Cationic amphiphilic drugs cause a marked expansion of apparent lysosomal volume: Implications for an intracellular distribution-based drug interaction

Molecular Pharmaceutics

Volumn 9, Issue 5, 2012, Pages 1384-1395

  Funk, Ryan S ^a   Krise, Jeffrey P ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

cationic amphiphillic drug; drug interaction; lysosomal volume; lysosome; lysosomotropic; phospholipidosis

Indexed keywords

AMIODARONE; CHLORPROMAZINE; DAUNORUBICIN; IMIPRAMINE; IONOPHORE; METHYLAMINE; PROPRANOLOL;

ARTICLE; CELL PH; CELL VOLUME; CONTROLLED STUDY; DRUG ACCUMULATION; DRUG DISTRIBUTION; DRUG INTERACTION; HUMAN; HUMAN CELL; INTRACELLULAR DISTRIBUTION BASED DRUG INTERACTION; LYSOSOME; MICROSCOPY; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS;

BETA-CYCLODEXTRINS; CELL LINE; DRUG INTERACTIONS; HUMANS; HYDROGEN-ION CONCENTRATION; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; LYSOSOMES;

EID: 84860725460     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp200641e     Document Type: Article

References (58)

1. de Duve, C.; de Barsy, T.; Poole, B.; Trouet, A.; Tulkens, P.; Van Hoof, F. Commentary. Lysosomotropic agents Biochem. Pharmacol. 1974, 23 (18) 2495-531
2. Dean, R. T.; Jessup, W.; Roberts, C. R. Effects of exogenous amines on mammalian cells, with particular reference to membrane flow Biochem. J. 1984, 217 (1) 27-40
3. Hein, L.; Lullmann-Rauch, R.; Mohr, K. Human accumulation potential of xenobiotics: potential of catamphiphilic drugs to promote their accumulation via inducing lipidosis or mucopolysaccharidosis Xenobiotica 1990, 20 (11) 1259-67
4. Poole, B.; Ohkuma, S. Effect of weak bases on the intralysosomal pH in mouse peritoneal macrophages J. Cell Biol. 1981, 90 (3) 665-9
5. Ohkuma, S.; Poole, B. Cytoplasmic vacuolation of mouse peritoneal macrophages and the uptake into lysosomes of weakly basic substances J. Cell Biol. 1981, 90 (3) 656-64
6. Ohkuma, S.; Poole, B. Fluorescence probe measurement of the intralysosomal pH in living cells and the perturbation of pH by various agents Proc. Natl. Acad. Sci. U.S.A. 1978, 75 (7) 3327-31
7. Lullmann, H.; Lullmann-Rauch, R.; Wassermann, O. Drug-induced phospholipidoses. II. Tissue distribution of the amphiphilic drug chlorphentermine CRC Crit. Rev. Toxicol. 1975, 4 (2) 185-218
8. Halliwell, W. H. Cationic amphiphilic drug-induced phospholipidosis Toxicol. Pathol. 1997, 25 (1) 53-60
9. Reasor, M. J. Phospholipidosis in the alveolar macrophage induced by cationic amphiphilic drugs Fed. Proc. 1984, 43 (11) 2578-81
10. Yamamoto, A.; Adachi, S.; Kitani, T.; Shinji, Y.; Seki, K. Drug-induced lipidosis in human cases and in animal experiments. Accumulation of an acidic glycerophospholipid J. Biochem. 1971, 69 (3) 613-5
11. Yamamoto, A.; Adachi, S.; Ishikawa, K.; Yokomura, T.; Kitani, T. Studies on drug-induced lipidosis. 3. Lipid composition of the liver and some other tissues in clinical cases of "Niemann-Pick-like syndrome" induced by 4,4′-diethylaminoethoxyhexestrol J. Biochem. 1971, 70 (5) 775-84
12. Yoshikawa, H. Effects of drugs on cholesterol esterification in normal and Niemann-Pick type C fibroblasts: AY-9944, other cationic amphiphilic drugs and DMSO Brain Dev. 1991, 13 (2) 115-20
13. Roff, C. F.; Goldin, E.; Comly, M. E.; Cooney, A.; Brown, A.; Vanier, M. T.; Miller, S. P.; Brady, R. O.; Pentchev, P. G. Type C Niemann-Pick disease: use of hydrophobic amines to study defective cholesterol transport Dev. Neurosci. 1991, 13 (4-5) 315-9
14. Sakuragawa, N.; Sakuragaw, M.; Kuwabara, T.; Pentchev, P. G.; Barranger, J. A.; Brady, R. O. Niemann-Pick disease experimental model: sphingomyelinase reduction induced by AY-9944 Science 1977, 196 (4287) 317-9
15. Kaufmann, A. M.; Krise, J. P. Niemann-Pick C1 functions in regulating lysosomal amine content J. Biol. Chem. 2008, 283 (36) 24584-93
16. Kopitz, J.; Harzer, K.; Kohlschutter, A.; Zoller, B.; Blenck, N.; Cantz, M. Methylamine accumulation in cultured cells as a measure of the aqueous storage compartment in the laboratory diagnosis of genetic lysosomal diseases Am. J. Med. Genet. 1996, 63 (1) 198-202
17. Zheng, N.; Zhang, X.; Rosania, G. R. Effect of phospholipidosis on the cellular pharmacokinetics of chloroquine J. Pharmacol Exp. Ther. 2011, 336 (3) 661-71
18. Reasor, M. J. Influence of a pre-existing phospholipidosis on the accumulation of amiodarone and desethylamiodarone in rat alveolar macrophages Res. Commun. Chem. Pathol. Pharmacol. 1991, 72 (2) 169-81
19. Singh, S. S. Preclinical pharmacokinetics: an approach towards safer and efficacious drugs Curr. Drug Metab. 2006, 7 (2) 165-82
20. Ogu, C. C.; Maxa, J. L. Drug interactions due to cytochrome P450 Proc. (Baylor Univ. Med. Cent.) 2000, 13 (4) 421-3
21. Giacomini, K. M. Membrane transporters in drug disposition J. Pharmacokinet. Biopharm. 1997, 25 (6) 731-41
22. Kornhuber, J.; Henkel, A. W.; Groemer, T. W.; Stadtler, S.; Welzel, O.; Tripal, P.; Rotter, A.; Bleich, S.; Trapp, S. Lipophilic cationic drugs increase the permeability of lysosomal membranes in a cell culture system J. Cell. Physiol. 2010, 224 (1) 152-64
23. Daniel, W. A. Mechanisms of cellular distribution of psychotropic drugs. Significance for drug action and interactions Prog. Neuro-Psychopharmacol. Biol. Psychiatry 2003, 27 (1) 65-73
24. Daniel, W. A.; Wojcikowski, J. The role of lysosomes in the cellular distribution of thioridazine and potential drug interactions Toxicol. Appl. Pharmacol. 1999, 158 (2) 115-24
25. Bickel, M. H.; Graber, B. E.; Moor, M. Distribution of chlorpromazine and imipramine in adipose and other tissues of rats Life Sci. 1983, 33 (20) 2025-31
26. Ndolo, R. A.; Forrest, M. L.; Krise, J. P. The role of lysosomes in limiting drug toxicity in mice J. Pharmacol. Exp. Ther. 2010, 333 (1) 120-8
27. Altan, N.; Chen, Y.; Schindler, M.; Simon, S. M. Defective acidification in human breast tumor cells and implications for chemotherapy J. Exp. Med. 1998, 187 (10) 1583-98
28. Neun, B. W.; Stern, S. T. Monitoring lysosomal activity in nanoparticle-treated cells Methods Mol. Biol. 2011, 697, 207-12
29. Shi, H.; He, X.; Yuan, Y.; Wang, K.; Liu, D. Nanoparticle-based biocompatible and long-life marker for lysosome labeling and tracking Anal. Chem. 2010, 82 (6) 2213-20
30. Gong, Y.; Duvvuri, M.; Krise, J. P. Separate roles for the Golgi apparatus and lysosomes in the sequestration of drugs in the multidrug-resistant human leukemic cell line HL-60 J. Biol. Chem. 2003, 278 (50) 50234-9
31. Cramb, G. Selective lysosomal uptake and accumulation of the beta-adrenergic antagonist propranolol in cultured and isolated cell systems Biochem. Pharmacol. 1986, 35 (8) 1365-72
32. Duvvuri, M.; Gong, Y.; Chatterji, D.; Krise, J. P. Weak base permeability characteristics influence the intracellular sequestration site in the multidrug-resistant human leukemic cell line HL-60 J. Biol. Chem. 2004, 279 (31) 32367-72
33. Seydel, J. K.; Wassermann, O. NMR-studies on the molecular basis of drug-induced phospholipidosis - II. Interaction between several amphiphilic drugs and phospholipids Biochem. Pharmacol. 1976, 25 (21) 2357-64
34. Kopitz, J.; Gerhard, C.; Hofler, P.; Cantz, M. [14C]Methylamine accumulation in cultured human skin fibroblasts - a biochemical test for lysosomal storage and lysosomal diseases Clin. Chim. Acta 1994, 227 (1-2) 121-33
35. Langer, S. Z.; Moret, C.; Raisman, R.; Dubocovich, M. L.; Briley, M. High-affinity [3H]imipramine binding in rat hypothalamus: association with uptake of serotonin but not of norepinephrine Science 1980, 210 (4474) 1133-5
36. Ploemen, J. P.; Kelder, J.; Hafmans, T.; van de Sandt, H.; van Burgsteden, J. A.; Saleminki, P. J.; van Esch, E. Use of physicochemical calculation of pKa and CLogP to predict phospholipidosis-inducing potential: a case study with structurally related piperazines Exp. Toxicol. Pathol. 2004, 55 (5) 347-55
37. Gong, Y.; Duvvuri, M.; Duncan, M. B.; Liu, J.; Krise, J. P. Niemann-Pick C1 protein facilitates the efflux of the anticancer drug daunorubicin from cells according to a novel vesicle-mediated pathway J. Pharmacol. Exp. Ther. 2006, 316 (1) 242-7
38. Michalik, M.; Pierzchalska, M.; Pabianczyk-Kulka, A.; Korohoda, W. Procaine-induced enhancement of fluid-phase endocytosis and inhibition of exocytosis in human skin fibroblasts Eur. J. Pharmacol. 2003, 475 (1-3) 1-10
39. Willingham, M. C.; Cornwell, M. M.; Cardarelli, C. O.; Gottesman, M. M.; Pastan, I. Single cell analysis of daunomycin uptake and efflux in multidrug-resistant and -sensitive KB cells: effects of verapamil and other drugs Cancer Res. 1986, 46 (11) 5941-6
40. Dudley, A. J.; Brown, C. D. pH-dependent transport of procainamide in cultured renal epithelial monolayers of OK cells: consistent with nonionic diffusion Br. J. Pharmacol. 1995, 116 (1) 1685-91
41. Abi-Mosleh, L.; Infante, R. E.; Radhakrishnan, A.; Goldstein, J. L.; Brown, M. S. Cyclodextrin overcomes deficient lysosome-to-endoplasmic reticulum transport of cholesterol in Niemann-Pick type C cells Proc. Natl. Acad. Sci. U.S.A. 2009, 106 (46) 19316-21
42. Thomas, G. H.; Tuck-Muller, C. M.; Miller, C. S.; Reynolds, L. W. Correction of sphingomyelinase deficiency in Niemann-Pick type C fibroblasts by removal of lipoprotein fraction from culture media J. Inherited Metab. Dis 1989, 12 (2) 139-51
43. Appelqvist, H.; Nilsson, C.; Garner, B.; Brown, A. J.; Kagedal, K.; Ollinger, K. Attenuation of the lysosomal death pathway by lysosomal cholesterol accumulation Am. J. Pathol. 2011, 178 (2) 629-39
44. Wojcikowski, J.; Daniel, W. A. Thioridazine-fluoxetine interaction at the level of the distribution process in vivo Pol. J. Pharmacol. 2002, 54 (6) 647-54
45. Daniel, W. A.; 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 (4) 807-14
46. Wojcikowski, J.; Daniel, W. A. Distribution interactions between perazine and antidepressant drugs. In vivo studies Pol. J. Pharmacol. 2000, 52 (6) 449-57
47. Daniel, W. A.; Wojcikowski, J. Lysosomal trapping as an important mechanism involved in the cellular distribution of perazine and in pharmacokinetic interaction with antidepressants Eur. Neuropsychopharmacol. 1999, 9 (6) 483-91
48. Daniel, W. A.; Wojcikowski, J. Interactions between promazine and antidepressants at the level of cellular distribution Pharmacol. Toxicol. 1997, 81 (6) 259-64
49. 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 (3) 1088-98
50. Martin, W. J., 2nd; Kachel, D. L.; Vilen, T.; Natarajan, V. Mechanism of phospholipidosis in amiodarone pulmonary toxicity J. Pharmacol. Exp. Ther. 1989, 251 (1) 272-8
51. Liscum, L.; Faust, J. R. The intracellular transport of low density lipoprotein-derived cholesterol is inhibited in Chinese hamster ovary cells cultured with 3-beta-[2-(diethylamino)ethoxy]androst-5-en-17-one J. Biol. Chem. 1989, 264 (20) 11796-806
52. Yoshida, Y.; Arimoto, K.; Sato, M.; Sakuragawa, N.; Arima, M.; Satoyoshi, E. Reduction of acid sphingomyelinase activity in human fibroblasts induced by AY-9944 and other cationic amphiphilic drugs J. Biochem. 1985, 98 (6) 1669-79
53. Woo, J. T.; Shinohara, C.; Sakai, K.; Hasumi, K.; Endo, A. Isolation, characterization and biological activities of concanamycins as inhibitors of lysosomal acidification J. Antibiot. (Tokyo) 1992, 45 (7) 1108-16
54. Hollemans, M.; Elferink, R. O.; De Groot, P. G.; Strijland, A.; Tager, J. M. Accumulation of weak bases in relation to intralysosomal pH in cultured human skin fibroblasts Biochim. Biophys. Acta 1981, 643 (1) 140-51
55. Duvvuri, M.; Krise, J. P. A novel assay reveals that weakly basic model compounds concentrate in lysosomes to an extent greater than pH-partitioning theory would predict Mol. Pharmaceutics 2005, 2 (6) 440-8
56. Vestal, R. E.; Kornhauser, D. M.; Shand, D. G. Active uptake of propranolol by isolated rabbit alveolar macrophages and its inhibition by other basic amines J. Pharmacol. Exp. Ther. 1980, 214 (1) 106-11
57. Xia, Z.; Ying, G.; Hansson, A. L.; Karlsson, H.; Xie, Y.; Bergstrand, A.; DePierre, J. W.; Nassberger, L. Antidepressant-induced lipidosis with special reference to tricyclic compounds Prog. Neurobiol. 2000, 60 (6) 501-12
58. Riva, E.; Aarons, L.; Latini, R.; Neyroz, P.; Urso, R. Amiodarone kinetics after single i.v. bolus and multiple dosing in healthy volunteers Eur. J. Clin. Pharmacol. 1984, 27 (4) 491-4