메뉴 건너뛰기




Volumn 11, Issue 1, 2010, Pages

Interactions of unconjugated bilirubin with vesicles, cyclodextrins and micelles: New modeling and the role of high pKa values

Author keywords

[No Author keywords available]

Indexed keywords

ANION; BETA CYCLODEXTRIN; BILE SALT; BILIRUBIN; CARBOHYDRATE; CHOLESTEROL; CYCLODEXTRIN; DODECYL MALTOSIDE; OCTYL GLUCOSIDE; PHOSPHATIDYLCHOLINE; TAUROCHOLIC ACID; UNCLASSIFIED DRUG;

EID: 77951953672     PISSN: None     EISSN: 14712091     Source Type: Journal    
DOI: 10.1186/1471-2091-11-16     Document Type: Article
Times cited : (6)

References (49)
  • 1
    • 0028110519 scopus 로고
    • Structure and binding of unconjugated bilirubin: Relevance for physiological and pathophysiological function
    • Structure and binding of unconjugated bilirubin: relevance for physiological and pathophysiological function. Ostrow JD, Mukerjee P, Tiribelli C, J Lipid Res 1994 35 1715 1737 7852850 (Pubitemid 24331275)
    • (1994) Journal of Lipid Research , vol.35 , Issue.10 , pp. 1715-1737
    • Ostrow, J.D.1    Mukerjee, P.2    Tiribelli, C.3
  • 2
    • 77951965560 scopus 로고    scopus 로고
    • Review: Bilirubin pKa studies: New models and theories indicate high pKa values in water, dimethylformamide and DMSO
    • 20350305
    • Review: Bilirubin pKa studies: new models and theories indicate high pKa values in water, dimethylformamide and DMSO. Mukerjee P, Ostrow JD, BMC Biochemistry 2010 11 15 20350305
    • (2010) BMC Biochemistry , vol.11 , pp. 15
    • Mukerjee, P.1    Ostrow, J.D.2
  • 3
    • 10644253618 scopus 로고    scopus 로고
    • a and aggregation of bilirubin: Titrimetric and ultracentrifugation studies on water-soluble pegylated conjugates of bilirubin and fatty acids
    • DOI 10.1021/bi0481491
    • pKa and aggregation of bilirubin: titrimetric and ultracentrifugation studies on water-soluble pegylated conjugates of bilirubin and fatty acids. Boiadjiev SE, Watters K, Wolf S, Lai BN, Welch WH, McDonagh AF, Lightner DA, Biochemistry 2004 43 15617 15632 10.1021/bi0481491 15581375 (Pubitemid 39647488)
    • (2004) Biochemistry , vol.43 , Issue.49 , pp. 15617-15632
    • Boiadjiev, S.E.1    Watters, K.2    Wolf, S.3    Lai, B.N.4    Welch, W.H.5    McDonagh, A.F.6    Lightner, D.A.7
  • 4
    • 0026761329 scopus 로고
    • Ionization and self-association of unconjugated bilirubin, determined by rapid solvent partition from chloroform, with further studies of bilirubin solubility
    • 1431594
    • Ionization and self-association of unconjugated bilirubin, determined by rapid solvent partition from chloroform, with further studies of bilirubin solubility. Hahm JS, Ostrow JD, Mukerjee P, Celic L, J Lipid Res 1992 33 1123 1137 1431594
    • (1992) J Lipid Res , vol.33 , pp. 1123-1137
    • Hahm, J.S.1    Ostrow, J.D.2    Mukerjee, P.3    Celic, L.4
  • 5
    • 34249326928 scopus 로고    scopus 로고
    • Revalidation and rationale for high pKa values of unconjugated bilirubin
    • DOI 10.1186/1471-2091-8-7
    • Revalidation and rationale for high pKa values of unconjugated bilirubin. Ostrow JD, Mukerjee P, BMC Biochem 2007 8 7 10.1186/1471-2091-8-7 17475001 (Pubitemid 46817306)
    • (2007) BMC Biochemistry , vol.8 , pp. 7
    • Ostrow, J.D.1    Mukerjee, P.2
  • 7
    • 0014648275 scopus 로고
    • Bilirubin colloid formation in neutral aqueous solution
    • 10.3109/00365516909080178 5375744
    • Bilirubin colloid formation in neutral aqueous solution. Brodersen R, Theilgaard J, Scand J Clin Lab Invest 1969 24 395 398 10.3109/00365516909080178 5375744
    • (1969) Scand J Clin Lab Invest , vol.24 , pp. 395-398
    • Brodersen, R.1    Theilgaard, J.2
  • 8
    • 0018364450 scopus 로고
    • Solubilization of unconjugated bilirubin by bile salts
    • DOI 10.1007/BF01968199
    • Solubilization of unconjugated bilirubin by bile salts. Wosiewitz U, Schroebler S, Experientia 1979 35 717 718 10.1007/BF01968199 38133 (Pubitemid 9193859)
    • (1979) Experientia , vol.35 , Issue.6 , pp. 717-718
    • Wosiewitz, U.1    Schroebler, S.2
  • 9
    • 0023970342 scopus 로고
    • Molecular and micellar associations in the pH-dependent stable and metastable dissolution of unconjugated bilirubin by bile salts
    • 3379345
    • Molecular and micellar associations in the pH-dependent stable and metastable dissolution of unconjugated bilirubin by bile salts. Ostrow JD, Celic L, Mukerjee P, J Lipid Res 1988 29 335 348 3379345
    • (1988) J Lipid Res , vol.29 , pp. 335-348
    • Ostrow, J.D.1    Celic, L.2    Mukerjee, P.3
  • 12
    • 0018791450 scopus 로고
    • Binding to egg phosphatidylcholine of some organic anions (bromsulphophthalein, oestrone sulphate, haem and bilirubin) that bind to ligandin and aminoazo-dye binding protein A
    • 39548
    • Binding to egg phosphatidylcholine of some organic anions (bromsulphophthalein, oestrone sulphate, haem and bilirubin) that bind to ligandin and aminoazo-dye binding protein A. Tipping E, Ketterer B, Christodoulides L, Biochem J 1979 180 327 337 39548
    • (1979) Biochem J , vol.180 , pp. 327-337
    • Tipping, E.1    Ketterer, B.2    Christodoulides, L.3
  • 13
    • 37049075798 scopus 로고
    • Properties of alkyl -D-glucoside and alkyl -D-maltoside micelles
    • 10.1039/p29950001655
    • Properties of alkyl -D-glucoside and alkyl -D-maltoside micelles. Kano K, Ishimura T, J Chem Soc Perkin Trans II 1995 1655 1660 10.1039/p29950001655
    • (1995) J Chem Soc Perkin Trans II , pp. 1655-1660
    • Kano, K.1    Ishimura, T.2
  • 14
    • 37049069196 scopus 로고
    • Conformational enantiomerism of bilirubin and pamoic acid induced by protonated aminocyclodextrins
    • 10.1039/p29950001661
    • Conformational enantiomerism of bilirubin and pamoic acid induced by protonated aminocyclodextrins. Kano K, Arimoto S, Ishimura T, J Chem Soc Perkin Trans II 1995 1661 1667 10.1039/p29950001661
    • (1995) J Chem Soc Perkin Trans II , pp. 1661-1667
    • Kano, K.1    Arimoto, S.2    Ishimura, T.3
  • 15
    • 0000881594 scopus 로고
    • Micellar aggregates of sodium glycocholate and sodium taurocholate and their interaction complexes with bilirubin-IX
    • 10.1039/ft9949001523
    • Micellar aggregates of sodium glycocholate and sodium taurocholate and their interaction complexes with bilirubin-IX D'Alagni M, Galantini L, Giglio E, Gavuzzo E, Scaramuzza L, J Chem Soc Faraday Trans 1994 90 1523 1532 10.1039/ft9949001523
    • (1994) J Chem Soc Faraday Trans , vol.90 , pp. 1523-1532
    • D'Alagni, M.1    Galantini, L.2    Giglio, E.3    Gavuzzo, E.4    Scaramuzza, L.5
  • 16
    • 0019508086 scopus 로고
    • Bilirubin-liposome interaction. Binding of bilirubin dianion, protonization, and aggregation of bilirubin acid
    • Bilirubin-liposome interaction. Binding of bilirubin dianion, protonization and aggregation of bilirubin acid. Eriksen EF, Danielsen H, Brodersen R, J Biol Chem 1981 256 4269 4274 7194339 (Pubitemid 11089695)
    • (1981) Journal of Biological Chemistry , vol.256 , Issue.9 , pp. 4269-4274
    • Eriksen, E.F.1    Danielsen, H.2    Brodersen, R.3
  • 17
    • 0029901219 scopus 로고    scopus 로고
    • 13C-NMR. pK(a)s of mesobiliverdin-XIIIα and mesobilirubin-XIIIα
    • DOI 10.1007/BF01969747
    • as of mesobiliverdin-XIII and mesobilirubin-XIII Lightner DA, Holmes DL, McDonagh AF, Experientia 1996 51 639 642 10.1007/BF01969747 (Pubitemid 26229954)
    • (1996) Experientia , vol.52 , Issue.6 , pp. 639-642
    • Lightner, D.A.1    Holmes, D.L.2    McDonagh, A.F.3
  • 18
    • 0029968842 scopus 로고    scopus 로고
    • 13C-NMR
    • 10.1016/0040-4020(96)00153-6
    • 13C-NMR. Holmes DL, Lightner DA, Tetrahedron 1996 52 5319 5338 10.1016/0040-4020(96)00153-6
    • (1996) Tetrahedron , vol.52 , pp. 5319-5338
    • Holmes, D.L.1    Lightner, D.A.2
  • 20
  • 22
    • 0020818526 scopus 로고
    • Interaction of bilirubin with small unilamellar vesicles of dipalmitoylphosphatidylcholine
    • 6689320
    • Interaction of bilirubin with small unilamellar vesicles of dipalmitoylphosphatidylcholine. Cestaro B, Cervato G, Ferrari S, Di Silvestro G, Monti D, Manitto P, Ital J Biochem 1983 32 318 329 6689320
    • (1983) Ital J Biochem , vol.32 , pp. 318-329
    • Cestaro, B.1    Cervato, G.2    Ferrari, S.3    Di Silvestro, G.4    Monti, D.5    Manitto, P.6
  • 23
    • 82055185149 scopus 로고
    • The titration of some phosphatides and related compounds in a non-aqueous system
    • 13345811
    • The titration of some phosphatides and related compounds in a non-aqueous system. Garvin JE, Karnovsky ML, J Biol Chem 1956 221 211 222 13345811
    • (1956) J Biol Chem , vol.221 , pp. 211-222
    • Garvin, J.E.1    Karnovsky, M.L.2
  • 24
    • 82055172226 scopus 로고
    • The electrometric titration of lecithin and cephalin
    • The electrometric titration of lecithin and cephalin. Jukes TH, J Biol Chem 1934 107 783 787
    • (1934) J Biol Chem , vol.107 , pp. 783-787
    • Jukes, T.H.1
  • 25
    • 0002767421 scopus 로고
    • Physical chemistry of bile pigments and porphyrins with particular reference to bile
    • New York: Marcel Dekker Ostrow JD
    • Physical chemistry of bile pigments and porphyrins with particular reference to bile. Carey MC, Spivak W, Bile Pigments and Jaundice; Molecular, Metabolic and Medical Aspects New York: Marcel Dekker, Ostrow JD, 1986 81 132
    • (1986) Bile Pigments and Jaundice; Molecular, Metabolic and Medical Aspects , pp. 81-132
    • Carey, M.C.1    Spivak, W.2
  • 26
    • 0033951150 scopus 로고    scopus 로고
    • Mechanism of hepatocellular uptake of albumin-bound bilirubin
    • DOI 10.1016/S0005-2736(99)00196-0, PII S0005273699001960
    • Mechanism of hepatocellular uptake of albumin-bound bilirubin. Zucker SD, Gössling W, Biochim Biophys Acta 2000 1463 197 208 10.1016/S0005-2736(99) 00196-0 10675499 (Pubitemid 30081780)
    • (2000) Biochimica et Biophysica Acta - Biomembranes , vol.1463 , Issue.2 , pp. 197-208
    • Zucker, S.D.1    Goessling, W.2
  • 27
    • 0035655285 scopus 로고    scopus 로고
    • Localization of bilirubin in phospholipid bilayers by parallax analysis of fluorescence quenching
    • Localization of bilirubin in phospholipid bilayers by parallax analysis of fluorescence quenching. Zucker SD, Gössling W, Bootle EJ, Sterritt C, J Lipid Res 2001 42 1377 1388 11518756 (Pubitemid 34007667)
    • (2001) Journal of Lipid Research , vol.42 , Issue.9 , pp. 1377-1388
    • Zucker, S.D.1    Goessling, W.2    Bootle, E.J.3    Sterritt, C.4
  • 29
    • 0026766754 scopus 로고
    • Mechanism of the spontaneous transfer of unconjugated bilirubin between small unilamellar phosphatidylcholine vesicles
    • 10.1021/bi00127a020 1554704
    • Mechanism of the spontaneous transfer of unconjugated bilirubin between small unilamellar phosphatidylcholine vesicles. Zucker SD, Storch J, Zeidel ML, Gollan JL, Biochemistry 1992 31 3184 3192 10.1021/bi00127a020 1554704
    • (1992) Biochemistry , vol.31 , pp. 3184-3192
    • Zucker, S.D.1    Storch, J.2    Zeidel, M.L.3    Gollan, J.L.4
  • 31
    • 0025035966 scopus 로고
    • Bilirubin-neural cell interaction: Characterization of initial cell surface binding leading to toxicity in the neuroblastoma cell line N-115
    • DOI 10.1016/0167-4889(90)90088-U
    • Bilirubin-neural cell interaction: characterization of initial cell surface binding leading to toxicity in the neuroblastoma cell line N-115. Amit Y, Fedunec S, Thomas PD, Poznansky MJ, Schiff D, Biochim Biophys Acta 1990 1055 36 42 10.1016/0167-4889(90)90088-U 2223872 (Pubitemid 20323526)
    • (1990) Biochimica et Biophysica Acta - Molecular Cell Research , vol.1055 , Issue.1 , pp. 36-42
    • Amit, Y.1    Fedunec, S.2    Thomas, P.D.3    Poznansky, M.J.4    Schiff, D.5
  • 32
    • 0033735646 scopus 로고    scopus 로고
    • Effect of pH and temperature on the binding of bilirubin to human erythrocyte membranes
    • 10878856
    • Effect of pH and temperature on the binding of bilirubin to human erythrocyte membranes. Rashid H, Ali MK, Tayyab S, J Biosci 2000 25 157 161 10878856
    • (2000) J Biosci , vol.25 , pp. 157-161
    • Rashid, H.1    Ali, M.K.2    Tayyab, S.3
  • 33
    • 0020539559 scopus 로고
    • Interaction of bilirubin with human erythrocyte membranes
    • Interaction of bilirubin with human erythrocyte membranes. Sato H, Kashiwamata S, Biochem J 1983 210 489 496 6860307 (Pubitemid 13124442)
    • (1983) Biochemical Journal , vol.210 , Issue.2 , pp. 489-496
    • Sato, H.1    Kashiwamata, S.2
  • 34
    • 0002765270 scopus 로고
    • The effect of pH on bilirubin binding by human erythrocytes
    • 10.3109/00365517209080265
    • The effect of pH on bilirubin binding by human erythrocytes. Bratlid D, Scand J Clin Lab Invest 1972 29 453 459 10.3109/00365517209080265
    • (1972) Scand J Clin Lab Invest , vol.29 , pp. 453-459
    • Bratlid, D.1
  • 35
    • 0023906575 scopus 로고
    • The importance of free bilirubin acid salt in bilirubin uptake by erythrocytes and mitochondria
    • 10.1203/00006450-198804000-00021 3374999
    • The importance of free bilirubin acid salt in bilirubin uptake by erythrocytes and mitochondria. Wennberg RP, Pediatr Res 1988 23 443 447 10.1203/00006450-198804000-00021 3374999
    • (1988) Pediatr Res , vol.23 , pp. 443-447
    • Wennberg, R.P.1
  • 36
    • 33845379595 scopus 로고
    • Conformational enantiomerism in bilirubin. Selection by cyclodextrins
    • 10.1021/ja00294a042
    • Conformational enantiomerism in bilirubin. Selection by cyclodextrins. Lightner DA, Gawronski JK, Gawronska K, J Am Chem Soc 1985 107 2456 2461 10.1021/ja00294a042
    • (1985) J Am Chem Soc , vol.107 , pp. 2456-2461
    • Lightner, D.A.1    Gawronski, J.K.2    Gawronska, K.3
  • 37
    • 0021198313 scopus 로고
    • Bile acids and bile salts: Ionization and solubility properties
    • Bile acids and bile salts: ionization and solubility properties. Carey MC, Hepatology 1984 4 66S 71S 10.1002/hep.1840040812 6479887 (Pubitemid 14018146)
    • (1984) Hepatology , vol.4 , Issue.5 SUPPL.
    • Carey, M.C.1
  • 38
    • 37049072727 scopus 로고
    • Mechanisms for steroid-induced conformational enantio-merism of bilirubin in protic solvents
    • 10.1039/p29920001747
    • Mechanisms for steroid-induced conformational enantio-merism of bilirubin in protic solvents. Kano K, Tsujino N, Kim M, J Chem Soc Perkin Trans II 1992 1747 1752 10.1039/p29920001747
    • (1992) J Chem Soc Perkin Trans II , pp. 1747-1752
    • Kano, K.1    Tsujino, N.2    Kim, M.3
  • 39
    • 0027420890 scopus 로고
    • Micellar electrokinetic capillary chromatography analysis of the behavior of bilirubin in micellar solutions
    • DOI 10.1016/0021-9673(93)83274-V
    • Micellar electrokinetic capillary chromatography analysis of the behavior of bilirubin in micellar solutions. Harman AD, Kibbey RG, Sablik MA, Fintschenko Y, Kurtin WE, Bushey MM, J Chromatogr A 1993 652 525 533 10.1016/0021-9673(93)83274-V 8287141 (Pubitemid 23325532)
    • (1993) Journal of Chromatography , vol.652 , Issue.2 , pp. 525-533
    • Harman, A.D.1    Kibbey, R.G.2    Sablik, M.A.3    Fintschenko, Y.4    Kurtin, W.E.5    Bushey, M.M.6
  • 40
    • 0034282463 scopus 로고    scopus 로고
    • Acid dissociation constants of bilirubin and related carboxylic acid compounds in bile salt solutions
    • 10.1006/abbi.2000.1949 11019823
    • Acid dissociation constants of bilirubin and related carboxylic acid compounds in bile salt solutions. Kurtin WE, Enz J, Dunsmoor C, Evans N, Lightner DA, Arch Biochem Biophys 2000 381 83 91 10.1006/abbi.2000.1949 11019823
    • (2000) Arch Biochem Biophys , vol.381 , pp. 83-91
    • Kurtin, W.E.1    Enz, J.2    Dunsmoor, C.3    Evans, N.4    Lightner, D.A.5
  • 41
    • 0000365555 scopus 로고
    • A study of the interaction of bilirubin with sodium deoxycholate in aqueous solutions
    • 10.1021/j100204a073
    • A study of the interaction of bilirubin with sodium deoxycholate in aqueous solutions. D'Alagni M, Delfini M, Galantini L, Giglio E, J Phys Chem 1992 96 10520 10528 10.1021/j100204a073
    • (1992) J Phys Chem , vol.96 , pp. 10520-10528
    • D'Alagni, M.1    Delfini, M.2    Galantini, L.3    Giglio, E.4
  • 42
    • 0001363380 scopus 로고
    • Structure of sodium and rubidium taurodeoxycholate micellar aggregates and their interaction complexes with bilirubin-IX
    • 10.1021/j100052a056
    • Structure of sodium and rubidium taurodeoxycholate micellar aggregates and their interaction complexes with bilirubin-IX D'Alagni M, D'Archivio AA, Giglio E, Scaramuzza L, J Phys Chem 1994 98 343 353 10.1021/j100052a056
    • (1994) J Phys Chem , vol.98 , pp. 343-353
    • D'Alagni, M.1    D'Archivio, A.A.2    Giglio, E.3    Scaramuzza, L.4
  • 43
    • 0017717708 scopus 로고
    • Prevention of kernicterus, based on recent progress in bilirubin chemistry
    • 10.1111/j.1651-2227.1977.tb07959.x 19921
    • Prevention of kernicterus, based on recent progress in bilirubin chemistry. Brodersen R, Acta Paediatr Scand 1977 66 625 634 10.1111/j.1651-2227. 1977.tb07959.x 19921
    • (1977) Acta Paediatr Scand , vol.66 , pp. 625-634
    • Brodersen, R.1
  • 44
    • 0018812596 scopus 로고
    • Binding of bilirubin to albumin; Implications for prevention of bilirubin encephalopathy in the newborn
    • Binding of bilirubin to albumin; implications for prevention of bilirubin encephalopathy in the newborn. Brodersen R, CRC Crit Rev Clin Lab Sci 1979 11 305 399
    • (1979) CRC Crit Rev Clin Lab Sci , vol.11 , pp. 305-399
    • Brodersen, R.1
  • 45
    • 85053101680 scopus 로고
    • Physical chemistry of bilirubin: Binding to macromolecules and membranes
    • Boca Raton, FL: CRC Press Heirwegh KPM, Brown SB
    • Physical chemistry of bilirubin: Binding to macromolecules and membranes. Brodersen R, Bilirubin. Chemistry Boca Raton, FL: CRC Press, Heirwegh KPM, Brown SB, 1982 1 75 123
    • (1982) Bilirubin. Chemistry , vol.1 , pp. 75-123
    • Brodersen, R.1
  • 46
    • 0002931546 scopus 로고
    • Aqueous solubility, albumin binding and tissue distribution of bilirubin
    • New York: Marcel Dekker Ostrow JD
    • Aqueous solubility, albumin binding and tissue distribution of bilirubin. Brodersen R, Bile Pigments and Jaundice; Molecular, Metabolic and Medical Aspects New York: Marcel Dekker, Ostrow JD, 1986 157 181
    • (1986) Bile Pigments and Jaundice; Molecular, Metabolic and Medical Aspects , pp. 157-181
    • Brodersen, R.1
  • 47
    • 0025191179 scopus 로고
    • Deposition of bilirubin acid in the central nervous system - A hypothesis for the development of kernicterus
    • Deposition of bilirubin acid in the central nervous system-A hypothesis for the development of kernicterus. Brodersen R, Stern L, Acta Paediatr Scand 1990 79 12 19 10.1111/j.1651-2227.1990.tb11323.x 2180252 (Pubitemid 20040101)
    • (1990) Acta Paediatrica Scandinavica , vol.79 , Issue.1 , pp. 12-19
    • Brodersen, R.1    Stern, L.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.