Polyamine-Iron Chelator Conjugate

Journal of Medicinal Chemistry

Volumn 46, Issue 25, 2003, Pages 5478-5483

  Bergeron, Raymond J ^a   McManis, James S ^a   Franklin, April M ^a   Yao, Hua ^a   Weimar, William R ^a,b  

^a UNIVERSITY OF FLORIDA   (United States)

^b SOUTHERN UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 [12 AMINO 4,9 DIAZADODECYL 2 METHYL 3 HYDROXY 4(1H) PYRIDINONE]; 3 O BENZYLMALTOL; ACYLTRANSFERASE; ADENOSYLMETHIONINE DECARBOXYLASE; CARRIER PROTEIN; DEFERIPRONE; IRON; IRON CHELATE; LIGAND; MALTOL; ORNITHINE DECARBOXYLASE; POLYAMINE; POLYAMINE TRANSPORTER; PYRIDONE DERIVATIVE; SPERMIDINE SPERMINE N1 ACETYLTRANSFERASE; SPERMINE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CANCER; CELL LINE; COMPLEX FORMATION; DRUG DELIVERY SYSTEM; DRUG EFFICACY; DRUG STRUCTURE; ENZYME ACTIVITY; GROWTH INHIBITION; IRON CHELATION; LEUKEMIA CELL; MOUSE; NONHUMAN; UPREGULATION;

ACETYLTRANSFERASES; ADENOSYLMETHIONINE DECARBOXYLASE; ANIMALS; ANTINEOPLASTIC AGENTS; BINDING, COMPETITIVE; BIOLOGICAL TRANSPORT, ACTIVE; CARRIER PROTEINS; CELL DIVISION; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; FERRIC COMPOUNDS; IRON CHELATING AGENTS; LEUKEMIA L1210; MICE; ORNITHINE DECARBOXYLASE; POLYAMINES; PYRIDONES; SPERMINE; UP-REGULATION;

EID: 0344118711     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0302694     Document Type: Article

References (45)

1. Marton, L. J.; Pegg, A. E. Polyamines as Targets for Therapeutic Intervention. Annu. Rev. Pharm. Toxicol, 1995, 35, 55-91.
2. Thomas, T.; Balabhadrapathruni, S.; Gallo, M. A.; Thomas, T. J. Development of Polyamine Analogs as Cancer Therapeutic Agents. Oncol. Res. 2002, 13, 123-135.
3. Wallace, H. M.; Fraser, A. V. Polyamine Analogues as Anticancer Drugs. Biochem. Soc. Trans. 2003, 31, 393-396.
4. Jänne, J.; Pösö, H.; Raina, A. Polyamines in Rapid Growth and Cancer. Biochim. Biophys. Acta 1978, 473, 241-293.
5. Porter, C. W.; McManis, J.; Casero, R. A.; Bergeron, R. J. Relative Abilities of Bis(ethyl) Derivatives of Putrescine, Spermidine, and Spermine to Regulate Polyamine Biosynthesis and Inhibit L1210 Leukemia Cell Growth. Cancer Res. 1987, 47, 2821-2825.
6. Bergeron, R. J.; Neims, A. H.; McManis, J. S.; Hawthorne, T. R.; Vinson, J. R. T.; Bortell, R.; Ingeno, M. J. Synthetic Polyamine Analogues as Antineoplastics. J. Med. Chem. 1988, 31, 1183-1190.
7. Pegg, A. E.; Madhubala, R.; Kameji, T.; Bergeron, R. J. Control of Ornithine Decarboxylase Activity in α-Difluoromethylornithine-Resistant L1210 Cells by Polyamines and Synthetic Analogues. J. Biol. Chem. 1988, 263, 11008-11014.
8. Porter, C. W.; Bergeron, R. J. Enzyme Regulation as an Approach to Interference with Polyamine Biosynthesis-an Alternative to Enzyme Inhibition. Adv. Enzyme Regul. 1988, 27, 57-79.
9. Bergeron, R. J.; Hawthorne, T. R.; Vinson, J. R. T.; Beck, D. E., Jr.; Ingeno, M. J. Role of the Methylene Backbone in the Antiproliferative Activity of Polyamine Analogues on L1210 Cells. Cancer Res. 1989, 49, 2959-2964.
10. Libby, P. R.; Bergeron, R. J.; Porter, C. W. Structure-Function Correlations of Polyamine Analog-Induced Increases in Spermidine/Spermine Acetyltransferase Activity. Biochem. Pharmacol. 1989, 38, 1435-1442.
11. 12-Bis(ethyl)spermine. Biochem. J. 1990, 268, 207-212.
12. Bernacki, R. J.; Bergeron, R. J.; Porter, C. W. Antitumor Activity of N,N′-Bis(ethyl)spermine Homologues against Human MALME-3 Melanoma Xenografts. Cancer Res. 1992, 52, 2424-2430.
13. 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.
14. Bergeron, R. J.; McManis, J. S.; Weimar, W. R.; Schreier, K. M.; Gao, F. ; Wu, Q.; Ortiz-Ocasio, J.; Luchetta, G. R.; Porter, C.; Vinson, J. R. T. The Role of Charge in Polyamine Analogue Recognition. J. Med. Chem. 1995, 38, 2278-2285.
15. 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.
16. 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 Anti-proliferatives. J. Med. Chem. 2000, 43, 224-235.
17. Bergeron, R. J.; Müller, R.; Huang, G.; McManis, J. S.; Algee, S. E.; Yao, H.; Weimar, W. R.; Wiegand, J. Synthesis and Evaluation of Hydroxylated Polyamine Analogues as Antiproliferatives. J. Med. Chem. 2001, 44, 2451-2459.
18. Delcros, 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 Acridine. J. Med. Chem. 2002, 45, 5098-5111.
19. Bergeron, R. J.; Weimar, W. R.; Wu, Q.; Feng, Y.; McManis, J. S. Polyamine Analogue Regulation of NMDA MK-801 Binding: A Structure-Activity Study. J. Med. Chem. 1996, 39, 5257-5266.
20. Bergeron, R. J.; Yao, G. W.; Yao, H.; Weimar, W. R.; Sninsky, C. A.; Raisler, B.; Feng, Y.; Wu, Q.; Gao, F. Metabolically Programmed Polyamine Analogue Antidiarrheals. J. Med. Chem. 1996, 39, 2461-2471.
21. Holley, J. L.; Mather, A.; Wheelhouse, R. T.; Cullis, P. M.; Hartley, J. A.; Bingham, J. P.; Cohen, G. M. Targeting of Tumor Cells and DNA by a Chlorambucil-Spermidine Conjugate. Cancer Res. 1992, 52, 4190-4195.
22. Cullis, P. M.; Green, R. E.; Malone, M. E.; Merson-Davies, L.; Weaver, R. Targeting of Tumor Cells with Polyamine-Drug Conjugates. Biochem. Soc. Trans. 1994, 22, 402S.
23. Wang, L.; Price, H. L.; Juusola, J.; Kline, M.; Phanstiel, O., IV. Influence of Polyamine Architecture on the Transport and Topoisomerase II Inhibitory Properties of Polyamine DNA-Intercalator Conjugates. J. Med. Chem. 2001, 44, 3682-3691.
24. Burns, M. R.; Carlson, C. L.; Vanderwerf, S. M.; Ziemer, J. R.; Weeks, R. S.; Cai, F.; Webb, H. K.; Graminski, G. F. Amino Acid/Spermine Conjugates: Polyamine Amides as Potent Spermidine Uptake Inhibitors. J. Med. Chem. 2001, 44, 3632-3644.
25. Bergeron, R. J. Iron: A Controlling Nutrient in Proliferative Processes. Trends Biochem. Sci. 1986, 11, 133-136.
26. Bergeron, R. J.; Braylan, R.; Goldey, S.; Ingeno, M. J. Effects of the Vibrio cholerae Siderophore Vibriobactin on the Growth Characteristics of L1210 Cells. Biochem. Biophys. Res. Commun. 1986, 136, 273-280.
27. Hershko, C. Control of Disease by Selective Iron Depletion: A Novel Therapeutic Strategy Utilizing Iron Chelators. Bailliere's Clin. Haematol. 1994, 7, 965-1000.
28. Chenoufi, N.; Drenou, B.; Loreal, O.; Pigeon, C.; Brissot, P.; Lescoat, G. Antiproliferative Effect of Deferiprone on the Hep G2 Cell Line. Biochem. Pharmacol. 1998, 56, 431-437.
29. Bergeron, R. J.; Ingeno, M. J. Microbial Iron Chelator-Induced Cell Cycle Synchronization in L1210 Cells: Potential in Combination Chemotherapy. Cancer Res. 1987, 47, 6010-6016.
30. Taetle, R.; Honeysett, J. M.; Bergeron, R. J. Combination Iron Depletion Therapy. J. Natl. Cancer Inst. 1989, 81, 1229-1235.
31. Nyholm, S.; Mann, G. J.; Johannson, A. G.; Bergeron, R. J.; Graslund, A. ; Thelander, L. Role of Ribonucleotide Reductase in Inhibition of Mammalian Cell Growth by Potent Iron Chelators. J. Biol. Chem. 1993, 268, 26200-26205.
32. Porter, J. B.; Gyparaki, M.; Burke, L. C.; Huehns, E. R.; Sarpong, P.; Saez, V.; Hider, R. C. Iron Mobilization from Hepatocyte Monolayer Cultures by Chelators: The Importance of Membrane Permeability and the Iron-Binding Constant. Blood 1988, 72, 1497-1503.
33. Selig, R. A.; White, L.; Gramacho, C.; Sterling-Levis, K.; Fraser, I. W. ; Naidoo, D. Failure of Iron Chelators to Reduce Tumor Growth in Human Neuroblastoma Xenografts. Cancer Res. 1998, 58, 473-478.
34. Bergeron, R. J.; Huang, G.; Weimar, W. R.; Smith, R. E.; Wiegand, J.; McManis, J. S. Desferrithiocin Analogue-Based Hexacoordinate Iron(III) Chelators. J. Med. Chem. 2003, 46, 16-24.
35. Cragg, L.; Hebbel, R. P.; Miller, W.; Solovey, A.; Selby, S.; Enright, H. The Iron Chelator L1 Potentiates Oxidative DNA Damage in Iron-Loaded Liver Cells. Blood 1998, 92, 632-638.
36. Dean, R. T.; Nicholson, P. The Action of Nine Chelators on Iron-Dependent Radical Damage. Free Radic. Res. 1994, 20, 83-101.
37. Harris, R. L. N. Potential Wool Growth Inhibitors. Improved Syntheses of Mimosine and Related 4(1H)-Pyridones. Aust. J. Chem. 1976, 29, 1329-1334.
38. Geall, A. J.; Blagbrough, I. S. Homologation of Polyamines in the Rapid Synthesis of Lipospermine Conjugates and Related Lipoplexes. Tetrahedron 2000, 56, 2449-2460.
39. Nelson, W. O.; Karpishin, T. B.; Rettig, S. J.; Orvig, C. Physical and Structural Studies of N-Substituted 3-Hydroxy-2-methyl-4(1H)-pyridinones. Can. J. Chem. 1988, 66, 123-131.
40. Liu, G.; Miller, S. C.; Bruenger, F. W. Synthesis of Lipophilic 3-Hydroxy-2-methyl-4-pyridinone Derivatives. Synth. Commun. 1995, 25, 3247-3253.
41. Bergeron, R. J.; Wiegand, J.; Weimar, W. R.; Vinson, J. R. T.; Bussenius, J.; Yao, G. W.; McManis, J. S. Desazadesmethyldes-ferrithiocin Analogues as Orally Effective Iron Chelators. J. Med. Chem. 1999, 42, 95-108.
42. 11-Diethylnorspermine. Drug Metab. Dispos. 1995, 23, 1117-1125.
43. Goddard, J. G.; Kontoghiorghes, G. J. Development of an HPLC Method for Measuring Orally Administered 1-Substituted 2-Alkyl-3-hydroxypyrid-4-one Iron Chelators in Biological Fluids. Clin. Chem. 1990, 36, 5-8.
44. Seely, J. E.; Pegg, A. E. Ornithine Decarboxylase (Mouse Kidney). Methods Enzymol. 1983, 94, 158-161.
45. Pegg, A. E.; Pösö, H. S-Adenosylmethionine Decarboxylase (Rat Liver). Methods Enzymol. 1983, 94, 234-239.