메뉴 건너뛰기




Volumn 431, Issue 4, 2013, Pages 680-685

Lipophilicity of flavonoid complexes with iron(II) and their interaction with liposomes

Author keywords

Flavonoids; Iron chelators; Lipid phase transitions; Liposomes; Quercetin; Taxifolin

Indexed keywords

FERROUS ION; LIPOSOME; PHOSPHATIDYLETHANOLAMINE; QUERCETIN; TAXIFOLIN;

EID: 84875253240     PISSN: 0006291X     EISSN: 10902104     Source Type: Journal    
DOI: 10.1016/j.bbrc.2013.01.060     Document Type: Article
Times cited : (28)

References (43)
  • 1
    • 77952743304 scopus 로고    scopus 로고
    • Flavonoids and age-related disease: risk, benefits and critical windows
    • Prasain J.K., Carlson S.H., Wyss J.M. Flavonoids and age-related disease: risk, benefits and critical windows. Maturitas 2010, 66:163-171.
    • (2010) Maturitas , vol.66 , pp. 163-171
    • Prasain, J.K.1    Carlson, S.H.2    Wyss, J.M.3
  • 2
    • 36048962099 scopus 로고    scopus 로고
    • Investigation of metal-flavonoid chelates and the determination of flavonoids via metal-flavonoid complexing reactions
    • Malesev D., Kuntic V. Investigation of metal-flavonoid chelates and the determination of flavonoids via metal-flavonoid complexing reactions. J. Serb. Chem. Soc. 2007, 72:921-939.
    • (2007) J. Serb. Chem. Soc. , vol.72 , pp. 921-939
    • Malesev, D.1    Kuntic, V.2
  • 3
    • 34547618062 scopus 로고    scopus 로고
    • Synthesis and characterization of a metal complex containing naringin and Cu, and its antioxidant, antimicrobial antiinflammatory and tumor cell cytotoxicity
    • Pereira R.M., Andrades N.E., Paulino N., Sawaya A.C., Eberlin M.N., Marcucci M.C., Favero G.M., Novak E.M., Bydlowski S.P. Synthesis and characterization of a metal complex containing naringin and Cu, and its antioxidant, antimicrobial antiinflammatory and tumor cell cytotoxicity. Molecules 2007, 12:1352-1366.
    • (2007) Molecules , vol.12 , pp. 1352-1366
    • Pereira, R.M.1    Andrades, N.E.2    Paulino, N.3    Sawaya, A.C.4    Eberlin, M.N.5    Marcucci, M.C.6    Favero, G.M.7    Novak, E.M.8    Bydlowski, S.P.9
  • 4
    • 39849109530 scopus 로고    scopus 로고
    • Complexation of flavonoids with iron: structure and optical signatures
    • Ren J., Meng S., Lekka C., Kaxiras E. Complexation of flavonoids with iron: structure and optical signatures. J. Phys. Chem. B 2008, 112:1845-1850.
    • (2008) J. Phys. Chem. B , vol.112 , pp. 1845-1850
    • Ren, J.1    Meng, S.2    Lekka, C.3    Kaxiras, E.4
  • 6
    • 79959214007 scopus 로고    scopus 로고
    • Lipid peroxidation of poly-unsaturated fatty acids in normal and obese adipose tissues
    • Cohen G., Riahi Y., Sasson S. Lipid peroxidation of poly-unsaturated fatty acids in normal and obese adipose tissues. Arch. Physiol. Biochem. 2011, 117:131-139.
    • (2011) Arch. Physiol. Biochem. , vol.117 , pp. 131-139
    • Cohen, G.1    Riahi, Y.2    Sasson, S.3
  • 8
    • 14544278461 scopus 로고    scopus 로고
    • Recent methodologies for the estimation of n-octanol/water partition coefficients and their use in the prediction of membrane transport properties of drugs
    • Klopman G., Zhu H. Recent methodologies for the estimation of n-octanol/water partition coefficients and their use in the prediction of membrane transport properties of drugs. Mini-Rev. Med. Chem. 2005, 5:127-133.
    • (2005) Mini-Rev. Med. Chem. , vol.5 , pp. 127-133
    • Klopman, G.1    Zhu, H.2
  • 9
    • 84862829086 scopus 로고
    • Calcium-dependent aggregation and fusion of phosphatidylcholine liposomes induced by complexes of flavonoids with divalent iron
    • Tarahovsky Y.S., Yagolnik E.A., Muzafarov E.N., Abdrasilov B.S., Kim Y.A. Calcium-dependent aggregation and fusion of phosphatidylcholine liposomes induced by complexes of flavonoids with divalent iron. Biochim. Biophys. Acta 1818, 2012:695-702.
    • (1818) Biochim. Biophys. Acta , vol.2012 , pp. 695-702
    • Tarahovsky, Y.S.1    Yagolnik, E.A.2    Muzafarov, E.N.3    Abdrasilov, B.S.4    Kim, Y.A.5
  • 10
    • 33749000228 scopus 로고
    • New substituent constant, r{cyrillic}, derived from partition coefficients
    • Fujita T., Iwasa J., Hansch C.A. New substituent constant, r{cyrillic}, derived from partition coefficients. J. Am. Chem. Soc. 1964, 86:5175-5180.
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 5175-5180
    • Fujita, T.1    Iwasa, J.2    Hansch, C.A.3
  • 12
    • 67649939018 scopus 로고    scopus 로고
    • The lipophilicity indices of flavonoids estimated by reversed-phase liquid chromatography using different computation methods
    • Briciu R.D., Kot-Wasik A., Namiesnik J., Sarbu C. The lipophilicity indices of flavonoids estimated by reversed-phase liquid chromatography using different computation methods. J. Sep. Sci. 2009, 32:2066-2074.
    • (2009) J. Sep. Sci. , vol.32 , pp. 2066-2074
    • Briciu, R.D.1    Kot-Wasik, A.2    Namiesnik, J.3    Sarbu, C.4
  • 14
    • 0001759538 scopus 로고    scopus 로고
    • Flavonoids, coumarins, and cinnamic acids as antioxidants in a micellar system. Structure-activity relationship
    • Foti M., Piattelli M., Baratta M.N., Ruberto G. Flavonoids, coumarins, and cinnamic acids as antioxidants in a micellar system. Structure-activity relationship. J. Agric. Food Chem. 1996, 44:497-501.
    • (1996) J. Agric. Food Chem. , vol.44 , pp. 497-501
    • Foti, M.1    Piattelli, M.2    Baratta, M.N.3    Ruberto, G.4
  • 15
    • 28744436977 scopus 로고    scopus 로고
    • Structure-activity relationships of the inhibitory effects of flavonoids on P-glycoprotein-mediated transport in KB-C2 cells
    • Kitagawa S., Nabekura T., Takahashi T., Nakamura Y., Sakamoto H., Tano H., Hirai M., Tsukahara G. Structure-activity relationships of the inhibitory effects of flavonoids on P-glycoprotein-mediated transport in KB-C2 cells. Biol. Pharm. Bull. 2005, 28:2274-2278.
    • (2005) Biol. Pharm. Bull. , vol.28 , pp. 2274-2278
    • Kitagawa, S.1    Nabekura, T.2    Takahashi, T.3    Nakamura, Y.4    Sakamoto, H.5    Tano, H.6    Hirai, M.7    Tsukahara, G.8
  • 16
    • 20744444385 scopus 로고    scopus 로고
    • Experimental determination of octanol-water partition coefficients of quercetin and related flavonoids
    • Rothwell J.A., Day A.J., Morgan M.R. Experimental determination of octanol-water partition coefficients of quercetin and related flavonoids. J. Agric. Food Chem. 2005, 53:4355-4360.
    • (2005) J. Agric. Food Chem. , vol.53 , pp. 4355-4360
    • Rothwell, J.A.1    Day, A.J.2    Morgan, M.R.3
  • 17
    • 53649093981 scopus 로고    scopus 로고
    • Structure-activity relationships of flavonoids in the cellular antioxidant activity assay
    • Wolfe K.L., Liu R.H. Structure-activity relationships of flavonoids in the cellular antioxidant activity assay. J. Agric. Food Chem. 2008, 56:8404-8411.
    • (2008) J. Agric. Food Chem. , vol.56 , pp. 8404-8411
    • Wolfe, K.L.1    Liu, R.H.2
  • 18
    • 85022000280 scopus 로고    scopus 로고
    • Spectroscopic techniques applied to flavonoids
    • CRC Press, New York, O.M. Andersen, K.R. Markham (Eds.)
    • Fossen T., Andersen O.M. Spectroscopic techniques applied to flavonoids. Flavonoids: Chemistry, Biochemistry and Applications 2006, 37-142. CRC Press, New York. O.M. Andersen, K.R. Markham (Eds.).
    • (2006) Flavonoids: Chemistry, Biochemistry and Applications , pp. 37-142
    • Fossen, T.1    Andersen, O.M.2
  • 19
    • 84858267405 scopus 로고    scopus 로고
    • Quercetin-phospholipid complex: an amorphous pharmaceutical system in herbal drug delivery
    • Singh D., Rawat M.S., Semalty A., Semalty M. Quercetin-phospholipid complex: an amorphous pharmaceutical system in herbal drug delivery. Curr. Drug Discov. Technol. 2012, 9:17-24.
    • (2012) Curr. Drug Discov. Technol. , vol.9 , pp. 17-24
    • Singh, D.1    Rawat, M.S.2    Semalty, A.3    Semalty, M.4
  • 20
    • 5644262626 scopus 로고    scopus 로고
    • Encapsulation of naturally occurring flavonoids into liposomes: physicochemical properties and biological activity against human cancer cell lines
    • Goniotaki M., Hatziantoniou S., Dimas K., Wagner M., Demetzos C. Encapsulation of naturally occurring flavonoids into liposomes: physicochemical properties and biological activity against human cancer cell lines. J. Pharm. Pharmacol. 2004, 56:1217-1224.
    • (2004) J. Pharm. Pharmacol. , vol.56 , pp. 1217-1224
    • Goniotaki, M.1    Hatziantoniou, S.2    Dimas, K.3    Wagner, M.4    Demetzos, C.5
  • 23
    • 0037443719 scopus 로고    scopus 로고
    • The relationship between the antioxidant and the antibacterial properties of galloylated catechins and the structure of phospholipid model membranes
    • Caturla N., Vera-Samper E., Villalain J., Mateo C.R., Micol V. The relationship between the antioxidant and the antibacterial properties of galloylated catechins and the structure of phospholipid model membranes. Free Radic. Biol. Med. 2003, 34:648-662.
    • (2003) Free Radic. Biol. Med. , vol.34 , pp. 648-662
    • Caturla, N.1    Vera-Samper, E.2    Villalain, J.3    Mateo, C.R.4    Micol, V.5
  • 24
    • 45449107377 scopus 로고    scopus 로고
    • Rafts making and rafts braking: how plant flavonoids may control membrane heterogeneity
    • Tarahovsky Y.S., Muzafarov E.N., Kim Y.A. Rafts making and rafts braking: how plant flavonoids may control membrane heterogeneity. Mol. Cell Biochem. 2008, 314:65-71.
    • (2008) Mol. Cell Biochem. , vol.314 , pp. 65-71
    • Tarahovsky, Y.S.1    Muzafarov, E.N.2    Kim, Y.A.3
  • 25
    • 0036429444 scopus 로고    scopus 로고
    • Total iron binding capacity and transferrin concentration in the assessment of iron status
    • Kasvosve I., Delanghe J. Total iron binding capacity and transferrin concentration in the assessment of iron status. Clin. Chem. Lab. Med. 2002, 40:1014-1018.
    • (2002) Clin. Chem. Lab. Med. , vol.40 , pp. 1014-1018
    • Kasvosve, I.1    Delanghe, J.2
  • 26
    • 45049085738 scopus 로고    scopus 로고
    • Conformational and hydrational properties during the L(beta)- to L(alpha)- and L(alpha)- to H(II)-phase transition in phosphatidylethanolamine
    • Rappolt M., Hodzic A., Sartori B., Ollivon M., Laggner P. Conformational and hydrational properties during the L(beta)- to L(alpha)- and L(alpha)- to H(II)-phase transition in phosphatidylethanolamine. Chem. Phys. Lipids 2008, 154:46-55.
    • (2008) Chem. Phys. Lipids , vol.154 , pp. 46-55
    • Rappolt, M.1    Hodzic, A.2    Sartori, B.3    Ollivon, M.4    Laggner, P.5
  • 27
    • 0020359862 scopus 로고
    • Morphology of the intermediate stages in the lamellar to hexagonal lipid phase transition
    • Borovjagin V.L., Vergara J.A., McIntosh T.J. Morphology of the intermediate stages in the lamellar to hexagonal lipid phase transition. J. Membr. Biol. 1982, 69:199-212.
    • (1982) J. Membr. Biol. , vol.69 , pp. 199-212
    • Borovjagin, V.L.1    Vergara, J.A.2    McIntosh, T.J.3
  • 28
    • 77955522494 scopus 로고    scopus 로고
    • " Smart" liposomal nanocontainers in biology and medicine
    • Tarahovsky Y.S. " Smart" liposomal nanocontainers in biology and medicine. Biochemistry (Moscow) 2010, 75:811-824.
    • (2010) Biochemistry (Moscow) , vol.75 , pp. 811-824
    • Tarahovsky, Y.S.1
  • 29
    • 74849127501 scopus 로고    scopus 로고
    • Cell transfection by DNA-lipid complexes-lipoplexes
    • Tarahovsky Y.S. Cell transfection by DNA-lipid complexes-lipoplexes. Biochemistry (Moscow) 2009, 74:1293-1304.
    • (2009) Biochemistry (Moscow) , vol.74 , pp. 1293-1304
    • Tarahovsky, Y.S.1
  • 30
    • 78549261367 scopus 로고    scopus 로고
    • Comparative pharmacokinetics and bioavailability studies of quercetin, kaempferol and isorhamnetin after oral administration of Ginkgo biloba extracts, Ginkgo biloba extract phospholipid complexes and Ginkgo biloba extract solid dispersions in rats
    • Chen Z.P., Sun J., Chen H.X., Xiao Y.Y., Liu D., Chen J., Cai H., Cai B.C. Comparative pharmacokinetics and bioavailability studies of quercetin, kaempferol and isorhamnetin after oral administration of Ginkgo biloba extracts, Ginkgo biloba extract phospholipid complexes and Ginkgo biloba extract solid dispersions in rats. Fitoterapia 2010, 81:1045-1052.
    • (2010) Fitoterapia , vol.81 , pp. 1045-1052
    • Chen, Z.P.1    Sun, J.2    Chen, H.X.3    Xiao, Y.Y.4    Liu, D.5    Chen, J.6    Cai, H.7    Cai, B.C.8
  • 31
    • 0032554621 scopus 로고    scopus 로고
    • Synergistic effects of diacylglycerols and fatty acids on membrane structure and protein kinase C activity
    • Goldberg E.M., Zidovetzki R. Synergistic effects of diacylglycerols and fatty acids on membrane structure and protein kinase C activity. Biochemistry 1998, 37:5623-5632.
    • (1998) Biochemistry , vol.37 , pp. 5623-5632
    • Goldberg, E.M.1    Zidovetzki, R.2
  • 34
    • 79751528958 scopus 로고    scopus 로고
    • Genistein enhances relaxation of the spontaneously hypertensive rat aorta by transactivation of epidermal growth factor receptor following binding to membrane estrogen receptors-alpha and activation of a G protein-coupled, endothelial nitric oxide synthase-dependent pathway
    • Lin A.H., Leung G.P., Leung S.W., Vanhoutte P.M., Man R.Y. Genistein enhances relaxation of the spontaneously hypertensive rat aorta by transactivation of epidermal growth factor receptor following binding to membrane estrogen receptors-alpha and activation of a G protein-coupled, endothelial nitric oxide synthase-dependent pathway. Pharmacol. Res. 2011, 63:181-189.
    • (2011) Pharmacol. Res. , vol.63 , pp. 181-189
    • Lin, A.H.1    Leung, G.P.2    Leung, S.W.3    Vanhoutte, P.M.4    Man, R.Y.5
  • 35
    • 56949101468 scopus 로고    scopus 로고
    • PCR differential display-based identification of regulator of G protein signaling 10 as the target gene in human colon cancer cells induced by black tea polyphenol theaflavin monogallate
    • Lu J., Gosslau A., Liu A.Y., Chen K.Y. PCR differential display-based identification of regulator of G protein signaling 10 as the target gene in human colon cancer cells induced by black tea polyphenol theaflavin monogallate. Eur. J. Pharmacol. 2008, 601:66-72.
    • (2008) Eur. J. Pharmacol. , vol.601 , pp. 66-72
    • Lu, J.1    Gosslau, A.2    Liu, A.Y.3    Chen, K.Y.4
  • 36
  • 37
    • 11144354419 scopus 로고    scopus 로고
    • The hippocampal cholinergic neurostimulating peptide, the N-terminal fragment of the secreted phosphatidylethanolamine-binding protein, possesses a new biological activity on cardiac physiology
    • Goumon Y., Angelone T., Schoentgen F., Chasserot-Golaz S., Almas B., Fukami M.M., Langley K., Welters I.D., Tota B., Aunis D., Metz-Boutigue M.H. The hippocampal cholinergic neurostimulating peptide, the N-terminal fragment of the secreted phosphatidylethanolamine-binding protein, possesses a new biological activity on cardiac physiology. J. Biol. Chem. 2004, 279:13054-13064.
    • (2004) J. Biol. Chem. , vol.279 , pp. 13054-13064
    • Goumon, Y.1    Angelone, T.2    Schoentgen, F.3    Chasserot-Golaz, S.4    Almas, B.5    Fukami, M.M.6    Langley, K.7    Welters, I.D.8    Tota, B.9    Aunis, D.10    Metz-Boutigue, M.H.11
  • 38
    • 79960016323 scopus 로고    scopus 로고
    • Beta-N-oxalyl-L-alpha, beta-diaminopropionic acid regulates mitogen-activated protein kinase signaling by down-regulation of phosphatidylethanolamine-binding protein 1
    • Jammulamadaka N., Burgula S., Medisetty R., Ilavazhagan G., Rao S.L., Singh S.S. beta-N-oxalyl-L-alpha, beta-diaminopropionic acid regulates mitogen-activated protein kinase signaling by down-regulation of phosphatidylethanolamine-binding protein 1. J. Neurochem. 2011, 118:176-186.
    • (2011) J. Neurochem. , vol.118 , pp. 176-186
    • Jammulamadaka, N.1    Burgula, S.2    Medisetty, R.3    Ilavazhagan, G.4    Rao, S.L.5    Singh, S.S.6
  • 40
    • 36248976248 scopus 로고    scopus 로고
    • Promotion of cellular migration and apoptosis resistance by a mouse eye-specific phosphatidylethanolamine-binding protein
    • Zhang Y., Wang X., Xiang Z., Li H., Qiu J., Sun Q., Wan T., Li N., Cao X., Wang J. Promotion of cellular migration and apoptosis resistance by a mouse eye-specific phosphatidylethanolamine-binding protein. Int. J. Mol. Med. 2007, 19:55-63.
    • (2007) Int. J. Mol. Med. , vol.19 , pp. 55-63
    • Zhang, Y.1    Wang, X.2    Xiang, Z.3    Li, H.4    Qiu, J.5    Sun, Q.6    Wan, T.7    Li, N.8    Cao, X.9    Wang, J.10
  • 41
    • 8544229212 scopus 로고    scopus 로고
    • A novel human phosphatidylethanolamine-binding protein resists tumor necrosis factor alpha-induced apoptosis by inhibiting mitogen-activated protein kinase pathway activation and phosphatidylethanolamine externalization
    • Wang X., Li N., Liu B., Sun H., Chen T., Li H., Qiu J., Zhang L., Wan T., Cao X. A novel human phosphatidylethanolamine-binding protein resists tumor necrosis factor alpha-induced apoptosis by inhibiting mitogen-activated protein kinase pathway activation and phosphatidylethanolamine externalization. J. Biol. Chem. 2004, 279:45855-45864.
    • (2004) J. Biol. Chem. , vol.279 , pp. 45855-45864
    • Wang, X.1    Li, N.2    Liu, B.3    Sun, H.4    Chen, T.5    Li, H.6    Qiu, J.7    Zhang, L.8    Wan, T.9    Cao, X.10
  • 42
    • 68349091429 scopus 로고    scopus 로고
    • Unraveling the protective effect of a Drosophila phosphatidylethanolamine-binding protein upon bacterial infection by means of proteomics
    • Reumer A., Bogaerts A., Van Loy T., Husson S.J., Temmerman L., Choi C., Clynen E., Hassan B., Schoofs L. Unraveling the protective effect of a Drosophila phosphatidylethanolamine-binding protein upon bacterial infection by means of proteomics. Dev. Comp. Immunol. 2009, 33:1186-1195.
    • (2009) Dev. Comp. Immunol. , vol.33 , pp. 1186-1195
    • Reumer, A.1    Bogaerts, A.2    Van Loy, T.3    Husson, S.J.4    Temmerman, L.5    Choi, C.6    Clynen, E.7    Hassan, B.8    Schoofs, L.9
  • 43
    • 33344471456 scopus 로고    scopus 로고
    • Decreased phosphatidylethanolamine binding protein expression correlates with Abeta accumulation in the Tg2576 mouse model of Alzheimer's disease
    • George A.J., Holsinger R.M., McLean C.A., Tan S.S., Scott H.S., Cardamone T., Cappai R., Masters C.L., Li Q.X. Decreased phosphatidylethanolamine binding protein expression correlates with Abeta accumulation in the Tg2576 mouse model of Alzheimer's disease. Neurobiol. Aging 2006, 27:614-623.
    • (2006) Neurobiol. Aging , vol.27 , pp. 614-623
    • George, A.J.1    Holsinger, R.M.2    McLean, C.A.3    Tan, S.S.4    Scott, H.S.5    Cardamone, T.6    Cappai, R.7    Masters, C.L.8    Li, Q.X.9


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.