A putrescine-anthracene conjugate: A paradigm for selective drug delivery

Biochemical Journal

Volumn 424, Issue 3, 2009, Pages 431-438

  Palmer, Andrew J ^a   Ghani, Radiah A ^a   Kaur, Navneet ^b   Phanstiel, Otto ^b   Wallace, Heather M ^a  

^a UNIVERSITY OF ABERDEEN   (United Kingdom)

^b UNIVERSITY OF CENTRAL FLORIDA   (United States)

Author keywords

Apoptosis; Cancer; DNA damage; Druf conjugate; Leukemia; Polyamine

Indexed keywords

ADDITIONAL MODE; APOPTOSIS; CANCER CELLS; CYTOTOXIC AGENTS; CYTOTOXIC DRUGS; DNA DAMAGES; HUMAN CANCER CELLS; HUMAN CELL LINES; MECHANISTIC STUDIES; NOVEL METHODS; POLYAMINES; TRANSPORT SYSTEMS;

AMINES; ANTHRACENE; CELL CULTURE; CELL DEATH; DNA; DRUG DELIVERY; GENES; GROWTH KINETICS;

PHOTOTRANSISTORS;

ANTHRACENE; PUTRESCINE;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL; CELL CYCLE G0 PHASE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOTOXICITY TEST; DNA DAMAGE; DRUG POTENTIATION; DRUG SELECTIVITY; DRUG TARGETING; DRUG UPTAKE; HUMAN; HUMAN CELL; IC 50; OXIDATIVE STRESS; PHENOTYPE; PRIORITY JOURNAL;

APOPTOSIS; BIOLOGICAL TRANSPORT; CELL CYCLE; CELL PROLIFERATION; CELL SURVIVAL; DNA DAMAGE; DRUG DELIVERY SYSTEMS; FLOW CYTOMETRY; GLUTATHIONE; HL-60 CELLS; HUMANS; INTRACELLULAR SPACE; POLYAMINES; PUTRESCINE;

EID: 73149104152     PISSN: 02646021     EISSN: 14708728     Source Type: Journal    
DOI: 10.1042/BJ20090815     Document Type: Article

References (33)

1. Wallace, H. M., Fraser, A. V. and Hughes, A. (2003) A perspective of polyamine metabolism. Biochem. J. 376, 1-14
2. Martinez, M. E., O'Brien, T. G., Fultz, K. E., Babbar, N., Yerushalmi, H., Qu, N., Guo, Y., Boorman, D., Einspahr, J., Alberts, D. S. and Gerner, E. W. (2003) Pronounced reduction in adenoma recurrence associated with aspirin use and a polymorphism in the ornithine decarboxylase gene. Proc. Natl. Acad. Sci. 100, 7859-7864
3. Seiler, N., Sarhan, S., Grauffel, C., Jones, R., Knodgen, B. and Moulinoux, J. (1990) Endogenous and exogenous polyamines in support of tumor growth. Cancer Res. 50, 5077-5083
4. Bachrach, U. and Seiler, N. (1981) Formation of acetylpolyamines and putrescine from spermidine by normal and transformed chick embryo fibroblasts. Cancer Res. 41, 1205-1208
5. Wallace, H. M. and Kerr, H. M. (1982) A comparison of polyamine metabolism in normal and transformed baby-hamster-kidney cells. Biochem. J. 202, 785-790
6. Volkow, N., Goldman, S. S., Flamm, E. S., Cravioto, H., Wolf, A. P. and Brodie, J. D. (1983) Labeled putrescine as a probe in brain tumors. Science 221, 673-675
7. Walters, J. D. and Wojcik, M. S. (1994) Polyamine transport in human promyelocytic leukemia cells and polymorphonuclear leukocytes. Leuk. Res. 18, 703-708
8. Seiler, N. (1991) Pharmacological properties of the natural polyamines and their depletion by biosynthesis inhibitors as a therapeutic approach. Prog. Drug Res. 37, 107-159
9. Phanstiel, O., Kaur, N. and Delcros, J. G. (2007) Structure-activity investigations of polyamine-anthracene conjugates and their uptake via the polyamine transporter. Amino Acids 33, 305-313
10. Seiler, N. and Dezeure, F. (1990) Polyamine transport in mammalian cells. Int. J. Biochem. 22, 211-218
11. Gardner, R. A., Delcros, J. G., Konate, F., Breitbeil, F., Martin, B., Sigman, M., Huang, M. and Phanstiel, O. (2004) N1-substituent effects in the selective delivery of polyamine conjugates into cells containing active polyamine transporters. J. Med. Chem. 47, 6055-6069
12. Wang, C., Delcros, J., Cannon, L., Konate, F., Carias, H., Biggerstaff, J., Gardner, R. A. and Phanstiel, O. (2003) Defining the molecular requirements for the selective delivery of polyamine conjugates into cells containing active polyamine transporters. J. Med. Chem. 46, 5129-5138
13. Denizot, F. and Lang, R. (1986) Rapid colorimetric assay for cell growth and survival. Modifications to the tetrazolium dye procedure giving improved sensitivity and reliability. J. Immunol. Methods 89, 271-277
14. Mosmann, T. (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 65, 55-63
15. Lowry, O. H., Rosebrough, N. J., Farr, A. L. and Randall, R. J. (1951) Protein measurement with the folin phenol reagent. J. Biol. Chem. 193, 265-275
16. Cohn, V. H. and Lyle, J. (1966) A fluorometric assay for glutathione. Anal. Biochem. 14, 434-440
17. Hissin, P. J. and Hilf, R. (1976) A fluorometric method for determination of oxidized and reduced glutathione in tissues. Anal. Biochem. 74, 214-226
18. Singh, N. P., McCoy, M. T., Tice, R. R. and Schneider, E. L. (1988) A simple technique for quantitation of low levels of DNA damage in individual cells. Exp. Cell Res. 175, 184-191
19. Fraser, A. V., Woster, P. M. and Wallace, H. M. (2002) Induction of apoptosis in human leukaemic cells by IPENSpm, a novel polyamine analogue and anti-metabolite. Biochem. J. 367, 307-312
20. Wang, C., Delcros, J. G., Biggerstaff, J. and Phanstiel, O. (2003) Molecular requirements for targeting the polyamine transport system. synthesis and biological evaluation of polyamine-anthracene conjugates. J. Med. Chem. 46, 2672-2682
21. Xie, S., Cheng, P., Liu, G., Ma, Y., Zhao, J., Chehtane, M., Khaled, A. R., Phanstiel, IV, O. and Wang, C. (2007) Synthesis and bioevaluation of N-(arylalkyl)-homospermidine conjugates. Bioorg. Med. Chem. Lett. 17, 4471-4475
22. Porter, C. W., Miller, J. and Bergeron, R. J. (1984) Aliphatic chain length specificity of the polyamine transport system in ascites L1210 leukemia cells. Cancer Res. 44, 126-128
23. Byers, T. L., Kameji, R., Rannels, D. E. and Pegg, A. E. (1987) Multiple pathways for uptake of paraquat, methylglyoxal bis(guanylhydrazone), and polyamines. Am. J. Physiol. Cell Physiol. 252, C663-C669
24. Heston, W. D. W., Yang, C., Pliner, L., Russo, P. and Covey, D. F. (1987) Cytotoxic activity of a polyamine analogue, monoaziridinylputrescine, against the PC-3 human prostatic carcinoma cell line. Cancer Res. 47, 3627-3631
25. Guo, X., Rao, J. N., Liu, L., Zou, T., Turner, D. J., Bass, B. L. and Wang, J. (2003) Regulation of adherens junctions and epithelial paracellular permeability: a novel function for polyamines. Am. J. Physiol. Cell Physiol. 285, C1174-C1187
26. Bratton, D. L., Fadok, V. A., Richter, D. A., Kailey, J. M., Frasch, S. C., Nakamura, T. and Henson, P. M. (1999) Polyamine regulation of plasma membrane phospholipid flip-flop during apoptosis. J. Biol. Chem. 274, 28113-28120
27. Ray, R. M., Zimmerman, B. J., McCormack, S. A., Patel, T. B. and Johnson, L. R. (1999) Polyamine depletion arrests cell cycle and induces inhibitors p21Waf1/Cip1, p27Kip1, and p53 in IEC-6 cells. Am. J. Physiol. Cell Physiol. 276, C684-C691
28. Coffino, P. (2001) Regulation of cellular polyamines by antizyme. Nat. Rev. Mol. Cell Biol. 2, 188-194
29. Bergeron, R. J., Feng, Y., Weimar, W. R., McManis, J. S., Dimova, H., Porter, C., Raisler, B. and Phanstiel, O. (1997) A comparison of structure-activity relationships between spermidine and spermine analogue antineoplastics. J. Med. Chem. 40, 1475-1494
30. Phanstiel, O., Price, H. L., Wang, L., Juusola, J., Kline, M. and Shah, S. M. (2000) The effect of polyamine homologation on the transport and cytotoxicity properties of polyamine-(DNA-intercalator) conjugates. J. Org. Chem. 65, 5590-5599
31. Varghese, S., Senanayake, T., Murray-Stewart, T., Doering, K., Fraser, A., Casero, R. A. and Woster, P. M. (2008) Polyaminohydroxamic acids and polyaminobenzamides as isoform selective histone deacetylase inhibitors. J. Med. Chem. 51, 2447-2456
32. Xie, S., Liu, G., Ma, Y., Cheng, P., Wu, Y., Wang, M., Ji, B., Zhao, J. and Wang, C. (2008) Synergistic antitumor effects of anthracenylmethyl homospermidine and α-difluoromethylornithine on promyelocytic leukemia HL60 cells. Toxicol. In Vitro 22, 352-358
33. Ott, M., Gogvadze, V., Orrenius, S. and Zhivotovsky, B. (2007) Mitochondria, oxidative stress and cell death. Apoptosis 12, 913-922