of Science ®Google Scholar
• Brocks DR. Drug disposition in three dimensions: an update on stereoselectivity in pharmacokinetics. Biopharm Drug Dispos 2006;27:387-406
   PubMed Web of Science ®Google Scholar
• Suzuki T, Kato Y, Sasabe H, Mechanism for the tissue distribution of grepafloxacin, a fluoroquinolone antibiotic, in rats. Drug Metab Dispos 2002;30:1393-9
   PubMed Web of Science ®Google Scholar
• Sasabe H, Kato Y, Suzuki T, 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
   PubMed Web of Science ®Google Scholar
• Sasabe H, Kato Y, Suzuki T, Carrier-mediated uptake of grepafloxacin, a fluoroquinolone antibiotic, by the isolated rat lung cells. Drug Metab Pharmacokinet 2005;20:491-5
   PubMedGoogle Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Wojcikowski J, Daniel WA. Distribution interactions between perazine and antidepressant drugs. In vivo studies. Pol J Pharmacol 2000;52:449-57
   PubMedGoogle Scholar
• Wojcikowski J, Daniel WA. Thioridazine-fluoxetine interaction at the level of the distribution process in vivo. Pol J Pharmacol 2002;54:647-54
   PubMedGoogle Scholar
• 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
   PubMedGoogle Scholar
• Post C, Andersson RG. Interactions between lidocaine, norepinephrine and nortriptyline in rat lung slices. Acta Pharmacol Toxicol (Copenh) 1979;45:403-4
   PubMedGoogle Scholar
• Post C, Freedman J, Ramsay CH, Bonnevier A. Redistribution of lidocaine and bupivacaine after intrathecal injection in mice. Anesthesiology 1985;63:410-17
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Gueorguieva I, Nestorov IA, Murby S, 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Klein CD, Klingmuller M, Schellinski C, Synthesis, pharmacological and biophysical characterization, and membrane-interaction QSAR analysis of cationic amphiphilic model compounds. J Med Chem 1999;42:3874-88
   PubMed Web of Science ®Google Scholar
• Kaufmann AM, Krise JP. Lysosomal sequestration of amine-containing drugs: analysis and therapeutic implications. J Pharm Sci 2007;96:729-46
   PubMed Web of Science ®Google Scholar
• Duvvuri M, Konkar S, Funk RS, A chemical strategy to manipulate the intracellular localization of drugs in resistant cancer cells. Biochemistry 2005;44:15743-9
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Yokogawa K, Nakashima E, Ishizaki J, Relationships in the structure-tissue distribution of basic drugs in the rabbits. Pharm Res 1990;7:691-706
   PubMed Web of Science ®Google Scholar
• Yokogawa K, Nakashima E, Ishizaki J, Brain regional pharmacokinetics of biperiden in rats. Biopharm Drug Dispos 1992;13:131-40
   PubMed Web of Science ®Google Scholar
• Ishizaki J, Yokogawa K, Hirano M, Contribution of lysosomes to the subcellular distribution of basic drugs in the rat liver. Pharm Res 1996;13:902-6
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMedGoogle Scholar
• Daniel WA, Wojcikowski J. Interactions between promazine and antidepressants at the level of cellular distribution. Pharmacol Toxicol 1997;81:259-64
   PubMedGoogle Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Daniel WA. Mechanisms of cellular distribution of psychotropic drugs. Significance for drug action and interactions. Prog Neuropsychopharmacol Biol Psychiatry 2003;27:65-73
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Alakoskela JM, Vitovic P, Kinnunen PK. Screening for the drug-phospholipid interaction: correlation to phospholipidosis. ChemMedChem 2009;4:1224-51
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• Utsugi T, Shibata J, Sugimoto Y, Antitumor activity of a novel podophyllotoxin derivative (TOP-53) against lung cancer and lung metastatic cancer. Cancer Res 1996;56:2809-14
   PubMed Web of Science ®Google Scholar
• Duca M, Guianvarc'h D, Meresse P, Synthesis and biological study of a new series of 4′-demethylepipodophyllotoxin derivatives. J Med Chem 2005;48:593-603
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• de Wolf FA, Demel RA, Bets D, Characterization of the interaction of doxorubicin with (poly)phosphoinositides in model systems. Evidence for specific interaction with phosphatidylinositol-monophosphate and -diphosphate. FEBS Lett 1991;288:237-40
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar
• de Wolf FA, Staffhorst RW, Smits HP, 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
   PubMed Web of Science ®Google Scholar
• 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
   PubMed Web of Science ®Google Scholar