Biogenic and synthetic polyamines bind cationic dendrimers

PLoS ONE

Volumn 7, Issue 4, 2012, Pages

  Mandeville, Jean Sebastian ^a   Bourassa, Phillipe ^a   Thomas, Thekkumkattil John ^b   Tajmir Riahi, Heidar Ali ^a  

^a UNIVERSITÉ DU QUÉBEC À TROIS RIVIÈRES   (Canada)

^b ROBERT WOOD JOHNSON MEDICAL SCHOOL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3,7,11,15 TETRAZAHEPTADECANE; 3,7,11,15,19 PENTAZAHENICOSANE; BE 333; BE 3333; DENDRIMER; MACROGOL; POLYAMINE DERIVATIVE; SPERMIDINE; SPERMINE; UNCLASSIFIED DRUG; CATION; NYLON; PAMAM G4; PAMAM-G4; POLYAMINE;

ARTICLE; BINDING AFFINITY; BINDING KINETICS; COMPLEX FORMATION; CONFORMATION; CONTROLLED STUDY; HYDROPHILICITY; HYDROPHOBICITY; MOLECULAR DOCKING; MOLECULAR MODEL; MOLECULAR STABILITY; CHEMICAL PHENOMENA; CHEMICAL STRUCTURE; CHEMISTRY; INFRARED SPECTROSCOPY; KINETICS; METABOLISM; THERMODYNAMICS; ULTRAVIOLET SPECTROPHOTOMETRY;

BIOGENIC POLYAMINES; CATIONS; DENDRIMERS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; KINETICS; MODELS, MOLECULAR; NYLONS; SPECTROPHOTOMETRY, ULTRAVIOLET; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; THERMODYNAMICS;

EID: 84860443716     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0036087     Document Type: Article

References (51)

1. Huang Y, Keen JC, Pledgie A, Marton LJ, Zhu T, et al. (2006) Polyamine analogues down-regulate estrogen receptor α expression in human breast cancer cells. J Biol Chem 281: 19055-19063.
2. Huang Y, Keen JC, Hager E, Smith R, Hacker A, et al. (2004) Regulation of polyamine analogue cytotoxicity by c-jun in human MDA-MB-435 cancer cells. Mol Cancer Res 2: 81-88.
3. Casero RA, Woster PM, (2001) Terminally alkylated polyamine analogues as chemotherapeutic agents. J Med Chem 44: 1-26.
4. Gerner EW, Meyskens FL, (2004) Polyamines and cancer: old molecules, new understanding. Nat Rev Cancer 4: 781-792.
5. Bergeron RJ, Neims AT, McManis JS, Hawthorne TR, Vinson JRT, et al. (1988) Synthetic polyaminesanalogues as antineoplastics. J Med Chem 31: 1183-1190.
6. Bergeron RJ, McManis JS, Liu CZ, Frng Y, Weimar WR, et al. (1994) Antiproliferative properties of polyamine analogues: a structure-activity study. J Med Chem 37: 3464-3476.
7. Davidson NE, Mank AR, Prestigiacomo LJ, Bergeron JR, Casero RA, (1993) Growth inhabitation of hormone-responsive and resistant human breast cancer cells in culture by N1,N12-bis (ethyl)spermine. Cancer Res 53: 2071-2075.
8. Thomas T, Balabhadrapathruni S, Gallo MA, Thomas TJ, (2002) Development of polyamine analogues as cancer therapeutic agents. Oncol Res 13: 123-135.
9. Faaland CA, Thomas TJ, Balabhadrapathruni S, Langer T, Mian S, et al. (2000) Molecular correlates of the action of bis(ethyl)polyamines in breast cancer cell growth inhibition and apoptosis. Biochem Cell Biol 78: 415-426.
10. Thomas T, Thomas TJ, (2003) Polyamine metabolism and cancer. J Cell Mol Med 7: 113-126.
11. McCloskey DE, Pegg AE, (2003) Properties of the spermidine/spermine N1- acetyltransferase mutant L156F that decreases cellular sensitivity to the polyamine analogue N1, N11-bis(ethyl)norspermine. J Biol Chem 278: 13881-13887.
12. Ha HC, Woster PA, Yager JD, Castro RA, (1997) The role of polyamine catabolism in polyamine analogue-induced programmed cell death. Proc Natl Acad. Sci USA 94: 11557-11562.
13. Ha HC, Sirisoma NS, Kuppusamy P, Zweier LJ, Woster PM, et al. (1998) The natural polyamines spermine functions directly as a free radical scavenger. Proc Natl Acad Sci U S A 95: 11140-11145.
14. Tabor CW, Tabor H, (1984) Polyamines. Annu Rev Biochem 53: 749-790.
15. Pegg AE, (1988) Polyamine metabolism, and its importance in neoplastic growth and a target of chemotherapy. Cancer Res 48: 759-774.
16. Heby O, (1981) Role of polyamines in the control of cell proliferation and differentiation. Differentiation 19: 1-20.
17. Tkachenko AG, Nesterova LY, (2003) Polyamines as modulators of gene expression under oxidative stress in Escherichia coli. Biochemistry (Moscow) 68: 850-856.
18. Marton LJ, Pegg AE, (1995) Polyamines as targets for therapeutic intervention. Annu Rev Pharmacol Toxicol 35: 55-91.
19. Cohen SS, (1998) (1998) A Guide to the polyamines, Oxford Uni. Press, New York.
20. Thomas T, Thomas TJ, (2001) Polyamine in cell growth and death. Cell Mol Life Sci 58: 244-258.
21. Ahmed Ouameur A, Tajmir-Riahi HA, (2004) Structural analysis of DNA interactions with biogenic polyamines and cobalt (III) hexamine studied by Fourier transform infrared and capillary electrophoresis. J Biol Chem 279: 42041-42050.
22. Ahmed Ouameur A, Bourassa P, Tajmir-Riahi HA, (2010) Probing tRNA interaction with biogenic polyamines. RNA 16: 1968-1979.
23. N'soukpoé-Kossi CN, Ahmed Ouameur A, Thomas T, Shirahata A, Thomas TJ, et al. (2008) DNA interaction with antitumor polyamine analogues: Acomparison with biogenic polyamines. Biomacromolecules 9: 2712-2718.
24. N'soukpoé-Kossi CN, Ahmed Ouameur A, Thomas T, Thomas TJ, Tajmir-Riahi HA, (2009) Interaction tRNA with antitumor polyamine analogues. Biochem Cell Biol 87: 621-630.
25. D'Agostino L, di Pietro M, Di Luccia A, (2005) Nuclear aggregates of polyamines are supramolecular structures that play a crucial role in genomic DNA protection and conformation. FEBS J 272: 3777-3787.
26. Hardy JG, Mauri A, David K, Smith K, Gabrielson NP, et al. (2006) Dendrons with spermine surface groups as potential building blocks for nonviral vectors in gene therapy. Bioconjugate Chem 17: 172-178.
27. Galeazzi S, Hermans TM, Paolino M, Anzini M, Mennuni L, et al. (2010) Multivalent supramolecular dendriemr-based drugs. Biomacromolecules 11: 182-186.
28. Hu J, Fang M, Cheng Y, Zhang J, Wu Q, et al. (2010) Host-guest chemistry of dendrimer-drug complexes. 4. An in depth look into the binding/encapsulation of guanosine monophosphate by dendrimers. J Phys Chem B 114: 7148-7157.
29. Maiti PK, Caing T, Wang G, Goddard WA, (2004) Structure of PAMAM dendrimers: Generations 1 through 11. Macromolecules 37: 6236-6254.
30. Patri AK, Majoros IJ, Baker JR, (2002) Dendritic polymer macromolecular carriers for drug delivery. Curr Opinion Chem Biol 6: 466-471.
31. Tomilia DA, (2005) Birth of a new macromolecular architecture: dendrimers as quantized building blocks for nanoscale synthetic polymer chemistry. Prog Polymer Sci 30: 294-324.
32. Klajnert B, Bryszewska M, (2007) Dendrimers as delivery systems in gene therapy; In: Valon CL, editors. New developments in mutation research pp. 217-240 in: Chapter 9.
33. Lee CC, Mackay JA, Frechet JMJ, Szoka FC, (2005) Designing dendrimers for biological applications. Nature Biotech 23: 1517-1526.
34. Klajnert B, Bryszewska M, (2007) Dendrimers in Medeicines Nova Science publisher, Inc., New York (2007) in:.
35. Kojima C, Kono K, Maruyama K, Takagishi T, (2000) Synthesis of pollyamidoamine dendriemrs having poly(ethylene glycol) grafts and their ability to encapsulate anticancer drugs. Bioconjugate Chem 11: 910-917.
36. Zhuo RX, Du B, Lu ZR, (1999) In vitro release of 5-flurouracil with cyclic core dendritic polymer. J Control Release 57: 249-257.
37. Kono K, Liu M, Frechet JMJ, (1999) Design of dendritic macromolecules containing folate or methotrexate residues. Bioconjugate Chem 10: 1115-1121.
38. Jansen JFGA, Meijer EW, de Brabander-van den Berg EMM, (1995) The dendritic box: shape-selective liberation of encapsulated guests. J Am Chem Soc 117: 4417-4418.
39. Malik N, Wiwattanapatapee R, Klopsch R, Lorenz K, Frey H, et al. (2000) Dendrimers: relationship between structure and biocompatibility in vitro, and preliminary studies on the biodistribution of 125I-labeled poly (amido amine) dendrimers in vivo. J Control Release 65: 133-148.
40. Jevprascsphant R, Penny J, Jalal R, Atwood D, McKcown N, et al. (2000) The influence of surface modifications on the cytotoxicity of PAMAM dendrimers. Int J Pharm 252: 263-266.
41. Iyer J, Fleming K, Hammond PT, Paula TH, (1998) Synthesis and solution properties of new linear-dendritic diblock copolymers. Macromolecules 31: 8757-8765.
42. Froehlich E, Mandeville JS, Weinert CM, Kreplak L, Tajmir-Riahi HA, (2011) Bundling and aggregation of DNA by cationic dendrimers. Biomacromolecules 12: 511-517.
43. Popescu MC, Filip D, Vasile C, Cruz C, Rueff JM, et al. (2006) Characterization by Fourier transform infrared spectroscopy (FT-IR) and 2D IR correlation spectroscopy of PAMAM dendrimer. J Phys Chem B 110: 14198-14211.
44. Singh P, Gupta U, Asthana A, Jain NK, (2008) Folate and folate#PEG#PAMAM dendrimers: synthesis, characterization, and targeted anticancer drug delivery potential in tumor bearing mice. Bioconjugate Chem 19: 2239-2252.
45. Connors K., (1987) Binding constants: The measurement of molecular complex stability, John Wiley & Sons, New York.
46. Dubeau S, Bourassa P, Thomas TJ, Tajmir-Riahi HA, (2010) Biogenic and synthetic polyamines bind bovine serum albumin. Biomacromolecules 11: 1507-1515.
47. Esseminea J, Hasnia I, Carpentiera R, Thomas TJ, Tajmir-Riahi HA, (2011) Binding of biogenic and synthetic polyamines to beta-lactoglobulin. Intl J Biol Macromol 49: 201209.
48. Jansen JFGA, Meijer EW, de Brabander-van den Berg EMM, (1994) Encapsulation of guest molecules into a dendritic box. Science 266: 1226-1229.
49. Hawke CJ, Wooley KL, Fréchet JMJ, (1999) Unimolecular micells and globular amphiphiles;dendritic macromolecules as novel recyclable solubilization agents. J Chem Soc Perkin Trans pp. 1287-1297.
50. Twyman LJ, Beezer AE, Esfand R, Dardy MJ, Michell JC, (1999) The synthesis of water soluble dendrimers and their application as possible drug delivery systems. Tetrahedron Lett 40: 1743-1746.
51. Abderrezak A, Bourassa P, Mandeville JS, Sedaghat-Herati R, Tajmir-Riahi HA, (2012) Dendrimers bind antioxidant polyphenols and cisplatin drug. PLoS ONE 7: e33102, 1-12.