메뉴 건너뛰기




Volumn 150, Issue 2, 2011, Pages 165-171

Effects of alkyl chain length of gallate on self-association and membrane binding

Author keywords

alkyl gallate; lipid membrane; partition constant; self association; solubility

Indexed keywords

DODECYL GALLATE; GALLIC ACID BUTYL ESTER; GALLIC ACID CETYL ESTER; GALLIC ACID DERIVATIVE; GALLIC ACID OCTYL ESTER; GALLIC ACID PROPYL ESTER; STEARYL GALLATE; UNCLASSIFIED DRUG;

EID: 79961048691     PISSN: 0021924X     EISSN: 17562651     Source Type: Journal    
DOI: 10.1093/jb/mvr048     Document Type: Article
Times cited : (37)

References (46)
  • 1
    • 11144262700 scopus 로고    scopus 로고
    • The antiproliferative activity of prodelphinidin B-2 3′-O-gallate from green tea leaf is through cell cycle arrest and Fas-mediated apoptotic pathway in A549 cells
    • DOI 10.1016/j.fct.2004.11.002, PII S0278691504003266
    • Kuo, P.L., Hsu, Y.L., Lin, T.C., and Lin, C.C. (2005) The antiproliferative activity of prodelphinidin B-2 3'- O-gallate from green tea leaf is through cell cycle arrest and Fas-mediated apoptotic pathway in A549 cells. Food Chem. Toxicol. 43, 315-323 (Pubitemid 40037950)
    • (2005) Food and Chemical Toxicology , vol.43 , Issue.2 , pp. 315-323
    • Kuo, P.L.1    Hsu, Y.L.2    Lin, T.C.3    Lin, C.C.4
  • 2
    • 0031444312 scopus 로고    scopus 로고
    • Green tea constituent epigallocatechin-3-gallate and induction of apoptosis and cell cycle arrest in human carcinoma cells
    • Ahmad, N., Feyes, D.K., Nieminen, A.L., Agarwal, R., and Mukhtar, H. (1997) Green tea constituent epigallocatechin-3-gallate and induction of apoptosis and cell cycle arrest in human carcinoma cells. J. Natl Cancer Inst. 89, 1881-1886 (Pubitemid 28009824)
    • (1997) Journal of the National Cancer Institute , vol.89 , Issue.24 , pp. 1881-1886
    • Ahmad, N.1    Feyes, D.K.2    Nieminen, A.-L.3    Agarwal, R.4    Mukhtar, H.5
  • 4
    • 0345275879 scopus 로고    scopus 로고
    • Tea Polyphenol (-)-Epigallocatechin-3-Gallate Inhibits DNA Methyltransferase and Reactivates Methylation-Silenced Genes in Cancer Cell Lines
    • Fang, M.Z., Wang, Y.M., Ai, N., Hou, Z., Sun, Y., Lu, H., Welsh, W., and Yang, C.S. (2003) Tea polyphenol (-)-epigallocatechin-3-gallate inhibits DNA methyltransferase and reactivates methylation-silenced genes in cancer cell lines. Cancer Res. 63, 7563-7570 (Pubitemid 37466673)
    • (2003) Cancer Research , vol.63 , Issue.22 , pp. 7563-7570
    • Fang, M.Z.1    Wang, Y.2    Ai, N.3    Hou, Z.4    Sun, Y.5    Lu, H.6    Welsh, W.7    Yang, C.S.8
  • 5
    • 0030799810 scopus 로고    scopus 로고
    • (-)-epigallocatechin-3- gallate blocks the induction of nitric oxide synthase by down-regulating lipopolysaccharide-induced activity of transcription factor nuclear factor-kappa B
    • Lin, Y.L. and Lin, J.K. (1997) (-)-epigallocatechin-3- gallate blocks the induction of nitric oxide synthase by down-regulating lipopolysaccharide- induced activity of transcription factor nuclear factor-kappa B. Mol. Pharmacol. 52, 465-472
    • (1997) Mol. Pharmacol. , vol.52 , pp. 465-472
    • Lin, Y.L.1    Lin, J.K.2
  • 6
    • 0742324878 scopus 로고    scopus 로고
    • The tea polyphenol, (-)-epigallocatechin gallate effects on growth, apoptosis, and telomerase activity in cervical cell lines
    • DOI 10.1016/j.ygyno.2003.09.023
    • Yokoyama, M., Noguchi, M., Nakao, Y., Pater, A., and Iwasaka, T. (2004) The tea polyphenol, (-)-epigallocatechin gallate effects on growth, apoptosis, and telomerase activity in cervical cell lines. Gynecol. Oncol. 92, 197-204 (Pubitemid 38147391)
    • (2004) Gynecologic Oncology , vol.92 , Issue.1 , pp. 197-204
    • Yokoyama, M.1    Noguchi, M.2    Nakao, Y.3    Pater, A.4    Iwasaka, T.5
  • 8
    • 0037114268 scopus 로고    scopus 로고
    • Antifungal activity of octyl gallate
    • Fujita, K. and Kubo, I. (2002) Antifungal activity of octyl gallate. Int. J. Food Microbiol. 79, 193-201
    • (2002) Int. J. Food Microbiol. , vol.79 , pp. 193-201
    • Fujita, K.1    Kubo, I.2
  • 9
    • 0036094198 scopus 로고    scopus 로고
    • Plasma membrane injury induced by nonyl gallate in Saccharomyces cerevisiae
    • DOI 10.1046/j.1365-2672.2002.01614.x
    • Fujita, K. and Kubo, I. (2002) Plasma membrane injury induced by nonyl gallate in Saccharomyces cerevisiae. J. Appl. Microbiol. 92, 1035-1042 (Pubitemid 34535483)
    • (2002) Journal of Applied Microbiology , vol.92 , Issue.6 , pp. 1035-1042
    • Fujita, K.1    Kubo, I.2
  • 10
    • 61349117570 scopus 로고    scopus 로고
    • Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi
    • Leal, P.C., Mascarello, A., Derita, M., Zuljan, F., Nunes, R.J., Zacchino, S., and Yunes, R.A. (2009) Relation between lipophilicity of alkyl gallates and antifungal activity against yeasts and filamentous fungi. Bioorg. Med. Chem. Lett. 19, 1793-1796
    • (2009) Bioorg. Med. Chem. Lett. , vol.19 , pp. 1793-1796
    • Leal, P.C.1    Mascarello, A.2    Derita, M.3    Zuljan, F.4    Nunes, R.J.5    Zacchino, S.6    Yunes, R.A.7
  • 11
    • 67349095614 scopus 로고    scopus 로고
    • Effects of alkyl chain length of gallates on their antifungal property and potency as an environmentally benign preservative against wood-decay fungi
    • Hsu, F.L., Chen, P.S., Chang, H.T., and Chang, S.T. (2009) Effects of alkyl chain length of gallates on their antifungal property and potency as an environmentally benign preservative against wood-decay fungi. Int. Biodeter. Biodegrad. 63, 543-547
    • (2009) Int. Biodeter. Biodegrad. , vol.63 , pp. 543-547
    • Hsu, F.L.1    Chen, P.S.2    Chang, H.T.3    Chang, S.T.4
  • 12
    • 0035847688 scopus 로고    scopus 로고
    • Antifungal activity of octyl gallate: Structural criteria and mode of action
    • DOI 10.1016/S0960-894X(00)00656-9, PII S0960894X00006569
    • Kubo, I., Xiao, P., and Fujita, K. (2001) Antifungal activity of octyl gallate, Structural criteria and mode of action. Bioorg. Med. Chem. Lett. 11, 347-350 (Pubitemid 32115843)
    • (2001) Bioorganic and Medicinal Chemistry Letters , vol.11 , Issue.3 , pp. 347-350
    • Kubo, I.1    Xiao, P.2    Fujita, K.3
  • 13
    • 0042389540 scopus 로고    scopus 로고
    • Molecular design of multifunctional antibacterial agents against methicillin resistant Staphylococcus aureus (MRSA)
    • DOI 10.1016/S0968-0896(03)00433-4
    • Kubo, I., Fujita, K., and Nihei, K. (2003) Molecular design of multifunctional antibacterial agents against methicillin resistant Staphylococcus aureus (MRSA). Bioorg. Med. Chem. 11, 4255-4262 (Pubitemid 37013576)
    • (2003) Bioorganic and Medicinal Chemistry , vol.11 , Issue.19 , pp. 4255-4262
    • Kubo, I.1    Fujita, K.-I.2    Nihei, K.-I.3
  • 14
    • 0033848081 scopus 로고    scopus 로고
    • Propyl gallate increases in vitro antifungal imidazole activity against Candida albicans
    • DOI 10.1016/S0924-8579(00)00200-4, PII S0924857900002004
    • Strippoli, V., D'Auria, F.D., Tecca, M., Callari, A., and Simonetti, G. (2000) Propyl gallate increases in vitro antifungal imidazole activity against Candida albicans. Int. J. Antimicrob. Agents 16, 73-76 (Pubitemid 30665429)
    • (2000) International Journal of Antimicrobial Agents , vol.16 , Issue.1 , pp. 73-76
    • Strippoli, V.1    D'Auria, F.D.2    Tecca, M.3    Callari, A.4    Simonetti, G.5
  • 15
    • 0242317297 scopus 로고    scopus 로고
    • Rational design of antimicrobial agents: Antifungal activity of alk(en)yl dihydroxybenzoates and dihydroxyphenyl alkanoates
    • DOI 10.1016/j.bmcl.2003.08.057
    • Nihei, K., Nihei, A., and Kubo, I. (2003) Rational design of antimicrobial agents, antifungal activity of alk(en)yl dihydroxybenzoates and dihydroxyphenyl alkanoates. Bioorg. Med. Chem. Lett. 13, 3993-3996 (Pubitemid 37338434)
    • (2003) Bioorganic and Medicinal Chemistry Letters , vol.13 , Issue.22 , pp. 3993-3996
    • Nihei, K.-I.1    Nihei, A.2    Kubo, I.3
  • 16
    • 33748575599 scopus 로고    scopus 로고
    • Evaluation of antifungal properties of octyl gallate and its synergy with cinnamaldehyde
    • Hsu, F.L., Chang, H.T., and Chang, S.T. (2007) Evaluation of antifungal properties of octyl gallate and its synergy with cinnamaldehyde. Bioresour. Technol. 98, 734-738
    • (2007) Bioresour. Technol. , vol.98 , pp. 734-738
    • Hsu, F.L.1    Chang, H.T.2    Chang, S.T.3
  • 17
    • 1542377352 scopus 로고    scopus 로고
    • Antibacterial activity of akyl gallates against Bacillus subtilis
    • Kubo, I., Fujita, K., Nihei, K., and Nihei, A. (2004) Antibacterial activity of akyl gallates against Bacillus subtilis. J. Agric. Food. Chem. 52, 1072-1076
    • (2004) J. Agric. Food. Chem. , vol.52 , pp. 1072-1076
    • Kubo, I.1    Fujita, K.2    Nihei, K.3    Nihei, A.4
  • 19
    • 33846362237 scopus 로고    scopus 로고
    • Antiviral effect of octyl gallate against DNA and RNA viruses
    • DOI 10.1016/j.antiviral.2006.07.010, PII S0166354206002336
    • Uozaki, M., Yamasaki, H., Katsuyama, Y., Higuchi, M., Higuti, T., and Koyama, A.H. (2007) Antiviral effect of octyl gallate against DNA and RNA viruses. Antiviral Res. 73, 85-91 (Pubitemid 46135766)
    • (2007) Antiviral Research , vol.73 , Issue.2 , pp. 85-91
    • Uozaki, M.1    Yamasaki, H.2    Katsuyama, Y.3    Higuchi, M.4    Higuti, T.5    Koyama, A.H.6
  • 22
    • 0023939395 scopus 로고
    • Methyl gallate methyl-3,4,5-trihydoxybenzoate, is a potent and highly specific inhibitor of herpes simplex virus in vitro. II. Antiviral activity of methyl gallate and its derivatives
    • Kane, C.J.M., Menna, J.H., Sung, C.-C., and Yeh, Y.-C. (1988) Methyl gallate, methyl-3,4,5-trihydoxybenzoate, is a potent and highly specific inhibitor of herpes simplex virus in vitro. II. Antiviral activity of methyl gallate and its derivatives. Biosci. Rep. 8, 1
    • (1988) Biosci. Rep. , Issue.8 , pp. 1
    • Kane, C.J.M.1    Menna, J.H.2    Sung, C.-C.3    Yeh, Y.-C.4
  • 26
    • 50349101643 scopus 로고    scopus 로고
    • Antiproliferative and apoptosis-inducing activities of alkyl gallate and gallamide derivatives related to (-)-epigallocatechin gallate
    • Dodo, K., Minato, T., Noguchi-Yachide, T., Suganuma, M., and Hashimoto, Y. (2008) Antiproliferative and apoptosis-inducing activities of alkyl gallate and gallamide derivatives related to (-)-epigallocatechin gallate. Bioorg. Med. Chem. 16, 7975-7982
    • (2008) Bioorg. Med. Chem. , vol.16 , pp. 7975-7982
    • Dodo, K.1    Minato, T.2    Noguchi-Yachide, T.3    Suganuma, M.4    Hashimoto, Y.5
  • 27
    • 0014209817 scopus 로고
    • Fluorescence and protein structure X. Reappraisal of solvent and structural effects
    • Cowgill, R.W. (1967) Fluorescence and protein structure, X. Reappraisal of solvent and structural effects. Biochim. Biophys. Acta 133, 6-18
    • (1967) Biochim. Biophys. Acta , vol.133 , pp. 6-18
    • Cowgill, R.W.1
  • 28
    • 65249174105 scopus 로고    scopus 로고
    • Magainin 2-induced pore formation in the lipid membranes depends on its concentration in the membrane interface
    • Tamba, Y. and Yamazaki, M. (2009) Magainin 2-induced pore formation in the lipid membranes depends on its concentration in the membrane interface. J. Phys. Chem. B. 113, 4846-4852
    • (2009) J. Phys. Chem. B. , vol.113 , pp. 4846-4852
    • Tamba, Y.1    Yamazaki, M.2
  • 29
    • 0034681140 scopus 로고    scopus 로고
    • Membrane binding and pore formation of the antibacterial peptide PGLa: Thermodynamic and mechanistic aspects
    • DOI 10.1021/bi992146k
    • Wieprecht, T., Apostolov, O., Beyermann, M., and Seelig, J. (2000) Membrane binding and pore formation of the antibacterial peptide PGLa, thermodynamic and mechanistic aspects. Biochemistry 39, 442-452 (Pubitemid 30056480)
    • (2000) Biochemistry , vol.39 , Issue.2 , pp. 442-452
    • Wieprecht, T.1    Apostolov, O.2    Beyermann, M.3    Seelig, J.4
  • 31
    • 77950351987 scopus 로고    scopus 로고
    • Quantitative analysis of protein-lipid interactions using tryptophan fluorescence
    • Kraft, C.A., Garrido, J.L., Leiva-Vega, L., and Romero, G. (2009) Quantitative analysis of protein-lipid interactions using tryptophan fluorescence. Sci. Signal 2, pl4
    • (2009) Sci. Signal , vol.2
    • Kraft, C.A.1    Garrido, J.L.2    Leiva-Vega, L.3    Romero, G.4
  • 32
    • 0021671706 scopus 로고
    • Role of peptide structure in lipid-peptide interactions: A fluorescence study of the binding of pentagastrin-related pentapeptides to phospholipid vesicles
    • DOI 10.1021/bi00320a026
    • Surewicz, W.K. and Epand, R.M. (1984) Role of peptide structure in lipid-peptide interactions, a fluorescence study of the binding of pentagastrin-related pentapeptides to phospholipid vesicles. Biochemistry 23, 6072-6077 (Pubitemid 15153481)
    • (1984) Biochemistry , vol.23 , Issue.25 , pp. 6072-6077
    • Surewicz, W.K.1    Epand, R.M.2
  • 33
    • 56749157982 scopus 로고    scopus 로고
    • Ground and excited state proton transfer and antioxidant activity of 7-hydroxyflavone in model membranes, absorption and fluorescence spectroscopic studies
    • Chaudhuri, S., Pahari, B., and Sengupta, P.K. (2009) Ground and excited state proton transfer and antioxidant activity of 7-hydroxyflavone in model membranes, absorption and fluorescence spectroscopic studies. Biophys. Chem. 139, 29-26
    • (2009) Biophys. Chem. , vol.139 , pp. 29-26
    • Chaudhuri, S.1    Pahari, B.2    Sengupta, P.K.3
  • 34
    • 0036849912 scopus 로고    scopus 로고
    • Novel two-band ratiometric fluorescence probes with different location and orientation in phospholipid membranes
    • DOI 10.1016/S1074-5521(02)00244-2, PII S1074552102002442
    • Klymchenko, A.S., Duportail, G., Ozturk, T., Pivovarenko, V.G., Mely, Y., and Demchenko, A.P. (2002) Novel two-band ratiometric fluorescence probes with different location and orientation in phospholipid membranes. Chem. Biol. 9, 1199-1208 (Pubitemid 35348273)
    • (2002) Chemistry and Biology , vol.9 , Issue.11 , pp. 1199-1208
    • Klymchenko, A.S.1    Duportail, G.2    Ozturk, T.3    Pivovarenko, V.G.4    Mely, Y.5    Demchenko, A.P.6
  • 35
    • 1642290918 scopus 로고    scopus 로고
    • Relationship between antibacterial activity of (+)-catechin derivatives and their interaction with a model membrane
    • Kajiya, K., Hojo, H., Suzuki, M., Nanjo, F., Kumazawa, S., and Nakayama, T. (2004) Relationship between antibacterial activity of (+)-catechin derivatives and their interaction with a model membrane. J. Agric. Food. Chem. 52, 1514-1519
    • (2004) J. Agric. Food. Chem. , vol.52 , pp. 1514-1519
    • Kajiya, K.1    Hojo, H.2    Suzuki, M.3    Nanjo, F.4    Kumazawa, S.5    Nakayama, T.6
  • 36
    • 66149102784 scopus 로고    scopus 로고
    • Triple combinations of lower and longer alkyl gallates and oxacillin improve antibiotic synergy against methicillin-resistant Staphylococcus aureus
    • Shibata, H., Nakano, T., Parvez, M.A., Furukawa, Y., Tomoishi, A., Niimi, S., Arakaki, N., and Higuti, T. (2009) Triple combinations of lower and longer alkyl gallates and oxacillin improve antibiotic synergy against methicillin-resistant Staphylococcus aureus. Antimicrob. Agents Chemother. 53, 2218-2220
    • (2009) Antimicrob. Agents Chemother. , vol.53 , pp. 2218-2220
    • Shibata, H.1    Nakano, T.2    Parvez, M.A.3    Furukawa, Y.4    Tomoishi, A.5    Niimi, S.6    Arakaki, N.7    Higuti, T.8
  • 37
    • 79953232697 scopus 로고    scopus 로고
    • Arginine increases the solubility of alkyl gallates through interaction with the aromatic ring
    • Ariki, R., Hirano, A., Arakawa, T., and Shiraki, K. (2011) Arginine increases the solubility of alkyl gallates through interaction with the aromatic ring. J. Biochem. 149, 389-394
    • (2011) J. Biochem. , vol.149 , pp. 389-394
    • Ariki, R.1    Hirano, A.2    Arakawa, T.3    Shiraki, K.4
  • 38
    • 0033750754 scopus 로고    scopus 로고
    • Cluster formation in aqueous electrolyte solutions observed by dynamic light scattering
    • Georgalis, Y., Kierzek, A.M., and Saenger, W. (2000) Cluster formation in aqueous electrolyte solutions observed by dynamic light scattering. J. Phys. Chem. B. 104, 3405-3406
    • (2000) J. Phys. Chem. B. , vol.104 , pp. 3405-3406
    • Georgalis, Y.1    Kierzek, A.M.2    Saenger, W.3
  • 39
    • 77958500340 scopus 로고    scopus 로고
    • Arginine-assisted solubilization system for drug substances, solubility experiment and simulation
    • Hirano, A., Kameda, T., Arakawa, T., and Shiraki, K. (2010) Arginine-assisted solubilization system for drug substances, solubility experiment and simulation. J. Phys. Chem. B. 114, 13455-13462
    • (2010) J. Phys. Chem. B. , vol.114 , pp. 13455-13462
    • Hirano, A.1    Kameda, T.2    Arakawa, T.3    Shiraki, K.4
  • 40
    • 0242385346 scopus 로고    scopus 로고
    • Separation of Liquid Phases in Giant Vesicles of Ternary Mixtures of Phospholipids and Cholesterol
    • Veatch, S.L. and Keller, S.L. (2003) Separation of liquid phases in giant vesicles of ternary mixtures of phospholipids and cholesterol. Biophys. J. 85, 3074-3083 (Pubitemid 37345795)
    • (2003) Biophysical Journal , vol.85 , Issue.5 , pp. 3074-3083
    • Veatch, S.L.1    Keller, S.L.2
  • 41
    • 0038287894 scopus 로고    scopus 로고
    • Correlation and simple linear regression
    • DOI 10.1148/radiol.2273011499
    • Zou, K.H., Tuncali, K., and Silverman, S.G. (2003) Correlation and simple linear regression. Radiology 227, 617-622 (Pubitemid 36583011)
    • (2003) Radiology , vol.227 , Issue.3 , pp. 617-622
    • Zou, K.H.1    Tuncali, K.2    Silverman, S.G.3
  • 42
    • 12244270658 scopus 로고    scopus 로고
    • Organization in lipid membranes containing cholesterol
    • Veatch, S.L. and Keller, S.L. (2002) Organization in lipid membranes containing cholesterol. Phys. Rev. Lett. 89, 268101
    • (2002) Phys. Rev. Lett. , vol.89 , pp. 268101
    • Veatch, S.L.1    Keller, S.L.2
  • 43
    • 29144531904 scopus 로고    scopus 로고
    • Seeing spots: Complex phase behavior in simple membranes
    • DOI 10.1016/j.bbamcr.2005.06.010, PII S0167488905001473, Lipid Refts: From Model Membranes to Cells
    • Veatch, S.L. and Keller, S.L. (2005) Seeing spots, complex phase behavior in simple membranes. Biochim. Biophys. Acta 1746, 172-185 (Pubitemid 41815014)
    • (2005) Biochimica et Biophysica Acta - Molecular Cell Research , vol.1746 , Issue.3 , pp. 172-185
    • Veatch, S.L.1    Keller, S.L.2
  • 44
    • 18144386926 scopus 로고    scopus 로고
    • Miscibility phase diagrams of giant vesicles containing sphingomyelin
    • Veatch, S.L. and Keller, S.L. (2005) Miscibility phase diagrams of giant vesicles containing sphingomyelin. Phys. Rev. Lett. 94, 148101
    • (2005) Phys. Rev. Lett. , vol.94 , pp. 148101
    • Veatch, S.L.1    Keller, S.L.2
  • 45
    • 34247531351 scopus 로고    scopus 로고
    • Diffusion of liquid domains in lipid bilayer membranes
    • DOI 10.1021/jp0702088
    • Cicuta, P., Keller, S.L., and Veatch, S.L. (2007) Diffusion of liquid domains in lipid bilayer membranes. J. Phys. Chem. B. 111, 3328-3331 (Pubitemid 46652682)
    • (2007) Journal of Physical Chemistry B , vol.111 , Issue.13 , pp. 3328-3331
    • Cicuta, P.1    Keller, S.L.2    Veatch, S.L.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.