Calorimetric studies of the effect of cis-carotenoids on the thermotropic phase behavior of phosphatidylcholine bilayers

Gruszecki, 2004, Carotenoids in health and disease, 151 Gruszecki, 1999, The photochemistry of carotenoids, 363 Gruszecki, 1991, Does the xanthophyll cycle take part in the regulation of fluidity of the thylakoid membrane, Biochim. Biophys. Acta, 1060, 310, 10.1016/S0005-2728(05)80322-6 Subczynski, 1992, Effects of polar carotenoids on dimyristoylphosphatidylcholine membranes: a spin-label study, Biochim. Biophys. Acta, 1105, 97, 10.1016/0005-2736(92)90167-K Wisniewska, 2006, Carotenoid–membrane interactions in liposomes: effect of dipolar, monopolar, and nonpolar carotenoids, Acta. Biochim. Pol., 53, 475, 10.18388/abp.2006_3318 Kostecka-Gugala, 2003, Thermotropic phase behaviour of α-dipalmitoylphosphatidylcholine multibilayers is influenced to various extents by carotenoids containing different structural features — evidence from differential scanning calorimetry, Biochim. Biophys. Acta, 1609, 193, 10.1016/S0005-2736(02)00688-0 Subczynski, 1992, Effect of carotenoids on oxygen transport within and across model membranes, Curr. Top. Biophys., 16, 62 Wisniewska, 1998, Effects of polar carotenoids on the shape of the hydrophobic barrier of phospholipid bilayers, Biochim. Biophys. Acta, 1368, 235, 10.1016/S0005-2736(97)00182-X Bone, 1983, Dichroism of lutein: a possible basis for Haidinger's brushes, Appl. Opt., 22, 775, 10.1364/AO.22.000775 Bone, 1984, Macular pigment in Henle fiber membranes: a model for Haidinger's brushes, Vis. Res., 24, 103, 10.1016/0042-6989(84)90094-4 Rapp, 2000, Lutein and zeaxanthin concentrations in rod outer segment membranes from perifoveal and peripheral human retina, Invest. Ophthalmol. Vis. Sci., 41, 1200 Yokoyama, 1996, Thermocryptoxanthins: novel intermediates in the carotenoid biosynthetic pathway of Thermus thermophilus, Arch. Microbiol., 165, 342, 10.1007/s002030050336 Huang, 1974, Regulation of membrane lipid fluidity in Acholeplasma laidlawii: effect of carotenoid pigment content, Biochim. Biophys. Acta, 352, 361, 10.1016/0005-2736(74)90228-4 Rottem, 1979, Carotenoids acts as reinforcers of the Acholeplasma laidlawii lipid bilayer, J. Bacteriol., 140, 944, 10.1128/JB.140.3.944-948.1979 Gombos, 1986, Primary role of the cytoplasmic membrane in thermal acclimation evidenced in nitrate-starved cells of the blue-green alga, Anacystis nidulans, Plant. Physiol., 80, 415, 10.1104/pp.80.2.415 Siefermann-Harms, 1978, Light-induced changes of the carotenoid levels in chloroplast envelopes, Plant Physiol., 61, 530, 10.1104/pp.61.4.530 Havaux, 2003, Carotenoids as membrane stabilizers in chloroplasts, Trends Plant Sci., 3, 147, 10.1016/S1360-1385(98)01200-X Wisniewska, 2006, Distribution of macular xanthophylls between domains in a model of photoreceptor outer segment membranes, Free Radic. Biol. Med., 41, 1257, 10.1016/j.freeradbiomed.2006.07.003 Kolev, 1986, Miscibility of beta-carotene and zeaxanthin with dipalmitoylphosphatidylcholine in multilamellar vesicles: a calorimetric and spectroscopic study, Photobiochem. Photobiophys., 11, 257 Socaciu, 2000, Competitive carotenoid and cholesterol incorporation into liposomes: effects on membrane phase transition, fluidity, polarity and anisotropy, Chem. Phys. Lipids, 106, 79, 10.1016/S0009-3084(00)00135-3 Gabrielska, 1996, Zeaxanthin (dihydroxy-beta-carotene) but not beta-carotene rigidifies lipid membranes: a 1H-NMR study of carotenoid-egg phosphatidylcholine liposomes, Biochim. Biophys. Acta, 1285, 167, 10.1016/S0005-2736(96)00152-6 McNulty, 2007, Differential effects of carotenoids on lipid peroxidation due to membrane interactions: X-ray diffraction analysis, Biochim. Biophys. Acta, 1768, 167, 10.1016/j.bbamem.2006.09.010 Suwalsky, 2002, Comparative X-ray studies on the interaction of carotenoids with a model phosphatidylcholine membrane, Z. Naturforsch., 57, 129, 10.1515/znc-2002-1-222 Sujak, 2000, Organization of mixed monomolecular layers formed with the xanthophyll pigments lutein or zeaxanthin and dipalmitoylphosphatidylcholine at the argon–water interface, J. Photochem. Photobiol. B, 59, 42, 10.1016/S1011-1344(00)00133-0 Milanowska, 2003, Interaction of isomeric forms of xanthophyll pigment zeaxanthin with dipalmitoylphosphatidylcholine studied in monomolecular layers, J. Photochem. Photobiol. B, 72, 1, 10.1016/j.jphotobiol.2003.08.009 Widomska, 2008, Transmembrane localization of cis-isomers of zeaxanthin in the host dimyristoylphosphatidylcholine bilayer membrane, Biochim. Biophys. Acta, 1778, 10, 10.1016/j.bbamem.2007.08.021 Molnar, 1993, (Z/E)-Photoisomerization of C40-carotenoids by iodine, Perkin Trans., 2, 261, 10.1039/P29930000261 Koyama, 1990, Configurations of carotenoids in the reaction center and the light-harvesting complex of Rhodospirillum rubrum. Natural selection of carotenoid configurations by pigment protein complexes, Photochem. Photobiol., 51, 119, 10.1111/j.1751-1097.1990.tb01692.x Boileau, 1999, Cis-lycopene is more bioavailable than trans-lycopene in vitro an in vivo in lymph-cannulated ferrets, J. Nutr., 129, 1176, 10.1093/jn/129.6.1176 Stahl, 1992, Cis–trans isomers of lycopene and beta-carotene in human serum and tissues, Arch. Biochem. Biophys., 294, 173, 10.1016/0003-9861(92)90153-N Berstein, 2001, Identification and quantitation of carotenoids and their metabolites in the tissues of human eye, Exp. Eye Res., 72, 215, 10.1006/exer.2000.0954 Khachik, 1997, Identification of lutein and zeaxanthin oxidation products in human and monkey retinas, Invest, Ophthalmol. Vis. Sci., 38, 1802 Dachtler, 2001, Combined HPLC-MS and HPLC-NMR on-line coupling for the separation and determination of lutein and zeaxanthin stereoisomers in spinach and in retina, Anal. Chem., 73, 667, 10.1021/ac000635g Subczynski, 1989, Oxygen permeability of phosphatidylcholine-cholesterol membranes, Proc. Natl. Acad. Sci. USA, 86, 4474, 10.1073/pnas.86.12.4474 Stahl, 2005, Bioactivity and protective effects of natural carotenoids, Biochim. Biophys. Acta, 1740, 101, 10.1016/j.bbadis.2004.12.006 Britton, 1995, Carotenoids, vol. 1B, 13 Koyama, 1999, The photochemistry of carotenoids, 161 Ichimori, 1997, Thermotropic and barotropic phase transition on bilayer membranes of phospholipids with varying acyl chain-lengths, Chem. Phys. Lipids, 89, 97, 10.1016/S0009-3084(97)00067-4 Socaciu, 2000, Different ways to insert carotenoids into liposomes affect structure and dynamics of the bilayer differently, Chem. Phys. Lipids, 106, 79, 10.1016/S0009-3084(00)00135-3 Milon, 1986, Organization of carotenoid–phospholipid bilayer systems: incorporation of zeaxanthin, astaxanthin, and their homologues into dimyristoylphosphatidylcholine vesicles, Helv. Chim. Acta, 69, 12, 10.1002/hlca.19860690104 Gruszecki, 1990, Orientation of xanthophylls in phosphatidylcholine multibilayers, Biochim. Biophys. Acta, 1023, 405, 10.1016/0005-2736(90)90133-9 Birge, 1999, Transition dipole orientation of linear polyenes: semiempirical models and extrapolation to the infinite chain limit, J. Phys. Chem. A, 103, 2251, 10.1021/jp983588t McNulty, 2008, Biological activity of carotenoids related to distinct membrane physicochemical interactions, Am. J. Cardiol., 101, 20D, 10.1016/j.amjcard.2008.02.004