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Volumn 15, Issue 4, 2004, Pages 738-746

Amphiphilic corroles bind tightly to human serum albumin

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; BINDING SITES; BODY FLUIDS; DICHROISM; GALLIUM COMPOUNDS; MANGANESE COMPOUNDS; POLYPYRROLES;

EID: 3242800519     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc034179p     Document Type: Article
Times cited : (164)

References (53)
  • 3
    • 0034830855 scopus 로고    scopus 로고
    • Photochemotherapy in the treatment of cancer
    • Via, L. D., and Magno, S. M. (2001) Photochemotherapy in the treatment of cancer. Curr. Med. Chem. 8, 1405-1418.
    • (2001) Curr. Med. Chem. , vol.8 , pp. 1405-1418
    • Via, L.D.1    Magno, S.M.2
  • 6
    • 0001674837 scopus 로고    scopus 로고
    • Syntheses of Corroles
    • (Kadish, K. M., Smith, K. M., and Guilard, R., Eds.), Academic Press, New York
    • Paolesse, R. (2000) Syntheses of Corroles. The Porphyrin Handbook, Vol. II. (Kadish, K. M., Smith, K. M., and Guilard, R., Eds.) pp 201-232, Academic Press, New York.
    • (2000) The Porphyrin Handbook , vol.2 , pp. 201-232
    • Paolesse, R.1
  • 7
    • 0033577883 scopus 로고    scopus 로고
    • The first direct synthesis of corroles from pyrrole
    • Gross, Z., Galili, N., and Saltsman, I. (1999) The first direct synthesis of corroles from pyrrole. Angew. Chem., Int. Ed. 38, 1427-1429.
    • (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 1427-1429
    • Gross, Z.1    Galili, N.2    Saltsman, I.3
  • 8
    • 0000534548 scopus 로고    scopus 로고
    • Solvent-free condensation of pyrrole and pentafluorobenzaldehyde: A novel synthetic pathway to corrole and oligopyrromethenes
    • Gross, Z., Galili, N., Simkhovich, L., Saltsman, I., Botoshansky, M., Bläser, D., Boese, R., and Goldberg, I. (1999) Solvent-free condensation of pyrrole and pentafluorobenzaldehyde: A novel synthetic pathway to corrole and oligopyrromethenes. Org. Lett. 1, 599-602.
    • (1999) Org. Lett. , vol.1 , pp. 599-602
    • Gross, Z.1    Galili, N.2    Simkhovich, L.3    Saltsman, I.4    Botoshansky, M.5    Bläser, D.6    Boese, R.7    Goldberg, I.8
  • 10
    • 0034233476 scopus 로고    scopus 로고
    • First syntheses and X-ray structures of a meso-alkyl substituted corrole and its Ga(III) complex
    • Simkhovich, L., Goldberg, I., and Gross, Z. (2000) First syntheses and X-ray structures of a meso-alkyl substituted corrole and its Ga(III) complex. J. Inorg. Biochem. 80, 235-238.
    • (2000) J. Inorg. Biochem. , vol.80 , pp. 235-238
    • Simkhovich, L.1    Goldberg, I.2    Gross, Z.3
  • 11
    • 0034728127 scopus 로고    scopus 로고
    • Customized, core-modified corroles from [2+2] condensation of dipyrromethanes
    • Cho, W.-S., and Lee, C.-H. (2000) Customized, core-modified corroles from [2+2] condensation of dipyrromethanes. Tetrahedron Lett. 41, 697-701.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 697-701
    • Cho, W.-S.1    Lee, C.-H.2
  • 12
    • 0034700222 scopus 로고    scopus 로고
    • A simple, rational synthesis of meso-substituted A(2)B-corroles
    • Gryko, D. T. (2000) A simple, rational synthesis of meso-substituted A(2)B-corroles. Chem. Commun. 2243-2244.
    • (2000) Chem. Commun. , pp. 2243-2244
    • Gryko, D.T.1
  • 13
    • 0035099928 scopus 로고    scopus 로고
    • Triarylcorroles by oxidative coupling of triaryltetrapyrranes
    • Briñas, R. P., and Brückner, C. (2001) Triarylcorroles by oxidative coupling of triaryltetrapyrranes. Synlett 442-444.
    • (2001) Synlett , pp. 442-444
    • Briñas, R.P.1    Brückner, C.2
  • 14
    • 0035874714 scopus 로고    scopus 로고
    • A simple and versatile one-pot synthesis of meso-substituted trans-A(2)B-corroles
    • Gryko, D. T., and Jadach, K. (2001) A simple and versatile one-pot synthesis of meso-substituted trans-A(2)B-corroles. J. Org. Chem. 66, 4267-4275.
    • (2001) J. Org. Chem. , vol.66 , pp. 4267-4275
    • Gryko, D.T.1    Jadach, K.2
  • 15
    • 0034649139 scopus 로고    scopus 로고
    • Expedient synthesis of corroles by oxidant-mediated, direct α-α′ coupling of tetrapyrromethanes
    • Ka, J.-W., Cho, W.-S., and Lee, C.-H. (2000) Expedient synthesis of corroles by oxidant-mediated, direct α-α′ coupling of tetrapyrromethanes. Tetrahedron Lett. 41, 8121-8125.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 8121-8125
    • Ka, J.-W.1    Cho, W.-S.2    Lee, C.-H.3
  • 16
    • 0035951561 scopus 로고    scopus 로고
    • Synthesis and functionalization of meso-aryl-substituted corroles
    • Paolesse, R., Nardis, S., Sagone, F., and Khoury, R. G. (2001) Synthesis and functionalization of meso-aryl-substituted corroles. J. Org. Chem. 66, 550-556.
    • (2001) J. Org. Chem. , vol.66 , pp. 550-556
    • Paolesse, R.1    Nardis, S.2    Sagone, F.3    Khoury, R.G.4
  • 17
    • 0035797057 scopus 로고    scopus 로고
    • Sterically encumbered triarylcorroles from aryldipyrromethanes and aromatic aldehydes
    • Asokan, C. V., Smeets, S., and Dehaen, W. (2001) Sterically encumbered triarylcorroles from aryldipyrromethanes and aromatic aldehydes. Tetrahedron Lett. 42, 4483-4485.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 4483-4485
    • Asokan, C.V.1    Smeets, S.2    Dehaen, W.3
  • 18
    • 0033531758 scopus 로고    scopus 로고
    • First catalysis by corrole metal complexes: Epoxidation, hydroxylation, and cyclopropanation
    • Gross, Z., Simkhovich, L., and Galili, N. (1999) First Catalysis by corrole metal complexes: epoxidation, hydroxylation, and cyclopropanation. J. Chem. Soc., Chem. Commun. 599-600.
    • (1999) J. Chem. Soc., Chem. Commun. , pp. 599-600
    • Gross, Z.1    Simkhovich, L.2    Galili, N.3
  • 19
    • 0034680594 scopus 로고    scopus 로고
    • Epoxidation catalysis by a manganese(III) corrole and isolation of an oxomanganese(V) corrole
    • Gross, Z., Golubkov, G., and Simkhovich, L. (2000) Epoxidation catalysis by a manganese(III) corrole and isolation of an oxomanganese(V) corrole. Angew. Chem., Int. Ed. 39, 4045-4047.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 4045-4047
    • Gross, Z.1    Golubkov, G.2    Simkhovich, L.3
  • 20
    • 0035793809 scopus 로고    scopus 로고
    • Synthesis and characterization of germanium, tin, phosphorous, iron, and rhodium complexes of tris(pentafluorophenyl)corrole, and the utilization of the iron and rhodium corroles as cyclopropanation catalysts
    • Simkhovich, L., Mahammed, A., Goldberg, I., and Gross, Z. (2001) Synthesis and characterization of germanium, tin, phosphorous, iron, and rhodium complexes of tris(pentafluorophenyl)corrole, and the utilization of the iron and rhodium corroles as cyclopropanation catalysts. Chem. Eur. J. 7, 1041-1055.
    • (2001) Chem. Eur. J. , vol.7 , pp. 1041-1055
    • Simkhovich, L.1    Mahammed, A.2    Goldberg, I.3    Gross, Z.4
  • 22
    • 0035813420 scopus 로고    scopus 로고
    • Iron(IV) corroles are potent catalysts for aziridination of olefins by chloramine-T
    • Simkhovich, L., and Gross, Z. (2001) Iron(IV) corroles are potent catalysts for aziridination of olefins by chloramine-T. Tetrahedron Lett. 42, 8089-8092.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 8089-8092
    • Simkhovich, L.1    Gross, Z.2
  • 23
    • 0034680541 scopus 로고    scopus 로고
    • Structural, electrochemical, and photophysical properties of gallium(III) 5,10,15-tris(pentafluorophenyl)corrole
    • Bendix, J., Dmochowski, I. J., Gray, H. B., Mahammed, A., Simkhovich, L., and Gross, Z. (2000) Structural, electrochemical, and photophysical properties of gallium(III) 5,10,15-tris(pentafluorophenyl)corrole. Angew. Chem., Int. Ed. 39, 4048-4051.
    • (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 4048-4051
    • Bendix, J.1    Dmochowski, I.J.2    Gray, H.B.3    Mahammed, A.4    Simkhovich, L.5    Gross, Z.6
  • 24
    • 0036189333 scopus 로고    scopus 로고
    • Aluminum corrolin, a novel chlorophyll analogue
    • Mahammed, A., and Gross, Z. (2002) Aluminum corrolin, a novel chlorophyll analogue. J. Inorg. Biochem. 88, 305-309.
    • (2002) J. Inorg. Biochem. , vol.88 , pp. 305-309
    • Mahammed, A.1    Gross, Z.2
  • 25
    • 0035515328 scopus 로고    scopus 로고
    • Highly selective chlorosulfonation of tris(pentafluorophenyl)corrole as a synthetic tool for the preparation of amphiphilic corroles and metal complexes of chiral planarity
    • Mahammed, A., Goldberg, I., and Gross, Z. (2001) Highly selective chlorosulfonation of tris(pentafluorophenyl)corrole as a synthetic tool for the preparation of amphiphilic corroles and metal complexes of chiral planarity. Org. Lett. 3, 3443-3446.
    • (2001) Org. Lett. , vol.3 , pp. 3443-3446
    • Mahammed, A.1    Goldberg, I.2    Gross, Z.3
  • 27
  • 28
    • 0030237186 scopus 로고    scopus 로고
    • Structure and biodistribution relationships of photodynamic sensitizers
    • Boyle, R. W., and Dolphin, D. (1996) Structure and biodistribution relationships of photodynamic sensitizers. Photochem. Photobiol. 64, 469-485.
    • (1996) Photochem. Photobiol. , vol.64 , pp. 469-485
    • Boyle, R.W.1    Dolphin, D.2
  • 29
    • 0032941945 scopus 로고    scopus 로고
    • Photodynamic therapy in historical perspective
    • Bonnett, R. (1999) Photodynamic therapy in historical perspective. Rev. Contemp. Pharmacother. 10, 1-17.
    • (1999) Rev. Contemp. Pharmacother. , vol.10 , pp. 1-17
    • Bonnett, R.1
  • 30
    • 0036001387 scopus 로고    scopus 로고
    • Pharmaceutical strategies utilizing recombinant human serum albumin
    • Chuang, V. T. G., Kragh-Hansen, U., and Otagiri, M. (2002) Pharmaceutical strategies utilizing recombinant human serum albumin. Pharm. Res. 19, 569-577.
    • (2002) Pharm. Res. , vol.19 , pp. 569-577
    • Chuang, V.T.G.1    Kragh-Hansen, U.2    Otagiri, M.3
  • 31
    • 0036599564 scopus 로고    scopus 로고
    • Practical aspects of the ligand-binding and enzymatic properties of human serum albumin
    • Kragh-Hansen, U., Chuang, V. T. G., and Otagiri, M. (2002) Practical aspects of the ligand-binding and enzymatic properties of human serum albumin. Biol. Pharm. Bull. 25, 695-704.
    • (2002) Biol. Pharm. Bull. , vol.25 , pp. 695-704
    • Kragh-Hansen, U.1    Chuang, V.T.G.2    Otagiri, M.3
  • 33
    • 0033062612 scopus 로고    scopus 로고
    • Crystal structure of human serum albumin at 2.5 angstrom resolution
    • and references therein
    • Sugio, S., Kashima, A., Mochizuki, S., Noda, M., and Kobayashi, K. (1999) Crystal structure of human serum albumin at 2.5 angstrom resolution. Protein Eng. 12, 439-446 and references therein.
    • (1999) Protein Eng. , vol.12 , pp. 439-446
    • Sugio, S.1    Kashima, A.2    Mochizuki, S.3    Noda, M.4    Kobayashi, K.5
  • 35
    • 0035992779 scopus 로고    scopus 로고
    • Reversible and covalent binding of drugs to human serum albumin: Methodological approaches and physiological relevance
    • Bertucci, C. and Domenici, E. (2002) Reversible and covalent binding of drugs to human serum albumin: Methodological approaches and physiological relevance. Curr. Med. Chem. 9, 1463-1481.
    • (2002) Curr. Med. Chem. , vol.9 , pp. 1463-1481
    • Bertucci, C.1    Domenici, E.2
  • 36
    • 0034921094 scopus 로고    scopus 로고
    • Binding sudies of porphyrins to human serum albumin using affinity capillary electrophoresis
    • Ding, Y. S., Lin, B. C., and Huie, C. W. (2001) Binding sudies of porphyrins to human serum albumin using affinity capillary electrophoresis. Electrophoresis 22, 2210-2216.
    • (2001) Electrophoresis , vol.22 , pp. 2210-2216
    • Ding, Y.S.1    Lin, B.C.2    Huie, C.W.3
  • 37
    • 0019178958 scopus 로고
    • The interaction of human serum albumin and hemopexin with porphyrins
    • Morgan, W. T., Smith, A., and Koskelo, P. (1980) The interaction of human serum albumin and hemopexin with porphyrins Biochim. Biophys. Acta 624, 271-285.
    • (1980) Biochim. Biophys. Acta , vol.624 , pp. 271-285
    • Morgan, W.T.1    Smith, A.2    Koskelo, P.3
  • 38
    • 0024590044 scopus 로고
    • Binding studies of 4 free base porphyrins and 6 Fe(III) porphyrins with human serum albumin
    • Datta-Gupta, N., Malakar, D., and Dozier, J. (1989) Binding studies of 4 free base porphyrins and 6 Fe(III) porphyrins with human serum albumin. Res. Commun. Chem. Pathol. Pharmacol. 63, 289-292.
    • (1989) Res. Commun. Chem. Pathol. Pharmacol. , vol.63 , pp. 289-292
    • Datta-Gupta, N.1    Malakar, D.2    Dozier, J.3
  • 39
    • 0023445190 scopus 로고
    • Thermodynamics of porphyrin binding to serum-albumin - Effects of temperature, of porphyrin species and of albumin-carried fatty-acids
    • Rotenberg, M., Cohen, S., and Margalit, R. (1987) Thermodynamics of porphyrin binding to serum-albumin - Effects of temperature, of porphyrin species and of albumin-carried fatty-acids. Photochem. Photobiol. 46, 689-693.
    • (1987) Photochem. Photobiol. , vol.46 , pp. 689-693
    • Rotenberg, M.1    Cohen, S.2    Margalit, R.3
  • 40
    • 0015993964 scopus 로고
    • Spectroscopic study of hemin-human serum albumin system
    • Beaven, G. H., Chen, S. H., Dalbis, A., and Garatzer, B. W. (1974) Spectroscopic study of hemin-human serum albumin system. Eur. J. Biochem. 41, 539-546,
    • (1974) Eur. J. Biochem. , vol.41 , pp. 539-546
    • Beaven, G.H.1    Chen, S.H.2    Dalbis, A.3    Garatzer, B.W.4
  • 41
    • 0342417965 scopus 로고    scopus 로고
    • Difference in the transport of metal and free-base porphyrins: Steady-state and time-resolved fluorescence studies
    • Bardos-Nagy, I., Galantai, R., Kaposi, A. D., and Fidy, J. (1998) Difference in the transport of metal and free-base porphyrins: Steady-state and time-resolved fluorescence studies. Int. J. Pharm. 175, 255-267.
    • (1998) Int. J. Pharm. , vol.175 , pp. 255-267
    • Bardos-Nagy, I.1    Galantai, R.2    Kaposi, A.D.3    Fidy, J.4
  • 42
    • 0033150807 scopus 로고    scopus 로고
    • Binding interactions and conformational changes induced by sulfonated aluminum phthalocyanines in human serum albumin
    • Gantchev, T. G., Ouellet, R., and van Lier, J. E. (1999) Binding interactions and conformational changes induced by sulfonated aluminum phthalocyanines in human serum albumin. Arch. Biochem. Biophys. 366, 21-30.
    • (1999) Arch. Biochem. Biophys. , vol.366 , pp. 21-30
    • Gantchev, T.G.1    Ouellet, R.2    Van Lier, J.E.3
  • 43
    • 0028349923 scopus 로고
    • Time-resolved fluorescence spectroscopy and intracellular imaging of disulfonated aluminum phthalocyanine
    • Ambroz, M., MacRobert, A. J., Morgan, J., Rumbles, G., Foley, M. S. C., and Phillips, D. (1994) Time-resolved fluorescence spectroscopy and intracellular imaging of disulfonated aluminum phthalocyanine. J. Photochem. Photobiol. B22, 105-117.
    • (1994) J. Photochem. Photobiol. B , vol.22 , pp. 105-117
    • Ambroz, M.1    MacRobert, A.J.2    Morgan, J.3    Rumbles, G.4    Foley, M.S.C.5    Phillips, D.6
  • 44
    • 0036198482 scopus 로고    scopus 로고
    • Spectroscopic studies on the interaction of a water soluble porphyrin and two drug carrier proteins
    • Andrade, S. M., and Costa, S. M. B. (2002) Spectroscopic studies on the interaction of a water soluble porphyrin and two drug carrier proteins. Biophys. J. 82, 1607-1619.
    • (2002) Biophys. J. , vol.82 , pp. 1607-1619
    • Andrade, S.M.1    Costa, S.M.B.2
  • 45
    • 0025347990 scopus 로고
    • Photochemical and radiolytic oxidation of a zinc porphyrin bound to human serum albumin
    • Davila, J., and Harriman, A. (1990) Photochemical and radiolytic oxidation of a zinc porphyrin bound to human serum albumin. J. Am. Chem. Soc. 112, 2680-2690.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 2680-2690
    • Davila, J.1    Harriman, A.2
  • 46
    • 0027260405 scopus 로고
    • Characterization of the photochemotherapeutic agent disulfonated aluminum phthalocyanine and its high-performance liquid-chromatographic separated components
    • Bishop, S. M., Khoo, B. J., MacRobert, A. J., Simpson, M. S. C., and Phillips, D. (1993) Characterization of the photochemotherapeutic agent disulfonated aluminum phthalocyanine and its high-performance liquid-chromatographic separated components. J. Chromatogr. 646, 345-350.
    • (1993) J. Chromatogr. , vol.646 , pp. 345-350
    • Bishop, S.M.1    Khoo, B.J.2    MacRobert, A.J.3    Simpson, M.S.C.4    Phillips, D.5
  • 48
    • 0033647373 scopus 로고    scopus 로고
    • Spectral investigations of the interaction of some porphyrins with bovine serum albumin
    • Chatterjee, S., and Srivastava, T. S. (2000) Spectral investigations of the interaction of some porphyrins with bovine serum albumin. J. Porphyrins Phthalocyanines 4, 147-157.
    • (2000) J. Porphyrins Phthalocyanines , vol.4 , pp. 147-157
    • Chatterjee, S.1    Srivastava, T.S.2
  • 49
    • 0344899932 scopus 로고    scopus 로고
    • Conformational analysis of proteins and peptides
    • Cai, X. and Dass, C. (2003) Conformational analysis of proteins and peptides. Curr. Org. Chem. 7, 1841-1854.
    • (2003) Curr. Org. Chem. , vol.7 , pp. 1841-1854
    • Cai, X.1    Dass, C.2
  • 50
    • 0037207250 scopus 로고    scopus 로고
    • Species-dependency in chiral-drug recognition of serum albumin studied by chromatographic methods
    • and references therein
    • Fitos, I., Visy, J., and Simonyi, M. J. (2002) Species-dependency in chiral-drug recognition of serum albumin studied by chromatographic methods. J. Biochem. Biophys. Methods 54, 71-84 and references therein.
    • (2002) J. Biochem. Biophys. Methods , vol.54 , pp. 71-84
    • Fitos, I.1    Visy, J.2    Simonyi, M.J.3
  • 51
    • 0141919816 scopus 로고    scopus 로고
    • Nanosecond photoreduction of cytochrome P450cam by channel-specific Ru-diimine electron tunneling wires
    • Dunn, A. R., Dmochowski, I. J., Winkler, J. R., and Gray, H. B. (2003) Nanosecond photoreduction of cytochrome P450cam by channel-specific Ru-diimine electron tunneling wires. J. Am. Chem. Soc. 125, 12450-12456.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 12450-12456
    • Dunn, A.R.1    Dmochowski, I.J.2    Winkler, J.R.3    Gray, H.B.4
  • 53
    • 85168750477 scopus 로고    scopus 로고
    • note
    • Structural models were built using the Accelrys DS ViewerPro erpro 5.0 software package. The structure of 2-Ga was obtained by addition of two sulfonate groups and removal of the axial pyridine from the published crystal structure (ref 23): 2-Ga was then inserted into putative HSA binding sites (crystal structure from ref 34).


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