Designing the polyamine pharmacophore: Influence of N-substituents on the transport behavior of polyamine conjugates

Journal of Medicinal Chemistry

Volumn 51, Issue 8, 2008, Pages 2551-2560

  Kaur, Navneet ^b   Deleros, Jean Guy ^a   Archer, Jennifer ^b   Weagraff, Nathan Z ^b   Martin, Bénédicte ^a   Phanstiel IV, Otto ^b,c  

^a UNIVERSITÉ DE RENNES 1   (France)

^b UNIVERSITY OF CENTRAL FLORIDA   (United States)

^c UNIVERSITY OF CENTRAL FLORIDA COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYAMINE;

AMINE TRANSPORT; ANIMAL CELL; ARTICLE; CHO CELL; CYTOTOXICITY; LEUKEMIA CELL; METHYLATION; MOUSE; NONHUMAN; PHARMACOPHORE; SYNTHESIS;

ANIMALS; CELL LINE, TUMOR; CHO CELLS; CRICETINAE; CRICETULUS; ENZYME INHIBITORS; GUANIDINES; MAGNETIC RESONANCE SPECTROSCOPY; MICE; POLYAMINES; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT;

EID: 43049137323     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm701341k     Document Type: Article

References (33)

1. (a) Cullis, P. M.; Green, R. E.; Merson-Davies, L.; Travis, N. Probing the mechanism of transport and compartmentalisation of polyamines in mammalian cells. Chem. Biol. 1999, 6, 717-729, and refs therein.
2. (b) Seiler, N.; Dezeure, F. Polyamine transport in mammalian cells. Int. J. Biochem. 1990, 22, 211-218.
3. (c) Seiler, N.; Deleros, J.-G.; Moulinoux, J. P. Polyamine transport in mammalian cells. An update. Int. J. Biochem. Cell Biol. 1996, 28, 843-861.
4. Phanstiel, O., IV; Price, H. L.; Wang, L.; Juusola, J.; Kline, M.; Shah, S. M. The effect of polyamine homologation on the transport and cytotoxicity properties of polyamine-(DNA-intercalator) conjugates. J. Org. Chem. 2000, 65, 5590-5599.
5. Wang, L.; Price, H. L.; Juusola, J.; Kline, M.; Phanstiel, O., IV. The influence of polyamine architecture on the transport and topoisomerase II inhibitory properties of polyamine DNA-intercalator conjugates. J. Med. Chem. 2001, 44, 3682-3691.
6. 1-(anthracen-9-ylmethyl) triamines as molecular recognition elements for the polyamine transporter. J. Med. Chem. 2003, 46, 2663-2671.
7. Wang, C.; Deleros, J.-G.; Biggerstaff, J.; Phanstiel, O., IV. Molecular requirements for targeting the polyamine transport system: Synthesis and biological evaluation of polyamine-anthracene conjugates. J. Med. Chem. 2003, 46, 2672-2682.
8. Wang, C.; Deleros, J.-G.; Cannon, L.; Konate, F.; Carias, H.; Biggerstaff, J.; Gardner, R. A.; Phanstiel, O., IV. Defining the molecular requirements for the selective delivery of polyamine-conjugutes into cells containing active polyamine transporters. J. Med. Chem. 2003, 46, 5129-5138.
9. Kaur, N.; Deleros, J.-G.; Martin, B.; Phanstiel, O., IV. Synthesis and biological evaluation of dihydromotuporamine derivatives in cells containing active polyamine transporters. J. Med. Chem. 2005, 48, 3832-3839.
10. 1-Substituent effects in the selective delivery of polyamine-conjugates into cells containing active polyamine transporters. J. Med. Chem. 2004, 47, 6055-6069.
11. Deleros, J.-G.; Tomasi, S.; Carrington, S.; Martin, B.; Renault, J.; Blagbrough, I. S.; Uriac, P. Effect of spermine conjugation on the cytotoxicity and cellular transport of aeridine. J. Med. Chem. 2002, 45, 5098-5111.
12. (a) Bergeron, R. J.; Feng, Y.; Weimar, W. R.; McManis, J. S.; Dimova, H.; Porter, C.; Raisler, B.; Phanstiel, O. A comparison of structure - activity relationships between spermidine and spermine analogue antineoplastics. J. Med. Chem. 1997, 40, 1475-1494.
13. (b) Kramer, D. L.; Miller, J. T.; Bergeron, R. J.; Khomutov, R.; Khomutov, A.; Porter, C. W. Regulation of polyamine transport by polyamines and polyamine analogs. J. Cell. Physiol. 1993, 155, 399-407.
14. (c) Bergeron, R. J.; McManis, J. S.; Liu, C. Z.; Feng, Y.; Weimar, W. R.; Luchetta, G. R.; Wu, Q.; Ortiz-Ocasio, J.; Vinson, J. R. T.; Kramer, D.; Porter, C. Antiproliferative properties of polyamine analogues: A structure - activity study. J. Med. Chem. 1994, 37, 3464-3476.
15. (d) Bergeron, R. J.; Müller, R.; Bussenius, J.; McManis, J. S.; Merriman, R. L.; Smith, R. E.; Yao, H.; Weimar, W. R. Synthesis and evaluation of hydroxylated polyamine analogues as antiproliferatives. J. Med. Chem. 2000, 43, 224-235.
16. (a) Covassin, L.; Desjardins, M.; Charest-Gaudreault, R.; Audette, M.; Bonneau, M. J.; Poulin, R. Synthesis of spermidine and norspermidine dimers as high affinity polyamine transport inhibitors. Bioorg. Med. Chem. Lett. 1999, 9, 1709-1714.
17. Huber, M.; Pelletier, J. G.; Torossian, K.; Dionne, P.; Gamache, I.; Charest-Gaudreault, R.; Audette, M.; Poulin, R. 2,2′-Dithiobis(N- ethyl-spermine-5-carboxamide) is a high affinity, membrane-impermeant antagonist of the mammalian polyamine transport system. J. Biol. Chem. 1996, 271, 27556-27563.
18. Mandel, J. L.; Flintoff, W. F. Isolation of mutant mammalian cells altered in polyamine transport. J. Cell. Physiol. 1978, 97, 335-344.
19. Byers, T. L.; Wechter, R.; Nuttall, M. E.; Pegg, A. E. Expression of a human gene for polyamine transport in Chinese hamster ovary cells. Biochem. J. 1989, 263, 745-752.
20. Williams, D. E.; Craig, K. S.; Patrick, B.; McHardy, L. M.; Soest, R.v.; Roberge, M.; Anderson, R. J. Motuporamines, anti-invasion and anti-angiogenic alkaloids from the marine sponge Xestospongia exigna (Kirkpatrick): Isolation, structure elucidation, anologue synthesis, and conformational analysis. J. Org. Chem. 2002, 67, 245-258.
21. Breitbeil, F., III; Kaur, N.; Deleros, J.-G.; Martin, B.; Abboud, K. A.; Phanstiel, O., IV. Modeling the preferred shapes of polyamine transporter ligands and dihydromotuporamine-C mimics: Shovel versus hoe. J. Med. Chem. 2006, 49, 2407-2416.
22. 1-acetyltransferase in a human large cell lung carcinoma. Biochem. J. 1990, 270, 615-620.
23. 1-acetyltransferase activity by novel spermine analogs. Mol. Pharmacol. 1997, 52, 69-74.
24. 1-acetyltransferase and prevent its targeting to the proteasome for degradation. Biochem. J. 2001,358, 137-145.
25. (d) Kramer, D. L.; F-Petrovic, M.; Diegelman, P.; Cooley, J. M.; Bernacki, R. J.; McManis, J. S.; Bergeron, R. J.; Porter, C. W. Effects of novel spermine analogues on cell cycle progression and apoptosis in MALME-3M human melanoma cells. Cancer Res. 1997, 57, 5521-5527.
26. (e) Gahl, W. A.; Pitot, H. C. Reversal by aminoguanidine of the inhibition of proliferation of human fibroblasts by spermidine and spermine. Chem.-Biol. Interact. 1978, 22, 91-98.
27. (f) Morgan, D. M. Polyamine Oxidases and Oxidized Polyamines. In The Physiology of Polyamines; Bachrach, U., Heimer, Y. M., Eds.; CRC Press: Boca Raton, FL. 1989; Vol I, Chapter 13, pp 203-229.
28. Salvatore, R. N.; Nagle, A. S.; Jung, K. W. Cesium effect: High chemoselcctivitv in direct N-alkylation of amines. J. Org. Chem. 2002, 67, 674-683.
29. Gardner, R. A.; Belting, M.; Svensson, K.; Phanstiel, O., IV. Synthesis and transfection efficiencies of new lipophilic polyamines. J. Med. Chem. 2007, 50, 308-318.
30. Mosmann, T. Rapid colorimetric assay for cellular growth and survival: Application to proliferation and cytotoxicity assays. J. Immunol. Methods 1983, 65, 55-63.
31. Clément, S.; Deleros, J. G.; Feuerstein, B. G. Spermine uptake is necessary to induce haemoglobin synthesis in murine erythroleukemia cells. Biochem. J. 1995, 312, 933-938.
32. 50) of an enzymatic reaction. Biochem. Pharmacol. 1973, 22, 3099-3108.
33. Torossian, K.; Audette, M.; Poulin, R. Substrate protection against inactivation of the mammalian polyamine transport system by 1-ethyl-3-(3- dimethylan:inopropyl)-carbodiimide. Biochem. J. 1996, 319, 21-26.