Changes induced by malathion, methylparathion and parathion on membrane lipid physicochemical properties correlate with their toxicity

R. Metcalf, The chemistry and biology of pesticides, in: R. White-Stevens (Ed.), Pesticides in the Environment, Marcel Dekker, New York, 1971, pp. 67–124.

G.W. Ware, Pesticides, Theory and Applications, W.H. Freeman and Company, San Francisco, CA, 1983, pp. 35–67.

M. Eto, Organophosphorus Pesticides: Organic and Biological Chemistry, CRC Press, Cleveland, OH, 1974, pp. 123–133.

Kardos, 2000, Interactions of the organophosphorus paraoxon and methylparaoxon with mouse acetylcholinesterase, Toxicol. Sci., 58, 118, 10.1093/toxsci/58.1.118

H. Ohkawa, Stereoselectivity of organophosphorus insecticides, in: J.R. Coats (Ed.), Insecticide Mode of Action, Academic Press, London, 1982, pp. 163–185.

Volpe, 1985, In vitro modulation of bovine caudate muscarinic receptor number by organophosphorus and carbamates, Toxicol. Appl. Pharmacol., 78, 226, 10.1016/0041-008X(85)90286-8

Antunes-Madeira, 1989, Membrane partitioning of organophosphorus and organochlorine insecticides and its implications for mechanisms of toxicity, Pestic. Sci., 26, 167, 10.1002/ps.2780260208

Videira, 1996, Interaction of ethylazinphos with the physical organization of model and native membranes, Biochim. Biophys. Acta, 128, 65, 10.1016/0005-2736(96)00012-0

Antunes-Madeira, 1979, Interaction of insecticides with lipid membranes, Biochim. Biophys. Acta, 550, 384, 10.1016/0005-2736(79)90143-3

Antunes-Madeira, 1981, Interaction of insecticides with erythrocyte membranes, Pestic. Biochem. Physiol., 15, 79, 10.1016/0048-3575(81)90036-5

Antunes-Madeira, 1982, Interaction of insecticides with Ca2+-pump activity of sarcoplasmic reticulum, Pestic. Biochem. Physiol., 17, 185, 10.1016/0048-3575(82)90024-4

Moreno, 1990, Interference of parathion with mitochondrial bioenergetics, Biochim. Biophys. Acta, 1015, 166

Brown, 1976, Synaptosomal adenosine triphosphatase (ATPase) inhibition by organophosphates, Experientia, 32, 1540, 10.1007/BF01924440

Sitkiewicz, 1980, Effect of organophosphorus insecticides on the oxidative processes in rat brain synaptosomes, J. Neurochem., 34, 619, 10.1111/j.1471-4159.1980.tb11189.x

Mobley, 1988, Effects of organophosphorus agents on sarcoplasmic reticulum in skinned skeletal muscle fibers, Toxicol. Appl. Pharmacol., 94, 407, 10.1016/0041-008X(88)90281-5

Swann, 1996, The effects of organophosphorus insecticides dursban and lorsban on the ciliated epithelium of the frog palate in vitro, Arch. Environ. Contam. Toxicol., 30, 188, 10.1007/BF00215797

Lee, 1975, Functional properties of biological membranes: a physical-chemical approach, Prog. Biophys. Mol. Biol., 29, 5

Tocanne, 1994, Lipid domains and lipid/protein interactions in biological membranes, Chem. Phys. Lipids, 73, 139, 10.1016/0009-3084(94)90179-1

Sikkema, 1995, Mechanisms of membrane toxicity of hydrocarbons, Microbiol. Rev., 59, 201, 10.1128/MR.59.2.201-222.1995

Mouritsen, 1998, A new look at lipid-membrane structure in relation to drug research, Pharm. Res., 15, 1507, 10.1023/A:1011986613392

Antunes-Madeira, 1989, Membrane fluidity as affected by the insecticide lindane, Biochim. Biophys. Acta, 982, 161, 10.1016/0005-2736(89)90187-9

Shinitzky, 1978, Fluidity parameters of lipid regions determined by fluorescence polarization, Biochim. Biophys. Acta, 515, 367, 10.1016/0304-4157(78)90010-2

Litman, 1982, Fluorescent probe: diphenylhexatriene, Methods Enzymol., 81, 678, 10.1016/S0076-6879(82)81093-8

Kinosita, 1977, A theory of fluorescence polarization decay in membrane, Biophys. J., 20, 289, 10.1016/S0006-3495(77)85550-1

Lakowicz, 1978, Detection of hindered rotations of 1,6-diphenyl-1,3,5-hexatriene in lipid bilayers by differential polarization phasefluorometry, Biophys. J., 24, 213, 10.1016/S0006-3495(78)85357-0

Lentz, 1989, Membrane ‘fluidity’ as detected by diphenylhexatriene probes, Chem. Phys. Lipids, 50, 171, 10.1016/0009-3084(89)90049-2

Van Dijck, 1976, The preference of cholesterol for phosphatidylcholine in mixed phosphatidylcholine–phosphatidylethanolamine bilayers, Biochim. Biophys. Acta, 455, 576, 10.1016/0005-2736(76)90326-6

Bartlett, 1959, Phosphorus assay in column chromatography, J. Biol. Chem., 234, 466, 10.1016/S0021-9258(18)70226-3

Böttcher, 1961, A rapid and sensitive sub-micro phosphorus determination, Anal. Chim. Acta, 24, 203, 10.1016/0003-2670(61)80041-X

Trotter, 1989, 3-[p-(6-phenyl)-1,3,5-hexatrienyl] phenylpropionic acid (PA-DPH): characterization as a fluorescent membrane probe and binding to fatty acid binding proteins, Biochim. Biophys. Acta, 982, 131, 10.1016/0005-2736(89)90183-1

Antunes-Madeira, 1994, Effects of parathion on membrane organization and its implications for the mechanisms of toxicity, Biochim. Biophys. Acta, 1190, 149, 10.1016/0005-2736(94)90044-2

Videira, 1994, Effects of malathion on membrane fluidity and its implications for the mechanisms of toxicity, Med. Sci. Res., 22, 551

Lopes, 1997, Effects of methylparathion on membrane fluidity and its implications for the mechanisms of toxicity, Toxicol. Vitro, 11, 337, 10.1016/S0887-2333(97)00024-6

RTECS, Registry of Toxic Effects of Chemical Substances, 1997, NIOSH, US Department of Health and Human Services, Cincinnati, OH.

M.A. Hollinger, Tables of toxicological importance, in: M.J. Derelako, M.A. Hollinger (Eds.), Handbook of Toxicology, CRC Press, Inc., Boca Raton, FL, 1995, p. 804.

Jain, 1977, Effect of small molecules on the dipalmitoyl lecithin liposomal bilayer: III phase transition in lipid bilayer, J. Membr. Biol., 34, 157, 10.1007/BF01870299

Engelman, 1972, The planar organization of lecithin-cholesterol bilayers, J. Biol. Chem., 247, 3694, 10.1016/S0021-9258(19)45196-X

Ipsen, 1987, Phase equilibria in the phosphatidylcholine-cholesterol system, Biochim. Biophys. Acta, 905, 162, 10.1016/0005-2736(87)90020-4

Vist, 1990, Phase equilibria of cholesterol/dipalmitoylphosphatidylcholine mixtures: 2H nuclear magnetic resonance and differential scanning calorimetry, Biochemistry, 29, 415, 10.1021/bi00454a021

Videira, 1999, Biophysical perturbations induced by ethylazinphos in lipid membranes, Chem. Phys. Lipids, 97, 139, 10.1016/S0009-3084(98)00105-4

Videira, 1999, Perturbations induced by α- and β-endosulfan in lipid membranes: a DSC and fluorescence polarization study, Biochim. Biophys. Acta, 1419, 151, 10.1016/S0005-2736(99)00060-7

Sabra, 1995, Calorimetric and theoretical studies of the effects of lindane on lipid bilayers of different acyl chain length, Biochim. Biophys. Acta, 1233, 89, 10.1016/0005-2736(94)00244-J

Sabra, 1996, Lindane suppresses the lipid-bilayer permeability in the main transition region, Biochim. Biophys. Acta, 1282, 85, 10.1016/0005-2736(96)00042-9

Mavromoustakos, 1995, Effects of anesthetic steroid alphaxalone and its inactive Δ16-analog on the thermotropic properties of membrane bilayers. A model for membrane perturbation, Biochim. Biophys. Acta, 1239, 257, 10.1016/0005-2736(95)00153-T

Jørgensen, 1993, The effect of anaesthetics on the dynamic heterogeneity of lipid membranes, Chem. Phys. Lipids, 65, 205, 10.1016/0009-3084(93)90018-X

Zeng, 1993, Effects of alcohol-induced lipid interdigitation on proton permeability in L-α-dipalmitoylphosphatidylcholine vesicles, Biophys. J., 65, 1404, 10.1016/S0006-3495(93)81204-9

Söderlund, 1999, Interactions of cyclosporin A with phospholipid membranes: effects of cholesterol, Mol. Pharmacol., 55, 32, 10.1124/mol.55.1.32

Almeida, 1992, Lateral diffusion and percolation in two-phase, two-component lipid bilayers. Topology of the solid-phase domains in-plane and across the lipid bilayer, Biochemistry, 31, 7198, 10.1021/bi00146a024

Williams, 1998, Membrane lipids: what membrane physical properties are conserved during physicochemically-induced membrane restructuring?, Am. Zool., 38, 280, 10.1093/icb/38.2.280