메뉴 건너뛰기




Volumn 146, Issue 2, 2007, Pages 125-135

Membrane composition modulates the interaction between a new class of antineoplastic agents deriving from aromatic 2-chloroethylureas and lipid bilayers: a solid-state NMR study

Author keywords

Arylchloroethylureas; Cardiolipin; Endoplasmic reticulum; Mitochondria; Model membranes; Solid state NMR spectroscopy

Indexed keywords

1 (2 CHLOROETHYL) 3 (4 CYCLOHEXYLPHENYL)UREA; 1 (2 CHLOROETHYL) 3 (4 HEPTYLPHENYL)UREA; 1 (2 CHLOROETHYL) 3 [3 (HYDROXYPENTYL)PHENYL]UREA; 1 (4 TERT BUTYLPHENYL) 3 (2 CHLOROETHYL)UREA; 1 (4 TERT BUTYLPHENYL) 3 ETHYLUREA; 2 CHLOROETHYLUREA DERIVATIVE; 4 CYCLOPHENYL(4,5 DIHYDROOXAZOL 2 YL)AMINE; 4 HEPTYLPHENYL(4,5 DIHYDROOXAZOL 2 YL)AMINE; ANTINEOPLASTIC AGENT; CARDIOLIPIN; CHOLESTEROL; DEUTERIUM; PHOSPHATIDYLCHOLINE; PHOSPHATIDYLETHANOLAMINE; PHOSPHATIDYLINOSITOL; PHOSPHATIDYLSERINE; PHOSPHOLIPID; PHOSPHORUS 31; SPHINGOMYELIN; UNCLASSIFIED DRUG;

EID: 33847182465     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2007.01.002     Document Type: Article
Times cited : (11)

References (39)
  • 1
    • 0028606719 scopus 로고
    • Synthesis and cytotoxic activity of new alkyl 3-(2-chloroethyl(ureido))benzene derivatives
    • Béchard P., Lacroix J., Poyet P., and C.-Gaudreault R. Synthesis and cytotoxic activity of new alkyl 3-(2-chloroethyl(ureido))benzene derivatives. Eur. J. Med. Chem. 29 (1994) 963-966
    • (1994) Eur. J. Med. Chem. , vol.29 , pp. 963-966
    • Béchard, P.1    Lacroix, J.2    Poyet, P.3    C.-Gaudreault, R.4
  • 5
    • 0023829524 scopus 로고
    • 1-Aryl-3-(2-chloroethyl) ureas: synthesis and in vitro assay as potential anticancer agents
    • C-Gaudreault R., Lacroix J., Pagé M., and Joly L.P. 1-Aryl-3-(2-chloroethyl) ureas: synthesis and in vitro assay as potential anticancer agents. J. Pharm. Sci. 77 (1988) 185-187
    • (1988) J. Pharm. Sci. , vol.77 , pp. 185-187
    • C-Gaudreault, R.1    Lacroix, J.2    Pagé, M.3    Joly, L.P.4
  • 6
    • 0141483378 scopus 로고    scopus 로고
    • Cholesterol impair the adenine nucleotide translocator-mediated mitochondrial permeability transition through altered membrane fluidity
    • 928-933, 935
    • Colell A., Garcia-Ruiz C., Lluis J.M., Coll O., Mari M., and Fernandez-Checa J.C. Cholesterol impair the adenine nucleotide translocator-mediated mitochondrial permeability transition through altered membrane fluidity. J. Biol. Chem. 278 33 (2003) 928-933, 935
    • (2003) J. Biol. Chem. , vol.278 , Issue.33
    • Colell, A.1    Garcia-Ruiz, C.2    Lluis, J.M.3    Coll, O.4    Mari, M.5    Fernandez-Checa, J.C.6
  • 7
    • 0842345400 scopus 로고    scopus 로고
    • VDAC: the channel at the interface between mitochondria and the cytosol
    • Colombini M. VDAC: the channel at the interface between mitochondria and the cytosol. Mol. Cell. Biochem. 256/257 (2004) 107-115
    • (2004) Mol. Cell. Biochem. , vol.256-257 , pp. 107-115
    • Colombini, M.1
  • 8
    • 0018797519 scopus 로고
    • Lipid polymorphism and the functional roles of lipids in biological membranes
    • Cullis P.R., and de Kruijff B. Lipid polymorphism and the functional roles of lipids in biological membranes. Biochim. Biophys. Acta 559 (1979) 339-420
    • (1979) Biochim. Biophys. Acta , vol.559 , pp. 339-420
    • Cullis, P.R.1    de Kruijff, B.2
  • 9
    • 0018510430 scopus 로고
    • Deuterium magnetic resonance study of the gel and liquid crystalline phases of dipalmitoyl phosphatidylcholine
    • Davis J.H. Deuterium magnetic resonance study of the gel and liquid crystalline phases of dipalmitoyl phosphatidylcholine. Biophys. J. 27 (1979) 339-358
    • (1979) Biophys. J. , vol.27 , pp. 339-358
    • Davis, J.H.1
  • 10
    • 0000745176 scopus 로고
    • Quadrupolar echo deuteron magnetic resonance spectrsocopy in ordered hydrocarbon chains
    • Davis J.H., Jeffrey K.R., Bloom M., and Valic M.I. Quadrupolar echo deuteron magnetic resonance spectrsocopy in ordered hydrocarbon chains. Chem. Phys. Lett. 42 (1976) 390-394
    • (1976) Chem. Phys. Lett. , vol.42 , pp. 390-394
    • Davis, J.H.1    Jeffrey, K.R.2    Bloom, M.3    Valic, M.I.4
  • 11
    • 0030588176 scopus 로고    scopus 로고
    • Interaction of 4-tert- butyl- 3-(2-chloroethyl) ureido benzene with phosphatidylcholine bilayers: a differential scanning calorimetry and infrared spectroscopy study
    • Gicquaud C., Auger M., Wong P.T.T., Poyet P., Boudreau N., and C.-Gaudreault R. Interaction of 4-tert- butyl- 3-(2-chloroethyl) ureido benzene with phosphatidylcholine bilayers: a differential scanning calorimetry and infrared spectroscopy study. Arch. Biochem. Biophys. 334 (1996) 193-199
    • (1996) Arch. Biochem. Biophys. , vol.334 , pp. 193-199
    • Gicquaud, C.1    Auger, M.2    Wong, P.T.T.3    Poyet, P.4    Boudreau, N.5    C.-Gaudreault, R.6
  • 15
    • 0000516361 scopus 로고
    • Deuterium isotope effect on the stability of molecules: phospholipids
    • Guard-Friar D., Chen C.-H., and Engle A.S. Deuterium isotope effect on the stability of molecules: phospholipids. J. Phys. Chem. 89 (1985) 1810-1813
    • (1985) J. Phys. Chem. , vol.89 , pp. 1810-1813
    • Guard-Friar, D.1    Chen, C.-H.2    Engle, A.S.3
  • 16
    • 33749622370 scopus 로고
    • Spin echoes
    • Hahn E.L. Spin echoes. Phys. Rev. 80 (1950) 580-594
    • (1950) Phys. Rev. , vol.80 , pp. 580-594
    • Hahn, E.L.1
  • 17
    • 0019391603 scopus 로고
    • Interaction of the alkylating antitumor agent 2,3,5-tris(ethyleneimino)benzoquinone with the plasma membrane of Ehrlich ascites tumor cells
    • Ihlenfeldt M., Gantner G., Harrer M., Puschendorf B., Putzer H., and Grunicke H. Interaction of the alkylating antitumor agent 2,3,5-tris(ethyleneimino)benzoquinone with the plasma membrane of Ehrlich ascites tumor cells. Cancer Res. 41 (1981) 289-293
    • (1981) Cancer Res. , vol.41 , pp. 289-293
    • Ihlenfeldt, M.1    Gantner, G.2    Harrer, M.3    Puschendorf, B.4    Putzer, H.5    Grunicke, H.6
  • 18
    • 33749859921 scopus 로고    scopus 로고
    • Induction of a apoptosis by YTX in myoblast cell lines via mitochondrial signalling transduction pathway
    • Korsnes M.S., Hetland D.L., Espenes A., and Aune T. Induction of a apoptosis by YTX in myoblast cell lines via mitochondrial signalling transduction pathway. Toxicol. in Vitro 20 (2006) 1419-1426
    • (2006) Toxicol. in Vitro , vol.20 , pp. 1419-1426
    • Korsnes, M.S.1    Hetland, D.L.2    Espenes, A.3    Aune, T.4
  • 19
    • 0023795327 scopus 로고
    • In vitro and in vivo activity of 1-aryl-3-(2-chloroethyl) ureas derivatives as new antineoplastic agents
    • Lacroix J., C.-Gaudreault R., Pagé M., and Joly L.P. In vitro and in vivo activity of 1-aryl-3-(2-chloroethyl) ureas derivatives as new antineoplastic agents. Anticancer Res. 8 (1988) 595-598
    • (1988) Anticancer Res. , vol.8 , pp. 595-598
    • Lacroix, J.1    C.-Gaudreault, R.2    Pagé, M.3    Joly, L.P.4
  • 20
    • 0037009030 scopus 로고    scopus 로고
    • Solid-state NMR spectroscopic methods in chemistry
    • Laws D.D.L., Bitter H.M., and Jerschow A. Solid-state NMR spectroscopic methods in chemistry. Angew. Chem. Int. Ed. 41 (2002) 3096-3129
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 3096-3129
    • Laws, D.D.L.1    Bitter, H.M.2    Jerschow, A.3
  • 21
    • 0034652719 scopus 로고    scopus 로고
    • Microtubule disruption induced in vivo by alkylation of β-tubulin by 1-aryl-3-(2-chloroethyl)ureas, a novel class of soft alkylating agents
    • Legault J., Gaulin J.-F., Mounetou E., Bolduc S., Lacroix J., Poyet P., and C.-Gaudreault R. Microtubule disruption induced in vivo by alkylation of β-tubulin by 1-aryl-3-(2-chloroethyl)ureas, a novel class of soft alkylating agents. Cancer Res. 60 (2000) 985-992
    • (2000) Cancer Res. , vol.60 , pp. 985-992
    • Legault, J.1    Gaulin, J.-F.2    Mounetou, E.3    Bolduc, S.4    Lacroix, J.5    Poyet, P.6    C.-Gaudreault, R.7
  • 22
    • 0031024171 scopus 로고    scopus 로고
    • Experimental and computational approaches to estimate solubility and permeability in drug discovery and development setting
    • Lipinski C.A., Lombardo F., Dominy B.W., and Feeney P.J. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development setting. Adv. Drug Delivery Rev. 23 (1997) 3-25
    • (1997) Adv. Drug Delivery Rev. , vol.23 , pp. 3-25
    • Lipinski, C.A.1    Lombardo, F.2    Dominy, B.W.3    Feeney, P.J.4
  • 23
    • 0024918105 scopus 로고
    • Tubulin synthesis, structure, function: what are the relationship?
    • MacRae T.H., and Langdon C.M. Tubulin synthesis, structure, function: what are the relationship?. Biochem. Cell Biol. 67 (1989) 770-790
    • (1989) Biochem. Cell Biol. , vol.67 , pp. 770-790
    • MacRae, T.H.1    Langdon, C.M.2
  • 24
    • 0031916782 scopus 로고    scopus 로고
    • Disposition and metabolism of a novel antineoplastic agent, 4-tert-butyl-3-(2-chloroethyl) ureido] benzene, in mice
    • Maurizis J.-C., Rapp M., Azim E.M., C.-Gaudreault R., Veyre A., and Madelmont J.-C. Disposition and metabolism of a novel antineoplastic agent, 4-tert-butyl-3-(2-chloroethyl) ureido] benzene, in mice. Drug Metab. Dispos. 26 (1998) 146-151
    • (1998) Drug Metab. Dispos. , vol.26 , pp. 146-151
    • Maurizis, J.-C.1    Rapp, M.2    Azim, E.M.3    C.-Gaudreault, R.4    Veyre, A.5    Madelmont, J.-C.6
  • 25
    • 0035282634 scopus 로고    scopus 로고
    • Antimiotic antitumor agents: synthesis, structure-activity relationships, and biological characterization of n-aryl-n-(2-chloroethyl)ureas as new selective alkylating agents
    • Mounetou E., Legault J., Lacroix J., and C.-Gaudreault R. Antimiotic antitumor agents: synthesis, structure-activity relationships, and biological characterization of n-aryl-n-(2-chloroethyl)ureas as new selective alkylating agents. J. Med. Chem. 44 (2001) 694-702
    • (2001) J. Med. Chem. , vol.44 , pp. 694-702
    • Mounetou, E.1    Legault, J.2    Lacroix, J.3    C.-Gaudreault, R.4
  • 26
    • 0242267903 scopus 로고    scopus 로고
    • Antimiotic antitumor agents: a new generation of n-aryl-n-(1-alkyl-2-chloroethyl)ureas as microtubule disruptors: synthesis, antiproliferative activity, and β-tubulin alkylation
    • Mounetou E., Legault J., Lacroix J., and C.-Gaudreault R. Antimiotic antitumor agents: a new generation of n-aryl-n-(1-alkyl-2-chloroethyl)ureas as microtubule disruptors: synthesis, antiproliferative activity, and β-tubulin alkylation. J. Med. Chem. 46 (2003) 5055-5063
    • (2003) J. Med. Chem. , vol.46 , pp. 5055-5063
    • Mounetou, E.1    Legault, J.2    Lacroix, J.3    C.-Gaudreault, R.4
  • 28
    • 0027358651 scopus 로고
    • Effect of an aryl chloroethyl ureas on tubulin and vimentin syntheses in human breast cancer cell line
    • Poyet P., Ritchot N., Béchard P., and C.-Gaudreault R. Effect of an aryl chloroethyl ureas on tubulin and vimentin syntheses in human breast cancer cell line. Anticancer Res. 13 (1993) 1447-1452
    • (1993) Anticancer Res. , vol.13 , pp. 1447-1452
    • Poyet, P.1    Ritchot, N.2    Béchard, P.3    C.-Gaudreault, R.4
  • 30
    • 0034926843 scopus 로고    scopus 로고
    • Membrane interactions of a new class of anticancer agents derived from arylchloroethylurea: a FTIR spectroscopic study
    • Saint-Laurent A., Boudreau N., Larivière D., Legault J., C.-Gaudreault R., and Auger M. Membrane interactions of a new class of anticancer agents derived from arylchloroethylurea: a FTIR spectroscopic study. Chem. Phys. Lipids 111 (2001) 163-175
    • (2001) Chem. Phys. Lipids , vol.111 , pp. 163-175
    • Saint-Laurent, A.1    Boudreau, N.2    Larivière, D.3    Legault, J.4    C.-Gaudreault, R.5    Auger, M.6
  • 31
    • 0017752553 scopus 로고
    • Deuterium magnetic resonance: theory and application to lipid membranes
    • Seelig J. Deuterium magnetic resonance: theory and application to lipid membranes. Q. Rev. Biophys. 10 (1977) 353-418
    • (1977) Q. Rev. Biophys. , vol.10 , pp. 353-418
    • Seelig, J.1
  • 32
    • 0017902280 scopus 로고
    • 31P nuclear magnetic resonance and the head group structure of phospholipids in membranes
    • 31P nuclear magnetic resonance and the head group structure of phospholipids in membranes. Biochim. Biophys. Acta 515 (1978) 105-140
    • (1978) Biochim. Biophys. Acta , vol.515 , pp. 105-140
    • Seelig, J.1
  • 33
    • 0018982584 scopus 로고
    • Lipid conformation in model membrane and biological membranes
    • Seelig J., and Seelig A. Lipid conformation in model membrane and biological membranes. Q. Rev. Biophys. 13 (1980) 19-61
    • (1980) Q. Rev. Biophys. , vol.13 , pp. 19-61
    • Seelig, J.1    Seelig, A.2
  • 34
    • 84940938972 scopus 로고
    • Phosphorus-31 NMR of phospholipids in membranes
    • Gorenstein D.G. (Ed), Academic Press, London
    • Smith I.C.P., and Ekiel I.H. Phosphorus-31 NMR of phospholipids in membranes. In: Gorenstein D.G. (Ed). In Phosphorus-31 NMR: Principles and Applications (1984), Academic Press, London 447-475
    • (1984) In Phosphorus-31 NMR: Principles and Applications , pp. 447-475
    • Smith, I.C.P.1    Ekiel, I.H.2
  • 36
    • 7044232102 scopus 로고    scopus 로고
    • Nonbilayer lipids affect peripheral and integral membrane proteins via changes in the lateral pressure profile
    • van den Brink-van der Laan E., Killian J.A., and de Kruijff B. Nonbilayer lipids affect peripheral and integral membrane proteins via changes in the lateral pressure profile. Biochim. Biophys. Acta 1666 (2004) 275-288
    • (2004) Biochim. Biophys. Acta , vol.1666 , pp. 275-288
    • van den Brink-van der Laan, E.1    Killian, J.A.2    de Kruijff, B.3
  • 38
    • 0032071355 scopus 로고    scopus 로고
    • Solid-state NMR for the study of membrane systems: the use of anisotropic interactions
    • Warschawski D.E., Traikia M., Devaux P.F., and Bodenhausen G. Solid-state NMR for the study of membrane systems: the use of anisotropic interactions. Biochimie 80 (1998) 437-450
    • (1998) Biochimie , vol.80 , pp. 437-450
    • Warschawski, D.E.1    Traikia, M.2    Devaux, P.F.3    Bodenhausen, G.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.