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Volumn 15, Issue 2, 2009, Pages 95-106

Effect of structural parameters of peptides on dimer formation and highly oxidized side products in the oxidation of thiols of linear analogues of human β-defensin 3 by DMSO

Author keywords

Antimicrobial peptides; Dimers; DMSO; Highly oxidized side products; Human defensin 3 (hBD3); Molecular hydrophobicity; Molecular modelling

Indexed keywords

BETA DEFENSIN; CYSTEINE; DIMER; DIMETHYL SULFOXIDE; DISULFIDE; HOMODIMER; PEPTIDE DERIVATIVE; THIOL DERIVATIVE; BETA DEFENSIN 3, HUMAN; BETA-DEFENSIN 3, HUMAN; PEPTIDE; SOLVENT;

EID: 61449100509     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.1100     Document Type: Article
Times cited : (20)

References (37)
  • 1
    • 1042278915 scopus 로고    scopus 로고
    • The relationship between peptide structure and antibacterial activity
    • Powers JP, Hancock REW. The relationship between peptide structure and antibacterial activity. Peptides 2003; 24(11): 1681-1691.
    • (2003) Peptides , vol.24 , Issue.11 , pp. 1681-1691
    • Powers, J.P.1    Hancock, R.E.W.2
  • 3
    • 0037406799 scopus 로고    scopus 로고
    • Defensin expression by the cornea: Multiple signalling pathways mediate IL-1beta stimulation of hBD-2 expression by human corneal epithelial cells
    • McDermott AM, Redfern RL, Zhang B, Pei Y, Huang L, Proske RJ. Defensin expression by the cornea: multiple signalling pathways mediate IL-1beta stimulation of hBD-2 expression by human corneal epithelial cells. Invest. Ophthalmol. Vis. Sci. 2003; 44(5): 1859-1865.
    • (2003) Invest. Ophthalmol. Vis. Sci , vol.44 , Issue.5 , pp. 1859-1865
    • McDermott, A.M.1    Redfern, R.L.2    Zhang, B.3    Pei, Y.4    Huang, L.5    Proske, R.J.6
  • 5
    • 33749127871 scopus 로고    scopus 로고
    • Defensins HNP1 and HBD2 stimulation of wound-associated responses in human conjunctival fibroblasts
    • Li J, Raghunath M, Tan D, Lareu RR, Chen Z, Beuerman RW. Defensins HNP1 and HBD2 stimulation of wound-associated responses in human conjunctival fibroblasts. Invest. Ophthalmol. Vis. Sci. 2006; 47: 3811-3819.
    • (2006) Invest. Ophthalmol. Vis. Sci , vol.47 , pp. 3811-3819
    • Li, J.1    Raghunath, M.2    Tan, D.3    Lareu, R.R.4    Chen, Z.5    Beuerman, R.W.6
  • 8
    • 33749525670 scopus 로고    scopus 로고
    • Human beta-defensin-3: A promising antimicrobial peptide
    • Batoni G, Maisetta G, Esin S, Campa M. Human beta-defensin-3: a promising antimicrobial peptide. Mini. Rev. Med. Chem. 2006; 6: 1063-1073.
    • (2006) Mini. Rev. Med. Chem , vol.6 , pp. 1063-1073
    • Batoni, G.1    Maisetta, G.2    Esin, S.3    Campa, M.4
  • 9
    • 0037040913 scopus 로고    scopus 로고
    • The solution structures of the human β defensins lead to a better understanding of the potent bactericidal activity of the HBD3 against staphylococcusaureus
    • Schibli DJ, Hunter HN, Aseyev V, Starner TD, Wiencek JM, McCray PB Jr, Tack BF, Vogel HJ. The solution structures of the human β defensins lead to a better understanding of the potent bactericidal activity of the HBD3 against staphylococcusaureus. J. Biol. Chem. 2002; 277: 8279-8289.
    • (2002) J. Biol. Chem , vol.277 , pp. 8279-8289
    • Schibli, D.J.1    Hunter, H.N.2    Aseyev, V.3    Starner, T.D.4    Wiencek, J.M.5    McCray Jr, P.B.6    Tack, B.F.7    Vogel, H.J.8
  • 10
    • 33947383052 scopus 로고    scopus 로고
    • Modelling study of dimerization in mammalian defensins
    • Suresh A, Verma C. Modelling study of dimerization in mammalian defensins. BMC Bioinformatics 2006; 7: S17.
    • (2006) BMC Bioinformatics , vol.7
    • Suresh, A.1    Verma, C.2
  • 12
    • 10344240423 scopus 로고    scopus 로고
    • Structure-activity relationships in defensin dimers, a novel link between β-defensin tertiary structure and antimicrobial activity
    • Campopiano DJ, Clarke DJ, Polfer NC, Barran PE, Langley RJ, Govan JR, Maxwell A, Dorin JR. Structure-activity relationships in defensin dimers, a novel link between β-defensin tertiary structure and antimicrobial activity. J. Biol. Chem. 2004; 279: 48671-48679.
    • (2004) J. Biol. Chem , vol.279 , pp. 48671-48679
    • Campopiano, D.J.1    Clarke, D.J.2    Polfer, N.C.3    Barran, P.E.4    Langley, R.J.5    Govan, J.R.6    Maxwell, A.7    Dorin, J.R.8
  • 14
    • 23444437935 scopus 로고    scopus 로고
    • A review of antimicrobial peptides and their therapeutic potential as antiinfective drugs
    • Gordon YJ, Romanowski EG, McDermott AM. A review of antimicrobial peptides and their therapeutic potential as antiinfective drugs. Curr. Eye Res. 2005; 30: 505-515.
    • (2005) Curr. Eye Res , vol.30 , pp. 505-515
    • Gordon, Y.J.1    Romanowski, E.G.2    McDermott, A.M.3
  • 15
    • 33845699790 scopus 로고    scopus 로고
    • Antimicrobial and host-defense peptides as new anti-infective therapeutic strategies
    • Hancock REW, Sahl HG. Antimicrobial and host-defense peptides as new anti-infective therapeutic strategies. Nat. Biotechnol. 2006; 24: 1551-1557.
    • (2006) Nat. Biotechnol , vol.24 , pp. 1551-1557
    • Hancock, R.E.W.1    Sahl, H.G.2
  • 16
    • 0035821314 scopus 로고    scopus 로고
    • Fatal attraction evaded: How pathogenic bacteria resist cationic polypeptides
    • Ganz T. Fatal attraction evaded: how pathogenic bacteria resist cationic polypeptides. J. Exp. Med. 2001; 193: F31-F34.
    • (2001) J. Exp. Med , vol.193
    • Ganz, T.1
  • 19
    • 22244480342 scopus 로고    scopus 로고
    • Structure-activity relation of human beta-defensin 3: Influence of disulfide bonds and cysteine substitution on antimicrobial activity and cytotoxicity
    • Kluver E, Schulz-Maronde S, Scheid S, Meyer B, Forssmann WG, Adermann K. Structure-activity relation of human beta-defensin 3: influence of disulfide bonds and cysteine substitution on antimicrobial activity and cytotoxicity. Biochemistry 2005; 44: 9804-9816.
    • (2005) Biochemistry , vol.44 , pp. 9804-9816
    • Kluver, E.1    Schulz-Maronde, S.2    Scheid, S.3    Meyer, B.4    Forssmann, W.G.5    Adermann, K.6
  • 20
    • 44049109194 scopus 로고    scopus 로고
    • Linear analogues of human beta-defensin 3: Concepts for design of antimicrobial peptides with reduced cytotoxicity to mammalian cells
    • Liu SP, Zhou L, Li J, Suresh A, Verma C, Foo YH, Yap E, Tan D, Beuerman R. Linear analogues of human beta-defensin 3: concepts for design of antimicrobial peptides with reduced cytotoxicity to mammalian cells. ChemBioChem 2008; 9: 964-973.
    • (2008) ChemBioChem , vol.9 , pp. 964-973
    • Liu, S.P.1    Zhou, L.2    Li, J.3    Suresh, A.4    Verma, C.5    Foo, Y.H.6    Yap, E.7    Tan, D.8    Beuerman, R.9
  • 21
    • 65949095588 scopus 로고    scopus 로고
    • For an extensive and earlier review of the course and mechanism of oxidation of biologically important SH groups see Friedman M. The Chemistry and Biochemistry of the Sulfhydryl Group in Amino Acids, Peptides, and Proteins. Pergramon Press: New York, 1973; Chapter 3
    • For an extensive and earlier review of the course and mechanism of oxidation of biologically important SH groups see Friedman M. The Chemistry and Biochemistry of the Sulfhydryl Group in Amino Acids, Peptides, and Proteins. Pergramon Press: New York, 1973; Chapter 3.
  • 22
    • 12044255356 scopus 로고
    • Disulfide bond formation in peptides by dimethyl sulfoxide. Scope and applications
    • Tam JP, Wu CR, Liu W, Zhang JW. Disulfide bond formation in peptides by dimethyl sulfoxide. Scope and applications. 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
  • 25
    • 20644449471 scopus 로고    scopus 로고
    • Modification of the generalized born model suitable for macromolecules
    • Onufriev A, Bashford D, Case DA. Modification of the generalized born model suitable for macromolecules. J. Phys. Chem. B 2000; 104: 3712-3720.
    • (2000) J. Phys. Chem. B , vol.104 , pp. 3712-3720
    • Onufriev, A.1    Bashford, D.2    Case, D.A.3
  • 26
    • 0037110472 scopus 로고    scopus 로고
    • Effective Born radii in the generalized Born approximation: The importance of being perfect
    • Onufriev A, Case DA, Bashford D. Effective Born radii in the generalized Born approximation: the importance of being perfect. J. Comput. Chem. 2002; 23: 1297-1304.
    • (2002) J. Comput. Chem , vol.23 , pp. 1297-1304
    • Onufriev, A.1    Case, D.A.2    Bashford, D.3
  • 27
    • 33646940952 scopus 로고
    • Numerical-integration of Cartesian equations of motions of a system with constraints molecular dynamics of n-alkanes
    • Ryckaert JP, Cicotti G, Berendsen HJC. Numerical-integration of Cartesian equations of motions of a system with constraints molecular dynamics of n-alkanes. J. Comput. Phys. 1977;23:327-341.
    • (1977) J. Comput. Phys , vol.23 , pp. 327-341
    • Ryckaert, J.P.1    Cicotti, G.2    Berendsen, H.J.C.3
  • 29
    • 0027043261 scopus 로고
    • Design of model amphipathic peptides having potent antimicrobial activities
    • Blondelle SE, Houghten RA. Design of model amphipathic peptides having potent antimicrobial activities. Biochemistry 1992; 31: 12688-12694.
    • (1992) Biochemistry , vol.31 , pp. 12688-12694
    • Blondelle, S.E.1    Houghten, R.A.2
  • 30
    • 0037202210 scopus 로고    scopus 로고
    • Structure-activity studies of 14-helical antimicrobial beta-peptides: Probing the relationship between conformational stability and antimicrobial potency
    • Raguse TL, Porter EA, Weisblum B, Gellman SH. Structure-activity studies of 14-helical antimicrobial beta-peptides: probing the relationship between conformational stability and antimicrobial potency. J. Am. Chem. Soc. 2002; 124: 12774-12785.
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 12774-12785
    • Raguse, T.L.1    Porter, E.A.2    Weisblum, B.3    Gellman, S.H.4
  • 31
    • 33846251959 scopus 로고    scopus 로고
    • Interplay among folding, sequence and lipophilicity in the antibacterial and hemolytic activities of alpha/ beta-Peptides
    • Schmitt MA, Weisblum B, Gellman SH. Interplay among folding, sequence and lipophilicity in the antibacterial and hemolytic activities of alpha/ beta-Peptides. J. Am. Chem. Soc. 2007; 129: 417-428.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 417-428
    • Schmitt, M.A.1    Weisblum, B.2    Gellman, S.H.3
  • 32
    • 27744493759 scopus 로고    scopus 로고
    • Correlation between the activities of alpha-helical antimicrobial peptides and hydrophobicities represented as RP HPLC retention times
    • Kim S, Kim SS, Lee BJ. Correlation between the activities of alpha-helical antimicrobial peptides and hydrophobicities represented as RP HPLC retention times. Peptides 2005; 26: 2050-2056.
    • (2005) Peptides , vol.26 , pp. 2050-2056
    • Kim, S.1    Kim, S.S.2    Lee, B.J.3
  • 33
    • 5644235408 scopus 로고    scopus 로고
    • Monitoring the hydrophilicity/ hydrophobicity of amino acid side-chains in the non-polar and polar faces of amphipathic alpha-helices by reversed-phase and hydrophilic interaction/cation-exchange chromatography
    • Hodges RS, Chen Y, Kopecky E, Mant CT. Monitoring the hydrophilicity/ hydrophobicity of amino acid side-chains in the non-polar and polar faces of amphipathic alpha-helices by reversed-phase and hydrophilic interaction/cation-exchange chromatography. J. Chromatogr., A 2004; 1053: 161-172.
    • (2004) J. Chromatogr., A , vol.1053 , pp. 161-172
    • Hodges, R.S.1    Chen, Y.2    Kopecky, E.3    Mant, C.T.4
  • 34
    • 0000448982 scopus 로고
    • Prediction of protein antigenic determinants from amino acid sequences
    • Hopp TP, Woods KR. Prediction of protein antigenic determinants from amino acid sequences. Proc. Natl. Acad. Sci. U.S.A. 1981; 78: 3824-3828.
    • (1981) Proc. Natl. Acad. Sci. U.S.A , vol.78 , pp. 3824-3828
    • Hopp, T.P.1    Woods, K.R.2
  • 35
    • 0038957558 scopus 로고
    • Oxidation of thiols and disulfides to sulfonic acids by dimethyl sulfoxide
    • Lowe OG. Oxidation of thiols and disulfides to sulfonic acids by dimethyl sulfoxide. J. Org. Chem. 1976; 41: 2061-2064.
    • (1976) J. Org. Chem , vol.41 , pp. 2061-2064
    • Lowe, O.G.1
  • 36
    • 0001110135 scopus 로고
    • Reactions of thiols with sulfoxides. I. Scope of the reaction and synthetic applications
    • Wallace TJ. Reactions of thiols with sulfoxides. I. Scope of the reaction and synthetic applications. J. Am. Chem. Soc. 1964; 86: 2018-2021.
    • (1964) J. Am. Chem. Soc , vol.86 , pp. 2018-2021
    • Wallace, T.J.1
  • 37
    • 0000443850 scopus 로고
    • Reactions of thiols with sulfoxides. II. Kinetics and mechanistic implications
    • Wallace TJ, Mahon JJ. Reactions of thiols with sulfoxides. II. Kinetics and mechanistic implications. J. Am. Chem. Soc. 1964; 86:4099-4103.
    • (1964) J. Am. Chem. Soc , vol.86 , pp. 4099-4103
    • Wallace, T.J.1    Mahon, J.J.2


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