Lysosomotropic Properties of Weakly Basic Anticancer Agents Promote Cancer Cell Selectivity In Vitro

PLoS ONE

Volumn 7, Issue 11, 2012, Pages

  Ndolo, Rosemary A ^a   Luan, Yepeng ^b   Duan, Shaofeng ^a   Forrest, M Laird ^a   Krise, Jeffrey P ^a  

^a UNIVERSITY OF KANSAS   (United States)

^b SHANDONG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CHLORAMBUCIL; DAUNORUBICIN; FLUOROURACIL; GELDANAMYCIN; GELDANAMYCIN DERIVATIVE; HEAT SHOCK PROTEIN 90; MITOXANTRONE; PROTON TRANSPORTING ADENOSINE TRIPHOSPHATASE; SMALL INTERFERING RNA; UNCLASSIFIED DRUG;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BINDING AFFINITY; CANCER CELL; CANCER CELL CULTURE; CELL STRAIN HEK293; CELL STRAIN HL 60; CONTROLLED STUDY; DISSOCIATION CONSTANT; DRUG CYTOTOXICITY; DRUG PROTEIN BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; FIBROBLAST; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; LYSOSOME; PH; PROTEIN EXPRESSION;

ANTINEOPLASTIC AGENTS; BENZOQUINONES; BIOLOGICAL TRANSPORT; CYTOSOL; DRUG DESIGN; HL-60 CELLS; HUMANS; LACTAMS, MACROCYCLIC; LYSOSOMES;

EID: 84868691252     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0049366     Document Type: Article

References (47)

1. Kroemer G, Pouyssegur J, (2008) Tumor cell metabolism: cancer's Achilles' heel. Cancer Cell 13: 472-482.
2. Dutcher JP, Novik Y, O'Boyle K, Marcoullis G, Secco C, et al. (2000) 20th-century advances in drug therapy in oncology-Part I. J Clin Pharmacol. 40: 1007-1024.
3. Dutcher JP, Novik Y, O'Boyle K, Marcoullis G, Secco C, et al. (2000) 20th-century advances in drug therapy in oncology-Part. II. J Clin Pharmacol 40: 1079-1092.
4. Imai K, Takaoka A, (2006) Comparing antibody and small-molecule therapies for cancer. Nat Rev Cancer 6: 714-727.
5. Houshmand P, Zlotnik A, (2003) Targeting tumor cells. Curr Opin Cell Biol 15: 640-644.
6. Petrak K, (2005) Essential properties of drug-targeting delivery systems. Drug Discov Today 10: 1667-1673.
7. 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: 32367-32372.
8. 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. Biochemistry 44: 15743-15749.
9. Trapp S, Rosania G, Horobin R, Kornhuber J, (2008) Quantitative modeling of selective lysosomal targeting for drug design. Eur Biophys J 37: 1317-1328.
10. Egorin MJ, Clawson RE, Cohen JL, Ross LA, Bachur NR, (1980) Cytofluorescence localization of anthracycline antibiotics. Cancer Res 40: 4669-4676.
11. Kaufmann AM, Krise JP, (2008) Niemann-Pick C1 functions in regulating lysosomal amine content. J Biol Chem 283: 24584-24593.
12. Duvvuri M, Konkar S, Hong KH, Blagg BS, Krise JP, (2006) A new approach for enhancing differential selectivity of drugs to cancer cells. ACS Chem Biol 1: 309-315.
13. Kang BH, Altieri DC, (2009) Compartmentalized cancer drug discovery targeting mitochondrial Hsp90 chaperones. Oncogene 28: 3681-3688.
14. Lansiaux A, Tanious F, Mishal Z, Dassonneville L, Kumar A, et al. (2002) Distribution of furamidine analogues in tumor cells: targeting of the nucleus or mitochondria depending on the amidine substitution. Cancer Res 62: 7219-7229.
15. Fernandez-Carneado J, Van Gool M, Martos V, Castel S, Prados P, et al. (2005) Highly efficient, nonpeptidic oligoguanidinium vectors that selectively internalize into mitochondria. J Am Chem Soc 127: 869-874.
16. Kang BH, Tavecchio M, Goel HL, Hsieh CC, Garlick DS, et al. (2011) Targeted inhibition of mitochondrial Hsp90 suppresses localised and metastatic prostate cancer growth in a genetic mouse model of disease. Brit J Cancer 104: 629-634.
17. de Duve C, de Barsy T, Trouet A, Tulkens P, van Hoof F, (1974) Lysosomotropic agents. Biochem Pharmacol 23: 2495-2531.
18. Bulychev A, Trouet A, Tulkens P, (1978) Uptake and intracellular distribution of neutral red in cultured fibroblasts. Exp Cell Res 115: 343-355.
19. Jiang LW, Maher VM, McCormick JJ, Schindler M, (1990) Alkalinization of the lysosomes is correlated with ras transformation of murine and human fibroblasts. J Biol Chem 265: 4775-4777.
20. Altan N, Chen Y, Schindler M, Simon SM, (1998) Defective acidification in human breast tumor cells and implications for chemotherapy. J Exp Med 187: 1583-1598.
21. Kokkonen N, Rivinoja A, Kauppila A, Suokas M, Kellokumpu I, et al. (2004) Defective acidification of intracellular organelles results in aberrant secretion of cathepsin D in cancer cells. J Biol Chem 279: 39982-39988.
22. Gong Y, Duvvuri M, Krise JP, (2003) Separate roles for the Golgi apparatus and lysosomes in the sequestration of drugs in the multi-drug resistant human leukemic cell line HL-60. J Biol Chem 278: 50234-50239.
23. Ndolo RA, Jacobs DT, Forrest ML, Krise JP, (2010) Intracellular distribution-based anticancer drug targeting: Exploiting a lysosomal acidification defect associated with cancer cells. Mol Cell Pharmacol 2: 131-136.
24. Bocchetta M, Eliasz S, De Marco MA, Rudzinski J, Zhang L, et al. (2008) The SV40 large T antigen-p53 complexes bind and activate the insulin-like growth factor-I promoter stimulating cell growth. Cancer Res 68: 1022-1029.
25. Tian Z-Q, Liu Y, Zhang D, Wang Z, Dong SD, et al. (2004) Synthesis and biological activities of novel 17-aminogeldanamycin derivatives. Bioorg Med Chem 12: 5317-5329.
26. 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: 440-448.
27. Nilsson C, Kågedal K, Johansson U, Öllinger K, (2004) Analysis of cytosolic and lysosomal pH in apoptotic cells by flow cytometry. Methods Cell Sci 25: 185-194.
28. Nikolovska-Coleska Z, Wang R, Fang X, Pan H, Tomita Y, et al. (2004) Development and optimization of a binding assay for the XIAP BIR3 domain using fluorescence polarization. Anal Biochem 332: 261-273.
29. Howes R, Barril X, Dymock BW, Grant K, Northfield CJ, et al. (2006) A fluorescence polarization assay for inhibitors of Hsp90. Anal Biochem 350: 202-213.
30. Young JC, Moarefi I, Hartl FU, (2001) Hsp90: a specialized but essential protein-folding tool. J Cell Biol 154: 267-274.
31. Lu X, Qin W, Li J, Tan N, Pan D, et al. (2005) The growth and metastasis of human hepatocellular carcinoma xenografts are inhibited by small interfering RNA targeting to the subunit ATP6L of proton pump. Cancer Res 65: 6843-6849.
32. Mahoney BP, Raghunand N, Baggett B, Gillies RJ, (2003) Tumor acidity, ion trapping and chemotherapeutics: I. Acid pH affects the distribution of chemotherapeutic agents in vitro. Biochem Pharmacol 66: 1207-1218.
33. Milano G, Thyss A, Santini J, Frenay M, Francois E, et al. (1989) Salivary passage of 5-fluorouracil during continuous infusion. Cancer Chemother Pharmacol 24: 197-199.
34. Adair CG, McElnay JC, (1986) Studies on the mechanism of gastrointestinal absorption of melphalan and chlorambucil. Cancer Chemother Pharmacol 17: 95-98.
35. Schindler M, Grabski S, Hoff E, Simon SM, (1996) Defective pH regulation of acidic compartments in human breast cancer cells (MCF-7) is normalized in adriamycin-resistant cells (MCF-7adr). Biochemistry 35: 2811-2817.
36. Gillies RJ, Liu Z, Bhujwalla Z, (1994) 31P-MRS measurements of extracellular pH of tumors using 3-aminopropylphosphonate. Am J Physiol- Cell Physiol 267: C195-C203.
37. Reasor MJ, Kacew S, (2001) Drug-induced phospholipidosis: are there functional consequences? Exp Biol M 226: 825-830.
38. Bickerton GR, Paolini GV, Besnard J, Muresan S, Hopkins AL, (2012) Quantifying the chemical beauty of drugs. Nat Chem 4: 90-98.
39. Hann MM, Keseru GM, (2012) Finding the sweet spot: the role of nature and nurture in medicinal chemistry. Nat Rev Drug Discov 11: 355-365.
40. Lipinski CA, Lombardo F, Dominy BW, Feeney PJ, (2001) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliver Rev 46: 3-26.
41. Meanwell NA, (2011) Improving drug candidates by design: a focus on physicochemical properties as a means of improving compound disposition and safety. Chem Res Toxicol 24: 1420-1456.
42. Liao Z, Lin J, Luo D, (2008) Expressions and significance of uPA and V-ATPase mRNA in hepatocellular carcinoma. Chin-Germ J Clin Oncol 7: 631-634.
43. Szakács Z, Hägele G, (2004) Accurate determination of low pK values by 1H NMR titration. Talanta 62: 819-825.
44. Grycová L, Dommisse R, Pieters L, Marek R, (2009) NMR determination of pKa values of indoloquinoline alkaloids. Magn Res Chem 47: 977-981.
45. Krezel A, Bal W, (2004) A formula for correlating pKa values determined in D2O and H2O. J Inorg Biochem 98: 161-166.
46. Llauger-Bufi L, Felts SJ, Huezo H, Rosen N, Chiosis G, (2003) Synthesis of novel fluorescent probes for the molecular chaperone Hsp90. Bioorg Med Chem Lett 13: 3975-3978.
47. Borrok MJ, Kiessling LL, (2007) Non-carbohydrate inhibitors of the lectin DC-SIGN. J Am Chem Soc 129: 12780-12785.