메뉴 건너뛰기




Volumn 45, Issue 20, 2002, Pages 4494-4504

Antimicrobial peptides: Synthesis and antibacterial activity of linear and cyclic drosocin and apidaecin 1b analogues

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; APIDAECIN 1B DERIVATIVE; APIDAECIN DERIVATIVE; DROSOCIN; DROSOCIN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037179619     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm020861d     Document Type: Article
Times cited : (69)

References (43)
  • 1
    • 0027311126 scopus 로고
    • The humoral antibacterial response of Drosophila
    • Hoffmann, J. A.; Hetru, C.; Reichhart J. M. The humoral antibacterial response of Drosophila. FEBS Lett. 1993, 335, 63-66.
    • (1993) FEBS Lett. , vol.335 , pp. 63-66
    • Hoffmann, J.A.1    Hetru, C.2    Reichhart, J.M.3
  • 2
    • 0027318549 scopus 로고
    • Immune reactions in Drosophila and other insects: A model for innate immunity
    • Hultmark, D. Immune reactions in Drosophila and other insects: a model for innate immunity. Trends Genet. 1993, 9, 178-183.
    • (1993) Trends Genet. , vol.9 , pp. 178-183
    • Hultmark, D.1
  • 4
    • 0033754189 scopus 로고    scopus 로고
    • Antibacterial peptides isolated from insects
    • Otvos, L., Jr. Antibacterial Peptides isolated from insects. J. Pept. Sci. 2000, 6, 497-511.
    • (2000) J. Pept. Sci. , vol.6 , pp. 497-511
    • Otvos L., Jr.1
  • 5
    • 0002532947 scopus 로고
    • Antibacterial peptides/polypeptides in the insect host defense: A comparison with vertebrate antibacterial peptides/polypeptides
    • Hoffmann, J. A., Janeway, C. A., Natari, S., Eds.; R. G. Laudes Company: Texas
    • Hetru, C.; Bulet, P.; Cociancich, S.; Dimarcq, J.-L.; Hoffmann, D.; Hoffmann, J. A. Antibacterial peptides/polypeptides in the insect host defense: a comparison with vertebrate antibacterial peptides/polypeptides. In Phylogenetic Perspectives in Immunity: The Insect Host Defense; Hoffmann, J. A., Janeway, C. A., Natari, S., Eds.; R. G. Laudes Company: Texas, 1994; pp 43-65.
    • (1994) Phylogenetic Perspectives in Immunity: The Insect Host Defense , pp. 43-65
    • Hetru, C.1    Bulet, P.2    Cociancich, S.3    Dimarcq, J.-L.4    Hoffmann, D.5    Hoffmann, J.A.6
  • 6
    • 0032412381 scopus 로고    scopus 로고
    • Animal antimicrobial peptides: An overview
    • Andreu, D.; Rivas, L. Animal antimicrobial peptides: an overview. Biopolymers 1999, 47, 415-434.
    • (1999) Biopolymers , vol.47 , pp. 415-434
    • Andreu, D.1    Rivas, L.2
  • 8
    • 0028304808 scopus 로고
    • Novel inducible antibacterial peptides from a hemipteran insect, the sap-sucking bug Pyrrhocoris apterus
    • Cociancich, S.; Dupont, A.; Hegy, G.; Lanot, R.; Holder, F.; Hetru, C.; Hoffmann, J. A.; Bulet, P. Novel inducible antibacterial peptides from a hemipteran insect, the sap-sucking bug Pyrrhocoris apterus. Biochem. J. 1994, 300, 567-575.
    • (1994) Biochem. J. , vol.300 , pp. 567-575
    • Cociancich, S.1    Dupont, A.2    Hegy, G.3    Lanot, R.4    Holder, F.5    Hetru, C.6    Hoffmann, J.A.7    Bulet, P.8
  • 9
    • 0032513209 scopus 로고    scopus 로고
    • Isolation from an ant Myrmecia gulosa of two inducible O-glycosylated proline-rich antibacterial peptides
    • Mackintosh, J. A.; Veal, D. A.; Beattie, A. J.; Gooley, A. A. Isolation from an ant Myrmecia gulosa of two inducible O-glycosylated proline-rich antibacterial peptides. J. Biol. Chem. 1998, 273, 6139-6143.
    • (1998) J. Biol. Chem. , vol.273 , pp. 6139-6143
    • Mackintosh, J.A.1    Veal, D.A.2    Beattie, A.J.3    Gooley, A.A.4
  • 10
    • 0029055842 scopus 로고
    • Insect immunity. The inducibile antibacterial peptide diptericin carries two O-glycans necessary for biological activity
    • Bulet, P.; Hegy, G.; Van Dorsselear, A.; Hofmann, J. A.; Hetru, C. Insect immunity. The inducibile antibacterial peptide diptericin carries two O-glycans necessary for biological activity. Biochemistry 1995, 34, 7394-7410.
    • (1995) Biochemistry , vol.34 , pp. 7394-7410
    • Bulet, P.1    Hegy, G.2    Van Dorsselear, A.3    Hofmann, J.A.4    Hetru, C.5
  • 11
    • 0029051008 scopus 로고
    • A novel antibacterial peptide family isolated from silkworm, Bombyx mori
    • Hara, S,; Yamakawa, M, A novel antibacterial peptide family isolated from silkworm, Bombyx mori. Biochem. J. 1995, 310, 651-656.
    • (1995) Biochem. J. , vol.310 , pp. 651-656
    • Hara, S.1    Yamakawa, M.2
  • 12
    • 0029929079 scopus 로고    scopus 로고
    • Enlarged scale chemical synthesis and range of activity of drosocin, an O-glycosylated antibacterial peptide of Drosphila
    • Bulet, P.; Urge, L.; Ohresser, S.; Hetru, C.; Otvos, L., Jr. Enlarged scale chemical synthesis and range of activity of drosocin, an O-glycosylated antibacterial peptide of Drosphila. Eur. J. Biochem. 1996, 238, 64-69.
    • (1996) Eur. J. Biochem. , vol.238 , pp. 64-69
    • Bulet, P.1    Urge, L.2    Ohresser, S.3    Hetru, C.4    Otvos L., Jr.5
  • 13
    • 0032992923 scopus 로고
    • Range of activity and metabolic stability of synthetic antibacterial glycopeptides from insects
    • Hoffmann, R.; Bulet, P.; Urge, L.; Otvos, L., Jr. Range of activity and metabolic stability of synthetic antibacterial glycopeptides from insects. Biochem. Biophys. Acta 1995, 1426, 459-467.
    • (1995) Biochem. Biophys. Acta , vol.1426 , pp. 459-467
    • Hoffmann, R.1    Bulet, P.2    Urge, L.3    Otvos L., Jr.4
  • 14
    • 0033547753 scopus 로고    scopus 로고
    • Conformational studies by NMR of the antimicrobial peptide, drosocin, and its nonglycosylated derivative: Effect of glycosylation on solution conformation
    • McManus, A. M.; Otvos, L.; Hoffmann, R.; Craik, D. J. Conformational studies by NMR of the antimicrobial peptide, drosocin, and its nonglycosylated derivative: effect of glycosylation on solution conformation. Biochemistry 1999, 38, 705-714.
    • (1999) Biochemistry , vol.38 , pp. 705-714
    • McManus, A.M.1    Otvos, L.2    Hoffmann, R.3    Craik, D.J.4
  • 15
    • 0028286667 scopus 로고
    • Apidaecin-type peptide antibiotics function through a nonporeforming mechanism involving stereospecificity
    • Casteels, P.; Tempst, P. Apidaecin-type peptide antibiotics function through a nonporeforming mechanism involving stereospecificity. Biochem. Biophys. Res. Commun. 1994, 199, 339-345.
    • (1994) Biochem. Biophys. Res. Commun. , vol.199 , pp. 339-345
    • Casteels, P.1    Tempst, P.2
  • 16
    • 0032748297 scopus 로고    scopus 로고
    • Lethal effect of apidaecin on Escherichia coli involve sequential molecular interactions with diverse targets
    • Castle, M.; Nazarian, A.; Yi, S. S.; Tempst, P. Lethal effect of apidaecin on Escherichia coli involve sequential molecular interactions with diverse targets. J. Biol. Chem. 1999, 274, 33555-33564.
    • (1999) J. Biol. Chem. , vol.274 , pp. 33555-33564
    • Castle, M.1    Nazarian, A.2    Yi, S.S.3    Tempst, P.4
  • 17
    • 0024454751 scopus 로고
    • Apidaecins: Antibacterial peptides from honeybees
    • Casteels, P.; Ampe, C.; Jacobs, F.; Vaeck, M.; Tempst, P. Apidaecins: antibacterial peptides from honeybees. EMBO J. 1989, 8, 2387-2391.
    • (1989) EMBO J. , vol.8 , pp. 2387-2391
    • Casteels, P.1    Ampe, C.2    Jacobs, F.3    Vaeck, M.4    Tempst, P.5
  • 18
    • 0033433992 scopus 로고    scopus 로고
    • SMAP-29: A potent antibacterial and antifungal peptide from sheep leukocytes
    • Skerlavaj, B.; Benincasa, M.; Risso, A.; Zanetti, M.; Gennaro, R. SMAP-29: a potent antibacterial and antifungal peptide from sheep leukocytes. FEBS Lett. 1999, 463, 58-62.
    • (1999) FEBS Lett. , vol.463 , pp. 58-62
    • Skerlavaj, B.1    Benincasa, M.2    Risso, A.3    Zanetti, M.4    Gennaro, R.5
  • 19
    • 0025066842 scopus 로고
    • Rapid membrane permeabilization and inhibition of vital functions of gram-negative bacteria by bactenecins
    • Skerlavaj, B.; Romeo, D.; Gennaro, R. Rapid membrane permeabilization and inhibition of vital functions of gram-negative bacteria by bactenecins. Infect. Immun. 1990, 58, 3824-3730.
    • (1990) Infect. Immun. , vol.58 , pp. 3824-3730
    • Skerlavaj, B.1    Romeo, D.2    Gennaro, R.3
  • 20
    • 0002677942 scopus 로고
    • Interchain reactions (cyclo-oligomerizations) during the cyclization of resin-bound peptides
    • Goodman, M., Meienhofer, J., Eds.; J. Wiley & Sons: New York
    • Rothe, M.; Sander, A.; Fisher, W.; Mästle, W.; Nelson, B. Interchain reactions (cyclo-oligomerizations) during the cyclization of resin-bound peptides. In Peptides-Proceedings of the 5th American Peptide Symposium; Goodman, M., Meienhofer, J., Eds.; J. Wiley & Sons: New York, 1977; pp 506-509.
    • (1977) Peptides-Proceedings of the 5th American Peptide Symposium , pp. 506-509
    • Rothe, M.1    Sander, A.2    Fisher, W.3    Mästle, W.4    Nelson, B.5
  • 21
    • 0028475713 scopus 로고
    • Influence of solid support, solvent and coupling reagent on the head-to-tail cyclization of resin-bound peptides
    • McMurray, J. S.; Lewis, C. A.; Obeyesekere, N. U. Influence of solid support, solvent and coupling reagent on the head-to-tail cyclization of resin-bound peptides. Pept. Research 1994, 7, 195-206.
    • (1994) Pept. Research , vol.7 , pp. 195-206
    • McMurray, J.S.1    Lewis, C.A.2    Obeyesekere, N.U.3
  • 22
    • 12044255356 scopus 로고
    • Disulfide bond formation in peptides by dimethyl sulfoxide. Scope and limitations
    • Tam, J. P.; Wu, C. R.; Liu, W.; Zhang, J. W. Disulfide bond formation in peptides by dimethyl sulfoxide. Scope and limitations. J. Am. Chem. Soc. 1991, 113, 6657-6662.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 6657-6662
    • Tam, J.P.1    Wu, C.R.2    Liu, W.3    Zhang, J.W.4
  • 23
    • 0002940495 scopus 로고
    • Studies of theoretical circular dicroism of polypeptides
    • Blout, E. R., Bovey, F. A., Goodman, M., Lotan, M., Eds.; Wiley & Sons: New York, NY
    • Woody, R. W. Studies of theoretical circular dicroism of polypeptides. In Peptides, Polypeptides and Proteins; Blout, E. R., Bovey, F. A., Goodman, M., Lotan, M., Eds.; Wiley & Sons: New York, NY, 1994; pp 338-360.
    • (1994) Peptides, Polypeptides and Proteins , pp. 338-360
    • Woody, R.W.1
  • 24
    • 0032511944 scopus 로고    scopus 로고
    • Synthesis of an oxime-linked neoglycopeptide with glycosylation-dependent activity similar to its native counterpart
    • Marcaurelle, L. A.; Rodriguez, E. C.; Bertozzi, C. R. Synthesis of an oxime-linked neoglycopeptide with glycosylation-dependent activity similar to its native counterpart. Tetrahedron Lett. 1998, 39, 8417-8420.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 8417-8420
    • Marcaurelle, L.A.1    Rodriguez, E.C.2    Bertozzi, C.R.3
  • 27
    • 0035853022 scopus 로고    scopus 로고
    • The antibacterial peptide pyrrhocoricin inhibits the ATPase actions of DnaK and prevents chaperone-assisted protein folding
    • Kragol, G.; Lovas, S.; Varadi, G.; Condie, B. A.; Hoffmann, R.; Otvos, L., Jr. The antibacterial peptide pyrrhocoricin inhibits the ATPase actions of DnaK and prevents chaperone-assisted protein folding. Biochemistry 2001, 40, 3016-3026.
    • (2001) Biochemistry , vol.40 , pp. 3016-3026
    • Kragol, G.1    Lovas, S.2    Varadi, G.3    Condie, B.A.4    Hoffmann, R.5    Otvos L., Jr.6
  • 28
    • 0020163940 scopus 로고
    • Conformational and biological activity of cyclic peptides
    • Kessler, H. Conformational and biological activity of cyclic peptides. Angew. Chem, Int. Ed. Engl. 1982, 21, 512-523.
    • (1982) Angew. Chem., Int. Ed. Engl. , vol.21 , pp. 512-523
    • Kessler, H.1
  • 30
    • 0023920225 scopus 로고
    • Concurrent assessment of inner and outer membrane permeabilization and bacteriolysis in E. coli by multiple wavelength spectrophotometry
    • Lehrer, R. I.; Barton, A.; Ganz, T. Concurrent assessment of inner and outer membrane permeabilization and bacteriolysis in E. coli by multiple wavelength spectrophotometry. J. Immunol. Methods 1988, 108, 153-158.
    • (1988) J. Immunol. Methods , vol.108 , pp. 153-158
    • Lehrer, R.I.1    Barton, A.2    Ganz, T.3
  • 31
    • 0025051195 scopus 로고
    • Synthesis of O-glycosylated tuftsins by utilizing threonine derivatives containing an unprotected monosaccharide moiety
    • Filira, F.; Biondi, L.; Cavaggion, F.; Scolaro, B.; Rocchi, R. Synthesis of O-glycosylated tuftsins by utilizing threonine derivatives containing an unprotected monosaccharide moiety. Int. J. Pept. Protein Res. 1990, 36, 86-96.
    • (1990) Int. J. Pept. Protein Res. , vol.36 , pp. 86-96
    • Filira, F.1    Biondi, L.2    Cavaggion, F.3    Scolaro, B.4    Rocchi, R.5
  • 32
    • 0026013512 scopus 로고
    • Synthesis of glycosylated tuftsins and tuftsin-containing IgC fragment undecapeptide
    • Biondi, L.; Filira, F.; Gobbo, M.; Scolaro, B.; Rocchi, R. Synthesis of glycosylated tuftsins and tuftsin-containing IgC fragment undecapeptide. Int. J. Pept. Protein Res. 1991, 37, 112-121.
    • (1991) Int. J. Pept. Protein Res. , vol.37 , pp. 112-121
    • Biondi, L.1    Filira, F.2    Gobbo, M.3    Scolaro, B.4    Rocchi, R.5
  • 33
    • 33748233897 scopus 로고
    • Synthesis of C-glycopeptides via free radical addition of glycosyl bromides to dehydroalanine derivatives
    • Kessler, H.; Wittmann, V.; Kock, M.; Kottenhahn, M. Synthesis of C-glycopeptides via free radical addition of glycosyl bromides to dehydroalanine derivatives. Angew. Chem., Int. Ed. Engl. 1992, 31, 902-904.
    • (1992) Angew. Chem., Int. Ed. Engl. , vol.31 , pp. 902-904
    • Kessler, H.1    Wittmann, V.2    Kock, M.3    Kottenhahn, M.4
  • 34
    • 0024707204 scopus 로고
    • Unusually stable helix formation in short alanine-based peptides
    • Marqusee, S.; Robbins, V. H.; Baldwin, R. L. Unusually stable helix formation in short alanine-based peptides. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 5286-5290.
    • (1989) Proc. Natl. Acad. Sci. U.S.A. , vol.86 , pp. 5286-5290
    • Marqusee, S.1    Robbins, V.H.2    Baldwin, R.L.3
  • 35
    • 84912702945 scopus 로고
    • Quantitative monitoring of solid-phase synthesis by the ninhydrin reaction
    • Rich, D. M., Gross, E., Eds.; Pierce Chemical Co.: Rockford, IL
    • Sarin, V. K.; Kent, S. B.; Tam, J. P.; Merrifield, R. B. Quantitative monitoring of solid-phase synthesis by the ninhydrin reaction. In Peptide Structure and Biological Function; Rich, D. M., Gross, E., Eds.; Pierce Chemical Co.: Rockford, IL, 1981; pp 221-224.
    • (1981) Peptide Structure and Biological Function , pp. 221-224
    • Sarin, V.K.1    Kent, S.B.2    Tam, J.P.3    Merrifield, R.B.4
  • 36
    • 84986648460 scopus 로고
    • Head-to-tail cyclization of hexapeptide using different coupling reagents
    • Zimmer, S.; Hoffmann, E.; Jung, G.; Kessler, H. Head-to-tail cyclization of hexapeptide using different coupling reagents. Liebigs Ann. Chem. 1993, 497-501.
    • (1993) Liebigs Ann. Chem. , pp. 497-501
    • Zimmer, S.1    Hoffmann, E.2    Jung, G.3    Kessler, H.4
  • 37
    • 0025014627 scopus 로고
    • PyBOP: A new coupling reagent devoid of toxic byproducts
    • Coste, J.; Le-Nguyen, D.; Castro, B. PyBOP: a new coupling reagent devoid of toxic byproducts. Tetrahedron Lett. 1990, 31, 205-208.
    • (1990) Tetrahedron Lett. , vol.31 , pp. 205-208
    • Coste, J.1    Le-Nguyen, D.2    Castro, B.3
  • 39
    • 3042934967 scopus 로고
    • Quantitative monitoring of sufhydryl groups
    • Ellman, G. L. Quantitative monitoring of sufhydryl groups. Arch. Biochem. Biophys. 1959, 82, 70-77.
    • (1959) Arch. Biochem. Biophys. , vol.82 , pp. 70-77
    • Ellman, G.L.1
  • 40
    • 0031725844 scopus 로고    scopus 로고
    • Biological characterization of a novel mammalian antimicrobial peptide
    • Gennaro, R.; Scocchi, M.; Merluzzi, M; Zanetti, M. Biological characterization of a novel mammalian antimicrobial peptide. Biochim. Biophys. Acta 1998, 1425, 361-368.
    • (1998) Biochim. Biophys. Acta , vol.1425 , pp. 361-368
    • Gennaro, R.1    Scocchi, M.2    Merluzzi, M.3    Zanetti, M.4
  • 41
    • 0025175731 scopus 로고
    • Hemolysis of erythrocytes and fluorescence polarization changes elicited by peptide toxins, aliphatic alcohols, related glycols and benzylidene derivatives
    • Osorio e Castro, V. R.; Ashwood, E. R.; Wood, S. G.; Vernon, L. P. Hemolysis of erythrocytes and fluorescence polarization changes elicited by peptide toxins, aliphatic alcohols, related glycols and benzylidene derivatives. Biochim. Biophys. Acta 1990, 1029, 252-258.
    • (1990) Biochim. Biophys. Acta , vol.1029 , pp. 252-258
    • Osorio e Castro, V.R.1    Ashwood, E.R.2    Wood, S.G.3    Vernon, L.P.4
  • 42
    • 0028876215 scopus 로고
    • Enhanced membrane-perturbing activities of bundled amphiphilic α-helical polypeptides on interaction with phospholipid bilayer
    • Sakamoto, S.; Mihara, H.; Matsuo, E.; Niidome, T.; Anzai, K.; Kirino, Y.; Aoyagi, H. Enhanced membrane-perturbing activities of bundled amphiphilic α-helical polypeptides on interaction with phospholipid bilayer. Bull. Chem. Soc. Jpn. 1995, 68, 2931-2939.
    • (1995) Bull. Chem. Soc. Jpn. , vol.68 , pp. 2931-2939
    • Sakamoto, S.1    Mihara, H.2    Matsuo, E.3    Niidome, T.4    Anzai, K.5    Kirino, Y.6    Aoyagi, H.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.