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Volumn 27, Issue 9, 2010, Pages 1329-1349

Synthesis and biological evaluation of amphotericin B derivatives

Author keywords

[No Author keywords available]

Indexed keywords

AMPHOTERICIN B; ANTIFUNGAL AGENT; DRUG DERIVATIVE;

EID: 77955801125     PISSN: 02650568     EISSN: 14604752     Source Type: Journal    
DOI: 10.1039/b820743g     Document Type: Review
Times cited : (105)

References (112)
  • 2
    • 0028108885 scopus 로고
    • Epidemiology and control of fungal infections
    • M. A. Pfaller Epidemiology and control of fungal infections Clin. Infect. Dis. 1994 19 S8 13
    • (1994) Clin. Infect. Dis. , vol.19 , pp. 8-13
    • Pfaller, M.A.1
  • 3
    • 3943093972 scopus 로고    scopus 로고
    • Nosocomial bloodstream infections in US hospitals: Analysis of 24,179 cases from a prospective nationwide surveillance study
    • H. Wisplinghoff et al. Nosocomial bloodstream infections in US hospitals: analysis of 24,179 cases from a prospective nationwide surveillance study Clin. Infect. Dis. 2004 39 309 317
    • (2004) Clin. Infect. Dis. , vol.39 , pp. 309-317
    • Wisplinghoff, H.1
  • 4
    • 18544401585 scopus 로고    scopus 로고
    • The effect of aggregation state of amphotericin-B on its interactions with cholesterol- or ergosterol-containing phosphatidylcholine monolayers
    • J. Barwicz P. Tancrede The effect of aggregation state of amphotericin-B on its interactions with cholesterol- or ergosterol-containing phosphatidylcholine monolayers Chem. Phys. Lipids 1997 85 145 155
    • (1997) Chem. Phys. Lipids , vol.85 , pp. 145-155
    • Barwicz, J.1    Tancrede, P.2
  • 5
    • 0043270593 scopus 로고    scopus 로고
    • Candida albicans mutations in the ergosterol biosynthetic pathway and resistance to several antifungal agents
    • D. Sanglard F. Ischer T. Parkinson D. Falconer J. Bille Candida albicans mutations in the ergosterol biosynthetic pathway and resistance to several antifungal agents Antimicrob. Agents Chemother. 2003 47 2404 2412
    • (2003) Antimicrob. Agents Chemother. , vol.47 , pp. 2404-2412
    • Sanglard, D.1    Ischer, F.2    Parkinson, T.3    Falconer, D.4    Bille, J.5
  • 6
    • 0032882718 scopus 로고    scopus 로고
    • Antifungal agents: Mode of action, mechanisms of resistance, and correlation of these mechanisms with bacterial resistance
    • M. A. Ghannoum L. B. Rice Antifungal agents: mode of action, mechanisms of resistance, and correlation of these mechanisms with bacterial resistance Clin. Microbiol. Rev. 1999 12 501 517
    • (1999) Clin. Microbiol. Rev. , vol.12 , pp. 501-517
    • Ghannoum, M.A.1    Rice, L.B.2
  • 8
    • 0035937109 scopus 로고    scopus 로고
    • Characterization of histatin 5 with respect to amphipathicity, hydrophobicity, and effects on cell and mitochondrial membrane integrity excludes a candidacidal mechanism of pore formation
    • E. J. Helmerhorst et al. Characterization of histatin 5 with respect to amphipathicity, hydrophobicity, and effects on cell and mitochondrial membrane integrity excludes a candidacidal mechanism of pore formation J. Biol. Chem. 2001 276 5643 5649
    • (2001) J. Biol. Chem. , vol.276 , pp. 5643-5649
    • Helmerhorst, E.J.1
  • 10
    • 10444285332 scopus 로고    scopus 로고
    • Multidrug resistance in yeast Candida
    • R. Prasad K. Kapoor Multidrug resistance in yeast Candida Int. Rev. Cytol. 2004 242 215 248
    • (2004) Int. Rev. Cytol. , vol.242 , pp. 215-248
    • Prasad, R.1    Kapoor, K.2
  • 12
    • 0024401331 scopus 로고
    • The role of the carboxyl and amino-groups of polyene macrolides in their interactions with sterols and their selective toxicity - A P-31-NMR study
    • M. Herve J. C. Debouzy E. Borowski B. Cybulska C. M. Garybobo The role of the carboxyl and amino-groups of polyene macrolides in their interactions with sterols and their selective toxicity - a P-31-NMR study Biochim. Biophys. Acta, Biomembr. 1989 980 261 272
    • (1989) Biochim. Biophys. Acta, Biomembr. , vol.980 , pp. 261-272
    • Herve, M.1    Debouzy, J.C.2    Borowski, E.3    Cybulska, B.4    Garybobo, C.M.5
  • 14
    • 0015800484 scopus 로고
    • Chemistry and biology of the polyene macrolide antibiotics
    • J. M. Hamilton-Miller Chemistry and biology of the polyene macrolide antibiotics Bacteriol. Rev. 1973 37 166 196
    • (1973) Bacteriol. Rev. , vol.37 , pp. 166-196
    • Hamilton-Miller, J.M.1
  • 16
    • 0001348302 scopus 로고
    • Amphotericins A and B, antifungal antibiotics produced by a streptomycete. I. in vitro studies
    • W. Gold H. A. Stout J. F. Pagano R. Donovick Amphotericins A and B, antifungal antibiotics produced by a streptomycete. I. In vitro studies Antibiot. Annu. 1955 3 579 586
    • (1955) Antibiot. Annu. , vol.3 , pp. 579-586
    • Gold, W.1    Stout, H.A.2    Pagano, J.F.3    Donovick, R.4
  • 17
    • 77049236540 scopus 로고
    • Amphotericins A and B, antifungal antibiotics produced by a streptomycete. II. The isolation and properties of the crystalline amphotericins
    • J. Vandeputte J. L. Wachtel E. T. Stiller Amphotericins A and B, antifungal antibiotics produced by a streptomycete. II. The isolation and properties of the crystalline amphotericins Antibiot. Annu. 1955 3 587 591
    • (1955) Antibiot. Annu. , vol.3 , pp. 587-591
    • Vandeputte, J.1    Wachtel, J.L.2    Stiller, E.T.3
  • 18
    • 33645379105 scopus 로고    scopus 로고
    • Amphotericin B: 50 years of chemistry and biochemistry
    • D. M. Cereghetti E. M. Carreira Amphotericin B: 50 years of chemistry and biochemistry Synthesis 2006 914 942
    • (2006) Synthesis , pp. 914-942
    • Cereghetti, D.M.1    Carreira, E.M.2
  • 19
    • 33645335146 scopus 로고
    • Chemical studies on amphotericin B. II. 2-Methylheptadecanedioic acid from perhydrogenated amphotericin B
    • E. Borowski W. Mechlinski L. Falkowski T. Ziminski J. D. Dutcher Chemical studies on amphotericin B. II. 2-Methylheptadecanedioic acid from perhydrogenated amphotericin B Tetrahedron Lett. 1965 6 473 478
    • (1965) Tetrahedron Lett. , vol.6 , pp. 473-478
    • Borowski, E.1    Mechlinski, W.2    Falkowski, L.3    Ziminski, T.4    Dutcher, J.D.5
  • 20
    • 0003105359 scopus 로고
    • Amphotericin B. I. Carbon skeleton ring size and partial structure
    • A. C. Cope U. Axen E. P. Burrows J. Weinlich Amphotericin B. I. Carbon skeleton ring size and partial structure J. Am. Chem. Soc. 1966 88 4228
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 4228
    • Cope, A.C.1    Axen, U.2    Burrows, E.P.3    Weinlich, J.4
  • 21
    • 49849110339 scopus 로고
    • Structure and absolute configuration of polyene macrolide antibiotic amphotericin-B
    • W. Mechlins Cp. Schaffne P. Ganis G. Avitabil Structure and absolute configuration of polyene macrolide antibiotic amphotericin-B Tetrahedron Lett. 1970 11 3873
    • (1970) Tetrahedron Lett. , vol.11 , pp. 3873
    • Mechlins, W.1    Schaffne, Cp.2    Ganis, P.3    Avitabil, G.4
  • 22
    • 0015215440 scopus 로고
    • Polyene macrolide antibiotic amphotericin B. Crystal structure of the N-iodoacetyl derivative
    • P. Ganis G. Avitabile W. Mechlinski C. P. Schaffner Polyene macrolide antibiotic amphotericin B. Crystal structure of the N-iodoacetyl derivative J. Am. Chem. Soc. 1971 93 4560 4564
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 4560-4564
    • Ganis, P.1    Avitabile, G.2    Mechlinski, W.3    Schaffner, C.P.4
  • 24
    • 0013951783 scopus 로고
    • Interaction of polyene antibiotics with natural and artificial membrane systems
    • S. C. Kinsky S. A. Luse L. Vandeene Interaction of polyene antibiotics with natural and artificial membrane systems Federation Proceedings 1966 25 1503
    • (1966) Federation Proceedings , vol.25 , pp. 1503
    • Kinsky, S.C.1    Luse, S.A.2    Vandeene, L.3
  • 26
    • 0036177169 scopus 로고    scopus 로고
    • Amphotericin B nephrotoxicity
    • G. Deray Amphotericin B nephrotoxicity J. Antimicrob. Chemother. 2002 49 suppl 1 37 41 (Pubitemid 34162655)
    • (2002) Journal of Antimicrobial Chemotherapy , vol.49 , Issue.SUPPL. S1 , pp. 37-41
    • Deray, G.1
  • 27
    • 0025330593 scopus 로고
    • Influence of net charge on the aggregation and solubility behaviour of amphotericin B and its derivatives in aqueous media
    • J. Mazerski J. Grzybowska E. Borowski Influence of net charge on the aggregation and solubility behaviour of amphotericin B and its derivatives in aqueous media Eur. Biophys. J. 1990 18 159 164
    • (1990) Eur. Biophys. J. , vol.18 , pp. 159-164
    • Mazerski, J.1    Grzybowska, J.2    Borowski, E.3
  • 28
    • 0030608163 scopus 로고    scopus 로고
    • Aggregation of polyene antibiotics as studied by electronic absorption and circular dichroism spectroscopies
    • Z. Shervani H. Etori K. Taga T. Yoshida H. Okabayashi Aggregation of polyene antibiotics as studied by electronic absorption and circular dichroism spectroscopies Colloids Surf., B 1996 7 31 38
    • (1996) Colloids Surf., B , vol.7 , pp. 31-38
    • Shervani, Z.1    Etori, H.2    Taga, K.3    Yoshida, T.4    Okabayashi, H.5
  • 30
    • 0026437668 scopus 로고
    • Effects of aggregation and solvent on the toxicity of amphotericin B to human erythrocytes
    • P. Legrand E. A. Romero B. E. Cohen J. Bolard Effects of aggregation and solvent on the toxicity of amphotericin B to human erythrocytes Antimicrob. Agents Chemother. 1992 36 2518 2522
    • (1992) Antimicrob. Agents Chemother. , vol.36 , pp. 2518-2522
    • Legrand, P.1    Romero, E.A.2    Cohen, B.E.3    Bolard, J.4
  • 31
    • 0015980909 scopus 로고
    • Polyene antibiotic-sterol interactions in membranes of Acholeplasma laidlawii cells and lecithin liposomes. 3. Molecular structure of the polyene antibiotic-cholesterol complexes
    • B. de Kruijff R. A. Demel Polyene antibiotic-sterol interactions in membranes of Acholeplasma laidlawii cells and lecithin liposomes. 3. Molecular structure of the polyene antibiotic-cholesterol complexes Biochim. Biophys. Acta, Biomembr. 1974 339 57 70
    • (1974) Biochim. Biophys. Acta, Biomembr. , vol.339 , pp. 57-70
    • De Kruijff, B.1    Demel, R.A.2
  • 32
    • 0015992898 scopus 로고
    • Polyene antibiotic-sterol interactions in membranes of Acholeplasma laidlawii cells and lecithin liposomes. I. Specificity of the membrane permeability changes induced by the polyene antibiotics
    • B. de Kruijff W. J. Gerritsen A. Oerlemans R. A. Demel L. L. van Deenen Polyene antibiotic-sterol interactions in membranes of Acholeplasma laidlawii cells and lecithin liposomes. I. Specificity of the membrane permeability changes induced by the polyene antibiotics Biochim. Biophys. Acta 1974 339 30 43
    • (1974) Biochim. Biophys. Acta , vol.339 , pp. 30-43
    • De Kruijff, B.1    Gerritsen, W.J.2    Oerlemans, A.3    Demel, R.A.4    Van Deenen, L.L.5
  • 33
    • 34447294856 scopus 로고    scopus 로고
    • + and calcein release from liposomes and the determination of pore size formed in a membrane
    • + and calcein release from liposomes and the determination of pore size formed in a membrane Anal. Sci. 2007 23 517 522
    • (2007) Anal. Sci. , vol.23 , pp. 517-522
    • Katsu, T.1    Imamura, T.2    Komagoe, K.3    Masuda, K.4    Mizushima, T.5
  • 35
    • 0016158807 scopus 로고
    • Structure and function of amphotericin B-cholesterol pores in lipid bilayer membranes
    • T. E. Andreoli Structure and function of amphotericin B-cholesterol pores in lipid bilayer membranes Ann. N. Y. Acad. Sci. 1974 235 448 468
    • (1974) Ann. N. Y. Acad. Sci. , vol.235 , pp. 448-468
    • Andreoli, T.E.1
  • 38
  • 39
    • 23844514081 scopus 로고    scopus 로고
    • Structure and fluctuations of a single floating lipid bilayer
    • J. Daillant et al. Structure and fluctuations of a single floating lipid bilayer Proc. Natl. Acad. Sci. U. S. A. 2005 102 11639 11644
    • (2005) Proc. Natl. Acad. Sci. U. S. A. , vol.102 , pp. 11639-11644
    • Daillant, J.1
  • 40
    • 0030844744 scopus 로고    scopus 로고
    • Molecular properties of amphotericin B membrane channel: A molecular dynamics simulation
    • M. Baginski H. Resat J. A. McCammon Molecular properties of amphotericin B membrane channel: a molecular dynamics simulation Mol. Pharmacol. 1997 52 560 570
    • (1997) Mol. Pharmacol. , vol.52 , pp. 560-570
    • Baginski, M.1    Resat, H.2    McCammon, J.A.3
  • 41
    • 0023156357 scopus 로고
    • Spin-labeled amphotericin B: Synthesis, characterization, biological and spectroscopic properties
    • J. A. Urbina B. E. Cohen E. Perozo L. Cornivelli Spin-labeled amphotericin B: synthesis, characterization, biological and spectroscopic properties Biochim. Biophys. Acta, Biomembr. 1987 897 467 473
    • (1987) Biochim. Biophys. Acta, Biomembr. , vol.897 , pp. 467-473
    • Urbina, J.A.1    Cohen, B.E.2    Perozo, E.3    Cornivelli, L.4
  • 42
    • 33847772829 scopus 로고    scopus 로고
    • Ergosterol in POPC membranes: Physical properties and comparison with structurally similar sterols
    • Y. W. Hsueh et al. Ergosterol in POPC membranes: physical properties and comparison with structurally similar sterols Biophys. J. 2007 92 1606 1615
    • (2007) Biophys. J. , vol.92 , pp. 1606-1615
    • Hsueh, Y.W.1
  • 43
    • 53849121653 scopus 로고    scopus 로고
    • Synthesis and in vitro biological properties of novel cationic derivatives of amphotericin B
    • V. Paquet A. A. Volmer E. M. Carreira Synthesis and in vitro biological properties of novel cationic derivatives of amphotericin B Chem.-Eur. J. 2008 14 2465 2481
    • (2008) Chem.-Eur. J. , vol.14 , pp. 2465-2481
    • Paquet, V.1    Volmer, A.A.2    Carreira, E.M.3
  • 44
    • 0022646239 scopus 로고
    • Mechanism of anion-cation selectivity of amphotericin B channels
    • M. P. Borisova R. A. Brutyan L. N. Ermishkin Mechanism of anion-cation selectivity of amphotericin B channels J. Membr. Biol. 1986 90 13 20
    • (1986) J. Membr. Biol. , vol.90 , pp. 13-20
    • Borisova, M.P.1    Brutyan, R.A.2    Ermishkin, L.N.3
  • 45
    • 0017866923 scopus 로고
    • Electrostatic calculations for an ion channel. 1. Energy and potential profiles and interactions between ions
    • D. G. Levitt Electrostatic calculations for an ion channel. 1. Energy and potential profiles and interactions between ions Biophys. J. 1978 22 209 219
    • (1978) Biophys. J. , vol.22 , pp. 209-219
    • Levitt, D.G.1
  • 46
    • 33845204824 scopus 로고    scopus 로고
    • Biologically active amphotericin B-calix[4]arene conjugates
    • V. Paquet A. Zumbuehl E. M. Carreira Biologically active amphotericin B-calix[4]arene conjugates Bioconjugate Chem. 2006 17 1460 1463
    • (2006) Bioconjugate Chem. , vol.17 , pp. 1460-1463
    • Paquet, V.1    Zumbuehl, A.2    Carreira, E.M.3
  • 47
    • 0022253426 scopus 로고
    • Cation Permeability induced by valinomycin, gramicidin-D and amphotericin-B in large lipidic unilamellar vesicles studied by P-31-NMR
    • M. Herve B. Cybulska C. M. Garybobo Cation Permeability induced by valinomycin, gramicidin-D and amphotericin-B in large lipidic unilamellar vesicles studied by P-31-NMR Eur. Biophys. J. Biophys. Lett. 1985 12 121 128
    • (1985) Eur. Biophys. J. Biophys. Lett. , vol.12 , pp. 121-128
    • Herve, M.1    Cybulska, B.2    Garybobo, C.M.3
  • 48
    • 0018152154 scopus 로고
    • Effect of amphotericin B on cholesterol-containing liposomes of egg phosphatidylcholine and didocosenoyl phosphatidylcholine. A refinement of the model for the formation of pores by amphotericin B in membranes
    • P. van Hoogevest B. de Kruijff Effect of amphotericin B on cholesterol-containing liposomes of egg phosphatidylcholine and didocosenoyl phosphatidylcholine. A refinement of the model for the formation of pores by amphotericin B in membranes Biochim. Biophys. Acta, Biomembr. 1978 511 397 407
    • (1978) Biochim. Biophys. Acta, Biomembr. , vol.511 , pp. 397-407
    • Van Hoogevest, P.1    De Kruijff, B.2
  • 49
    • 44449087557 scopus 로고    scopus 로고
    • Natamycin blocks fungal growth by binding specifically to ergosterol without permeabilizing the membrane
    • Y. M. T. Welscher et al. Natamycin blocks fungal growth by binding specifically to ergosterol without permeabilizing the membrane J. Biol. Chem. 2008 283 6393 6401
    • (2008) J. Biol. Chem. , vol.283 , pp. 6393-6401
    • Welscher, Y.M.T.1
  • 51
    • 0025808089 scopus 로고
    • One-sided action of amphotericin B on cholesterol-containing membranes is determined by its self-association in the medium
    • J. Bolard P. Legrand F. Heitz B. Cybulska One-sided action of amphotericin B on cholesterol-containing membranes is determined by its self-association in the medium Biochemistry 1991 30 5707 5715
    • (1991) Biochemistry , vol.30 , pp. 5707-5715
    • Bolard, J.1    Legrand, P.2    Heitz, F.3    Cybulska, B.4
  • 52
    • 0015861634 scopus 로고
    • Equilibrium dialysis of ions in nystatin-treated red-cells
    • A. Cass M. Dalmark Equilibrium dialysis of ions in nystatin-treated red-cells Nature 1973 244 47 49
    • (1973) Nature , vol.244 , pp. 47-49
    • Cass, A.1    Dalmark, M.2
  • 53
    • 6044220226 scopus 로고    scopus 로고
    • An amphotericin B-fluorescein conjugate as a powerful probe for biochemical studies of the membrane
    • A. Zumbuehl et al. An amphotericin B-fluorescein conjugate as a powerful probe for biochemical studies of the membrane Angew. Chem., Int. Ed. 2004 43 5181 5185
    • (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 5181-5185
    • Zumbuehl, A.1
  • 54
    • 38849205715 scopus 로고    scopus 로고
    • Self-assembled amphotericin B is probably surrounded by ergosterol: Bimolecular interactions as evidenced by solid-state NMR and CD spectra
    • Y. Kasai et al. Self-assembled amphotericin B is probably surrounded by ergosterol: Bimolecular interactions as evidenced by solid-state NMR and CD spectra Chem.-Eur. J. 2008 14 1178 1185
    • (2008) Chem.-Eur. J. , vol.14 , pp. 1178-1185
    • Kasai, Y.1
  • 55
    • 0019891830 scopus 로고
    • Fluorescence quenching in model membranes. 3. Relationship between calcium adenosine-triphosphatase enzyme-activity and the affinity of the protein for phosphatidylcholines with different acyl chain characteristics
    • M. Caffrey G. W. Feigenson Fluorescence quenching in model membranes. 3. Relationship between calcium adenosine-triphosphatase enzyme-activity and the affinity of the protein for phosphatidylcholines with different acyl chain characteristics Biochemistry 1981 20 1949 1961
    • (1981) Biochemistry , vol.20 , pp. 1949-1961
    • Caffrey, M.1    Feigenson, G.W.2
  • 56
    • 0021839275 scopus 로고
    • Mechanism of inactivation of the polyene antibiotic amphotericin-B - Evidence for radical formation in the process of autooxidation
    • M. T. Lamy-Freund V. F. N. Ferreira S. Schreier Mechanism of inactivation of the polyene antibiotic amphotericin-B - evidence for radical formation in the process of autooxidation J. Antibiot. 1985 38 753 757
    • (1985) J. Antibiot. , vol.38 , pp. 753-757
    • Lamy-Freund, M.T.1    Ferreira, V.F.N.2    Schreier, S.3
  • 57
    • 0018223663 scopus 로고
    • Kinetics of amphotericin-B decay in a liquid-medium and characterization of the decay process
    • W. H. Beggs Kinetics of amphotericin-B decay in a liquid-medium and characterization of the decay process Curr. Microbiol. 1978 1 301 304
    • (1978) Curr. Microbiol. , vol.1 , pp. 301-304
    • Beggs, W.H.1
  • 58
    • 0022482179 scopus 로고
    • Amphotericin B-induced oxidative damage and killing of Candida albicans
    • M. L. Sokol-Anderson J. Brajtburg G. Medoff Amphotericin B-induced oxidative damage and killing of Candida albicans J. Infect. Dis. 1986 154 76 83
    • (1986) J. Infect. Dis. , vol.154 , pp. 76-83
    • Sokol-Anderson, M.L.1    Brajtburg, J.2    Medoff, G.3
  • 59
    • 0019485471 scopus 로고
    • Increase in colony-forming units of Candida albicans after treatment with polyene antibiotics
    • J. Brajtburg S. Elberg G. Medoff G. S. Kobayashi Increase in colony-forming units of Candida albicans after treatment with polyene antibiotics Antimicrob. Agents Chemother. 1981 19 199 200
    • (1981) Antimicrob. Agents Chemother. , vol.19 , pp. 199-200
    • Brajtburg, J.1    Elberg, S.2    Medoff, G.3    Kobayashi, G.S.4
  • 61
    • 0242404225 scopus 로고    scopus 로고
    • Conditional response to stress in yeast
    • M. Siderius W. H. Mager Conditional response to stress in yeast Monatsh. Chem. 2003 134 1433 1444
    • (2003) Monatsh. Chem. , vol.134 , pp. 1433-1444
    • Siderius, M.1    Mager, W.H.2
  • 62
    • 0034930476 scopus 로고    scopus 로고
    • Amphotericin biosynthesis in Streptomyces nodosus: Deductions from analysis of polyketide synthase and late genes
    • P. Caffrey S. Lynch E. Flood S. Finnan M Oliynyk Amphotericin biosynthesis in Streptomyces nodosus: deductions from analysis of polyketide synthase and late genes Chem. Biol. 2001 8 713 723
    • (2001) Chem. Biol. , vol.8 , pp. 713-723
    • Caffrey, P.1    Lynch, S.2    Flood, E.3    Finnan, S.4    Oliynyk, M.5
  • 65
    • 0034995348 scopus 로고    scopus 로고
    • Methods for the recovery and purification of polyene antifungals
    • D. R. Worthen M. Jay P. M. Bummer Methods for the recovery and purification of polyene antifungals Drug Dev. Ind. Pharm. 2001 27 277 286
    • (2001) Drug Dev. Ind. Pharm. , vol.27 , pp. 277-286
    • Worthen, D.R.1    Jay, M.2    Bummer, P.M.3
  • 66
    • 0142028153 scopus 로고    scopus 로고
    • High frequency transformation of the amphotericin-producing bacterium Streptomyces nodosus
    • J. Nikodinovic K. D. Barrow J. A. Chuck High frequency transformation of the amphotericin-producing bacterium Streptomyces nodosus J. Microbiol. Methods 2003 55 273 277
    • (2003) J. Microbiol. Methods , vol.55 , pp. 273-277
    • Nikodinovic, J.1    Barrow, K.D.2    Chuck, J.A.3
  • 67
    • 0346968196 scopus 로고    scopus 로고
    • Biosynthesis of deoxyamphotericins and deoxyamphoteronolides by engineered strains of Streptomyces nodosus
    • B. Byrne M. Carmody E. Gibson B. Rawlings P. Caffrey Biosynthesis of deoxyamphotericins and deoxyamphoteronolides by engineered strains of Streptomyces nodosus Chem. Biol. 2003 10 1215 1224
    • (2003) Chem. Biol. , vol.10 , pp. 1215-1224
    • Byrne, B.1    Carmody, M.2    Gibson, E.3    Rawlings, B.4    Caffrey, P.5
  • 68
    • 47249110302 scopus 로고    scopus 로고
    • Biosynthetic engineering of polyene macrolides towards generation of improved antifungal and antiparasitic agents
    • P. Caffrey J. F. Aparicio F. Malpartida S. B. Zotchev Biosynthetic engineering of polyene macrolides towards generation of improved antifungal and antiparasitic agents Curr. Top. Med. Chem. 2008 8 639 653
    • (2008) Curr. Top. Med. Chem. , vol.8 , pp. 639-653
    • Caffrey, P.1    Aparicio, J.F.2    Malpartida, F.3    Zotchev, S.B.4
  • 69
    • 36148980794 scopus 로고    scopus 로고
    • A post-PKS oxidation of the amphotericin B skeleton predicted to be critical for channel formation is not required for potent antifungal activity
    • D. S. Palacios T. M. Anderson M. D. Burke A post-PKS oxidation of the amphotericin B skeleton predicted to be critical for channel formation is not required for potent antifungal activity J. Am. Chem. Soc. 2007 129 13804 13805
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 13804-13805
    • Palacios, D.S.1    Anderson, T.M.2    Burke, M.D.3
  • 70
    • 0023836455 scopus 로고
    • Quantitative structure-activity relationships in amphotericin B derivatives
    • M. Cheron et al. Quantitative structure-activity relationships in amphotericin B derivatives Biochem. Pharmacol. 1988 37 827 836
    • (1988) Biochem. Pharmacol. , vol.37 , pp. 827-836
    • Cheron, M.1
  • 71
    • 0022544617 scopus 로고
    • N-Dimethylaminoacyl derivatives of polyene macrolide antibiotics
    • A. Czerwinski J. Grzybowska E. Borowski N-Dimethylaminoacyl derivatives of polyene macrolide antibiotics J. Antibiot. (Tokyo) 1986 39 1025 1027
    • (1986) J. Antibiot. (Tokyo) , vol.39 , pp. 1025-1027
    • Czerwinski, A.1    Grzybowska, J.2    Borowski, E.3
  • 72
    • 0030828996 scopus 로고    scopus 로고
    • N-Methyl-N-d-fructopyranosylamphotericin B methyl ester, new amphotericin B derivative of low toxicity
    • J. Grzybowska P. Sowinski J. Gumieniak T. Zieniawa E. Borowski N-Methyl-N-d-fructopyranosylamphotericin B methyl ester, new amphotericin B derivative of low toxicity J. Antibiot. (Tokyo) 1997 50 709 711
    • (1997) J. Antibiot. (Tokyo) , vol.50 , pp. 709-711
    • Grzybowska, J.1    Sowinski, P.2    Gumieniak, J.3    Zieniawa, T.4    Borowski, E.5
  • 73
    • 19944366318 scopus 로고    scopus 로고
    • N-(1-Piperidinepropionyl)amphotericin B methyl ester (PAME) - A new derivative of the antifungal antibiotic amphotericin B: Searching for the mechanism of its reduced toxicity
    • K. Hac-Wydro P. Dynarowicz-Latka J. Grzybowska E. Borowski N-(1-Piperidinepropionyl)amphotericin B methyl ester (PAME) - a new derivative of the antifungal antibiotic amphotericin B: searching for the mechanism of its reduced toxicity J. Colloid Interface Sci. 2005 287 476 484
    • (2005) J. Colloid Interface Sci. , vol.287 , pp. 476-484
    • Hac-Wydro, K.1    Dynarowicz-Latka, P.2    Grzybowska, J.3    Borowski, E.4
  • 74
    • 0019422592 scopus 로고
    • Comparative in vitro susceptibility of yeasts to amphotericin B and three methyl ester derivatives
    • D. L. Oblack W. L. Hewitt W. J. Martin Comparative in vitro susceptibility of yeasts to amphotericin B and three methyl ester derivatives Antimicrob. Agents Chemother. 1981 19 106 109
    • (1981) Antimicrob. Agents Chemother. , vol.19 , pp. 106-109
    • Oblack, D.L.1    Hewitt, W.L.2    Martin, W.J.3
  • 75
    • 0019985934 scopus 로고
    • N-Aminoacyl derivatives of polyene macrolide antibiotics and their esters
    • J. J. K. Wright J. A. Albarella L. R. Krepski D. Loebenberg N-Aminoacyl derivatives of polyene macrolide antibiotics and their esters J. Antibiot. 1982 35 911 914
    • (1982) J. Antibiot. , vol.35 , pp. 911-914
    • Wright, J.J.K.1    Albarella, J.A.2    Krepski, L.R.3    Loebenberg, D.4
  • 76
  • 77
    • 33646475260 scopus 로고    scopus 로고
    • Significant improvement of antifungal activity of polyene macrolides by bisalkylation of the mycosamine
    • V. Paquet E. M. Carreira Significant improvement of antifungal activity of polyene macrolides by bisalkylation of the mycosamine Org. Lett. 2006 8 1807 1809
    • (2006) Org. Lett. , vol.8 , pp. 1807-1809
    • Paquet, V.1    Carreira, E.M.2
  • 79
    • 4043071644 scopus 로고
    • Cyanohydridoborate anion as a selective reducing agent
    • R. F. Borch Md. Bernstei H. D. Durst Cyanohydridoborate anion as a selective reducing agent J. Am. Chem. Soc. 1971 93 2897
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 2897
    • Borch, R.F.1    Bernstei, Md.2    Durst, H.D.3
  • 80
    • 33846014067 scopus 로고
    • Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeast, M27-A2
    • Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeast, M27-A2, Approved Standard (2nd edn), 1995, vol. 22, no. 15
    • (1995) Approved Standard (2nd Edn)
  • 83
    • 37049071379 scopus 로고
    • A versatile strategy for the derivatization of the carboxy group of amphotericin-B - The preparation of C-16 ketone analogs
    • M. J. Driver A. R. Greenlees D. T. Macpherson A versatile strategy for the derivatization of the carboxy group of amphotericin-B - the preparation of C-16 ketone analogs J. Chem. Soc., Perkin Trans. 1 1992 3155 3157
    • (1992) J. Chem. Soc., Perkin Trans. 1 , pp. 3155-3157
    • Driver, M.J.1    Greenlees, A.R.2    MacPherson, D.T.3
  • 84
    • 33746356860 scopus 로고    scopus 로고
    • Recent advances (1995-2005) in fluorinated pharmaceuticals based on natural products
    • J. P. Begue D. Bonnet-Delpon Recent advances (1995-2005) in fluorinated pharmaceuticals based on natural products J. Fluorine Chem. 2006 127 992 1012
    • (2006) J. Fluorine Chem. , vol.127 , pp. 992-1012
    • Begue, J.P.1    Bonnet-Delpon, D.2
  • 87
    • 0347287011 scopus 로고    scopus 로고
    • Study of the toxicity of a new lipid complex formulation of amphotericin B
    • M. Larabi et al. Study of the toxicity of a new lipid complex formulation of amphotericin B J. Antimicrob. Chemother. 2004 53 81 88
    • (2004) J. Antimicrob. Chemother. , vol.53 , pp. 81-88
    • Larabi, M.1
  • 90
    • 0032819384 scopus 로고    scopus 로고
    • A novel injectable water-soluble amphotericin B-arabinogalactan conjugate
    • R. Falk A. J. Domb I. Polacheck A novel injectable water-soluble amphotericin B-arabinogalactan conjugate Antimicrob. Agents Chemother. 1999 43 1975 1981
    • (1999) Antimicrob. Agents Chemother. , vol.43 , pp. 1975-1981
    • Falk, R.1    Domb, A.J.2    Polacheck, I.3
  • 91
    • 0036497983 scopus 로고    scopus 로고
    • Synthesis and characterization of novel water-soluble amphotericin B-arabinogalactan conjugates
    • T. Ehrenfreund-Kleinman et al. Synthesis and characterization of novel water-soluble amphotericin B-arabinogalactan conjugates Biomaterials 2002 23 1327 1335
    • (2002) Biomaterials , vol.23 , pp. 1327-1335
    • Ehrenfreund-Kleinman, T.1
  • 92
    • 0001067584 scopus 로고
    • Arabinogalactan. A review of the literature
    • M. F. Adams C. Douglas Arabinogalactan. A review of the literature TAPPI J. 1963 46 544 558
    • (1963) TAPPI J. , vol.46 , pp. 544-558
    • Adams, M.F.1    Douglas, C.2
  • 93
    • 1142297579 scopus 로고    scopus 로고
    • Conjugation of amino-containing drugs to polysaccharides by tosylation: Amphotericin B-arabinogalactan conjugates
    • T. Ehrenfreund-Kleinman J. Golenser A. J. Domb Conjugation of amino-containing drugs to polysaccharides by tosylation: amphotericin B-arabinogalactan conjugates Biomaterials 2004 25 3049 3057
    • (2004) Biomaterials , vol.25 , pp. 3049-3057
    • Ehrenfreund-Kleinman, T.1    Golenser, J.2    Domb, A.J.3
  • 94
    • 0035814050 scopus 로고    scopus 로고
    • Synthesis and characterisation of a new amphotericin B- methoxypoly(ethylene glycol) conjugate
    • M. Sedlak et al. Synthesis and characterisation of a new amphotericin B-methoxypoly(ethylene glycol) conjugate Bioorg. Med. Chem. Lett. 2001 11 2833 2835
    • (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 2833-2835
    • Sedlak, M.1
  • 95
  • 96
    • 0033539039 scopus 로고    scopus 로고
    • Drug delivery systems employing 1,4- or 1,6-elimination: Poly(ethylene glycol) prodrugs of amine-containing compounds
    • R. B. Greenwald et al. Drug delivery systems employing 1,4- or 1,6-elimination: poly(ethylene glycol) prodrugs of amine-containing compounds J. Med. Chem. 1999 42 3657 3667
    • (1999) J. Med. Chem. , vol.42 , pp. 3657-3667
    • Greenwald, R.B.1
  • 97
    • 34247568837 scopus 로고    scopus 로고
    • Synthesis of pH-sensitive amphotericin B-poly(ethylene glycol) conjugates and study of their controlled release in vitro
    • M. Sedlak et al. Synthesis of pH-sensitive amphotericin B-poly(ethylene glycol) conjugates and study of their controlled release in vitro Bioorg. Med. Chem. 2007 15 4069 4076
    • (2007) Bioorg. Med. Chem. , vol.15 , pp. 4069-4076
    • Sedlak, M.1
  • 98
    • 2642544178 scopus 로고    scopus 로고
    • An amphotericin B-ergosterol covalent conjugate with powerful membrane permeabilizing activity
    • N. Matsumori et al. An amphotericin B-ergosterol covalent conjugate with powerful membrane permeabilizing activity Chem. Biol. 2004 11 673 679
    • (2004) Chem. Biol. , vol.11 , pp. 673-679
    • Matsumori, N.1
  • 99
    • 0344946181 scopus 로고    scopus 로고
    • Amphotericin B-phospholipid covalent conjugates: Dependence of membrane-permeabilizing activity on acyl-chain length
    • S. Matsuoka N. Matsumori M. Murata Amphotericin B-phospholipid covalent conjugates: dependence of membrane-permeabilizing activity on acyl-chain length Org. Biomol. Chem. 2003 1 3882 3884
    • (2003) Org. Biomol. Chem. , vol.1 , pp. 3882-3884
    • Matsuoka, S.1    Matsumori, N.2    Murata, M.3
  • 100
    • 34247555860 scopus 로고    scopus 로고
    • A novel strategy for bioconjugation: Synthesis and preliminary evaluation with amphotericin B
    • A. Zumbuehl et al. A novel strategy for bioconjugation: synthesis and preliminary evaluation with amphotericin B Org. Biomol. Chem. 2007 5 1339 1342
    • (2007) Org. Biomol. Chem. , vol.5 , pp. 1339-1342
    • Zumbuehl, A.1
  • 101
    • 70349558315 scopus 로고    scopus 로고
    • Synthesis and investigation of tryptophan-amphotericin B conjugates
    • A. Zumbuehl et al. Synthesis and investigation of tryptophan-amphotericin B conjugates ChemBioChem 2009 10 1617 1620
    • (2009) ChemBioChem , vol.10 , pp. 1617-1620
    • Zumbuehl, A.1
  • 102
    • 0037165756 scopus 로고    scopus 로고
    • Amphotericin B covalent dimers forming sterol-dependent ion-permeable membrane channels
    • N. Matsumori N. Yamaji S. Matsuoka T. Oishi M. Murata Amphotericin B covalent dimers forming sterol-dependent ion-permeable membrane channels J. Am. Chem. Soc. 2002 124 4180 4181
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 4180-4181
    • Matsumori, N.1    Yamaji, N.2    Matsuoka, S.3    Oishi, T.4    Murata, M.5
  • 103
    • 6044227903 scopus 로고    scopus 로고
    • Amphotericin B covalent dimers bearing a tartarate linkage
    • N. Matsumori R. Masuda M. Murata Amphotericin B covalent dimers bearing a tartarate linkage Chem. Biodiversity 2004 1 346 352
    • (2004) Chem. Biodiversity , vol.1 , pp. 346-352
    • Matsumori, N.1    Masuda, R.2    Murata, M.3
  • 104
    • 0037071946 scopus 로고    scopus 로고
    • Amphotericin B dimers with bisamide linkage bearing powerful membrane-permeabilizing activity
    • N. Yamaji N. Matsumori S. Matsuoka T. Oishi M. Murata Amphotericin B dimers with bisamide linkage bearing powerful membrane-permeabilizing activity Org. Lett. 2002 4 2087 2089
    • (2002) Org. Lett. , vol.4 , pp. 2087-2089
    • Yamaji, N.1    Matsumori, N.2    Matsuoka, S.3    Oishi, T.4    Murata, M.5
  • 105
    • 26844536241 scopus 로고    scopus 로고
    • Targeted delivery of amphotericin B to cells by using functionalized carbon nanotubes
    • W. Wu et al. Targeted delivery of amphotericin B to cells by using functionalized carbon nanotubes Angew. Chem., Int. Ed. 2005 44 6358 6362
    • (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 6358-6362
    • Wu, W.1
  • 106
    • 33644914163 scopus 로고    scopus 로고
    • A central strategy for converting natural products into fluorescent probes
    • M. D. Alexander et al. A central strategy for converting natural products into fluorescent probes ChemBioChem 2006 7 409 416
    • (2006) ChemBioChem , vol.7 , pp. 409-416
    • Alexander, M.D.1
  • 107
    • 33750464876 scopus 로고    scopus 로고
    • Small molecule natural products in the discovery of therapeutic agents: The synthesis connection
    • R. M. Wilson S. J. Danishefsky Small molecule natural products in the discovery of therapeutic agents: the synthesis connection J. Org. Chem. 2006 71 8329 8351
    • (2006) J. Org. Chem. , vol.71 , pp. 8329-8351
    • Wilson, R.M.1    Danishefsky, S.J.2
  • 109
    • 0035051937 scopus 로고    scopus 로고
    • Asymmetric synthesis of the C(33)-C(37) fragment of amphotericin B
    • J. Tholander E. M. Carreira Asymmetric synthesis of the C(33)-C(37) fragment of amphotericin B Helv. Chim. Acta 2001 84 613 622
    • (2001) Helv. Chim. Acta , vol.84 , pp. 613-622
    • Tholander, J.1    Carreira, E.M.2
  • 110
    • 29044435380 scopus 로고    scopus 로고
    • Scalable synthesis of a mycosamine donor. Overcoming difficult reactivity in allose systems
    • J. M. Manthorpe A. M. Szpilman E. M. Carreira Scalable synthesis of a mycosamine donor. Overcoming difficult reactivity in allose systems Synthesis 2005 3380 3388
    • (2005) Synthesis , pp. 3380-3388
    • Manthorpe, J.M.1    Szpilman, A.M.2    Carreira, E.M.3
  • 111
    • 46749087921 scopus 로고    scopus 로고
    • Synthesis and biological studies of 35-deoxy amphotericin B methyl ester
    • A. M. Szpilman J. M. Manthorpe E. M. Carreira Synthesis and biological studies of 35-deoxy amphotericin B methyl ester Angew. Chem., Int. Ed. 2008 47 4339 4342
    • (2008) Angew. Chem., Int. Ed. , vol.47 , pp. 4339-4342
    • Szpilman, A.M.1    Manthorpe, J.M.2    Carreira, E.M.3


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