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Volumn 99, Issue 3, 2002, Pages 229-243

Spectroscopic evidence for a preferential location of lidocaine inside phospholipid bilayers

Author keywords

Lidocaine; Membrane; Nuclear magnetic resonance

Indexed keywords

AROMATIC COMPOUND; CHOLINE; ESTER DERIVATIVE; FATTY ACID DERIVATIVE; FLUORESCENT DYE; GLYCEROL; LIDOCAINE; LOCAL ANESTHETIC AGENT; METHYL GROUP; PEPTIDE; PHOSPHATIDYLCHOLINE; PHOSPHOLIPID; PROTON;

EID: 0037032531     PISSN: 03014622     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0301-4622(02)00202-8     Document Type: Article
Times cited : (64)

References (54)
  • 1
    • 0025263891 scopus 로고
    • Molecular mechanisms of local-anesthesia - A review
    • Butterworth J.F., Strichartz G.R. Molecular mechanisms of local-anesthesia - a review. Anesthesiology. 72:1990;711-734.
    • (1990) Anesthesiology , vol.72 , pp. 711-734
    • Butterworth, J.F.1    Strichartz, G.R.2
  • 2
    • 0030016938 scopus 로고    scopus 로고
    • Molecular and physicochemical aspects of local anesthetic-membrane interaction
    • de Paula E., Schreier S. Molecular and physicochemical aspects of local anesthetic-membrane interaction. Braz. J. Med. Biol. Res. 29:1996;877-894.
    • (1996) Braz. J. Med. Biol. Res. , vol.29 , pp. 877-894
    • De Paula, E.1    Schreier, S.2
  • 3
    • 0016795433 scopus 로고
    • Effects of local-anesthetics on membrane properties. 1. Changes in fluidity of phospholipids bilayers
    • Papahadjoupoulos D., Jacobson K., Poste G., Shepherd G. Effects of local-anesthetics on membrane properties. 1. Changes in fluidity of phospholipids bilayers. Biochim. Biophys. Acta. 394:1975;504-519.
    • (1975) Biochim. Biophys. Acta , vol.394 , pp. 504-519
    • Papahadjoupoulos, D.1    Jacobson, K.2    Poste, G.3    Shepherd, G.4
  • 4
    • 0017144599 scopus 로고
    • Interactions between anesthetics and lipid mixtures amines
    • Lee A.G. Interactions between anesthetics and lipid mixtures amines. Biochim. Biophys. Acta. 448:1976;34-44.
    • (1976) Biochim. Biophys. Acta , vol.448 , pp. 34-44
    • Lee, A.G.1
  • 5
    • 0019789698 scopus 로고
    • Molecular details of anesthetic-lipid interaction as seen by deuterium and P-31 nuclear magnetic resonance
    • Boulanger Y., Schreier S., Smith I.C.P. Molecular details of anesthetic-lipid interaction as seen by deuterium and P-31 nuclear magnetic resonance. Biochemistry. 20:1981;6824-6830.
    • (1981) Biochemistry , vol.20 , pp. 6824-6830
    • Boulanger, Y.1    Schreier, S.2    Smith, I.C.P.3
  • 6
    • 0021343046 scopus 로고
    • Effect of lipid-membranes on the apparent pK of local-anesthetic tetracaine - Spin label and titration studies
    • Schreier S., Frezzatti W. Jr., Araujo P.S., Chaimovich H., Cuccovia I.M. Effect of lipid-membranes on the apparent pK of local-anesthetic tetracaine - spin label and titration studies. Biochim. Biophys. Acta. 769:1984;231-237.
    • (1984) Biochim. Biophys. Acta , vol.769 , pp. 231-237
    • Schreier, S.1    Frezzatti W., Jr.2    Araujo, P.S.3    Chaimovich, H.4    Cuccovia, I.M.5
  • 8
    • 0022518455 scopus 로고
    • A 2H-NMR study on the interactions of the local anesthetic tetracaine with membranes containing phosphatidylserine
    • Kelusky E.C., Boulanger Y., Schreier S., Smith I.C.P. A 2H-NMR study on the interactions of the local anesthetic tetracaine with membranes containing phosphatidylserine. Biochim. Biophys. Acta. 856:1986;85-90.
    • (1986) Biochim. Biophys. Acta , vol.856 , pp. 85-90
    • Kelusky, E.C.1    Boulanger, Y.2    Schreier, S.3    Smith, I.C.P.4
  • 9
    • 0024232041 scopus 로고
    • Membrane-buffer partition-coeficients of tetracaine for liquid-crystal and solid-gel membranes estimated by direct ultraviolet spectrophotometry
    • Kaminoh Y., Inone T., Ma S.M., Ueda I., Lin S.H. Membrane-buffer partition-coeficients of tetracaine for liquid-crystal and solid-gel membranes estimated by direct ultraviolet spectrophotometry. Biochim. Biophys. Acta. 946:1988;337-344.
    • (1988) Biochim. Biophys. Acta , vol.946 , pp. 337-344
    • Kaminoh, Y.1    Inone, T.2    Ma, S.M.3    Ueda, I.4    Lin, S.H.5
  • 10
    • 0023884308 scopus 로고
    • Use of membrane spin label spectra to monitor rates of reaction of partitioning compounds - Hydrolysis of a local-anesthetic analog
    • Bianconi M.L., Amaral A.T., Schreier S. Use of membrane spin label spectra to monitor rates of reaction of partitioning compounds - hydrolysis of a local-anesthetic analog. Biochem. Biophys. Res. Commun. 152:1988;344-350.
    • (1988) Biochem. Biophys. Res. Commun. , vol.152 , pp. 344-350
    • Bianconi, M.L.1    Amaral, A.T.2    Schreier, S.3
  • 11
    • 0025253914 scopus 로고
    • High-pressure infrared study of phosphatidylserine bilayers and their interactions with the local-anesthetic tetracaine
    • Auger M., Smith I.C.P., Mantsch H., Wong P.T.T. High-pressure infrared study of phosphatidylserine bilayers and their interactions with the local-anesthetic tetracaine. Biochemistry. 29:1990;2008-2015.
    • (1990) Biochemistry , vol.29 , pp. 2008-2015
    • Auger, M.1    Smith, I.C.P.2    Mantsch, H.3    Wong, P.T.T.4
  • 12
    • 0028818451 scopus 로고
    • Use of a novel method for determination of partition-coeficients to compare the effect of local-anesthetics on membrane-structure
    • de Paula E., Schreier S. Use of a novel method for determination of partition-coeficients to compare the effect of local-anesthetics on membrane-structure. Biochim. Biophys. Acta. 1240:1995;25-33.
    • (1995) Biochim. Biophys. Acta , vol.1240 , pp. 25-33
    • De Paula, E.1    Schreier, S.2
  • 15
    • 0017087276 scopus 로고
    • Model for action of local-anesthetics
    • Lee A.G. Model for action of local-anesthetics. Nature. 262:1976;545-548.
    • (1976) Nature , vol.262 , pp. 545-548
    • Lee, A.G.1
  • 16
    • 0018900245 scopus 로고
    • Structure-activity relations for frequency-dependent sodium-channel block in nerve by local-anesthetics
    • Courtney K.R. Structure-activity relations for frequency-dependent sodium-channel block in nerve by local-anesthetics. J. Pharmacol. Exp. Ther. 213:1980;114-119.
    • (1980) J. Pharmacol. Exp. Ther. , vol.213 , pp. 114-119
    • Courtney, K.R.1
  • 18
    • 84860748568 scopus 로고
    • Quantitative structure-activity relationship studies on local-anesthetics
    • Gupta S.P. Quantitative structure-activity relationship studies on local-anesthetics. Chem. Rev. 91:1991;1109-1119.
    • (1991) Chem. Rev. , vol.91 , pp. 1109-1119
    • Gupta, S.P.1
  • 19
    • 0017350085 scopus 로고
    • PH-dependent rate of action of local-anesthetics on node of ranvier
    • Hille B. pH-dependent rate of action of local-anesthetics on node of ranvier. J. Gen. Physiol. 69:1977;497-515.
    • (1977) J. Gen. Physiol. , vol.69 , pp. 497-515
    • Hille, B.1
  • 23
    • 0014681420 scopus 로고
    • Cationic forms of local anaesthetics block action potentials from inside nerve membrane
    • Narahashi T., Yamada M., Frazier D.T. Cationic forms of local anaesthetics block action potentials from inside nerve membrane. Nature. 223:1969;748-749.
    • (1969) Nature , vol.223 , pp. 748-749
    • Narahashi, T.1    Yamada, M.2    Frazier, D.T.3
  • 24
    • 0014709320 scopus 로고
    • Site of action and active form of local anesthetics. 1. Theory and pH experiments with tertiary compounds
    • Narahashi T., Frazier D.T., Yamada M. Site of action and active form of local anesthetics. 1. Theory and pH experiments with tertiary compounds. J. Pharmacol. Exp. Ther. 171:1970;32-44.
    • (1970) J. Pharmacol. Exp. Ther. , vol.171 , pp. 32-44
    • Narahashi, T.1    Frazier, D.T.2    Yamada, M.3
  • 27
    • 0014779155 scopus 로고
    • Two dimensional thin layer chromatographic separation of polar lipids and determination of phospholipids by phosphorus analysis of spots
    • Rouser G., Fleicher S., Yamamoto A. Two dimensional thin layer chromatographic separation of polar lipids and determination of phospholipids by phosphorus analysis of spots. Lipids. 5:1970;494-496.
    • (1970) Lipids , vol.5 , pp. 494-496
    • Rouser, G.1    Fleicher, S.2    Yamamoto, A.3
  • 28
    • 0022552590 scopus 로고
    • Spin label study of local anesthetic-lipid membrane interactions - Phase-separation of the uncharged form and bilayer micellization by the charged form of tetracaine
    • Frezzatti W. Jr., Toselli W.R., Schreier S. Spin label study of local anesthetic-lipid membrane interactions - phase-separation of the uncharged form and bilayer micellization by the charged form of tetracaine. Biochim. Biophys. Acta. 860:1986;531-538.
    • (1986) Biochim. Biophys. Acta , vol.860 , pp. 531-538
    • Frezzatti W., Jr.1    Toselli, W.R.2    Schreier, S.3
  • 29
    • 5144229966 scopus 로고
    • Pratical aspects of two-dimensional transverse NOE spectroscopy
    • Bax A., Davis D.G. Pratical aspects of two-dimensional transverse NOE spectroscopy. J. Magn. Res. 63:1985;207-213.
    • (1985) J. Magn. Res. , vol.63 , pp. 207-213
    • Bax, A.1    Davis, D.G.2
  • 30
    • 0021285895 scopus 로고
    • Intramolecular and intermolecular H1-H1 nuclear Overhauser effect studies on the interactions of chlorpromazine with lecithin vesicles
    • Kuroda Y., Kitamura K. Intramolecular and intermolecular H1-H1 nuclear Overhauser effect studies on the interactions of chlorpromazine with lecithin vesicles. J. Am. Chem. Soc. 106:1984;1-6.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 1-6
    • Kuroda, Y.1    Kitamura, K.2
  • 31
    • 0029066881 scopus 로고
    • Distribution of general-anesthetics in phospholipids-bilayers determined using H-2 NMR and H1-H1 NOE spectroscopy
    • Baber J., Ellena J.F., Cafiso D.S. Distribution of general-anesthetics in phospholipids-bilayers determined using H-2 NMR and H1-H1 NOE spectroscopy. Biochemistry. 34:1995;6533-6539.
    • (1995) Biochemistry , vol.34 , pp. 6533-6539
    • Baber, J.1    Ellena, J.F.2    Cafiso, D.S.3
  • 32
    • 0015947272 scopus 로고
    • Dynamics structure of lipid-membranes - C13 nuclear magnetic resonance study using spin labels
    • Godici P.E., Landsberger F.R. Dynamics structure of lipid-membranes - C13 nuclear magnetic resonance study using spin labels. Biochemistry. 13:1974;362-368.
    • (1974) Biochemistry , vol.13 , pp. 362-368
    • Godici, P.E.1    Landsberger, F.R.2
  • 33
    • 0016804330 scopus 로고
    • Bilayers of dipalmitoyl-3-sn-phosphatidylcholine - Conformational differences between fatty acyl chains
    • Seelig A., Seelig J. Bilayers of dipalmitoyl-3-sn-phosphatidylcholine - conformational differences between fatty acyl chains. Biochim. Biophys. Acta. 406:1975;1-5.
    • (1975) Biochim. Biophys. Acta , vol.406 , pp. 1-5
    • Seelig, A.1    Seelig, J.2
  • 34
    • 0025828647 scopus 로고
    • Pressure effects on dipalmitoylphosphatidylcholine bilayers measured by H-2 nuclear-magnetic-resonance
    • Driscoll D.A., Samarasinghe S., Adamy S., Jonas J., Jonas A. Pressure effects on dipalmitoylphosphatidylcholine bilayers measured by H-2 nuclear-magnetic-resonance. Biochemistry. 30:1991;3322-3327.
    • (1991) Biochemistry , vol.30 , pp. 3322-3327
    • Driscoll, D.A.1    Samarasinghe, S.2    Adamy, S.3    Jonas, J.4    Jonas, A.5
  • 35
    • 0023887910 scopus 로고
    • Localizing the nitroxide group of fatty-acid and voltage-sensitive spin-labels in phopholipid-bilayers
    • Ellena J.F., Archer S.J., Dominey R.N., Hill B.D., Cafiso D.S. Localizing the nitroxide group of fatty-acid and voltage-sensitive spin-labels in phopholipid-bilayers. Biochim. Biophys. Acta. 940:1988;63-70.
    • (1988) Biochim. Biophys. Acta , vol.940 , pp. 63-70
    • Ellena, J.F.1    Archer, S.J.2    Dominey, R.N.3    Hill, B.D.4    Cafiso, D.S.5
  • 36
    • 0015693295 scopus 로고
    • Nuclear magnetic resonance studies of structure of model membranes systems - Effect of surface curvature
    • Chan S.I., Sheetz M.P., Seiter C.H.A., et al. Nuclear magnetic resonance studies of structure of model membranes systems - effect of surface curvature. Ann. NY Acad. Sci. 222:1973;499-522.
    • (1973) Ann. NY Acad. Sci. , vol.222 , pp. 499-522
    • Chan, S.I.1    Sheetz, M.P.2    Seiter, C.H.A.3
  • 38
    • 0019959862 scopus 로고
    • The interaction of local-anesthetic with synthetic phospholipids-bilayers
    • Sikaris K.A., Sawyer W.H. The interaction of local-anesthetic with synthetic phospholipids-bilayers. Biochem. Pharmacol. 31:1982;2625-2631.
    • (1982) Biochem. Pharmacol. , vol.31 , pp. 2625-2631
    • Sikaris, K.A.1    Sawyer, W.H.2
  • 39
    • 0025100904 scopus 로고
    • Methods for the determination of partition-coefficients based on the effect of solutes upon membrane-structure
    • Lissi E., Bianconi M.L., Amaral A.T., de Paula E., Blanch L.E.B., Schreier S. Methods for the determination of partition-coefficients based on the effect of solutes upon membrane-structure. Biochim. Biophys. Acta. 1021:1990;46-50.
    • (1990) Biochim. Biophys. Acta , vol.1021 , pp. 46-50
    • Lissi, E.1    Bianconi, M.L.2    Amaral, A.T.3    De Paula, E.4    Blanch, L.E.B.5    Schreier, S.6
  • 40
    • 0023200371 scopus 로고
    • Locations and dynamic perturbations for lipids of cationic forms of procaine, tetracaine and dibucaine in small unilamellar phosphatidylcholine vesicles as studied by nuclear Overhauser effects in H-1 nuclear magnetic resonance spectroscopy
    • Kuroda Y., Fujiwara Y. Locations and dynamic perturbations for lipids of cationic forms of procaine, tetracaine and dibucaine in small unilamellar phosphatidylcholine vesicles as studied by nuclear Overhauser effects in H-1 nuclear magnetic resonance spectroscopy. Biochim. Biophys. Acta. 903:1987;395-410.
    • (1987) Biochim. Biophys. Acta , vol.903 , pp. 395-410
    • Kuroda, Y.1    Fujiwara, Y.2
  • 41
    • 0028297760 scopus 로고
    • Local-anesthetics destabilize lipid-membranes by breaking hydration shell - Infrared and calorimetry studies
    • Ueda I., Chiou J.S., Krishma P.R., Kamaya H. Local-anesthetics destabilize lipid-membranes by breaking hydration shell - infrared and calorimetry studies. Biochim. Biophys. Acta. 1190:1994;421-429.
    • (1994) Biochim. Biophys. Acta , vol.1190 , pp. 421-429
    • Ueda, I.1    Chiou, J.S.2    Krishma, P.R.3    Kamaya, H.4
  • 42
    • 0024291319 scopus 로고
    • Fourier-transform infrared-spectroscopy of C-13=O-labeled phospholipids hydrogen-bonding to carbonyl groups
    • Blume A., Hübner W., Messner G. Fourier-transform infrared-spectroscopy of C-13=O-labeled phospholipids hydrogen-bonding to carbonyl groups. Biochemistry. 27:1988;8239-8249.
    • (1988) Biochemistry , vol.27 , pp. 8239-8249
    • Blume, A.1    Hübner, W.2    Messner, G.3
  • 43
    • 0031761606 scopus 로고    scopus 로고
    • Evidence for the specific interaction of a lipid molecule with rhodopsin which is altered in the transition to the active state metarhodopsin II
    • Beck M., Siebert F., Sakmar T.P. Evidence for the specific interaction of a lipid molecule with rhodopsin which is altered in the transition to the active state metarhodopsin II. FEBS Lett. 436:1998;304-308.
    • (1998) FEBS Lett. , vol.436 , pp. 304-308
    • Beck, M.1    Siebert, F.2    Sakmar, T.P.3
  • 44
    • 0032552880 scopus 로고    scopus 로고
    • The preference of tryptophan for membrane interfaces
    • Yau W.M., Wimley W.C., Gawrisch K., White S.H. The preference of tryptophan for membrane interfaces. Biochemistry. 37:1998;14713-14718.
    • (1998) Biochemistry , vol.37 , pp. 14713-14718
    • Yau, W.M.1    Wimley, W.C.2    Gawrisch, K.3    White, S.H.4
  • 45
    • 0026664796 scopus 로고
    • Conformations of dibucaine and tetracaine in small unilamellar phosphatidylcholine vesicles as studied by nuclear Overhauser effects in H-1 nuclear magnetic resonance spectroscopy
    • Wakita M., Kuroda Y., Fujiwara Y., Nakagawa T. Conformations of dibucaine and tetracaine in small unilamellar phosphatidylcholine vesicles as studied by nuclear Overhauser effects in H-1 nuclear magnetic resonance spectroscopy. Chem. Phys. Lipids. 62:1992;45-54.
    • (1992) Chem. Phys. Lipids , vol.62 , pp. 45-54
    • Wakita, M.1    Kuroda, Y.2    Fujiwara, Y.3    Nakagawa, T.4
  • 46
    • 0028352680 scopus 로고
    • Direct NMR evidence for ethanol binding to the lipid-water interface of phospholipids-bilayers
    • Barry J.A., Gawrisch K. Direct NMR evidence for ethanol binding to the lipid-water interface of phospholipids-bilayers. Biochemistry. 33:1994;8082-8088.
    • (1994) Biochemistry , vol.33 , pp. 8082-8088
    • Barry, J.A.1    Gawrisch, K.2
  • 47
    • 0030888224 scopus 로고    scopus 로고
    • Determining ethanol distribution in phospholipid multilayers with MAS-NOESY spectra
    • Holte L.L., Gawrisch K. Determining ethanol distribution in phospholipid multilayers with MAS-NOESY spectra. Biochemistry. 36:1997;4669-4674.
    • (1997) Biochemistry , vol.36 , pp. 4669-4674
    • Holte, L.L.1    Gawrisch, K.2
  • 48
    • 0033541114 scopus 로고    scopus 로고
    • NOESY NMR crosspeaks between lipid headgroups and hydrocarbon chains: Spin diffusion or molecular disorder?
    • Huster D., Gawrish K. NOESY NMR crosspeaks between lipid headgroups and hydrocarbon chains: spin diffusion or molecular disorder? J. Am. Chem. Soc. 121:1999;1992-1992.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 1992-1992
    • Huster, D.1    Gawrish, K.2
  • 49
    • 0001726193 scopus 로고    scopus 로고
    • Investigation of lipid organization in biological membranes by two-dimensional nuclear overhauser enhancement spectroscopy
    • Huster D., Gawrish K. Investigation of lipid organization in biological membranes by two-dimensional nuclear overhauser enhancement spectroscopy. J. Phys. Chem. B. 103:1999;243-251.
    • (1999) J. Phys. Chem. B , vol.103 , pp. 243-251
    • Huster, D.1    Gawrish, K.2
  • 50
    • 0019419317 scopus 로고
    • The headgroup conformation of phospholipids in membranes
    • Büldt G., Wohlgemuth R. The headgroup conformation of phospholipids in membranes. J. Membr. Biol. 58:1981;81-100.
    • (1981) J. Membr. Biol. , vol.58 , pp. 81-100
    • Büldt, G.1    Wohlgemuth, R.2
  • 51
    • 0041197509 scopus 로고
    • Paramagnetic-resonance spectra of spin labels in phospholipids membranes
    • Gaffney B.J., McConnell H.M. Paramagnetic-resonance spectra of spin labels in phospholipids membranes. J. Magn. Res. 16:1974;1-30.
    • (1974) J. Magn. Res. , vol.16 , pp. 1-30
    • Gaffney, B.J.1    McConnell, H.M.2
  • 52
    • 0343118775 scopus 로고    scopus 로고
    • Molecular dynamics simulations of lipid bilayers
    • Merz K.M. Jr. Molecular dynamics simulations of lipid bilayers. Curr. Opin. Struct. Biol. 7:1997;511-517.
    • (1997) Curr. Opin. Struct. Biol. , vol.7 , pp. 511-517
    • Merz K.M., Jr.1
  • 53
  • 54
    • 0016160926 scopus 로고
    • Binding of spin-labeled local-anesthetics to phosphatidylcholine and phosphatidylserine liposomes
    • Giotta G.J., Chan D.S., Wang H.H. Binding of spin-labeled local-anesthetics to phosphatidylcholine and phosphatidylserine liposomes. Arch. Biochim. Biophys. 163:1974;453-458.
    • (1974) Arch. Biochim. Biophys. , vol.163 , pp. 453-458
    • Giotta, G.J.1    Chan, D.S.2    Wang, H.H.3


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