메뉴 건너뛰기




Volumn 164, Issue 2, 2011, Pages 131-143

Lipid bilayer molecular dynamics study of lipid-derived agonists of the putative cannabinoid receptor, GPR55

Author keywords

Cannabinoid; GPCR; GPR55; Lipid bilayer; Molecular dynamics

Indexed keywords

1 ALPHA LYSOPHOSPHATIDYLINOSITOL; 1 PALMITOYL 2 OLEOYL SN GLYCERO 3 PHOSPHOCHOLINE; 2 ARACHIDONOYL SN GLYCERO 3 PHOSPHOINOSITOL; ANANDAMIDE; CANNABINOID RECEPTOR; GLYCEROL; INOSITOL; ISOTHIOCYANIC ACID; PHOSPHATE; PHOSPHOLIPID; PHOSPHORYLCHOLINE; UNCLASSIFIED DRUG;

EID: 79951515395     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2010.12.003     Document Type: Article
Times cited : (15)

References (41)
  • 1
    • 0022444567 scopus 로고
    • Computer-based modeling of the conformation and packing properties of docosahexaenoic acid
    • K.R. Applegate, and J.A. Glomset Computer-based modeling of the conformation and packing properties of docosahexaenoic acid J. Lipid Res. 27 1986 658 680 (Pubitemid 16052420)
    • (1986) Journal of Lipid Research , vol.27 , Issue.6 , pp. 658-680
    • Applegate, K.R.1    Glomset, J.A.2
  • 2
    • 0031820877 scopus 로고    scopus 로고
    • Phospholipid component volumes: Determination and application to bilayer structure calculations
    • R.S. Armen, O.D. Uitto, and S.E. Feller Phospholipid component volumes: determination and application to bilayer structure calculations Biophys. J. 75 1998 734 744 (Pubitemid 28357515)
    • (1998) Biophysical Journal , vol.75 , Issue.2 , pp. 734-744
    • Armen, R.S.1    Uitto, O.D.2    Feller, S.E.3
  • 3
    • 0032548089 scopus 로고    scopus 로고
    • Exploration of biologically relevant conformations of anandamide, 2- arachidonylglycerol, and their analogues using conformational memories
    • DOI 10.1021/jm9803471
    • J. Barnett-Norris, F. Guarnieri, D.P. Hurst, and P.H. Reggio Exploration of biologically relevant conformations of anandamide, 2-arachidonylglycerol, and their analogues using conformational memories J. Med. Chem. 41 1998 4861 4872 (Pubitemid 28530461)
    • (1998) Journal of Medicinal Chemistry , vol.41 , Issue.24 , pp. 4861-4872
    • Barnett-Norris, J.1    Guarnieri, F.2    Hurst, D.P.3    Reggio, P.H.4
  • 4
    • 0024291319 scopus 로고
    • 13CO-labeled phospholipids hydrogen bonding to carbonyl groups
    • 13CO-labeled phospholipids hydrogen bonding to carbonyl groups Biochemistry 27 1988 8239 8249
    • (1988) Biochemistry , vol.27 , pp. 8239-8249
    • Blume, A.1    Hubner, W.2    Messner, G.3
  • 5
    • 18944363888 scopus 로고    scopus 로고
    • Conformational analysis of N-arachidonylethanolamide (anandamide) using nuclear magnetic resonance and theoretical calculations
    • C. Bonechi, A. Brizzi, V. Brizzi, M. Francoli, A. Donati, and C. Rossi Conformational analysis of N-arachidonylethanolamide (anandamide) using nuclear magnetic resonance and theoretical calculations Magn. Reson. Chem. 39 2001 432 437
    • (2001) Magn. Reson. Chem. , vol.39 , pp. 432-437
    • Bonechi, C.1    Brizzi, A.2    Brizzi, V.3    Francoli, M.4    Donati, A.5    Rossi, C.6
  • 6
    • 0032706178 scopus 로고    scopus 로고
    • Combined Monte Carlo and molecular dynamics simulation of fully hydrated dioleyl and palmitoyl-oleyl phosphatidylcholine lipid bilayers
    • S.W. Chiu, E. Jakobsson, S. Subramaniam, and H.L. Scott Combined Monte Carlo and molecular dynamics simulation of fully hydrated dioleyl and palmitoyl-oleyl phosphatidylcholine lipid bilayers Biophys. J. 77 1999 2462 2469 (Pubitemid 29519493)
    • (1999) Biophysical Journal , vol.77 , Issue.5 , pp. 2462-2469
    • Chiu, S.W.1    Jakobsson, E.2    Subramaniam, S.3    Scott, H.L.4
  • 7
    • 33846823909 scopus 로고
    • Particle Mesh Ewald. An Nlog(N) method for Ewald sums in large systems
    • T.A. Darden, D. York, and L. Pedersen Particle Mesh Ewald. An Nlog(N) method for Ewald sums in large systems J. Chem. Phys. 98 1993 10089 10092
    • (1993) J. Chem. Phys. , vol.98 , pp. 10089-10092
    • Darden, T.A.1    York, D.2    Pedersen, L.3
  • 8
    • 0037837613 scopus 로고    scopus 로고
    • Polyunsaturated docosahexaenoic vs docosapentaenoic acid - Differences in lipid matrix properties from the loss of one double bond
    • DOI 10.1021/ja029029o
    • N.V. Eldho, S.E. Feller, S. Tristram-Nagle, I.V. Polozov, and K. Gawrisch Polyunsaturated docosahexaenoic vs docosapentaenoic acid-differences in lipid matrix properties from the loss of one double bond J. Am. Chem. Soc. 125 2003 6409 6421 (Pubitemid 36605409)
    • (2003) Journal of the American Chemical Society , vol.125 , Issue.21 , pp. 6409-6421
    • Eldho, N.V.1    Feller, S.E.2    Tristram-Nagle, S.3    Polozov, I.V.4    Gawrisch, K.5
  • 9
    • 22744437702 scopus 로고    scopus 로고
    • Location, conformation and dynamics of anandamide in biomembranes
    • N.V. Eldho, and K. Gawrisch Location, conformation and dynamics of anandamide in biomembranes Biophys. J. 84 2003 49a
    • (2003) Biophys. J. , vol.84
    • Eldho, N.V.1    Gawrisch, K.2
  • 10
    • 0037116518 scopus 로고    scopus 로고
    • Polyunsaturated fatty acids in lipid bilayers: Intrinsic and environmental contributions to their unique physical properties
    • DOI 10.1021/ja0118340
    • S.E. Feller, K. Gawrisch, and A.D. MacKerell Jr. Polyunsaturated fatty acids in lipid bilayers: intrinsic and environmental contributions to their unique physical properties J. Am. Chem. Soc. 124 2002 318 326 (Pubitemid 34062762)
    • (2002) Journal of the American Chemical Society , vol.124 , Issue.2 , pp. 318-326
    • Feller, S.E.1    Gawrisch, K.2    MacKerell Jr., A.D.3
  • 11
    • 0034250744 scopus 로고    scopus 로고
    • An improved empirical potential energy function for molecular simulations of phospholipids
    • S.E. Feller, and J.A.D. MacKerell An improved empirical potential energy function for molecular simulations of phospholipids J. Phys. Chem. B 104 2000 7510 7515
    • (2000) J. Phys. Chem. B , vol.104 , pp. 7510-7515
    • Feller, S.E.1    MacKerell, J.A.D.2
  • 12
    • 0037633085 scopus 로고    scopus 로고
    • The structure of DHA in phospholipid membranes
    • DOI 10.1007/s11745-003-1082-0
    • K. Gawrisch, N.V. Eldho, and L.L. Holte The structure of docosahexaenoic acid in phospholipid membranes Lipids 38 2003 445 452 (Pubitemid 36724304)
    • (2003) Lipids , vol.38 , Issue.4 , pp. 445-452
    • Gawrisch, K.1    Eldho, N.V.2    Holte, L.L.3
  • 13
    • 2942675244 scopus 로고    scopus 로고
    • Lipid Bilayer pressure profiles and mechanosensitive channel gating
    • DOI 10.1529/biophysj.103.034322
    • J. Gullingsrud, and K. Schulten Lipid bilayer pressure profiles and mechanosensitive channel gating Biophys. J. 86 2004 3496 3509 (Pubitemid 38780232)
    • (2004) Biophysical Journal , vol.86 , Issue.6 , pp. 3496-3509
    • Gullingsrud, J.1    Schulten, K.2
  • 14
    • 34249282672 scopus 로고    scopus 로고
    • Study of the torsional potential energies of 2-methylpropane, n-butane, and 2-methylbutane with high level ab initio calculations
    • M.J. Hafezi, and F. Sharif Study of the torsional potential energies of 2-methylpropane, n-butane, and 2-methylbutane with high level ab initio calculations J. Mol. Struc. (Theochem.) 814 2007 43 49
    • (2007) J. Mol. Struc. (Theochem.) , vol.814 , pp. 43-49
    • Hafezi, M.J.1    Sharif, F.2
  • 16
    • 0028988796 scopus 로고
    • 2H nuclear magnetic resonance order parameter profiles suggest a change of molecular shape for phosphatidylcholines containing a polyunsaturated acyl chain
    • 2H nuclear magnetic resonance order parameter profiles suggest a change of molecular shape for phosphatidylcholines containing a polyunsaturated acyl chain Biophys. J. 68 1995 2396 2403
    • (1995) Biophys. J. , vol.68 , pp. 2396-2403
    • Holte, L.L.1    Peter, S.A.2    Sinnwell, T.M.3    Gawrisch, K.4
  • 19
    • 79951518162 scopus 로고    scopus 로고
    • In silico modeling of GPR55: Creation of an initial model and refinement based upon sequence divergences in TMH6 and TMH7
    • International Cannabinoid Research Society, vol. 16
    • D. Hurst, J. Barnett-Norris, M. Abood, and P. Reggio In silico modeling of GPR55: creation of an initial model and refinement based upon sequence divergences in TMH6 and TMH7 16th Annual Symposium on the Cannabinoids International Cannabinoid Research Society, vol. 16 2006 107
    • (2006) 16th Annual Symposium on the Cannabinoids , pp. 107
    • Hurst, D.1    Barnett-Norris, J.2    Abood, M.3    Reggio, P.4
  • 24
    • 33646446451 scopus 로고    scopus 로고
    • Structure of fully hydrated fluid phase lipid bilayers with monounsaturated chains
    • N. Kucerka, S. Tristram-Nagle, and J.F. Nagle Structure of fully hydrated fluid phase lipid bilayers with monounsaturated chains J. Membr. Biol. 208 2005 193 202
    • (2005) J. Membr. Biol. , vol.208 , pp. 193-202
    • Kucerka, N.1    Tristram-Nagle, S.2    Nagle, J.F.3
  • 26
    • 22744444204 scopus 로고    scopus 로고
    • Molecular dynamics simulations of the endocannabinoid N- arachidonoylethanolamine (anandamide) in a phospholipid bilayer: Probing structure and dynamics
    • DOI 10.1021/jm058185d
    • D.L. Lynch, and P.H. Reggio Molecular dynamics simulations of the endocannabinoid, N-arachidonoylethanolamine (anandamide) in a phospholipid bilayer: probing structure and dynamics J. Med. Chem. 48 2005 4824 4833 (Pubitemid 41033125)
    • (2005) Journal of Medicinal Chemistry , vol.48 , Issue.15 , pp. 4824-4833
    • Lynch, D.L.1    Reggio, P.H.2
  • 29
    • 58149138962 scopus 로고    scopus 로고
    • 2-Arachidonoyl-sn-glycero-3-phosphoinositol: A possible natural ligand for GPR55
    • S. Oka, T. Toshida, K. Maruyama, K. Nakajima, A. Yamashita, and T. Sugiura 2-Arachidonoyl-sn-glycero-3-phosphoinositol: a possible natural ligand for GPR55 J. Biochem. 145 2009 13 20
    • (2009) J. Biochem. , vol.145 , pp. 13-20
    • Oka, S.1    Toshida, T.2    Maruyama, K.3    Nakajima, K.4    Yamashita, A.5    Sugiura, T.6
  • 30
    • 56049101882 scopus 로고    scopus 로고
    • Ligand-binding architecture of human CB2 cannabinoid receptor: Evidence for receptor subtype-specific binding motif and modeling GPCR activation
    • Y. Pei, R.W. Mercier, J.K. Anday, G.A. Thakur, A.M. Zvonok, D. Hurst, P.H. Reggio, D.R. Janero, and A. Makriyannis Ligand-binding architecture of human CB2 cannabinoid receptor: evidence for receptor subtype-specific binding motif and modeling GPCR activation Chem. Biol. 15 2008 1207 1219
    • (2008) Chem. Biol. , vol.15 , pp. 1207-1219
    • Pei, Y.1    Mercier, R.W.2    Anday, J.K.3    Thakur, G.A.4    Zvonok, A.M.5    Hurst, D.6    Reggio, P.H.7    Janero, D.R.8    Makriyannis, A.9
  • 31
    • 27844505656 scopus 로고    scopus 로고
    • (-)-7′-isothiocyanato-11-hydroxy-1′,1′- dimethylheptylhexahydrocannabinol (AM841), a high-affinity electrophilic ligand, interacts covalently with a cysteine in helix six and activates the CB1 cannabinoid receptor
    • DOI 10.1124/mol.105.014407
    • R.P. Picone, A.D. Khanolkar, W. Xu, L.A. Ayotte, G.A. Thakur, D.P. Hurst, M.E. Abood, P.H. Reggio, D.J. Fournier, and A. Makriyannis (-)-7′- Isothiocyanato-11-hydroxy-1′,1′-dimethylheptylhexahydrocannabinol (AM841), a high-affinity electrophilic ligand, interacts covalently with a cysteine in helix six and activates the CB1 cannabinoid receptor Mol. Pharmacol. 68 2005 1623 1635 (Pubitemid 41654346)
    • (2005) Molecular Pharmacology , vol.68 , Issue.6 , pp. 1623-1635
    • Picone, R.P.1    Khanolkar, A.D.2    Xu, W.3    Ayotte, L.A.4    Thakur, G.A.5    Hurst, D.P.6    Abood, M.E.7    Reggio, P.H.8    Fournier, D.J.9    Makriyannis, A.10
  • 32
    • 0025737771 scopus 로고
    • On the conformational, physical properties and function of polyunsaturated acylchains
    • A.L. Rabinovich, and P.O. Ripatti On the conformational, physical properties and function of polyunsaturated acylchains Biochim. Biophys. Acta 1085 1991 53 56
    • (1991) Biochim. Biophys. Acta , vol.1085 , pp. 53-56
    • Rabinovich, A.L.1    Ripatti, P.O.2
  • 33
    • 0027179190 scopus 로고
    • Conformational analysis of arachidonic and related fatty acids using molecular dynamics simulations
    • DOI 10.1016/0167-4889(93)90113-4
    • M.R. Rich Conformational analysis of arachidonic and related fatty acids using molecular dynamics simulations Biochim. Biophys. Acta 1178 1993 87 96 (Pubitemid 23236100)
    • (1993) Biochimica et Biophysica Acta - Molecular Cell Research , vol.1178 , Issue.1 , pp. 87-96
    • Rich, M.R.1
  • 35
    • 0034962090 scopus 로고    scopus 로고
    • Structural properties of a highly polyunsaturated lipid bilayer from molecular dynamics simulations
    • L. Saiz, and M.L. Klein Structural properties of a highly polyunsaturated lipid bilayer from molecular dynamics simulations Biophys. J. 81 2001 204 216 (Pubitemid 32605963)
    • (2001) Biophysical Journal , vol.81 , Issue.1 , pp. 204-216
    • Saiz, L.1    Klein, M.L.2
  • 36
    • 0033524644 scopus 로고    scopus 로고
    • Identification and cloning of three novel human G protein-coupled receptor genes GPR52, ΨGPR53 and GPR55: GPR55 is extensively expressed in human brain
    • DOI 10.1016/S0169-328X(98)00277-0, PII S0169328X98002770
    • M. Sawzdargo, T. Nguyen, D.K. Lee, K.R. Lynch, R. Cheng, H.H. Heng, S.R. George, and B.F. O'Dowd Identification and cloning of three novel human G protein-coupled receptor genes GPR52, PsiGPR53 and GPR55: GPR55 is extensively expressed in human brain Brain Res. Mol. Brain Res. 64 1999 193 198 (Pubitemid 29052470)
    • (1999) Molecular Brain Research , vol.64 , Issue.2 , pp. 193-198
    • Sawzdargo, M.1    Nguyen, T.2    Lee, D.K.3    Lynch, K.R.4    Cheng, R.5    Heng, H.H.Q.6    George, S.R.7    O'Dowd, B.F.8
  • 37
    • 0022487880 scopus 로고
    • Depth of water penetration into lipid bilayers
    • S.A. Simon, and T.J. McIntosh Depth of water penetration into lipid bilayers Methods Enzymol. 127 1986 511 521
    • (1986) Methods Enzymol. , vol.127 , pp. 511-521
    • Simon, S.A.1    McIntosh, T.J.2
  • 39
    • 23844534427 scopus 로고    scopus 로고
    • The conformation, location, and dynamic properties of the endocannabinoid ligand anandamide in a membrane bilayer
    • DOI 10.1074/jbc.M502925200
    • X. Tian, J. Guo, F. Yao, D.P. Yang, and A. Makriyannis The conformation, location, and dynamic properties of the endocannabinoid ligand anandamide in a membrane bilayer J. Biol. Chem. 280 2005 29788 29795 (Pubitemid 41177056)
    • (2005) Journal of Biological Chemistry , vol.280 , Issue.33 , pp. 29788-29795
    • Tian, X.1    Guo, J.2    Yao, F.3    Yang, D.-P.4    Makriyannis, A.5
  • 41
    • 0026729232 scopus 로고
    • Structure of a fluid dioleoylphosphatidylcholine bilayer determined by joint refinement of X-ray and neutron diffraction data. III. Complete structure
    • M.C. Wiener, and S.H. White Structure of a fluid dioleoylphosphatidylcholine bilayer determined by joint refinement of X-ray and neutron diffraction data. III. Complete structure Biophys. J. 61 1992 434 447
    • (1992) Biophys. J. , vol.61 , pp. 434-447
    • Wiener, M.C.1    White, S.H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.