Time-dependent effects of hydrophobic amine-containing drugs on lysosome structure and biogenesis in cultured human fibroblasts

Journal of Pharmaceutical Sciences

Volumn 103, Issue 10, 2014, Pages 3287-3296

  Logan, Randall ^a   Kong, Alex C ^a   Krise, Jeffrey P ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

Cell culture; Chronopharmacokinetics; Lipids; Nonlinear pharmacokinetics; Pharmacokinetics; Physicochemical properties

Indexed keywords

AMINE; HALOFANTRINE; LYSOSOME ASSOCIATED MEMBRANE PROTEIN 1; PROPRANOLOL;

ACCUMULATION ASSAY; ARTICLE; BIOGENESIS; CELL ISOLATION; CELL LYSATE; CELL PH; CELL STRUCTURE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG ACCUMULATION; DRUG RELEASE; DRUG UPTAKE; FIBROBLAST; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; HYDROPHOBICITY; LIPOPHILICITY; LYSOSOME; PROTEIN EXPRESSION; PROTEIN LOCALIZATION; STEADY STATE; TRANSMISSION ELECTRON MICROSCOPY; WESTERN BLOTTING; CELL CULTURE; CHEMICAL PHENOMENA; CHEMISTRY; CYTOLOGY; DRUG EFFECTS; TIME;

AMINES; CELLS, CULTURED; FIBROBLASTS; HUMANS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; LYSOSOMES; TIME;

EID: 84923327435     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.24087     Document Type: Article

References (52)

1. Marceau F, Bawolak MT, Lodge R, Bouthillier J, Gagne-Henley A, Gaudreault RC, Morissette G. 2012. Cation trapping by cellular acidic compartments: Beyond the concept of lysosomotropic drugs. Toxicol Appl Pharmacol 259(1):1-12.
2. de Duve C, de Barsy T, Poole B, Trouet A, Tulkens P, Van Hoof F. 1974. Commentary. Lysosomotropic agents. Biochem Pharmacol 23(18):2495-2531.
3. Duvvuri M, Feng W, Mathis A, Krise JP. 2004. A cell fractionation approach for the quantitative analysis of subcellular drug disposition. Pharm Res 21(1):26-32.
4. Duvvuri M, Konkar S, Funk RS, Krise JM, Krise JP. 2005. A chemical strategy to manipulate the intracellular localization of drugs in resistant cancer cells. Biochem 44(48):15743-15749.
5. Duvvuri M, Krise JP. 2005. A novel assay reveals that weakly basic model compounds concentrate in lysosomes to an extent greater than pH-partitioning theory would predict. Mol Pharm 2(6):440-448.
6. Duvvuri M, Gong Y, Chatterji D, Krise JP. 2004. Weak base permeability characteristics influence the intracellular sequestration site in the multidrug-resistant human leukemic cell line HL-60. J Biol Chem 279(31):32367-32372.
7. Logan R, Kong AC, Axcell E, Krise JP. 2014. Amine-containing molecules and the induction of an expanded lysosomal volume phenotype: A structure-activity relationship study. J Pharm Sci 103(5):1572-1580.
8. Underwood KW, Andemariam B, McWilliams GL, Liscum L. 1996.Quantitative analysis of hydrophobic amine inhibition of intracellular cholesterol transport. J Lipid Res 37(7):1556-1568.
9. Roff CF, Goldin E, Comly ME, Cooney A, Brown A, VanierMT, Miller SP, Brady RO, Pentchev PG. 1991. Type C Niemann-Pick disease: Use of hydrophobic amines to study defective cholesterol transport. Dev Neurosci 13(4-5):315-319.
10. Honegger UE, Roscher AA,Wiesmann UN. 1983. Evidence for lysosomotropic action of desipramine in cultured human fibroblasts. J Pharmacol Exp Ther 225(2):436-441.
11. Yamamoto A, Adachi S, Ishikawa K, Yokomura T, Kitani T. 1971.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 70(5):775-784.
12. Black WC, Percival MD. 2006. The consequences of lysosomotropism on the design of selective cathepsin K inhibitors. Chembiochem 7(10):1525-1535.
13. Falgueyret JP, Desmarais S, Oballa R, Black WC, Cromlish W, Khougaz K, Lamontagne S, Masse F, Riendeau D, Toulmond S, Percival MD. 2005. Lysosomotropism of basic cathepsin K inhibitors contributes to increased cellular potencies against off-target cathepsins and reduced functional selectivity. J Med Chem 48(24):7535-7543.
14. Ndolo RA, Luan Y, Duan S, Forrest ML, Krise JP. 2012. Lysosomotropic properties of weakly basic anticancer agents promote cancer cell selectivity in vitro. PloS one 7(11):e49366.
15. Ndolo RA, Forrest ML, Krise JP. 2010. The role of lysosomes in limiting drug toxicity in mice. J Pharmacol Exp Ther 333(1):120-128.
16. Shepard RM, Falkner FC. 1990. Pharmacokinetics of azithromycin in rats and dogs. J Antimicrob Chemother 25(Suppl A):49-60.
17. Zheng N, Zhang X, Rosania GR. 2011. Effect of phospholipidosis on the cellular pharmacokinetics of chloroquine. J Pharmacol Exp Ther 336(3):661-671.
18. Gong Y, Zhao Z, McConn DJ, Beaudet B, Tallman M, Speake JD, Ignar DM, Krise JP. 2007. Lysosomes contribute to anomalous pharmacokinetic behavior of melanocortin-4 receptor agonists. Pharm Res 24(6):1138-1144.
19. Funk RS, Krise JP. 2012. Cationic amphiphilic drugs cause a marked expansion of apparent lysosomal volume: Implications for an intracellular distribution-based drug interaction. Mol Pharm 9(5):1384-1395.
20. Settembre C, Di Malta C, Polito VA, Garcia Arencibia M, Vetrini F, Erdin S, Erdin SU, Huynh T, Medina D, Colella P, Sardiello M, Rubinsztein DC, Ballabio A. 2011. TFEB links autophagy to lysosomal biogenesis. Science 332(6036):1429-1433.
21. nd ed. Philadelphia Pennsylvania: W. B. Saunders Company, pp viii, 862.
22. Demant EJ, Friche E. 1998. Kinetics of anthracycline accumulation in multidrug-resistant tumor cells: Relationship to drug lipophilicity and serum albumin binding. Biochem Pharmacol 56(9):1209-1217.
23. Leonessa F, Jacobson M, Boyle B, Lippman J, McGarvey M, Clarke R. 1994. Effect of tamoxifen on the multidrug-resistant phenotype in human breast cancer cells: Isobologram, drug accumulation, and M(r) 170,000 glycoprotein (gp170) binding studies. Cancer Res 54(2):441-447.
24. Sirotnak FM, Moccio DM, Kelleher LE, Goutas LJ. 1981. Relative frequency and kinetic properties of transport-defective phenotypes among methotrexate-resistant L1210 clonal cell lines derived in vivo. Cancer Res 41(11 Pt 1):4447-4452.
25. Sardiello M, Palmieri M, di Ronza A, Medina DL, Valenza M, Gennarino VA, Di Malta C, Donaudy F, Embrione V, Polishchuk RS, Banfi S, Parenti G, Cattaneo E, Ballabio A. 2009. A gene network regulating lysosomal biogenesis and function. Science 325(5939):473-477.
26. Logan R, Kong A, Krise JP. 2013. Evaluating the roles of autophagy and lysosomal trafficking defects in intracellular distributionbased drug-drug interactions involving lysosomes. J Pharm Sci 102(11):4173-4180.
27. Zheng N, Zhang X, Rosania GR. 2011. Effect of phospholipidosis on the cellular pharmacokinetics of chloroquine. J Pharmacol Exp Ther 336(3):661-671.
28. Gong Y, Zhao Z, McConn DJ, Beaudet B, Tallman M, Speake JD, Ignar DM, Krise JP. 2007. Lysosomes contribute to anomalous pharmacokinetic behavior of melanocortin-4 receptor agonists. Pharm Res 24(6):1138-1144.
29. Greenblatt DJ. 1985. Elimination half-life of drugs: Value and limitations. Annu Rev Med 36:421-427.
30. Funk RS, Krise JP. 2012. Cationic amphiphilic drugs cause a marked expansion of apparent lysosomal volume: Implications for an intracellular distribution-based drug interaction. Mol Pharm 9:1384-1395.
31. DanielWA,Wojcikowski J. 1999. The role of lysosomes in the cellular distribution of thioridazine and potential drug interactions. Toxicol Appl Pharmacol 158(2):115-124.
32. Daniel WA, Wojcikowski J. 1997. Interactions between promazine and antidepressants at the level of cellular distribution. Pharmacol Toxicol 81(6):259-264.
33. Obach RS, Lombardo F, Waters NJ. 2008. Trend analysis of a database of intravenous pharmacokinetic parameters in humans for670 drug compounds. Drug Metab Dispos 36(7):1385-1405.
34. Schneck DW, Pritchard JF, Hayes AH Jr. 1977. Studies on the uptake and binding of propranolol by rat tissues. J Pharmacol Exp Ther 203(3):621-629.
35. Levy A, Ngai SH, Finck AD, Kawashima K, Spector S. 1976. Disposition of propranolol isomers in mice. Eur J Pharmacol 40(1):93-100.
36. Walle UK, Thibodeaux H, Privitera PJ, Walle T. 1989. Stereochemistry of tissue distribution of racemic propranolol in the dog. Chirality 1(3):192-196.
37. th ed. New York: McGraw-Hill.
38. Glotzbach RK, Preskorn SH. 1982. Brain concentrations of tricyclic antidepressants: Single-dose kinetics and relationship to plasma concentrations in chronically dosed rats. Psychopharmacology (Berl) 78(1):25-27.
39. Yung L, Huang Y, Lessard P, Legname G, Lin ET, Baldwin M, Prusiner SB, Ryou C, Guglielmo BJ. 2004. Pharmacokinetics of quinacrine in the treatment of prion disease. BMC Infect Dis 4:53.
40. Scuntaro I, Kientsch U, Wiesmann UN, Honegger UE. 1996. Inhibition by vitamin E of drug accumulation and of phospholipidosis induced by desipramine and other cationic amphiphilic drugs in human cultured cells. Br J Pharmacol 119(5):829-834.
41. Honegger UE, Scuntaro I, Wiesmann UN. 1995. Vitamin E reduces accumulation of amiodarone and desethylamiodarone and inhibits phospholipidosis in cultured human cells. Biochem Pharmacol 49(12):1741-1745.
42. Baik J, Rosania GR. 2011. Molecular imaging of intracellular drugmembrane aggregate formation. Mol Pharm 8(5):1742-1749.
43. Ohkuma S, Poole B. 1981. Cytoplasmic vacuolation of mouse peritoneal macrophages and the uptake into lysosomes of weakly basic substances. J Cell Biol 90(3):656-664.
44. Yang WC, Strasser FF, Pomerat CM. 1965. Mechanism of druginduced vacuolization in tissue culture. Exp Cell Res 38:495-506.
45. Finnin BC, Reed BL, Ruffin NE. 1969. The effects of osmotic pressure on procaine-induced vacuolation in cell culture. J Pharm Pharmacol 21(2):114-117.
46. Anderson N, Borlak J. 2006. Drug-induced phospholipidosis. FEBS Lett 580(23):5533-5540.
47. Xia Z, Ying G, Hansson AL, Karlsson H, Xie Y, Bergstrand A, De-Pierre JW, Nassberger L. 2000. Antidepressant-induced lipidosis with special reference to tricyclic compounds. Prog Neurobiol 60(6):501-512.
48. Luzio JP, Poupon V, Lindsay MR, Mullock BM, Piper RC, Pryor PR. 2003. Membrane dynamics and the biogenesis of lysosomes. Mol Membr Biol 20(2):141-154.
49. Kornfeld S, Mellman I. 1989. The biogenesis of lysosomes. Annu Rev Cell Biol 5:483-525.
50. Saftig P, Klumperman J. 2009. Lysosome biogenesis and lysosomal membrane proteins: Trafficking meets function. Nat Rev Mol Cell Biol 10(9):623-635.
51. Luzio JP, Pryor PR, Gray SR, Gratian MJ, Piper RC, Bright NA.2005. Membrane traffic to and from lysosomes. Biochem Soc Symp (72):77-86.
52. Kaufmann AM, Krise JP. 2008. Niemann-Pick C1 functions in regulating lysosomal amine content. J Biol Chem 283(36):24584-24593.