Effect of Xanthone and 1-Hydroxy Xanthone on the Dipole Potential of Lipid Membranes
Tài liệu tham khảo
Chairungsrilerd, 1996, Mangostanol, a prenyl xanthone from Garcinia mangostana, Phytochemistry, 43, 1099, 10.1016/S0031-9422(96)00410-4
Markiewicz, 2017, Assessing gastric toxicity of xanthone derivatives of anti-inflammatory activity using simulation and experimental approaches, Biophys. Chem., 220, 20, 10.1016/j.bpc.2016.10.007
Pedraza-Chaverri, 2008, Medicinal properties of mangosteen (Garcinia mangostana), Food Chem. Toxicol., 46, 3227, 10.1016/j.fct.2008.07.024
Matsumoto, 2003, Induction of apoptosis by xanthones from mangosteen in human leukemia cell lines, J. Nat. Prod., 66, 1124, 10.1021/np020546u
Matsumoto, 2004, Preferential target is mitochondria in α-mangostin-induced apoptosis in human leukemia HL60 cells, Bioorg. Med. Chem., 12, 5799, 10.1016/j.bmc.2004.08.034
Pedro, 2002, Xanthones as inhibitors of growth of human cancer cell lines and their effects on the proliferation of human lymphocytes in vitro, Bioorg. Med. Chem., 10, 3725, 10.1016/S0968-0896(02)00379-6
Mahabusarakam, 2006, Prenylated xanthones as potential antiplasmodial substances, Planta Med., 72, 912, 10.1055/s-2006-947190
Laphookhieo, 2006, Cytotoxic and antimalarial prenylated xanthones from Cratoxylum cochinchinense, Chem. Pharm. Bull., 54, 745, 10.1248/cpb.54.745
Rassameemasmaung, 2007, Effects of herbal mouthwash containing the pericarp extract of Garcinia mangostana L on halitosis, plaque and papillary bleeding index, J. Int. Acad. Periodontol., 9, 19
de Koning, 1988, Convenient syntheses of the naturally occurring benzo [b] xanthen-12-one bikaverin. X-Ray crystallographic confirmation of the product regiochemistry, J. Chem. Soc. Perkin Trans., 1, 3209, 10.1039/p19880003209
Pickert, 1998, Substituted xanthones as antimycobacterial agents, part 2: antimycobacterial activity, Arch. Pharm., 331, 193, 10.1002/(SICI)1521-4184(199805)331:5<193::AID-ARDP193>3.0.CO;2-S
Groweiss, 2000, HIV-inhibitory prenylated xanthones and flavones from Maclura t inctoria 1, J. Nat. Prod., 63, 1537, 10.1021/np000175m
Zarena, 2009, Screening of xanthone from mangosteen (Garcinia mangostana L.) peels and their effect on cytochrome c reductase and phosphomolybdenum activity, J. Nat. Prod. India, 2, 23
Librowski, 1999, Chiral 2-amino-1-butanol xanthone derivatives as potential antiarrhythmic and hypotensive agents, Acta Pol. Pharm., 56, 87
El-Seedi, 2010, Recent insights into the biosynthesis and biological activities of natural xanthones, Curr. Med. Chem., 17, 854, 10.2174/092986710790712147
Wang, 2016, Natural xanthones from Garcinia mangostana with multifunctional activities for the therapy of Alzheimer's disease, Neurochem. Res., 41, 1806, 10.1007/s11064-016-1896-y
Wang, 2012, α-Mangostin, a polyphenolic xanthone derivative from mangosteen, attenuates β-amyloid oligomers-induced neurotoxicity by inhibiting amyloid aggregation, Neuropharmacology, 62, 871, 10.1016/j.neuropharm.2011.09.016
Kolokythas, 2002, Design and synthesis of some new pyranoxanthenone aminoderivatives with cytotoxic activity, Bioorg. Med. Chem. Lett., 12, 1443, 10.1016/S0960-894X(02)00218-4
Negi, 2013, Naturally occurring xanthones: Chemistry and biology, J. Appl. Chem., 2013, 10.1155/2013/621459
Zou, 2013, Design and synthesis of amphiphilic xanthone-based, membrane-targeting antimicrobials with improved membrane selectivity, J. Med. Chem., 56, 2359, 10.1021/jm301683j
Koh, 2013, Rapid bactericidal action of alpha-mangostin against MRSA as an outcome of membrane targeting, Biochim. Biophys. Acta (BBA)-Biomembr., 1828, 834, 10.1016/j.bbamem.2012.09.004
Koh, 2015, Nonpeptidic amphiphilic xanthone derivatives: structure–activity relationship and membrane-targeting properties, J. Med. Chem., 59, 171, 10.1021/acs.jmedchem.5b01500
Peres, 2000, Tetraoxygenated naturally occurring xanthones, Phytochemistry, 55, 683, 10.1016/S0031-9422(00)00303-4
Sierra, 2017, Effects of hydroxy-xanthones on dipalmitoylphosphatidylcholine lipid bilayers: a theoretical and experimental study, Chem. Phys. Lipids, 206, 1, 10.1016/j.chemphyslip.2017.05.004
Kotova, 2000, Two phases of gramicidin photoinactivation in bilayer lipid membranes in the presence of a photosensitizer, Membr. Cell Biol., 13, 411
Pellosi, 2013, 85, 1267
Sokolov, 1984, Measurements of the potential difference during adsorption of phloretin and fluorescein on the surface of lipid membranes using the method of inner field compensation, Biofizika, 29, 424
Grover, 1955, Xanthones. Part IV. A new synthesis of hydroxyxanthones and hydroxybenzophenones, J. Chem. Soc. Resumed, 3982, 10.1039/jr9550003982
MacDonald, 1987, Lipid monolayer states and their relationships to bilayers, Proc. Natl. Acad. Sci., 84, 4089, 10.1073/pnas.84.12.4089
Luzardo, 1998, Surface potential of lipid interfaces formed by mixtures of phosphatidylcholine of different chain lengths, Langmuir, 14, 5858, 10.1021/la971273j
Lairion, 2009, Effect of dipole potential variations on the surface charge potential of lipid membranes, J. Phys. Chem. B, 113, 1607, 10.1021/jp808007g
Rosa, 2015, Interaction of phenylalanine with DPPC model membranes: more than a hydrophobic interaction, J. Phys. Chem. B, 119, 15844, 10.1021/acs.jpcb.5b08490
Wolkers, 2010, Dehydrating phospholipid vesicles measured in real-time using ATR Fourier transform infrared spectroscopy, Cryobiology, 61, 108, 10.1016/j.cryobiol.2010.06.001
Case, 2012
Skjevik, 2012, LIPID11: a modular framework for LIPID simulations using amber, J. Phys. Chem. B, 116, 11124, 10.1021/jp3059992
Jorgensen, 1983, Comparison of simple potential functions for simulating liquid water, J. Chem. Phys., 79, 926, 10.1063/1.445869
Mahoney, 2000, A five-site model for liquid water and the reproduction of the density anomaly by rigid, nonpolarizable potential functions, J. Chem. Phys., 112, 8910, 10.1063/1.481505
Hansen, 2013
Harris, 2002, Use of laurdan fluorescence intensity and polarization to distinguish between changes in membrane fluidity and phospholipid order, Biochim. Biophys. Acta (BBA)-Biomembr., 1565, 123, 10.1016/S0005-2736(02)00514-X
Parasassi, 1994, Influence of cholesterol on phospholipid bilayers phase domains as detected by Laurdan fluorescence, Biophys. J., 66, 120, 10.1016/S0006-3495(94)80763-5
Lakowicz, 2006
Nickels, 2015, 45
Brockman, 1994, Dipole potential of lipid membranes, Chem. Phys. Lipids, 73, 57, 10.1016/0009-3084(94)90174-0
Parasassi, 1998, Laurdan and Prodan as polarity-sensitive fluorescent membrane probes, J. Fluoresc., 8, 365, 10.1023/A:1020528716621
Bagatoll, 1999, A model for the interaction of 6-Lauroyl-2-(N, N-dimethylamino) naphthalene with lipid environments: implications for spectral properties, Photochem. Photobiol., 70, 557, 10.1111/j.1751-1097.1999.tb08251.x
Parasassi, 1993, Modulation and dynamics of phase properties in phospholipid mixtures detected by Laurdan fluorescence, Photochem. Photobiol., 57, 403, 10.1111/j.1751-1097.1993.tb02309.x
Jurkiewicz, 2006, Headgroup hydration and mobility of DOTAP/DOPC bilayers: a fluorescence solvent relaxation study, Langmuir, 22, 8741, 10.1021/la061597k
Samanta, 2000, Excited state dipole moment of PRODAN as determined from transient dielectric loss measurements, J. Phys. Chem. A, 104, 8972, 10.1021/jp0009960
Almaleck, 2013, Water defects induced by expansion and electrical fields in DMPC and DMPE monolayers: contribution of hydration and confined water, Colloids Surf. B: Biointerfaces, 102, 871, 10.1016/j.colsurfb.2012.09.031
Berkowitz, 2011, Aqueous solutions at the interface with phospholipid bilayers, Acc. Chem. Res., 45, 74, 10.1021/ar200079x
Rawicz, 2008, Elasticity, strength, and water permeability of bilayers that contain raft microdomain-forming lipids, Biophys. J., 94, 4725, 10.1529/biophysj.107.121731
Frias Mde, 2009, Configuration of carbonyl groups at the lipid interphases of different topological arrangements of lipid dispersions, Langmuir, 25, 8187, 10.1021/la900554h
Arsov, 2015, 127
Mannock, 2003, Effects of natural and enantiomeric cholesterol on the thermotropic phase behavior and structure of egg sphingomyelin bilayer membranes, Biophys. J., 84, 1038, 10.1016/S0006-3495(03)74920-0
Lucas, 2012, Molecular dynamics simulation of hydrated DPPC monolayers using charge equilibration force fields, J. Comput. Chem., 33, 141, 10.1002/jcc.21927