Selegiline-functionalized, PEGylated poly(alkyl cyanoacrylate) nanoparticles: Investigation of interaction with amyloid-β peptide and surface reorganization

International Journal of Pharmaceutics

Volumn 416, Issue 2, 2011, Pages 453-460

  Le Droumaguet, Benjamin ^a   Souguir, Hayfa ^a   Brambilla, Davide ^a   Verpillot, Romain ^a   Nicolas, Julien ^a   Taverna, Myriam ^a   Couvreur, Patrick ^a   Andrieux, Karine ^a  

^a UNIV PARIS SUD   (France)

Author keywords

Alzheimer's disease; Amyloid peptide; Functionalization; Poly(alkyl cyanoacrylate) nanoparticles; Selegiline

Indexed keywords

AMYLOID BETA PROTEIN[1-42]; COPOLYMER; CYANOACRYLATE; MACROGOL; NANOPARTICLE; PEGYLATED POLY(ALKYL CYANOACRYLATE); RHODAMINE B; SELEGILINE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CAPILLARY ELECTROPHORESIS; CONTROLLED STUDY; DRUG FORMULATION; DRUG SYNTHESIS; HYDROPHOBICITY; KNOEVENAGEL CONDENSATION; MICHAEL ADDITION; MOLECULAR INTERACTION; PRIORITY JOURNAL; SURFACE PROPERTY; SURFACE REORGANIZATION; ZETA POTENTIAL;

ALZHEIMER DISEASE; AMYLOID BETA-PEPTIDES; COLLOIDS; CYANOACRYLATES; DRUG DELIVERY SYSTEMS; DRUG DESIGN; ELECTROPHORESIS, CAPILLARY; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; NANOPARTICLES; PEPTIDE FRAGMENTS; POLYETHYLENE GLYCOLS; RHODAMINES; SELEGILINE;

EID: 80051864819     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2011.01.015     Document Type: Article

References (50)

1. A. Aguzzi, and T. O'Connor Protein aggregation diseases: pathogenicity and therapeutic perspectives Nat. Rev. Drug Discov. 9 2010 237 248
2. G. Aliev, M.A. Smith, J.C. de la Torre, and G. Perry Mitochondria as a primary target for vascular hypoperfusion and oxidative stress in Alzheimer's disease Mitochondrion 4 2004 649 663 (Pubitemid 39650918)
3. J. Birks, J. Grimley Evans, V. Iakovidou, M. Tsolaki, and F.E. Holt Rivastigmine for Alzheimer's disease Cochrane Database Syst. Rev. 2009 CD001191
4. D. Brambilla, J. Nicolas, B. Le Droumaguet, K. Andrieux, V. Marsaud, P.-O. Couraud, and P. Couvreur Design of fluorescently tagged poly(alkyl cyanoacrylate) nanoparticles for human brain endothelial cell imaging Chem. Commun. 46 2010 2602 2604
5. D. Brambilla, R. Verpillot, M. Taverna, L. De Kimpe, B. Le Droumaguet, J. Nicolas, F. Mantegazza, M. Canovi, M. Gobbi, M. Salmona, V. Nicolas, W. Scheper, P. Couvreur, and K. Andrieux Capillary electrophoresis with laser-induced fluorescence detection (CE-LIF) as a new protocol to monitor interaction between nanoparticles and the amyloid-β peptide Anal. Chem. 82 2010 10083 10089
6. P. Calvo, B. Gouritin, H. Chacun, D. Desmaële, J. D'Angelo, J.-P. Noel, D. Georgin, E. Fattal, J.P. Andreux, and P. Couvreur Long-circulating PEGylated polycyanoacrylate nanoparticles as new drug carrier for brain delivery Pharm. Res. 18 2001 1157 1166 (Pubitemid 32900402)
7. D.B. Carter, and K.C. Chou A model for structure-dependent binding of Congo red to Alzheimer β-amyloid fibrils Neurobiol. Aging 19 1998 37 40 (Pubitemid 28167793)
8. V. Chow, M. Mattson, P. Wong, and M. Gleichmann An overview of APP processing enzymes and products Neuromol. Med. 12 2010 1 12
9. D.L. Christopher, J.J. Carolyn, F. Virginia, P. Marie-Christine, H.H. David, S. Scot, A.M. Chester, and E.K. William Visualization of fibrillar amyloid deposits in living, transgenic Caenorhabditis elegans animals using the sensitive amyloid dye, X-34 Neurobiol. Aging 22 2001 217 226
10. R. Colombo, A. Carotti, M. Catto, M. Racchi, C. Lanni, L. Verga, G. Caccialanza, and E. De Lorenzi CE can identify small molecules that selectively target soluble oligomers of amyloid β protein and display antifibrillogenic activity Electrophoresis 30 2009 1418 1429
11. J.C. de la Torre Is Alzheimer's disease a neurodegenerative or a vascular disorder? Data, dogma, and dialectics Lancet Neurol. 3 2004 184 190 (Pubitemid 38232669)
12. 2 conjugates of Chrysamine G, potential probes for the beta-amyloid protein of Alzheimer's disease J. Labelled Compd. Radiopharm. 42 1999 309 324 (Pubitemid 29150211)
13. 99mTc-MAMA-Chrysamine G, a probe for beta-amyloid protein of Alzheimer's disease Eur. J. Nucl. Med. Mol. Imaging 26 1999 1392 1399 (Pubitemid 29515599)
14. M. Garcia-Alloza, L.A. Borrelli, A. Rozkalne, B.T. Hyman, and B.J. Bacskai Curcumin labels amyloid pathology in vivo, disrupts existing plaques, and partially restores distorted neurites in an Alzheimer mouse model J. Neurochem. 102 2007 1095 1104 (Pubitemid 47174225)
15. E. Garcia-Garcia, K. Andrieux, S. Gil, and P. Couvreur Colloidal carriers and blood-brain barrier (BBB) translocation: a way to deliver drugs to the brain? Int. J. Pharm. 298 2005 274 292 (Pubitemid 40910731)
16. E. Garcia-Garcia, S. Gil, K. Andrieux, D. Desmaële, V. Nicolas, F. Taran, D. Georgin, J. Andreux, F. Roux, and P. Couvreur A relevant in vitro rat model for the evaluation of blood-brain barrier translocation of nanoparticles Cell. Mol. Life Sci. 62 2005 1400 1408 (Pubitemid 40853828)
17. S. García-Matas, N. de Vera, A.O. Aznar, J.M. Marimon, A. Adell, A.M. Planas, R. Cristfol, and C. Sanfeliu In vitro and in vivo activation of astrocytes by amyloid-β is potentiated by pro-oxidant agents J. Alzheimer's Dis. 20 2010 229 245
18. M. Gralle, M.G. Botelho, and F.S. Wouters Neuroprotective secreted amyloid precursor protein acts by disrupting amyloid precursor protein dimers J. Biol. Chem. 284 2009 15016 15025
19. M. Kato, H. Kinoshita, M. Enokita, Y. Hori, T. Hashimoto, T. Iwatsubo, and T. Toyo'oka Analytical method for β-amyloid fibrils using CE-laser induced fluorescence and its application to screening for inhibitors of β-amyloid protein aggregation Anal. Chem. 79 2007 4887 4891 (Pubitemid 47051441)
20. J.A. Kemp, and R.M. McKernan NMDA receptor pathways as drug targets Nat. Neurosci. 5 2002 1039 1042 (Pubitemid 35247194)
21. W.E. Klunk, M.L. Debnath, A.M.C. Koros, and J.W. Pettegrew Chrysamine-G, a lipophilic analogue of Congo red, inhibits Aβ-induced toxicity in PC12 cells Life Sci. 63 1998 1807 1814 (Pubitemid 28511613)
22. H.C. Kolb, M.G. Finn, and K.B. Sharpless Click chemistry: diverse chemical function from a few good reactions Angew. Chem. Int. Ed. 40 2001 2004 2021
23. M.A. Korolainen, T.A. Nyman, T. Aittokallio, and T. Pirttila An update on clinical proteomics in Alzheimer's research J. Neurochem. 112 2010 1386 1414
24. V.M.Y. Lee Amyloid binding ligands as Alzheimer's disease therapies Neurobiol. Aging 23 2002 1039 1042
25. G.P. Lim, T. Chu, F. Yang, W. Beech, S.A. Frautschy, and G.M. Cole The curry spice curcumin reduces oxidative damage and amyloid pathology in an Alzheimer transgenic mouse J. Neurosci. 21 2001 8370 8377 (Pubitemid 33051435)
26. A. Lorenzo, and B.A. Yankner Beta-amyloid neurotoxicity requires fibril formation and is inhibited by Congo red Proc. Natl. Acad. Sci. U.S.A. 91 1994 12243 12247 (Pubitemid 24368641)
27. D. Munoz-Torrero Acetylcholinesterase inhibitors as disease-modifying therapies for Alzheimer's disease Curr. Med. Chem. 15 2008 2433 2455
28. R. Narlawar, M. Pickhardt, S. Leuchtenberger, K. Baumann, S. Krause, T. Dyrks, S. Weggen, E. Mandelkow, and B. Schmidt Curcumin-derived pyrazoles and isoxazoles: Swiss army knives or blunt tools for Alzheimer's disease? ChemMedChem 3 2008 165 172
29. J. Nicolas, F. Bensaid, D. Desmaele, M. Grogna, C. Detrembleur, K. Andrieux, and P. Couvreur Synthesis of highly functionalized poly(alkyl cyanoacrylate) nanoparticles by means of click chemistry Macromolecules 41 2008 8418 8428
30. J. Nicolas, and P. Couvreur Synthesis of poly(alkyl cyanoacrylate)-based colloidal nanomedicines Wiley Interdiscipl. Rev.: Nanomed. Nanobiotechnol. 1 2009 111 127
31. A. Nordberg PET imaging of amyloid in Alzheimer's disease Lancet Neurol. 3 2004 519 527 (Pubitemid 39485859)
32. K. Ono, K. Hasegawa, H. Naiki, and M. Yamada Curcumin has potent anti-amyloidogenic effects for Alzheimer's β-amyloid fibrils in vitro J. Neurosci. Res. 75 2004 742 750 (Pubitemid 38296087)
33. F. Panza, V. Solfrizzi, V. Frisardi, B.P. Imbimbo, C. Capurso, A. D'Introno, A.M. Colacicco, D. Seripa, G. Vendemiale, A. Capurso, and A. Pilotto Beyond the neurotransmitter-focused approach in treating Alzheimer's disease: drugs targeting beta-amyloid and tau protein Aging Clin. Exp. Res. 21 2009 386 406
34. C.G. Parsons, W. Danysz, and G. Quack Memantine is a clinically well tolerated N-methyl-d-aspartate (NMDA) receptor antagonist - a review of preclinical data Neuropharmacology 38 1999 735 767 (Pubitemid 29187336)
35. ® PEGylated polycyanoacrylate nanoparticles for intravenous administration and splenic targeting J. Controlled Release 60 1999 121 128 (Pubitemid 29255834)
36. H.W. Querfurth, and F.M. LaFerla Alzheimer's disease N. Engl. J. Med. 362 2010 329 344
37. F. Re, C. Airoldi, C. Zona, M. Masserini, B.L. Ferla, N. Quattrocchi, and F. Nicotra Beta amyloid aggregation inhibitors: small molecules as candidate drugs for therapy of Alzheimers disease Curr. Med. Chem. 17 2010 2990 3006
38. B. Reisberg, R. Doody, A. Stoffler, F. Schmitt, S. Ferris, and H.J. Mobius Memantine in moderate-to-severe Alzheimer's disease N. Engl. J. Med. 348 2003 1333 1341 (Pubitemid 36384100)
39. S. Sabella, M. Quaglia, C. Lanni, M. Racchi, S. Govoni, G. Caccialanza, A. Calligaro, V. Bellotti, and E. De Lorenzi Capillary electrophoresis studies on the aggregation process of β-amyloid 1-42 and 1-40 peptides Electrophoresis 25 2004 3186 3194 (Pubitemid 39480887)
40. M. Sano, C. Ernesto, R.G. Thomas, M.R. Klauber, K. Schafer, M. Grundman, P. Woodbury, J. Growdon, C.W. Cotman, E. Pfeiffer, L.S. Schneider, and L.J. Thal A controlled trial of selegiline, alpha-tocopherol, or both as treatment for Alzheimer's disease N. Eng. J. Med. 336 1997 1216 1222 (Pubitemid 27183651)
41. S.D. Styren, R.L. Hamilton, G.C. Styren, and W.E. Klunk X-34, a fluorescent derivative of Congo red: a novel histochemical stain for Alzheimer's disease pathology J. Histochem. Cytochem. 48 2000 1223 1232
42. H. Sugimoto, Y. Iimura, Y. Yamanishi, and K. Yamatsu Synthesis and structure-activity relationships of acetylcholinesterase inhibitors: 1-benzyl-4-[(5,6-dimethoxy-1-oxoindan-2-yl)methyl]piperidine hydrochloride and related compounds J. Med. Chem. 38 1995 4821 4829
43. M. Sun, Y. Gao, C. Guo, F. Cao, Z. Song, Y. Xi, A. Yu, A. Li, and G. Zhai Enhancement of transport of curcumin to brain in mice by poly(n- butylcyanoacrylate) nanoparticle J. Nanopart. Res. 2010 1 12
44. J. Tetrud, and J. Langston The effect of deprenyl (selegiline) on the natural history of Parkinson's disease Science 245 1989 519 522 (Pubitemid 19204003)
45. T. Tom Monoamine oxidase-B inhibitors in the treatment of Alzheimers disease Neurobiol. Aging 21 2000 343 348
46. M.Y.L. Virginia Amyloid binding ligands as Alzheimer's disease therapies Neurobiol. Aging 23 2002 1039 1042
47. Y. Wang, W. Klunk, M. Debnath, G.-F. Huang, D. Holt, L. Shao, and C. Mathis Development of a PET/SPECT agent for amyloid imaging in Alzheimer's disease J. Mol. Neurosci. 24 2004 55 62 (Pubitemid 41359167)
48. Y. Wang, W. Klunk, G.-F. Huang, M. Debnath, D. Holt, and C. Mathis Synthesis and evaluation of 2-(3′-lodo-4′-aminophenyl)-6- hydroxybenzothiazole for in vivo quantitation of amyloid deposits in Alzheimer's disease J. Mol. Neurosci. 19 2002 11 16 (Pubitemid 35013328)
49. G.K. Wilcock, J. Birks, A. Whitehead, and S.J.G. Evans The effect of selegiline in the treatment of people with Alzheimer's disease: a meta-analysis of published trials Int. J. Geriatr. Psych. 17 2002 175 183 (Pubitemid 34130310)
50. Y. Xie, S. Deng, Z. Chen, S. Yan, and D.W. Landry Identification of small-molecule inhibitors of the Aβ-ABAD interaction Bioorg. Med. Chem. Lett. 16 2006 4657 4660 (Pubitemid 44094056)