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Volumn 7, Issue 7, 2016, Pages 692-696

Charged Nonclassical Antifolates with Activity Against Gram-Positive and Gram-Negative Pathogens

Author keywords

antifolate; Dihydrofolate reductase; Escherichia coli; methotrexate; MRSA; Staphylococcus aureus; trimethoprim

Indexed keywords

ANTIBIOTIC AGENT; CARBOXYLIC ACID; CIPROFLOXACIN; CYTOCHROME P450; CYTOCHROME P450 2D6; CYTOCHROME P450 3A4; FOLIC ACID ANTAGONIST; METHYL GROUP; PYRIMIDINE DERIVATIVE; QUINOLONE DERIVATIVE; TETRACYCLINE DERIVATIVE;

EID: 84978653695     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/acsmedchemlett.6b00120     Document Type: Article
Times cited : (26)

References (24)
  • 1
    • 79251469453 scopus 로고    scopus 로고
    • Cancer chemotherapy: Targeting folic acid synthesis
    • Hagner, N.; Joerger, M. Cancer chemotherapy: targeting folic acid synthesis Cancer Manage. Res. 2010, 2, 293-301 10.2147/CMAR.S10043
    • (2010) Cancer Manage. Res. , vol.2 , pp. 293-301
    • Hagner, N.1    Joerger, M.2
  • 2
    • 84878792340 scopus 로고    scopus 로고
    • Antifolates as effective antimicrobial agents: New generations of trimethoprim analogs
    • Zhou, W.; Scocchera, E.; Wright, D.; Anderson, A. Antifolates as effective antimicrobial agents: new generations of trimethoprim analogs MedChemComm 2013, 4, 908-915 10.1039/c3md00104k
    • (2013) MedChemComm , vol.4 , pp. 908-915
    • Zhou, W.1    Scocchera, E.2    Wright, D.3    Anderson, A.4
  • 3
    • 63649118857 scopus 로고    scopus 로고
    • X-ray structure of the ternary MTX.NADPH complex of the anthrax dihydrofolate reductase: A pharmacophore for dual-site inhibitor design
    • Bennett, B.; Wan, Q.; Ahmad, M.; Langan, P.; Dealwis, C. X-ray structure of the ternary MTX.NADPH complex of the anthrax dihydrofolate reductase: a pharmacophore for dual-site inhibitor design J. Struct. Biol. 2009, 166, 162-171 10.1016/j.jsb.2009.01.001
    • (2009) J. Struct. Biol. , vol.166 , pp. 162-171
    • Bennett, B.1    Wan, Q.2    Ahmad, M.3    Langan, P.4    Dealwis, C.5
  • 4
    • 0031015737 scopus 로고    scopus 로고
    • Loop and subdomain movements in the mechanism of Escherichia coli dihydrofolate reductase: Crystallographic evidence
    • Sawaya, M.; Kraut, J. Loop and subdomain movements in the mechanism of Escherichia coli dihydrofolate reductase: crystallographic evidence Biochemistry 1997, 36, 586-603 10.1021/bi962337c
    • (1997) Biochemistry , vol.36 , pp. 586-603
    • Sawaya, M.1    Kraut, J.2
  • 5
    • 0034645774 scopus 로고    scopus 로고
    • Three-dimensional structure of M. Tuberculosis dihydrofolate reductase reveals opportunities for the design of novel tuberculosis drugs
    • Li, R.; Sirawaraporn, R.; Chitnumsub, P.; Sirawaraporn, W.; Wooden, J.; Athappilly, F.; Turley, S.; Hol, W. Three-dimensional structure of M. tuberculosis dihydrofolate reductase reveals opportunities for the design of novel tuberculosis drugs J. Mol. Biol. 2000, 295, 307-323 10.1006/jmbi.1999.3328
    • (2000) J. Mol. Biol. , vol.295 , pp. 307-323
    • Li, R.1    Sirawaraporn, R.2    Chitnumsub, P.3    Sirawaraporn, W.4    Wooden, J.5    Athappilly, F.6    Turley, S.7    Hol, W.8
  • 6
    • 0001596638 scopus 로고
    • Inhibitor Binding Analysis of Dihydrofolate Reductases from Various Species
    • Burchall, J.; Hitchings, G. Inhibitor Binding Analysis of Dihydrofolate Reductases from Various Species Mol. Pharmacol. 1965, 1, 126-136
    • (1965) Mol. Pharmacol. , vol.1 , pp. 126-136
    • Burchall, J.1    Hitchings, G.2
  • 7
    • 0033743958 scopus 로고    scopus 로고
    • Resistance to methotrexate due to AcrAB-dependent export from Escherichia coli
    • Kopytek, S.; Dyer, J.; Knapp, G.; Hu, J. Resistance to methotrexate due to AcrAB-dependent export from Escherichia coli Antimicrob. Agents Chemother. 2000, 44, 3210-3212 10.1128/AAC.44.11.3210-3212.2000
    • (2000) Antimicrob. Agents Chemother. , vol.44 , pp. 3210-3212
    • Kopytek, S.1    Dyer, J.2    Knapp, G.3    Hu, J.4
  • 8
    • 84856755045 scopus 로고    scopus 로고
    • Toward new Therapeutics for Skin and Soft Tissue Infections: Propargyl-linked Antifolates Are Potent Inhibitors of MRSA and Streptococcus pyogenes
    • Viswanathan, K.; Frey, K.; Scocchera, E.; Martin, B.; Swain, P.; Alverson, J.; Priestley, N.; Anderson, A.; Wright, D. Toward new Therapeutics for Skin and Soft Tissue Infections: Propargyl-linked Antifolates Are Potent Inhibitors of MRSA and Streptococcus pyogenes PLoS One 2012, 7 (2) e29434 10.1371/journal.pone.0029434
    • (2012) PLoS One , vol.7 , Issue.2 , pp. e29434
    • Viswanathan, K.1    Frey, K.2    Scocchera, E.3    Martin, B.4    Swain, P.5    Alverson, J.6    Priestley, N.7    Anderson, A.8    Wright, D.9
  • 9
    • 0034496149 scopus 로고    scopus 로고
    • Antimicrobial activity of selected non-antibiotics - Activity of methotrexate against Staphylococcus aureus strains
    • Kruszewska, H.; Zareba, T.; Tyski, S. Antimicrobial activity of selected non-antibiotics-activity of methotrexate against Staphylococcus aureus strains Acta Polym. Pharm. 2000, 57S, 117-119
    • (2000) Acta Polym. Pharm. , vol.57 , pp. 117-119
    • Kruszewska, H.1    Zareba, T.2    Tyski, S.3
  • 10
    • 78649854733 scopus 로고    scopus 로고
    • Trimethoprim-sulfamethoxazole or clindamycin for community-associated MRSA (CA-MRSA) skin infections
    • Frei, C.; Miller, M.; Lewis, J.; Lawson, K.; Hunter, J.; Oramasionwu, C.; Talbert, R. Trimethoprim-sulfamethoxazole or clindamycin for community-associated MRSA (CA-MRSA) skin infections J. Am. Board Fam. Med. 2010, 23, 714-719 10.3122/jabfm.2010.06.090270
    • (2010) J. Am. Board Fam. Med. , vol.23 , pp. 714-719
    • Frei, C.1    Miller, M.2    Lewis, J.3    Lawson, K.4    Hunter, J.5    Oramasionwu, C.6    Talbert, R.7
  • 11
    • 77957766934 scopus 로고    scopus 로고
    • Empiric outpatient therapy with trimethoprim-sulfamethoxazole, cephalexin, or clindamycin for cellulitis
    • Khawcharoenporn, T.; Tice, A. Empiric outpatient therapy with trimethoprim-sulfamethoxazole, cephalexin, or clindamycin for cellulitis Am. J. Med. 2010, 123, 942-950 10.1016/j.amjmed.2010.05.020
    • (2010) Am. J. Med. , vol.123 , pp. 942-950
    • Khawcharoenporn, T.1    Tice, A.2
  • 12
    • 33845363001 scopus 로고    scopus 로고
    • Management of Community-Associated Methicillin-Resistant Staphylococcus aureus Infections in Children
    • Le, J.; Lieberman, J. Management of Community-Associated Methicillin-Resistant Staphylococcus aureus Infections in Children Pharmacotherapy 2006, 26, 1758-1770 10.1592/phco.26.12.1758
    • (2006) Pharmacotherapy , vol.26 , pp. 1758-1770
    • Le, J.1    Lieberman, J.2
  • 13
    • 84868019910 scopus 로고    scopus 로고
    • Has the emergence of community-associated methicillin-resistant Staphylococcus aureus increased trimethoprim-sulfamethoxazole use and resistance?: A 10-year time series analysis
    • Wood, J.; Smith, D.; Baker, E.; Brecher, S.; Gupta, K. Has the emergence of community-associated methicillin-resistant Staphylococcus aureus increased trimethoprim-sulfamethoxazole use and resistance?: a 10-year time series analysis Antimicrob. Agents Chemother. 2012, 56, 5655-5660 10.1128/AAC.01011-12
    • (2012) Antimicrob. Agents Chemother. , vol.56 , pp. 5655-5660
    • Wood, J.1    Smith, D.2    Baker, E.3    Brecher, S.4    Gupta, K.5
  • 14
    • 43949129098 scopus 로고    scopus 로고
    • Physicochemical properties of antibacterial compounds: Implications for drug discovery
    • O'Shea, R.; Moser, H. Physicochemical properties of antibacterial compounds: implications for drug discovery J. Med. Chem. 2008, 51, 2871-2878 10.1021/jm700967e
    • (2008) J. Med. Chem. , vol.51 , pp. 2871-2878
    • O'Shea, R.1    Moser, H.2
  • 15
    • 84937697847 scopus 로고    scopus 로고
    • Nonracemic antifolates stereoselectively recruit alternate cofactors and overcome resistance in S. Aureus
    • Keshipeddy, S.; Reeve, S.; Anderson, A.; Wright, D. Nonracemic antifolates stereoselectively recruit alternate cofactors and overcome resistance in S. aureus J. Am. Chem. Soc. 2015, 137, 8983-8990 10.1021/jacs.5b01442
    • (2015) J. Am. Chem. Soc. , vol.137 , pp. 8983-8990
    • Keshipeddy, S.1    Reeve, S.2    Anderson, A.3    Wright, D.4
  • 16
    • 84912142088 scopus 로고    scopus 로고
    • Crystal structures of Klebsiella pneumoniae dihydrofolate reductase bound to propargyl-linked antifolates reveal features for potency and selectivity
    • Lamb, K.; Lombardo, M.; Alverson, J.; Priestley, N.; Wright, D.; Anderson, A. Crystal structures of Klebsiella pneumoniae dihydrofolate reductase bound to propargyl-linked antifolates reveal features for potency and selectivity Antimicrob. Agents Chemother. 2014, 58, 7484-7491 10.1128/AAC.03555-14
    • (2014) Antimicrob. Agents Chemother. , vol.58 , pp. 7484-7491
    • Lamb, K.1    Lombardo, M.2    Alverson, J.3    Priestley, N.4    Wright, D.5    Anderson, A.6
  • 17
    • 84862538750 scopus 로고    scopus 로고
    • Prospectively screening novel antibacterial inhibitors of dihydrofolate reductase for mutational resistance
    • Frey, K.; Viswanathan, K.; Wright, D.; Anderson, A. Prospectively screening novel antibacterial inhibitors of dihydrofolate reductase for mutational resistance Antimicrob. Agents Chemother. 2012, 56, 3556-3562 10.1128/AAC.06263-11
    • (2012) Antimicrob. Agents Chemother. , vol.56 , pp. 3556-3562
    • Frey, K.1    Viswanathan, K.2    Wright, D.3    Anderson, A.4
  • 18
    • 84866459005 scopus 로고    scopus 로고
    • Acetylenic linkers in lead compounds: A study of the stability of the propargyl-linked antifolates
    • Zhou, W.; Viswanathan, K.; Hill, D.; Anderson, A.; Wright, D. Acetylenic linkers in lead compounds: A study of the stability of the propargyl-linked antifolates Drug Metab. Dispos. 2012, 40, 2002-2008 10.1124/dmd.112.046870
    • (2012) Drug Metab. Dispos. , vol.40 , pp. 2002-2008
    • Zhou, W.1    Viswanathan, K.2    Hill, D.3    Anderson, A.4    Wright, D.5
  • 19
    • 77950520151 scopus 로고    scopus 로고
    • Towards the Understanding of Resistance Mechanisms in Clinically Isolated Trimethoprim-resistant, Methicillin-resistant Staphylococcus aureus Dihydrofolate Reductase
    • Frey, K.; Lombardo, M.; Wright, D.; Anderson, A. Towards the Understanding of Resistance Mechanisms in Clinically Isolated Trimethoprim-resistant, Methicillin-resistant Staphylococcus aureus Dihydrofolate Reductase J. Struct. Biol. 2010, 170, 93-97 10.1016/j.jsb.2009.12.011
    • (2010) J. Struct. Biol. , vol.170 , pp. 93-97
    • Frey, K.1    Lombardo, M.2    Wright, D.3    Anderson, A.4
  • 20
    • 0028774535 scopus 로고
    • Old yellow enzyme at 2A resolution: Overall structure, ligand binding and comparison with related flavoproteins
    • Fox, K.; Karplus, A. Old yellow enzyme at 2A resolution: overall structure, ligand binding and comparison with related flavoproteins Structure 1994, 2, 1089-1105 10.1016/S0969-2126(94)00111-1
    • (1994) Structure , vol.2 , pp. 1089-1105
    • Fox, K.1    Karplus, A.2
  • 21
    • 0015914589 scopus 로고
    • The primary acid product of DPNH
    • Oppenheimer, N. The primary acid product of DPNH Biochem. Biophys. Res. Commun. 1973, 50, 683-690 10.1016/0006-291X(73)91298-9
    • (1973) Biochem. Biophys. Res. Commun. , vol.50 , pp. 683-690
    • Oppenheimer, N.1
  • 22
    • 1642311135 scopus 로고    scopus 로고
    • Clinical Relevance of Bacteriostatic versus Bactericidal Mechanisms of Action its the Treatment of Gram-Positive Bacterial Infections
    • Pankey, G.; Sabath, L. Clinical Relevance of Bacteriostatic versus Bactericidal Mechanisms of Action its the Treatment of Gram-Positive Bacterial Infections Clin. Infect. Dis. 2004, 38, 864-870 10.1086/381972
    • (2004) Clin. Infect. Dis. , vol.38 , pp. 864-870
    • Pankey, G.1    Sabath, L.2
  • 23
    • 81855199904 scopus 로고    scopus 로고
    • A b-(1,2)-glycosynthase and an attempted selection method for the directed evolution of glycosynthases
    • Jakeman, D.; Sadeghi-Khomami, A. A b-(1,2)-glycosynthase and an attempted selection method for the directed evolution of glycosynthases Biochemistry 2011, 50, 10359-10366 10.1021/bi201438q
    • (2011) Biochemistry , vol.50 , pp. 10359-10366
    • Jakeman, D.1    Sadeghi-Khomami, A.2
  • 24
    • 17444385981 scopus 로고    scopus 로고
    • Chemical conditionality: A genetic strategy to probe organelle assembly
    • Ruiz, N.; Falcone, B.; Kahne, D.; Silhavy, T. Chemical conditionality: a genetic strategy to probe organelle assembly Cell 2005, 121, 307-317 10.1016/j.cell.2005.02.014
    • (2005) Cell , vol.121 , pp. 307-317
    • Ruiz, N.1    Falcone, B.2    Kahne, D.3    Silhavy, T.4


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