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Volumn 38, Issue 17, 1995, Pages 3271-3281

Semisynthetic Chemical Modification of the Antifungal Lipopeptide Echinocandin B (ECB): Structure-Activity Studies of the Lipophilic and Geometric Parameters of Polyarylated Acyl Analogs of ECB

Author keywords

[No Author keywords available]

Indexed keywords

ACULEACIN A; AMPHOTERICIN B; ANIDULAFUNGIN; CILOFUNGIN; ECHINOCANDIN B; ECHINOCANDIN B DERIVATIVE; FLUCONAZOLE; GLUCAN SYNTHASE; ITRACONAZOLE; LINOLEIC ACID; LIPOPEPTIDE;

EID: 0029154315     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm00017a012     Document Type: Article
Times cited : (103)

References (45)
  • 2
    • 85047696806 scopus 로고
    • Opportunistic Mycoses in the Immunocompromised Host: Experience at the Cancer Center and Review
    • Anaissie, E. Opportunistic Mycoses in the Immunocompromised Host: Experience at the Cancer Center and Review. Clin. Infect. Dis. 1992, 14 (Suppl. 1), S43-S53.
    • (1992) Clin. Infect. Dis. , vol.14 , pp. S43-S53
    • Anaissie, E.1
  • 3
    • 0025256091 scopus 로고
    • Amphotericin B: 30 Years of Clinical Experience
    • Gallis, H. A.; Drew, R. H.; Pickard, W. W. Amphotericin B: 30 Years of Clinical Experience. Rev. Infect. Dis. 1990, 12, 308-329.
    • (1990) Rev. Infect. Dis. , vol.12 , pp. 308-329
    • Gallis, H.A.1    Drew, R.H.2    Pickard, W.W.3
  • 4
  • 5
    • 84912958397 scopus 로고
    • Systemic Azole Antifungal Drugs-Into the 1990’s
    • Ryley, J. F., Ed.; Springer-Verlag: New York
    • Graybill, J. R. Systemic Azole Antifungal Drugs-Into the 1990’s. In Handbook of Experimental Pharmocol. Vol. 96, Chemotherap. of Fungal Diseases; Ryley, J. F., Ed.; Springer-Verlag: New York, 1990; pp 455-482.
    • (1990) Handbook of Experimental Pharmocol. Chemotherap. of Fungal Diseases , vol.96 , pp. 455-482
    • Graybill, J.R.1
  • 7
    • 0021224331 scopus 로고
    • In Vitro and In Vivo Anti-Candida Activity and Toxicology of LY121019
    • Gordee, R. S.; Zeckner, D. J.; Ellis, L. F.; Thakkar, A. L.; Howard, L. C. In Vitro and In Vivo Anti-Candida Activity and Toxicology of LY121019. J. Antibiot. 1984, 37, 1054-1065.
    • (1984) J. Antibiot. , vol.37 , pp. 1054-1065
    • Gordee, R.S.1    Zeckner, D.J.2    Ellis, L.F.3    Thakkar, A.L.4    Howard, L.C.5
  • 8
    • 0020060160 scopus 로고
    • Studies of the Mechanism of Antifungal Action of Aculeacin A
    • Yamaguchi, H.; Hiratani, T.; Iwata, K.; Yamamoto, Y. Studies of the Mechanism of Antifungal Action of Aculeacin A. J. Antibiot. 1982, 35, 210-219.
    • (1982) J. Antibiot. , vol.35 , pp. 210-219
    • Yamaguchi, H.1    Hiratani, T.2    Iwata, K.3    Yamamoto, Y.4
  • 9
    • 0021145336 scopus 로고
    • Echinocandin Inhibition of 1, 3-Beta-D-glucan Synthase from Candida albicans
    • Sawistowska-Schroder, E. T.; Kerridge, D.; Perry, H. Echinocandin Inhibition of 1, 3-Beta-D-glucan Synthase from Candida albicans. FEBS Lett. 1984, 173, 134-138.
    • (1984) FEBS Lett. , vol.173 , pp. 134-138
    • Sawistowska-Schroder, E.T.1    Kerridge, D.2    Perry, H.3
  • 10
    • 0027439619 scopus 로고
    • Compounds Active Against Cell Walls of Medically Important Fungi
    • Hector, R. F. Compounds Active Against Cell Walls of Medically Important Fungi. Clin. Microbiol. Rev. 1993, 6, 1-21.
    • (1993) Clin. Microbiol. Rev. , vol.6 , pp. 1-21
    • Hector, R.F.1
  • 12
    • 0024509615 scopus 로고
    • Yeast Glucan in the Cyst Wall of Pneumocystis carinii
    • Matsumoto, Y.; Matsuda, S.; Tegoshi, T. Yeast Glucan in the Cyst Wall of Pneumocystis carinii. J. Protozool. 1989, 36, 21S-22S.
    • (1989) J. Protozool. , vol.36 , pp. 21S-22S
    • Matsumoto, Y.1    Matsuda, S.2    Tegoshi, T.3
  • 13
    • 0018418194 scopus 로고
    • Biosynthesis of Cell Walls of Fungi
    • Farkas, V. Biosynthesis of Cell Walls of Fungi. Microbiol. Rev. 1979, 43, 117-144.
    • (1979) Microbiol. Rev. , vol.43 , pp. 117-144
    • Farkas, V.1
  • 14
    • 0025079779 scopus 로고
    • Fungal Cell Walls: Their Structure, Biosynthesis and Biotechnological Aspects
    • Farkas, V. Fungal Cell Walls: Their Structure, Biosynthesis and Biotechnological Aspects. Acta Biotechnol. 1990, 10, 225-238.
    • (1990) Acta Biotechnol. , vol.10 , pp. 225-238
    • Farkas, V.1
  • 15
    • 0003007762 scopus 로고
    • Fungal Cell Walls - A Review
    • Kuhn, A., Trinci, P. J., Jung, M. J., Goosey, M. W., Copping, L. G., Eds.; Springer-Verlag: Berlin/New York
    • Peberdy, J. F. Fungal Cell Walls - A Review. In Biochemistry of Cell Walls and Membranes In Fungi; Kuhn, A., Trinci, P. J., Jung, M. J., Goosey, M. W., Copping, L. G., Eds.; Springer-Verlag: Berlin/New York, 1990; pp 5-24.
    • (1990) Biochemistry of Cell Walls and Membranes In Fungi , pp. 5-24
    • Peberdy, J.F.1
  • 16
    • 0023736454 scopus 로고
    • Cilofungin (LY121019) Inhibits Candida albicans (1-3)-β-D-Glucan Synthase Activity
    • Taft, C. S.; Stark, T.; Selitrennikoff, C. P. Cilofungin (LY121019) Inhibits Candida albicans (1-3)-β-D-Glucan Synthase Activity. Antimicrob. Agents Chemother. 1988, 32, 1901-1903.
    • (1988) Antimicrob. Agents Chemother. , vol.32 , pp. 1901-1903
    • Taft, C.S.1    Stark, T.2    Selitrennikoff, C.P.3
  • 17
    • 0022500297 scopus 로고
    • Cell Wall of Pathogenic Yeasts and Implication for Antimycotic Therapy
    • Cassone, A. Cell Wall of Pathogenic Yeasts and Implication for Antimycotic Therapy. Drugs Exp. Clin. Res. 1986, 12, 635-643.
    • (1986) Drugs Exp. Clin. Res. , vol.12 , pp. 635-643
    • Cassone, A.1
  • 18
    • 2842604602 scopus 로고
    • The Fungal Cell Wall - A Target for Lipopeptide Antifungal Agents
    • Fernandes, P. B., Ed.; Birkhauser: Boston, MA
    • Gordee, R. S.; Debono, M.; Parr, T. R., Jr. The Fungal Cell Wall - A Target for Lipopeptide Antifungal Agents. In New Approaches for Antifungal Drugs; Fernandes, P. B., Ed.; Birkhauser: Boston, MA, 1992; pp 46-63.
    • (1992) New Approaches for Antifungal Drugs , pp. 46-63
    • Gordee, R.S.1    Debono, M.2    Parr, T.R.3
  • 19
    • 0028004384 scopus 로고
    • Antibiotics That Inhibit Fungal Cell Wall Development
    • Debono, M.; Gordee, R. S. Antibiotics That Inhibit Fungal Cell Wall Development. Annu. Rev. Microbiol. 1994, 48, 471-497.
    • (1994) Annu. Rev. Microbiol. , vol.48 , pp. 471-497
    • Debono, M.1    Gordee, R.S.2
  • 20
    • 0028004384 scopus 로고
    • Antibiotics That Inhibit Fungal Cell Wall Development
    • Debono, M.; Gordee, R. S. Antibiotics That Inhibit Fungal Cell Wall Development. Annu. Rev. Microbiol. 1994, 48, 471-497.
    • (1994) Annu. Rev. Microbiol. , vol.48 , pp. 471-497
    • Debono, M.1    Gordee, R.S.2
  • 24
    • 0016338169 scopus 로고
    • Echinocandin B, a new polypeptide antibiotic from Aspergillus nidulans var echinulatus. Isolation and components
    • Echinocandin B, a new polypeptide antibiotic from Aspergillus nidulans var echinulatus. Isolation and components. Helv. Chim. Acta 1974, 57, 2459-2477.
    • (1974) Helv. Chim. Acta , vol.57 , pp. 2459-2477
  • 25
    • 0023134763 scopus 로고
    • Mulundocandin, a New Lipopeptide Antibiotic. I. Taxonomy, Fermentation, Isolation and Characterization
    • Roy, K.; Mukhopadhyay, T.; Reddy, G. C. S.; Desikan, K. R.; Ganguli, B. N. Mulundocandin, a New Lipopeptide Antibiotic. I. Taxonomy, Fermentation, Isolation and Characterization. J. Antibiot. 1987, 40, 275-280.
    • (1987) J. Antibiot. , vol.40 , pp. 275-280
    • Roy, K.1    Mukhopadhyay, T.2    Reddy, G.C.S.3    Desikan, K.R.4    Ganguli, B.N.5
  • 26
    • 0024502955 scopus 로고
    • 1-671, 329, a New Antifungal Agent. I. Fermentation and Isolation
    • Schwartz, R. E.; Giacobbe, R. A.; Bland, J. A.; Monaghan, R. L. 1-671, 329, a New Antifungal Agent. I. Fermentation and Isolation. J. Antibiot. 1989, 42, 163-167.
    • (1989) J. Antibiot. , vol.42 , pp. 163-167
    • Schwartz, R.E.1    Giacobbe, R.A.2    Bland, J.A.3    Monaghan, R.L.4
  • 30
    • 0002911070 scopus 로고
    • Chemical and Structure-Activity Studies of the Echinocandin Lipopeptides
    • Rippon, J. W., Fromtling, R. A., Eds.; Marcel Dekker: New York
    • Hammond, M. L. Chemical and Structure-Activity Studies of the Echinocandin Lipopeptides. In Cutaneous Antifungal Agents; Rippon, J. W., Fromtling, R. A., Eds.; Marcel Dekker: New York, 1993; pp 395-420.
    • (1993) Cutaneous Antifungal Agents , pp. 395-420
    • Hammond, M.L.1
  • 31
  • 32
    • 0025887095 scopus 로고
    • Efficacy of Cilofungin Alone and in Combination with Amphotericin B in a Murine Model of Disseminated Aspergillosis
    • Denning, D. W.; Stevens, D. A. Efficacy of Cilofungin Alone and in Combination with Amphotericin B in a Murine Model of Disseminated Aspergillosis. Antimicrob. Agents Chemother. 1991, 35, 1329-1333.
    • (1991) Antimicrob. Agents Chemother. , vol.35 , pp. 1329-1333
    • Denning, D.W.1    Stevens, D.A.2
  • 33
    • 0025292280 scopus 로고
    • Cilofungin Inhibition of (1, 3)-β-Glucan Synthase: The Lipophilic Side Chain is Essential for Inhibition of Enzyme Activity
    • Taft, C. S.; Selitrennikoff, C. P. Cilofungin Inhibition of (1, 3)-β-Glucan Synthase: The Lipophilic Side Chain is Essential for Inhibition of Enzyme Activity. J. Antibiot. 1990, 43, 433-437.
    • (1990) J. Antibiot. , vol.43 , pp. 433-437
    • Taft, C.S.1    Selitrennikoff, C.P.2
  • 34
    • 0024603393 scopus 로고
    • Deacylation of Echinocandin B by Actinoplanes utahensis
    • Boeck, L. D.; Fukuda, D. S.; Abbott, B. J.; Debono, M. Deacylation of Echinocandin B by Actinoplanes utahensis. J. Antibiot. 1989, 42, 382-388.
    • (1989) J. Antibiot. , vol.42 , pp. 382-388
    • Boeck, L.D.1    Fukuda, D.S.2    Abbott, B.J.3    Debono, M.4
  • 35
    • 0024519380 scopus 로고
    • Synthesis of New Analogs of Echinocandin B by Enzymatic Deacylation and Chemical Reacylation of the Echinocandin B Peptide: Synthesis of the Antifungal Agent Cilogungin (LY121019)
    • Debono, M.; Abbott, B. J.; Fukuda, D. S.; Barnhart, M.; Willard, K. E.; Molloy, R. M.; Michel, K. H.; Turner, J. R.; Butler, T. F.; Hunt, A. H. Synthesis of New Analogs of Echinocandin B by Enzymatic Deacylation and Chemical Reacylation of the Echinocandin B Peptide: Synthesis of the Antifungal Agent Cilogungin (LY121019). J. Antibiot. 1989, 42, 389-397.
    • (1989) J. Antibiot. , vol.42 , pp. 389-397
    • Debono, M.1    Abbott, B.J.2    Fukuda, D.S.3    Barnhart, M.4    Willard, K.E.5    Molloy, R.M.6    Michel, K.H.7    Turner, J.R.8    Butler, T.F.9    Hunt, A.H.10
  • 37
    • 84947151032 scopus 로고
    • The Palladium-catalyzed Cross-Coupling Reaction of Phenylboronic Acid with Haloarenes in the Presence of Bases
    • Suzuki, A.; Miyaura, N.; Yanagi, T. The Palladium-catalyzed Cross-Coupling Reaction of Phenylboronic Acid with Haloarenes in the Presence of Bases. Synth. Commun. 1981, 11, 513-519.
    • (1981) Synth. Commun. , vol.11 , pp. 513-519
    • Suzuki, A.1    Miyaura, N.2    Yanagi, T.3
  • 39
    • 0011492979 scopus 로고
    • Alkylation of Aromatics with Haloalkanes
    • Olah, G. A., Ed.; John Wiley & Sons Publishers: New York
    • Drahowzal, F. A. Alkylation of Aromatics with Haloalkanes. In Friedel-Crafts and Related Reactions Vol. 2 Part 1; Olah, G. A., Ed.; John Wiley & Sons Publishers: New York, 1964; pp 417-475.
    • (1964) Friedel-Crafts and Related Reactions , vol.2 , pp. 417-475
    • Drahowzal, F.A.1
  • 40
    • 0026060730 scopus 로고
    • W-1 Solubilization and Kinetics of Inhibition by Cilofungin of Candida albicans (1, 3)-β-D-Glucan Synthase
    • Tang, J.; Parr, T. R., Jr. W-1 Solubilization and Kinetics of Inhibition by Cilofungin of Candida albicans (1, 3)-β-D-Glucan Synthase. Antimicrob. Agents Chemother. 1991, 35, 99-103.
    • (1991) Antimicrob. Agents Chemother. , vol.35 , pp. 99-103
    • Tang, J.1    Parr, T.R.2
  • 41
    • 0023546523 scopus 로고
    • Hydrophobicity and Central Nervous System Agents: on the Principle of Minimal Hydrophobicity in Drug Design
    • Hansch, C.; Bjorkroth, J. P.; Leo, A. Hydrophobicity and Central Nervous System Agents: on the Principle of Minimal Hydrophobicity in Drug Design. J. Pharm. Sci. 1987, 79, 663-687.
    • (1987) J. Pharm. Sci. , vol.79 , pp. 663-687
    • Hansch, C.1    Bjorkroth, J.P.2    Leo, A.3
  • 43
    • 85022753895 scopus 로고
    • Unpublished work, Lilly Research Laboratories
    • Boyd, D. B. Unpublished work, Lilly Research Laboratories, 1984-1986.
    • (1984)
    • Boyd, D.B.1
  • 44
    • 0018607849 scopus 로고
    • The Hydrophobie Fragmental Constant: an Extension to a 1000 Data Point Set
    • Rekker, R. F.; de Kort, H. M. The Hydrophobie Fragmental Constant: an Extension to a 1000 Data Point Set. Eur. J. Med. Chem. 1979, 14, 479-488.
    • (1979) Eur. J. Med. Chem. , vol.14 , pp. 479-488
    • Rekker, R.F.1    de Kort, H.M.2
  • 45
    • 33745158157 scopus 로고
    • A Simple Method for Estimating 50 per cent Endpoints
    • Reed, F. J.; Muench, H. A Simple Method for Estimating 50 per cent Endpoints. Am. J. Hyg. 1938, 27, 493-497.
    • (1938) Am. J. Hyg. , vol.27 , pp. 493-497
    • Reed, F.J.1    Muench, H.2


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