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Spin label and 2H-NMR studies on the interaction of melanotropic peptides with lipid bilayers

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Abstract

The interaction of the cationic tridecapeptide α-melanocyte stimulating hormone (α-MSH) and the biologically more active analog [Nle4, DPhe7]-α-MSH with lipid membranes was investigated by means of ESR of spin probes incorporated in the bilayer, and NMR of deuterated lipids. All spin labels used here, stearic acid and phospholipid derivatives labeled at the 5th and 12th position of the hydrocarbon chain, and the cholestane label, incorporated into anionic vesicles of DMPG (1,2-dimyristoyl-sn-glycero-3-phosphoglycerol) in the liquid-crystalline phase, indicated that both peptides decrease the motional freedom of the acyl chains. No peptide effect was detected with neutral lipid bilayers. Changes in the α-deuteron quadrupolar splittings and spin lattice relaxation time of DMPG deuterated at the glycerol headgroup paralleled the results obtained with ESR, showing that the peptides cause a better packing both at the headgroup and at the acyl chain bilayer regions. The stronger effect caused by the more potent analog in the membrane structure, when compared to the native hormone, is discussed in terms of its larger lipid association constant and/or its deeper penetration into the bilayer.

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References

  • Beschiaschvili G, Seelig J (1990) Peptide binding to lipid membranes spectroscopic studies on the insertion of a cyclic somatostatin analog into phospholipid bilayers. Biochemistry 29:52–58

    Google Scholar 

  • Biaggi MH, Schreier S, Castrucci AML, Lamy-Freund MT (1993) Interaction of melanotropic peptides with lipid membranes. Ann NY Acad Sci 680:459–461

    Google Scholar 

  • Brown MF, Seelig J (1977) Ion-induced changes in head group conformation of lecitin bilayers. Nature (London) 269:721–723

    Google Scholar 

  • Brown MF, Seelig J, Häberlen U (1979) Structural dynamics in phospholipid bilayers from deuterium spin-lattice relaxation time measurements. J Chem Phys 70:5045–5053

    Google Scholar 

  • Castrucci AML, Sawyer TK, Al-Obeidi F, Hruby VJ, Hadley ME (1990) Melanotropic peptide antagonists: Recent discoveries and biomedical implications. Drugs of the Future 15:1–55

    Google Scholar 

  • Cevc G, Watts A, Marsh D (1983) Non-electrostatic contribution to the titration of the ordered-fluid phase transition of phosphatidylglycerol bilayers. FEBS Lett 120:267–270

    Google Scholar 

  • Davis JH (1983) The description of membrane lipid conformation, order and dynamics by 3H-NMR. Biochim Biophys Acta 737:117–171

    Google Scholar 

  • Ellena JF, Archer SJ, Dominey RN, Hill BD, Cafiso DS (1988) Localizing the nitroxide group of fatty acid and voltage-sensitive spin-labels in phospholipid bilayers. Biochim Biophys Acta 940:63–70

    Google Scholar 

  • Gaffney BJ (1976) Practical considerations for the calculation of order parameters for fatty acid or phospholipid spin labels in membranes. In: Berliner LJ (ed) Spin Labelling. Theory and Applications, vol 1. Academic Press, New York, pp 567–571

    Google Scholar 

  • Godici PE, Landsberger FR (1974) The dynamic structure of lipid membranes. A 13C nuclear magnetic resonance study using spin labels. Biochemistry 13:362–368

    Google Scholar 

  • Griffith OH, Jost PC (1976) Lipid spin labels in biological membranes. In: Berliner LJ (ed) Spin Labelling. Theory and Applications, vol 1. Academic Press, New York, pp 453–523

    Google Scholar 

  • Heimburg T, Biltonen RL (1994) Thermotropic behavior of dimyristoylphosphatidylglycerol and its interaction with cytochrome c. Biochemistry 33:9477–9488

    Google Scholar 

  • Ito AS, Castrucci AML, Hruby J, Hadley ME, Krajcarski T, Szabo A (1993) Structure-activity correlations of melanotropin peptides in model lipids by tryptophan fluorescence studies. Biochemistry 32:12264–12272

    Google Scholar 

  • Lange A, Marsh D, Wassmer K-H, Meier P, Kothe G (1985) Electron spin resonance study of phospholipid membranes employing a comprehensive line-shape model. Biochemistry 24:4383–4392

    Google Scholar 

  • Macêdo ZS, Furquim T, Ito AS (1996) Estimation of average depth of penetration of melanotropins in DMPG vesicles. Biophys Chem (in press)

  • Marassi FM, Macdonald PM (1991) Response of the headgroup of phosphatidylglycerol to membrane surface charge as studied by deuterium and phosphorus-31 nuclear magnetic resonance. Biochemistry 30:10558–10566

    Google Scholar 

  • Marsh D (1980) Molecular motion in phospholipd bilayers in gel phase: Long axis rotation. Biochemistry 19:1632–1637

    Google Scholar 

  • Marsh D (1981) Electron spin resonance: spin labels. In Greel E (ed) Membrane Spectroscopy. Springer, Berlin, pp 51–142

    Google Scholar 

  • Pascher I, Lundmark M, Nyholm P-G, Sundell S (1992) Crystal structures of membrane lipids. Biochim Biophys Acta 1113:339–373

    Google Scholar 

  • Pinheiro TJT, Duralski A, Watts A (1994) Phospholipid headgroup-headgroup eletrostatic interactions in mixed bilayers of cardiolipin with phosphatidylcholines studies by 2H NMR. Biochemistry 33:4896–4902

    Google Scholar 

  • Presti FT, Chan SI (1982) Cholesterol-phospholipid interaction in membranes. I. Cholestane spin-label studies of fase behavior of cholesterol-phospholipid liposomes. Biochemistry 21:3821–3830

    Google Scholar 

  • Ptak M, Egret-Charlier M, Sanson A, Boloussa O (1980) A NMR study of the ionization of fatty acids, fatty amines and N-acylamino acids incorporated in phosphatidylcholine vesicles. Biochim Biophys Acta 600:387–397

    Google Scholar 

  • Roux M, Neumann J-M, Bloom M, Devaux PF (1988) 2H and 31p NMR study of pentalysine interaction with headgroup deuterated phosphatidylcholine and phosphatidylserine. Eur Biophys J 16:267–273

    Google Scholar 

  • Sankaram MB, Brophy PJ, Marsh D (1989) Spin-label ESR studies on the interaction of bovine spinal cord myelin basic protein with dimiristoylphosphatidylglycerol dispersions. Biochemistry 28:9685–9691

    Google Scholar 

  • Sargent S, Schwyzer R (1986) Membrane lipid phase as catalyst for peptide-receptor interactions. Proc Natl Acad Sci USA 83:5774–5778

    Google Scholar 

  • Sawyer TK, Sanfilippo PJ, Hruby VJ, Engel MH, Heward CB, Burnett KB, Hadley ME (1980) 4-Norleucine, 7-D-phenylalanineα-melanocyte-stimating hormone: A highly potent α-melanotropin with ultra long biological activity. Proc Natl Acad Sci, USA 77:5754–5758

    Google Scholar 

  • Scherer PG, Seelig J (1989) Eletric charge effects on phospholipid headgroups. Phosphatidylcholine in mixtures with cationic and anionic amphiphiles. Biochemistry 28:7720–7728

    Google Scholar 

  • Schindler H, Seelig J (1973) ESR spectra of spin labels in lipid bilayers. J Chem Phys 59:1841–1850

    Google Scholar 

  • Schindler H, Seelig J (1974) ESR spectra of spin labels in lipid bilayers. II. Rotation of steroid spin probes. J Chem Phys 61:2946–2949

    Google Scholar 

  • Schwyzer R (1986) Molecular mechanism of opioid receptor selection. Biochemistry 25:6335–6341

    Google Scholar 

  • Seelig J (1977) Deuterium magnetic resonance: theory and application to lipid membranes. Q Rev Biophys 10:353–418

    Google Scholar 

  • Seelig J, Limacher H, Bader P (1972) Molecular architecture of liquid crystalline bilayers. J Am Chem Soc 94:6364–6371

    Google Scholar 

  • Seelig J, Macdonald PM, Scherer PG (1987) Phospholipid head groups as sensors of eletric charges in membranes. Biochemistry 26:7535–7541

    Google Scholar 

  • Sixl F, Watts A (1985) Deuterium and phosphorus nuclear magnetic resonance studies on the binding of polymyxin B to lipid bilayers-water interfaces. Biochemistry 24:7906–7910

    Google Scholar 

  • Sixl F, Brophy PJ, Watts A (1984) Selective protein-lipid interactions at membrane surfaces: a deuterium and phosphorus nuclear magnetic resonance study of the association of myelin basic protein with the bilayer head group of dimyristoylphosphatidyl-choline and dimyristoylphosphatidylglycerol. Biochemistry 23:2032–2039

    Google Scholar 

  • Subczynski WK, Markowska E, Gruszecki WI, Sielewiesiuk J (1992) Effects of polar carotenoids on dimyristoylphophatidylcholine membranes: a spin-label study. Biochim Biophys Acta 1105:97–108

    Google Scholar 

  • Watts A (1993) Magnetic resonance studies of phospholipid-protein interactions in bilayers. In: Cevc, G (eds) Phospholipids Handbook. Marcel Dekker, New York, pp 687–741

    Google Scholar 

  • Watts A, Harlos K, Maschke W, Marsh D (1978) Control of the structure and fluidity of phosphatidylglycerol bilayers by pH titration. Biochim Biophys Acta 510:63–74

    Google Scholar 

  • Yin J-J, Feix JB, Hyde JS (1988) Mapping of collision frequencies for stearic acid spin labels by saturation-recovery electron paramagnetic resonance. Biophys J 53:521–531

    Google Scholar 

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Author notes

  1. Teresa J. T. Pinheiro

    Present address: Department of Biological Sciences, University of Warwick, CV4 7AL, Coventry, UK

Authors and Affiliations

  1. Instituto de Física, Universidade de São Paulo, CP 66318, CEP 05389-970, São Paulo, Brasil

    Marcia H. Biaggi & M. Teresa Lamy-Freund

  2. Department of Biochemistry, University of Oxford, South Parks Road, OX1 3QU, Oxford, UK

    Teresa J. T. Pinheiro & Anthony Watts

Authors
  1. Marcia H. Biaggi
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  2. Teresa J. T. Pinheiro
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  3. Anthony Watts
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  4. M. Teresa Lamy-Freund
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Biaggi, M.H., Pinheiro, T.J.T., Watts, A. et al. Spin label and 2H-NMR studies on the interaction of melanotropic peptides with lipid bilayers. Eur Biophys J 24, 251–259 (1996). https://doi.org/10.1007/BF00205106

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  • DOI: https://doi.org/10.1007/BF00205106

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