Multifunctional nanoliposomes with curcumin–lipid derivative and brain targeting functionality with potential applications for Alzheimer disease

European Journal of Medicinal Chemistry - Tập 80 - Trang 175-183 - 2014
Spyridon Mourtas1, Adina N. Lazar2,3, Eleni Markoutsa1, Charles Duyckaerts2,3, Sophia G. Antimisiaris1,4
1Laboratory of Pharmaceutical Technology, Dept. of Pharmacy, School of Health Sciences, University of Patras, Rio 26510, Greece
2Laboratoire de Neuropathologie Escourolle, Hôpital de la Salpêtrière, AP-HP, 47 Bd de l'hôpital 75013 Paris, France
3Centre de recherche de l'ICM, (UPMC, INSERM UMR S 975, CNRS UMR 7225), 47 Bd de l'hôpital, 75013 Paris, France
4Institute of Chemical Engineering Sciences, FORTH/ICES, Rio, 26504 Patras, Greece

Tài liệu tham khảo

American Psychiatric Association, 2000 Hyman, 2012, National Institute on Aging-Alzheimer's Association guidelines for the neuropathologic assessment of Alzheimer's disease, Alzheimer's & Dementia: the Journal of the Alzheimer's Association, 8, 1, 10.1016/j.jalz.2011.10.007 Hardy, 2002, Testing times for the “amyloid cascade hypothesis”, Neurobiology of Aging, 23, 1073, 10.1016/S0197-4580(02)00042-8 Iwatsubo, 1994, Visualization of A beta 42(43) and A beta 40 in senile plaques with end-specific A beta monoclonals: evidence that an initially deposited species is A beta 42(43), Neuron, 13, 45, 10.1016/0896-6273(94)90458-8 Selkoe, 1998, The cell biology of beta-amyloid precursor protein and presenilin in Alzheimer's disease, Trends in Cell Biology, 8, 447, 10.1016/S0962-8924(98)01363-4 Selkoe, 2001, Alzheimer's disease: genes, proteins, and therapy, Physiological Reviews, 81, 741, 10.1152/physrev.2001.81.2.741 Klunk, 2004, Imaging brain amyloid in Alzheimer's disease with Pittsburgh Compound-B, Annals of Neurology, 55, 306, 10.1002/ana.20009 Yanagisawa, 2011, In vivo detection of amyloid beta deposition using (1)F magnetic resonance imaging with a (1)F-containing curcumin derivative in a mouse model of Alzheimer's disease, Neuroscience, 184, 120, 10.1016/j.neuroscience.2011.03.071 Koronyo-Hamaoui, 2011, Identification of amyloid plaques in retinas from Alzheimer's patients and noninvasive in vivo optical imaging of retinal plaques in a mouse model, Neuroimage, 54, S204, 10.1016/j.neuroimage.2010.06.020 Lee, 2011, Synthesis and evaluation of 1-(4-[(18)F] fluoroethyl)-7-(4'-methyl)curcumin with improved brain permeability for beta-amyloid plaque imaging, Bioorganic & Medicinal Chemistry Letters, 21, 5765, 10.1016/j.bmcl.2011.08.003 Lazar, 2013, Curcumin-conjugated nanoliposomes with high affinity for Aβ deposits: possible applications to Alzheimer disease, Nanomedicine: Nanotechnology, Biology, and Medicine, 9, 712, 10.1016/j.nano.2012.11.004 Begum, 2008, Curcumin structure-function, bioavailability, and efficacy in models of neuroinflammation and Alzheimer's disease, The Journal of Pharmacology and Experimental Therapeutics, 326, 196, 10.1124/jpet.108.137455 Ono, 2004, Curcumin has potent anti-amyloidogenic effects for Alzheimer's beta-amyloid fibrils in vitro, Journal of Neuroscience Research, 742, 10.1002/jnr.20025 Yang, 2005, Curcumin inhibits formation of amyloid beta oligomers and fibrils, binds plaques, and reduces amyloid in vivo, The Journal of Biological Chemistry, 280, 5892, 10.1074/jbc.M404751200 Antimisiaris, 2007, 443 Jolck, 2011, Engineering liposomes and nanoparticles for biological targeting, Advances in Biochemical Engineering/Biotechnology, 125, 251, 10.1007/10_2010_92 Costantino, 2009, Colloidal systems for CNS drug delivery, Progress in Brain Research, 180, 35, 10.1016/S0079-6123(08)80003-9 Mourtas, 2011, Curcumin-decorated nanoliposomes with very high affinity for amyloid-β1-42 peptide, Biomaterials, 32, 1635, 10.1016/j.biomaterials.2010.10.027 Mourtas, 2001, S-4-Methoxytrityl mercapto acids: synthesis and application, Tetrahedron Letters, 42, 6965, 10.1016/S0040-4039(01)01423-X Dittmer, 1964, Specific spray, for the detection of phospholipids on thin-layer chromatograms, Journal of Lipid Research, 15, 126, 10.1016/S0022-2275(20)40272-X Stewart, 1980, Colorimetric determination of phospholipids with ammonium ferro thiocyanate, Analytical Biochemistry, 104, 10, 10.1016/0003-2697(80)90269-9 Markoutsa, 2014, Mono and dually decorated nanoliposomes for brain targeting, in vitro and in vivo studies, Pharmaceutical Research, 10.1007/s11095-013-1249-3 Braak, 1991, Neuropathological stageing of Alzheimer-related changes, Acta Neuropathologica, 82, 239, 10.1007/BF00308809 Mirra, 1991, The consortium to establish a registry for Alzheimer's disease (CERAD). Part II. Standardization of the neuropathologic assessment of Alzheimer's disease, Neurology, 41, 479, 10.1212/WNL.41.4.479 Consensus recommendations for the postmortem diagnosis of Alzheimer's disease, 1997, The national Institute on aging, and Reagan Institute working group on diagnostic criteria for the neuropathological assessment of Alzheimer's disease, Neurobiology of Aging, 18, S1 Manzoni, 2009, Overcoming synthetic Aβ peptide aging: a new approach to an age old problem, Amyloid: the International Journal of Experimental and Clinical Investigation: the Official Journal of the International Society of Amyloidosis, 16, 71, 10.1080/13506120902879848 Weksler, 2013, The hCMEC/D3 cell line as a model of the human blood brain barrier, Fluids and Barriers of the CNS, 10, 16, 10.1186/2045-8118-10-16 Markoutsa, 2012, Anti-Aβ-MAb and dually decorated nanoliposomes: effect of Aβ1-42 peptides on interaction with hCMEC/D3 cells, European Journal of Pharmaceutics and Biopharmaceutics, 81, 49, 10.1016/j.ejpb.2012.02.006 Greenwald, 1996, Water soluble taxol: 2′-poly(ethyleneglycol) ester prodrugs-design and in vivo effectiveness, Journal of Medicinal Chemistry, 39, 424, 10.1021/jm950475e Mukherjee, 2005, Haloperidol-associated stealth liposomes. A potent carrier for delivering genes to human breast cancer cells, The Journal of Biological Chemistry, 280, 15619, 10.1074/jbc.M409723200 Taylor, 2011, Effect of curcumin-associated and lipid ligand-functionalized nanoliposomes on aggregation of the Alzheimer's Aβ peptide, Nanomedicine: Nanotechnology, Biology, and Medicine, 7, 541, 10.1016/j.nano.2011.06.015 Markoutsa, 2011, Uptake and permeability studies of BBB-targeting immunoliposomes using the hCMEC/D3 cell line, European Journal of Pharmaceutics and Biopharmaceutics: Official Journal of Arbeitsgemeinschaft Fur Pharmazeutische Verfahrenstechnik e.V, 77, 265, 10.1016/j.ejpb.2010.11.015 DeFrees, 1996, Sialyl Lewis × liposomes as a multivalent ligand and inhibitor of E-selectin mediated cellular adhesion, Journal of the American Chemical Society, 118, 6101, 10.1021/ja954122g Zalipsky, 1997, Poly(ethylene glycol)-grafted liposomes with oligopeptide or oligosaccharide ligands appended to the termini of the polymer chains, Bioconjugate Chemistry, 8, 111, 10.1021/bc9600832