메뉴 건너뛰기




Volumn 63, Issue 4, 2009, Pages 687-698

Increased hydrophobic interactions of iclaprim with Staphylococcus aureus dihydrofolate reductase are responsible for the increase in affinity and antibacterial activity

Author keywords

DHFR; MRSA; Trimethoprim; X ray crystallography

Indexed keywords

DIHYDROFOLATE REDUCTASE; ICLAPRIM; SULFAMETHOXAZOLE; TRIMETHOPRIM;

EID: 62549149036     PISSN: 03057453     EISSN: 14602091     Source Type: Journal    
DOI: 10.1093/jac/dkp024     Document Type: Article
Times cited : (93)

References (51)
  • 1
    • 14844342386 scopus 로고    scopus 로고
    • DNA and RNA synthesis: Antifolates
    • Kompis IM, Islam K, Then RL. DNA and RNA synthesis: Antifolates. Chem Rev 2005; 105: 593-620.
    • (2005) Chem Rev , vol.105 , pp. 593-620
    • Kompis, I.M.1    Islam, K.2    Then, R.L.3
  • 2
    • 1942423110 scopus 로고    scopus 로고
    • Antimicrobial dihydrofolate reductase inhibitors - achievements and future options: Review
    • Then RL. Antimicrobial dihydrofolate reductase inhibitors - achievements and future options: Review. J Chemother 2004; 16: 3-12.
    • (2004) J Chemother , vol.16 , pp. 3-12
    • Then, R.L.1
  • 3
    • 33644508373 scopus 로고    scopus 로고
    • Dihydrofolate reductase inhibitors as antibacterial agents
    • Hawser S, Lociuro S, Islam K. Dihydrofolate reductase inhibitors as antibacterial agents. Biochem Pharmacol 2006; 71: 941-8.
    • (2006) Biochem Pharmacol , vol.71 , pp. 941-948
    • Hawser, S.1    Lociuro, S.2    Islam, K.3
  • 4
  • 5
    • 0022623252 scopus 로고
    • Mechanism of inhibition of dihydrofolate reductases from bacterial and vertebrate sources by various classes of folate analogues
    • Stone SR, Morrison JF. Mechanism of inhibition of dihydrofolate reductases from bacterial and vertebrate sources by various classes of folate analogues. Biochim Biophys Acta 1986; 869: 275-85.
    • (1986) Biochim Biophys Acta , vol.869 , pp. 275-285
    • Stone, S.R.1    Morrison, J.F.2
  • 6
    • 1642458261 scopus 로고    scopus 로고
    • Trimethoprim/sulfamethoxazole for treatment of severe Staphylococcus aureus infections
    • Adra M, Lawrence KR. Trimethoprim/sulfamethoxazole for treatment of severe Staphylococcus aureus infections. Ann Pharmacother 2004; 38: 338-41.
    • (2004) Ann Pharmacother , vol.38 , pp. 338-341
    • Adra, M.1    Lawrence, K.R.2
  • 7
    • 13544252542 scopus 로고    scopus 로고
    • Trimethoprim-sulfamethoxazole as a viable treatment option for infections caused by methicillin-resistant Staphylococcus aureus
    • Grim SA, Rapp RP, Martin CA et al. Trimethoprim-sulfamethoxazole as a viable treatment option for infections caused by methicillin-resistant Staphylococcus aureus. Pharmacotherapy 2005; 25: 253-64.
    • (2005) Pharmacotherapy , vol.25 , pp. 253-264
    • Grim, S.A.1    Rapp, R.P.2    Martin, C.A.3
  • 8
    • 27744533014 scopus 로고    scopus 로고
    • Treatment approaches for community-acquired methicillin-resistant Staphylococcus aureus infections
    • Ellis MW, Lewis JS. Treatment approaches for community-acquired methicillin-resistant Staphylococcus aureus infections. Curr Opin Infect Dis 2005; 18: 496-501.
    • (2005) Curr Opin Infect Dis , vol.18 , pp. 496-501
    • Ellis, M.W.1    Lewis, J.S.2
  • 9
  • 10
    • 33645114935 scopus 로고    scopus 로고
    • The growing menace of community-acquired methicillin-resistant Staphylococcus aureus
    • Moellering RC. The growing menace of community-acquired methicillin-resistant Staphylococcus aureus. Ann Intern Med 2006; 144: 368-70.
    • (2006) Ann Intern Med , vol.144 , pp. 368-370
    • Moellering, R.C.1
  • 11
    • 0029942660 scopus 로고    scopus 로고
    • Co-trimoxazole: Rationale for re-examining its indication for use
    • Howe RA, Spencer RC. Co-trimoxazole: Rationale for re-examining its indication for use. Drug Saf 1996; 14: 213-8.
    • (1996) Drug Saf , vol.14 , pp. 213-218
    • Howe, R.A.1    Spencer, R.C.2
  • 12
    • 26444491047 scopus 로고    scopus 로고
    • Resistance to antibiotics: Are we in the post-antibiotic era?
    • Alanis AJ. Resistance to antibiotics: Are we in the post-antibiotic era? Arch Med Res 2005; 36: 697-705.
    • (2005) Arch Med Res , vol.36 , pp. 697-705
    • Alanis, A.J.1
  • 13
    • 33845719824 scopus 로고    scopus 로고
    • Antimicrobial resistance: Current status and future direction
    • Saubolle MA. Antimicrobial resistance: Current status and future direction. Am J Rhinol 2006; 20: 667-71.
    • (2006) Am J Rhinol , vol.20 , pp. 667-671
    • Saubolle, M.A.1
  • 14
    • 33645750989 scopus 로고    scopus 로고
    • The importance of the development of antibiotic resistance in Staphylococcus aureus
    • Schito GC. The importance of the development of antibiotic resistance in Staphylococcus aureus. Clin Microbiol Infect 2006; 12 Suppl 1: 3-8.
    • (2006) Clin Microbiol Infect , vol.12 , Issue.SUPPL. 1 , pp. 3-8
    • Schito, G.C.1
  • 15
    • 0035746934 scopus 로고    scopus 로고
    • The VISA/GISA problem: Therapeutic implications
    • Linares J. The VISA/GISA problem: Therapeutic implications. Clin Microbiol Infect 2001; 7 Suppl 4: 8-15.
    • (2001) Clin Microbiol Infect , vol.7 , Issue.SUPPL. 4 , pp. 8-15
    • Linares, J.1
  • 16
    • 0020561080 scopus 로고
    • Evidence for a slowing in trimethoprim resistance during 1981: A comparison with earlier years
    • Brumfitt W, Hamilton-Miller JM, Wood A. Evidence for a slowing in trimethoprim resistance during 1981: A comparison with earlier years. J Antimicrob Chemother 1983; 11: 503-9.
    • (1983) J Antimicrob Chemother , vol.11 , pp. 503-509
    • Brumfitt, W.1    Hamilton-Miller, J.M.2    Wood, A.3
  • 17
    • 0026566669 scopus 로고
    • Frequency and transferability of trimethoprim and sulfonamide resistance in methicillin-resistant Staphylococcus aureus and Staphylococcus epidermidis
    • Then RL, Kohl I, Burdeska A. Frequency and transferability of trimethoprim and sulfonamide resistance in methicillin-resistant Staphylococcus aureus and Staphylococcus epidermidis. J Chemother 1992; 4: 67-71.
    • (1992) J Chemother , vol.4 , pp. 67-71
    • Then, R.L.1    Kohl, I.2    Burdeska, A.3
  • 18
    • 45749153369 scopus 로고    scopus 로고
    • Susceptibility of Staphylococcus aureus isolated from skin and wound infections in the United States 2005-07: Laboratory-based surveillance study
    • Tillotson G, Draghi D, Sahm D et al. Susceptibility of Staphylococcus aureus isolated from skin and wound infections in the United States 2005-07: Laboratory-based surveillance study. J Antimicrob Chemother 2008; 62: 109-15.
    • (2008) J Antimicrob Chemother , vol.62 , pp. 109-115
    • Tillotson, G.1    Draghi, D.2    Sahm, D.3
  • 19
    • 0029166664 scopus 로고
    • Cloning and characterization of a novel, plasmid-encoded trimethoprim-resistant dihydrofolate reductase from Staphylococcus haemolyticus MUR313
    • Dale GE, Langen H, Page MG et al. Cloning and characterization of a novel, plasmid-encoded trimethoprim-resistant dihydrofolate reductase from Staphylococcus haemolyticus MUR313. Antimicrob Agents Chemother 1995; 39: 1920-4.
    • (1995) Antimicrob Agents Chemother , vol.39 , pp. 1920-1924
    • Dale, G.E.1    Langen, H.2    Page, M.G.3
  • 20
    • 0024458146 scopus 로고
    • Trimethoprim resistance transposon Tn4003 from Staphylococcus aureus encodes genes for a dihydrofolate reductase and thymidylate synthetase flanked by three copies of IS257
    • Rouch DA, Messerotti LJ, Loo LS et al. Trimethoprim resistance transposon Tn4003 from Staphylococcus aureus encodes genes for a dihydrofolate reductase and thymidylate synthetase flanked by three copies of IS257. Mol Microbiol 1989; 3: 161-75.
    • (1989) Mol Microbiol , vol.3 , pp. 161-175
    • Rouch, D.A.1    Messerotti, L.J.2    Loo, L.S.3
  • 21
    • 24144502081 scopus 로고    scopus 로고
    • Cloning and characterization of a novel trimethoprim-resistant dihydrofolate reductase from a nosocomial isolate of Staphylococcus aureus CM.S2 (IMCJ1454)
    • Sekiguchi J, Tharavichitkul P, Miyoshi-Akiyama T et al. Cloning and characterization of a novel trimethoprim-resistant dihydrofolate reductase from a nosocomial isolate of Staphylococcus aureus CM.S2 (IMCJ1454). Antimicrob Agents Chemother 2005; 49: 3948-51.
    • (2005) Antimicrob Agents Chemother , vol.49 , pp. 3948-3951
    • Sekiguchi, J.1    Tharavichitkul, P.2    Miyoshi-Akiyama, T.3
  • 22
    • 0029011953 scopus 로고
    • Characterization of the gene for the chromosomal dihydrofolate reductase (DHFR) of Staphylococcus epidermidis ATCC 14990: The origin of the trimethoprim-resistant S1 DHFR from Staphylococcus aureus?
    • Dale GE, Broger C, Hartman PG et al. Characterization of the gene for the chromosomal dihydrofolate reductase (DHFR) of Staphylococcus epidermidis ATCC 14990: The origin of the trimethoprim-resistant S1 DHFR from Staphylococcus aureus? J Bacteriol 1995; 177: 2965-70.
    • (1995) J Bacteriol , vol.177 , pp. 2965-2970
    • Dale, G.E.1    Broger, C.2    Hartman, P.G.3
  • 23
    • 0031566958 scopus 로고    scopus 로고
    • A single amino acid substitution in Staphylococcus aureus dihydrofolate reductase determines trimethoprim resistance
    • Dale GE, Broger C, D'Arcy A et al. A single amino acid substitution in Staphylococcus aureus dihydrofolate reductase determines trimethoprim resistance. J Mol Biol 1997; 266: 23-30.
    • (1997) J Mol Biol , vol.266 , pp. 23-30
    • Dale, G.E.1    Broger, C.2    D'Arcy, A.3
  • 24
    • 38849190721 scopus 로고    scopus 로고
    • Peppard WJ, Schuenke CD. Iclaprim, a diaminopyrimidine dihydrofolate reductase inhibitor for the potential treatment of antibiotic-resistant staphylococcal infections. Curr Opin Invest Drugs 2008; 9: 210-25.
    • Peppard WJ, Schuenke CD. Iclaprim, a diaminopyrimidine dihydrofolate reductase inhibitor for the potential treatment of antibiotic-resistant staphylococcal infections. Curr Opin Invest Drugs 2008; 9: 210-25.
  • 25
    • 0242569143 scopus 로고    scopus 로고
    • Schneider P, Hawser S, Islam K. Iclaprim, a novel diaminopyrimidine with potent activity on trimethoprim sensitive and resistant bacteria. Bioorg Med Chem Lett 2003; 13: 4217-21.
    • Schneider P, Hawser S, Islam K. Iclaprim, a novel diaminopyrimidine with potent activity on trimethoprim sensitive and resistant bacteria. Bioorg Med Chem Lett 2003; 13: 4217-21.
  • 28
    • 0028103275 scopus 로고
    • Number 4. The CCP4 suite: Programs for protein crystallography
    • Collaborative Computational Project
    • Collaborative Computational Project, Number 4. The CCP4 suite: Programs for protein crystallography. Acta Crystallogr D Biol Crystallogr 1994; 50: 760-3.
    • (1994) Acta Crystallogr D Biol Crystallogr , vol.50 , pp. 760-763
  • 29
    • 0026908615 scopus 로고
    • Peptide mechanics: A force field for peptides and proteins working with entire residues as smallest units
    • Gerber P. Peptide mechanics: A force field for peptides and proteins working with entire residues as smallest units. Biopolymers 1992; 32: 1003-17.
    • (1992) Biopolymers , vol.32 , pp. 1003-1017
    • Gerber, P.1
  • 31
    • 0007899146 scopus 로고
    • Accurate bond and angle parameters for X-ray protein refinement
    • Engh R, Huber R. Accurate bond and angle parameters for X-ray protein refinement. Acta Crystallogr 1991; A47: 961-3.
    • (1991) Acta Crystallogr , vol.A47 , pp. 961-963
    • Engh, R.1    Huber, R.2
  • 32
    • 0026597444 scopus 로고
    • R value: A novel statistical quantity for assessing the accuracy of crystal structures
    • Brünger AT. Free R value: A novel statistical quantity for assessing the accuracy of crystal structures. Nature 1992; 355: 472-5.
    • (1992) Nature , vol.355 , pp. 472-475
    • Free, B.A.T.1
  • 33
    • 0000243829 scopus 로고
    • PROCHECK: A program to check the stereochemical quality of protein structures
    • Laskowski RA, MacArthur MW, Moss DS et al. PROCHECK: A program to check the stereochemical quality of protein structures. J Appl Crystallogr 1993; 26: 283-91.
    • (1993) J Appl Crystallogr , vol.26 , pp. 283-291
    • Laskowski, R.A.1    MacArthur, M.W.2    Moss, D.S.3
  • 34
    • 0026244229 scopus 로고
    • MOLSCRIPT: A program to produce both detailed and schematic plots of protein structures
    • Kraulis PJ. MOLSCRIPT: A program to produce both detailed and schematic plots of protein structures. J Appl Crystallogr 1991; 26: 946-50.
    • (1991) J Appl Crystallogr , vol.26 , pp. 946-950
    • Kraulis, P.J.1
  • 35
    • 0030815133 scopus 로고    scopus 로고
    • Raster3D: Photorealistic molecular graphics
    • Merrit EA, Bacon DJ. Raster3D: Photorealistic molecular graphics. Methods Enzymol 1997; 277: 505-24.
    • (1997) Methods Enzymol , vol.277 , pp. 505-524
    • Merrit, E.A.1    Bacon, D.J.2
  • 38
  • 39
    • 34250641961 scopus 로고    scopus 로고
    • Isothermal titration calorimetry to determine association constants for high-affinity ligands
    • Velazquez-Campoy A, Freire E. Isothermal titration calorimetry to determine association constants for high-affinity ligands. Nat Protoc 2006; 1: 186-91.
    • (2006) Nat Protoc , vol.1 , pp. 186-191
    • Velazquez-Campoy, A.1    Freire, E.2
  • 40
    • 85005688722 scopus 로고
    • A comparison of the binding of the ligand trimethoprim to bacterial and vertebrate dihydrofolate reductase
    • Roberts VA, Dauber-Osguthorpe P, Osguthorpe DJ et al. A comparison of the binding of the ligand trimethoprim to bacterial and vertebrate dihydrofolate reductase. Isr J Chem 1986; 2: 198-210.
    • (1986) Isr J Chem , vol.2 , pp. 198-210
    • Roberts, V.A.1    Dauber-Osguthorpe, P.2    Osguthorpe, D.J.3
  • 41
    • 0026076664 scopus 로고
    • Extracting hydrophobic free energies from experimental data: Relationship to protein folding and theoretical models
    • Sharp KA, Nicholls A, Friedman R et al. Extracting hydrophobic free energies from experimental data: Relationship to protein folding and theoretical models. Biochemistry 1991; 30: 9686-97.
    • (1991) Biochemistry , vol.30 , pp. 9686-9697
    • Sharp, K.A.1    Nicholls, A.2    Friedman, R.3
  • 42
    • 0015156076 scopus 로고
    • Reversal of the antimicrobial activity of trimethoprim by thymidine in commercially prepared media
    • Koch AE, Burchall JJ. Reversal of the antimicrobial activity of trimethoprim by thymidine in commercially prepared media. Appl Microbiol 1971; 22: 812-7.
    • (1971) Appl Microbiol , vol.22 , pp. 812-817
    • Koch, A.E.1    Burchall, J.J.2
  • 43
    • 0024264540 scopus 로고
    • Trimethoprim resistance in enterococci: Microbiological and biochemical aspects
    • Hamilton-Miller JM, Stewart S. Trimethoprim resistance in enterococci: microbiological and biochemical aspects. Microbios 1988; 56: 45-55.
    • (1988) Microbios , vol.56 , pp. 45-55
    • Hamilton-Miller, J.M.1    Stewart, S.2
  • 44
    • 0015079612 scopus 로고
    • Effect of trimethoprim on macromolecular synthesis in Escherichia coli
    • Miovic M, Pizer LI. Effect of trimethoprim on macromolecular synthesis in Escherichia coli. J Bacteriol 1971; 106: 856-62.
    • (1971) J Bacteriol , vol.106 , pp. 856-862
    • Miovic, M.1    Pizer, L.I.2
  • 45
    • 0022340872 scopus 로고
    • Further studies on thymidine kinase: Distribution pattern of the enzyme in bacteria
    • Saito H, Tomioka H, Ohkido S. Further studies on thymidine kinase: distribution pattern of the enzyme in bacteria. J Gen Microbiol 1985; 13: 3091-8.
    • (1985) J Gen Microbiol , vol.13 , pp. 3091-3098
    • Saito, H.1    Tomioka, H.2    Ohkido, S.3
  • 46
    • 0023735186 scopus 로고
    • Reversal of activity of trimethoprim against Gram-positive cocci by thymidine, thymine and 'folates'
    • Hamilton-Miller JM. Reversal of activity of trimethoprim against Gram-positive cocci by thymidine, thymine and 'folates'. J Antimicrob Chemother 1988; 22: 35-9.
    • (1988) J Antimicrob Chemother , vol.22 , pp. 35-39
    • Hamilton-Miller, J.M.1
  • 48
    • 0031585986 scopus 로고    scopus 로고
    • Structure and function of the dihydropteroate synthase from Staphylococcus aureus
    • Hampele IC, D'Arcy A, Dale GE et al. Structure and function of the dihydropteroate synthase from Staphylococcus aureus. J Mol Biol 1997; 268: 21-30.
    • (1997) J Mol Biol , vol.268 , pp. 21-30
    • Hampele, I.C.1    D'Arcy, A.2    Dale, G.E.3
  • 49
    • 36448992626 scopus 로고    scopus 로고
    • In vitro activity of the novel diaminopyrimidine iclaprim, in combination with folate inhibitors and other antimicrobials with different mechanisms of action
    • Laue H, Weiss L, Bernardi A et al. In vitro activity of the novel diaminopyrimidine iclaprim, in combination with folate inhibitors and other antimicrobials with different mechanisms of action. J Antimicrob Chemother 2007; 60: 1391-4.
    • (2007) J Antimicrob Chemother , vol.60 , pp. 1391-1394
    • Laue, H.1    Weiss, L.2    Bernardi, A.3
  • 50
    • 0015349791 scopus 로고
    • Effect of the folic acid analogue, trimethoprim, on growth, macromolecular synthesis and incorporation of exogenous thymine in Escherichia coli
    • Dale BA, Greenberg GR. Effect of the folic acid analogue, trimethoprim, on growth, macromolecular synthesis and incorporation of exogenous thymine in Escherichia coli. J Bacteriol 1972; 110: 905-16.
    • (1972) J Bacteriol , vol.110 , pp. 905-916
    • Dale, B.A.1    Greenberg, G.R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.