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Volumn 57, Issue 1, 2011, Pages 100-108

Synthesis and evaluation of sesquiterpene lactone inhibitors of phospholipase A2 from Bothrops jararacussu

Author keywords

Bothrops jararacussu; Chemometrics; DFT; PLA2; Sesquiterpene lactone

Indexed keywords

COMPOUND LAC01; COMPOUND LAC02; COMPOUND LAC03; COMPOUND LAC04; COMPOUND LAC05; COMPOUND LAC06; COMPOUND LAC07; COMPOUND LAC08; PHOSPHOLIPASE A2; SESQUITERPENE LACTONE DERIVATIVE; SNAKE VENOM; UNCLASSIFIED DRUG;

EID: 78650678396     PISSN: 00410101     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.toxicon.2010.10.010     Document Type: Article
Times cited : (20)

References (51)
  • 2
    • 0029750725 scopus 로고    scopus 로고
    • Bromoenol lactone inhibits magnesium-dependent phosphatidate phosphohydrolase and blocks triacylglycerol biosynthesis in mouse P388D1 macrophages
    • Balsinde J., Dennis E.A. Bromoenol lactone inhibits magnesium-dependent phosphatidate phosphohydrolase and blocks triacylglycerol biosynthesis in mouse P388D1 macrophages. J. Biol. Chem. 1996, 271:31937-31941.
    • (1996) J. Biol. Chem. , vol.271 , pp. 31937-31941
    • Balsinde, J.1    Dennis, E.A.2
  • 3
    • 0037201940 scopus 로고    scopus 로고
    • Phospholipase A2 regulation of arachidonic acid mobilization
    • Balsinde J., Winstead M.V., Dennis E.A. Phospholipase A2 regulation of arachidonic acid mobilization. FEBS. Lett. 2002, 531:2-6.
    • (2002) FEBS. Lett. , vol.531 , pp. 2-6
    • Balsinde, J.1    Winstead, M.V.2    Dennis, E.A.3
  • 4
    • 85038571561 scopus 로고    scopus 로고
    • Beebe K.R., Pell R.J. In Chemometrics: A Practical Guide 1988, Wiley-Interscience. M.B. Seasholtz (Ed.).
  • 6
    • 0035492205 scopus 로고    scopus 로고
    • Structure-activity relationships in platelet-activating factor (PAF). 11-From PAF-antagonism to phospholipase A2 inhibition: syntheses and structure-activity relationships in 1-arylsulfamido-2-alkylpiperazines
    • Binisti C., Assogba L., Touboul E., Mounier C., Huet J., Ombetta J., Dong C.Z., Redeuilh C., Heymans F., Godfroid J.J. Structure-activity relationships in platelet-activating factor (PAF). 11-From PAF-antagonism to phospholipase A2 inhibition: syntheses and structure-activity relationships in 1-arylsulfamido-2-alkylpiperazines. Eur. J. Med. Chem. 2001, 36:809-828.
    • (2001) Eur. J. Med. Chem. , vol.36 , pp. 809-828
    • Binisti, C.1    Assogba, L.2    Touboul, E.3    Mounier, C.4    Huet, J.5    Ombetta, J.6    Dong, C.Z.7    Redeuilh, C.8    Heymans, F.9    Godfroid, J.J.10
  • 9
    • 0036296032 scopus 로고    scopus 로고
    • First structural evidence of a specific inhibition of phospholipase A2 by α-tocopherol (Vitamin E) and its implications in inflammation: crystal structure of the complex formed between phospholipase A2 and α-tocopherol at 1.8 A resolution
    • Chandra V., Kaur P., Jasti J., Betzel C., Srinivasan A., Singh T.P. First structural evidence of a specific inhibition of phospholipase A2 by α-tocopherol (Vitamin E) and its implications in inflammation: crystal structure of the complex formed between phospholipase A2 and α-tocopherol at 1.8 A resolution. J. Mol. Biol. 2002, 320:215-222.
    • (2002) J. Mol. Biol. , vol.320 , pp. 215-222
    • Chandra, V.1    Kaur, P.2    Jasti, J.3    Betzel, C.4    Srinivasan, A.5    Singh, T.P.6
  • 10
    • 0036714237 scopus 로고    scopus 로고
    • Structural basis of phospholipase A2 inhibition for the synthesis of prostaglandins by the plant alkaloid aristolochic acid from a 1.7 A crystal structure
    • Chandra V., Jasti J., Kaur P., Srinivasan A., Betzel C., Singh T.P. Structural basis of phospholipase A2 inhibition for the synthesis of prostaglandins by the plant alkaloid aristolochic acid from a 1.7 A crystal structure. Biochemistry 2002, 41:10914-10919.
    • (2002) Biochemistry , vol.41 , pp. 10914-10919
    • Chandra, V.1    Jasti, J.2    Kaur, P.3    Srinivasan, A.4    Betzel, C.5    Singh, T.P.6
  • 12
    • 0037696588 scopus 로고    scopus 로고
    • Neolignan analogues tested against leishmaniasis. A study of structure-activity relationships and a proposal for the shape of the receptor cavity
    • Costa M.C.A., Takahata Y. Neolignan analogues tested against leishmaniasis. A study of structure-activity relationships and a proposal for the shape of the receptor cavity. J. Mol. Struct. (Theochem) 2003, 625:257-263.
    • (2003) J. Mol. Struct. (Theochem) , vol.625 , pp. 257-263
    • Costa, M.C.A.1    Takahata, Y.2
  • 13
    • 5444272591 scopus 로고    scopus 로고
    • The influence of electronic, steric and hydrophobic properties of flavonoid compounds in the inhibition of the xanthine oxidase
    • Da Silva S.L., Silva A., Honório K.M., Marangoni S., Toyama M.H., Da Silva A.B.F. The influence of electronic, steric and hydrophobic properties of flavonoid compounds in the inhibition of the xanthine oxidase. J. Mol. Struct. (Theochem) 2004, 684:1-7.
    • (2004) J. Mol. Struct. (Theochem) , vol.684 , pp. 1-7
    • Da Silva, S.L.1    Silva, A.2    Honório, K.M.3    Marangoni, S.4    Toyama, M.H.5    Da Silva, A.B.F.6
  • 14
    • 35348871311 scopus 로고    scopus 로고
    • Chemotherapeutic potential of the volatile oils from Zanthoxylum rhoifolium Lam leaves
    • Da Silva S.L., Figueiredo P.M.S., Yano T. Chemotherapeutic potential of the volatile oils from Zanthoxylum rhoifolium Lam leaves. Eur. J. Pharmacol. 2006, 576:180-188.
    • (2006) Eur. J. Pharmacol. , vol.576 , pp. 180-188
    • Da Silva, S.L.1    Figueiredo, P.M.S.2    Yano, T.3
  • 15
    • 33751575354 scopus 로고    scopus 로고
    • Antibacterial and antifungal activities of volatile oils from Zanthoxylum rhoifolium leaves
    • Da Silva S.L., Figueiredo P.M.S., Yano T. Antibacterial and antifungal activities of volatile oils from Zanthoxylum rhoifolium leaves. Pharm. Biol. 2007, 44:657-659.
    • (2007) Pharm. Biol. , vol.44 , pp. 657-659
    • Da Silva, S.L.1    Figueiredo, P.M.S.2    Yano, T.3
  • 16
    • 53649089252 scopus 로고    scopus 로고
    • Isolation and characterization of ellagic acid derivatives isolated from Casearia sylvestris SW aqueous extract with anti-PLA2 activity
    • Da Silva S.L., Calgarotto A.K., Chaar J.S., Marangoni S. Isolation and characterization of ellagic acid derivatives isolated from Casearia sylvestris SW aqueous extract with anti-PLA2 activity. Toxicon 2008, 52:655-666.
    • (2008) Toxicon , vol.52 , pp. 655-666
    • Da Silva, S.L.1    Calgarotto, A.K.2    Chaar, J.S.3    Marangoni, S.4
  • 20
    • 0030041824 scopus 로고    scopus 로고
    • Pefabloc, 4-[2-aminoethyl] benzenesulfonyl fluoride, is a new, potent nontoxic and irreversible inhibitor of PAF-degrading acetylhydrolase
    • Dentan C., Tselepis A.D., Chapman M.J., Ninio E. Pefabloc, 4-[2-aminoethyl] benzenesulfonyl fluoride, is a new, potent nontoxic and irreversible inhibitor of PAF-degrading acetylhydrolase. Biochim. Biophys. Acta. 1996, 1299:353-357.
    • (1996) Biochim. Biophys. Acta. , vol.1299 , pp. 353-357
    • Dentan, C.1    Tselepis, A.D.2    Chapman, M.J.3    Ninio, E.4
  • 22
    • 85038566787 scopus 로고    scopus 로고
    • Dragon Molecular Descriptors Analysis for Windows, version 5.0, Talete srl, Milano, Italy.
  • 23
    • 0035976575 scopus 로고    scopus 로고
    • Prostaglandins and leukotrienes: advances in eicosanoid biology
    • Funk C.D. Prostaglandins and leukotrienes: advances in eicosanoid biology. Science 2001, 294:1871-1875.
    • (2001) Science , vol.294 , pp. 1871-1875
    • Funk, C.D.1
  • 24
    • 85038569337 scopus 로고    scopus 로고
    • Gaussian03 Software- Gaussian Inc., 340 Quinnipiac Street, Bldg 40 Wallingford, CT 06492 U.S.A.
  • 25
    • 0036597873 scopus 로고    scopus 로고
    • Comprendiendo los venenos de serpientes: 50 Anos de investigaciones en Amećrica Latina
    • Gutiérrez J.M. Comprendiendo los venenos de serpientes: 50 Anos de investigaciones en Amećrica Latina. Rev. Biol. Trop. 2002, 50:377-394.
    • (2002) Rev. Biol. Trop. , vol.50 , pp. 377-394
    • Gutiérrez, J.M.1
  • 26
    • 33748545144 scopus 로고
    • The influence of polarization functions on molecular orbital hydrogenation energies
    • Hariharan P.C., Pople J.A. The influence of polarization functions on molecular orbital hydrogenation energies. Theor. Chim. Acta. 1973, 28:213.
    • (1973) Theor. Chim. Acta. , vol.28 , pp. 213
    • Hariharan, P.C.1    Pople, J.A.2
  • 27
    • 85038560564 scopus 로고    scopus 로고
    • HyperChem, Release 7.51 for Windows - Molecular Modeling System, Hypercube, USA.
  • 28
    • 33644841098 scopus 로고    scopus 로고
    • Non-steroidal anti-inflammatory drugs as potent inhibitors of phospholipase A2: structure of the complex of phospholipase A2 with niflumic acid at 2.5 A resolution
    • Jabeen T., Singh N., Singh R.K., Sharma S., Somvanshi R.K., Dey S., Singh T.P. Non-steroidal anti-inflammatory drugs as potent inhibitors of phospholipase A2: structure of the complex of phospholipase A2 with niflumic acid at 2.5 A resolution. Biochim. Biophys. Acta. 2005, 61:1579-1586.
    • (2005) Biochim. Biophys. Acta. , vol.61 , pp. 1579-1586
    • Jabeen, T.1    Singh, N.2    Singh, R.K.3    Sharma, S.4    Somvanshi, R.K.5    Dey, S.6    Singh, T.P.7
  • 29
    • 0037031926 scopus 로고    scopus 로고
    • Identification of calcium-independent phospholipase A2 (iPLA2) beta, and not iPlA2 gamma, as the mediator of arginine vasopressin-induced arachidonic acid release in A-10 smooth muscle cells. Enantioselective mechanism-based discrimination of mammalian iPLA2s
    • Jenkins C.M., Han X., Mancuso D.J., Gross R.W. Identification of calcium-independent phospholipase A2 (iPLA2) beta, and not iPlA2 gamma, as the mediator of arginine vasopressin-induced arachidonic acid release in A-10 smooth muscle cells. Enantioselective mechanism-based discrimination of mammalian iPLA2s. J. Biol. Chem. 2002, 277:32807-32814.
    • (2002) J. Biol. Chem. , vol.277 , pp. 32807-32814
    • Jenkins, C.M.1    Han, X.2    Mancuso, D.J.3    Gross, R.W.4
  • 30
    • 0030218597 scopus 로고    scopus 로고
    • Density functional theory of electronic structure
    • Kohn W., Becke A.D., Parr R.G. Density functional theory of electronic structure. J. Phys. Chem. 1996, 10:12974-12980.
    • (1996) J. Phys. Chem. , vol.10 , pp. 12974-12980
    • Kohn, W.1    Becke, A.D.2    Parr, R.G.3
  • 33
    • 0032890010 scopus 로고    scopus 로고
    • Ability of wedelolactone, heparin, and para-bromophenacyl bromide to antagonize the myotoxic effects of two crotaline venoms and their PLA2 myotoxins
    • Melo P.A., Ownby C.L. Ability of wedelolactone, heparin, and para-bromophenacyl bromide to antagonize the myotoxic effects of two crotaline venoms and their PLA2 myotoxins. Toxicon 1999, 37:199-215.
    • (1999) Toxicon , vol.37 , pp. 199-215
    • Melo, P.A.1    Ownby, C.L.2
  • 35
    • 0347291894 scopus 로고
    • Absolute hardness: companion parameter to absolute electronegativity
    • Parr R.G., Pearson R.G. Absolute hardness: companion parameter to absolute electronegativity. J. Am. Chem. Soc. 1983, 105:7512-7516.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 7512-7516
    • Parr, R.G.1    Pearson, R.G.2
  • 37
    • 85038563339 scopus 로고    scopus 로고
    • Perrin D.D., Armarego W.L.F., Perrin D.R. Purification of Laboratory Chemicals 1980, Pergamon Press, London. second ed.
  • 38
    • 85038590139 scopus 로고    scopus 로고
    • Pirouette Multivariate Data Analysis for IBM PC Systems, Version 2.0, Infometrix, Seattle, WA.
  • 40
    • 0011083273 scopus 로고    scopus 로고
    • Harmonic vibrational frequencies: an evaluation of Hartree-Fock, Møller-Plesset, quadratic configuration interaction, density functional theory, and semiempirical scale factors
    • Scott P., Radom L. Harmonic vibrational frequencies: an evaluation of Hartree-Fock, Møller-Plesset, quadratic configuration interaction, density functional theory, and semiempirical scale factors. J. Phys. Chem. 1996, 100:16502.
    • (1996) J. Phys. Chem. , vol.100 , pp. 16502
    • Scott, P.1    Radom, L.2
  • 41
    • 0030615005 scopus 로고    scopus 로고
    • Phospholipase A2 engineering. Structural and functional roles of the highly conserved active site residue aspartate-99
    • Sekar K., Eswaramoorthy S., Jain M.K., Sundaralingam M. Phospholipase A2 engineering. Structural and functional roles of the highly conserved active site residue aspartate-99. Biochemistry 1997, 36:3104-3114.
    • (1997) Biochemistry , vol.36 , pp. 3104-3114
    • Sekar, K.1    Eswaramoorthy, S.2    Jain, M.K.3    Sundaralingam, M.4
  • 42
    • 7544222355 scopus 로고    scopus 로고
    • Harmonic vibrational frequencies: scaling factors for HF, B3LYP, and MP2 methods in combination with correlation consistent basis sets
    • Sinha P., Boesch S.E., Gu C., Wheeler R.A., Wilson A.K. Harmonic vibrational frequencies: scaling factors for HF, B3LYP, and MP2 methods in combination with correlation consistent basis sets. J. Phys. Chem. A. 2004, 108:9213-9217.
    • (2004) J. Phys. Chem. A. , vol.108 , pp. 9213-9217
    • Sinha, P.1    Boesch, S.E.2    Gu, C.3    Wheeler, R.A.4    Wilson, A.K.5
  • 43
    • 1042287118 scopus 로고    scopus 로고
    • Chemical modifications of phospholipases A2 from snake venoms: effects on catalytic and pharmacological properties
    • Soares A.M., Giglio J.R. Chemical modifications of phospholipases A2 from snake venoms: effects on catalytic and pharmacological properties. Toxicon 2003, 42:855-868.
    • (2003) Toxicon , vol.42 , pp. 855-868
    • Soares, A.M.1    Giglio, J.R.2
  • 45
    • 4444225227 scopus 로고    scopus 로고
    • Phospholipases A2 myotoxins from Bothrops snake venoms: structure-function relationship
    • Soares A.M., Fontes M.R.M., Giglio J.R. Phospholipases A2 myotoxins from Bothrops snake venoms: structure-function relationship. Curr. Org. Chem. 2004, 8:1677-1690.
    • (2004) Curr. Org. Chem. , vol.8 , pp. 1677-1690
    • Soares, A.M.1    Fontes, M.R.M.2    Giglio, J.R.3
  • 46
    • 31144458847 scopus 로고    scopus 로고
    • A bromoenol lactone suicide substrate inactivates group via phospholipase A2 by generating a diffiusible bromomethyl keto acid that alkylates cysteine thiols
    • Song H., Ramanadham S., Bao S., Fong-Fu Hsu F.F., Turk J. A bromoenol lactone suicide substrate inactivates group via phospholipase A2 by generating a diffiusible bromomethyl keto acid that alkylates cysteine thiols. Biochemistry 2006, 45:1061-1073.
    • (2006) Biochemistry , vol.45 , pp. 1061-1073
    • Song, H.1    Ramanadham, S.2    Bao, S.3    Fong-Fu Hsu, F.F.4    Turk, J.5
  • 49
    • 20844447289 scopus 로고    scopus 로고
    • Selection of quantum chemical descriptors by chemometric methods in the study of antioxidant activity of flavonoid compounds
    • Weber K.C., Da Silva S.L., Honório K.M., Da Silva A.B.F. Selection of quantum chemical descriptors by chemometric methods in the study of antioxidant activity of flavonoid compounds. Int. J. Quantum. Chem. 2005, 103:731-737.
    • (2005) Int. J. Quantum. Chem. , vol.103 , pp. 731-737
    • Weber, K.C.1    Da Silva, S.L.2    Honório, K.M.3    Da Silva, A.B.F.4
  • 51
    • 33750931768 scopus 로고    scopus 로고
    • Control of phospholipase A2 activities for the treatment of inflammatory conditions
    • Yedgar S., Cohen Y., Shoseyov D. Control of phospholipase A2 activities for the treatment of inflammatory conditions. Biochim. Biophys. Acta. 2006, 1761:1373-1382.
    • (2006) Biochim. Biophys. Acta. , vol.1761 , pp. 1373-1382
    • Yedgar, S.1    Cohen, Y.2    Shoseyov, D.3


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