메뉴 건너뛰기




Volumn 55, Issue 24, 2012, Pages 10896-10908

Coumarin-based inhibitors of bacillus anthracis and staphylococcus aureus replicative DNA helicase: Chemical optimization, biological evaluation, and antibacterial activities

Author keywords

[No Author keywords available]

Indexed keywords

3 [4,8 DIMETHYL 2 OXO 7 (PROP 2 YNYLOXY) 2H CHROMEN 3 YL]PROPANOIC ACID; 3 [4,8 DIMETHYL 2 OXO 7 (PYRIDIN 4 YLMETHOXY) 2H CHROMEN 3 YL]PROPANOIC ACID; 3 [4,8 DIMETHYL 2 OXO 7 [(4' TRIFLUOROMETHYLBIPHENYL 4 YL)METHOXY] 2H CHROMEN 3 YL]PROPANOIC ACID; 3 [4,8 DIMETHYL 7 (NAPHTHALEN 2 YLMETHOXY) 2 OXO 2H CHROMEN 3 YL]PROPANOIC ACID; 3 [7 (ALLYLOXY) 4,8 DIMETHYL 2 OXO 2H CHROMEN 3 YL]PROPANOIC ACID; 3 [7 (ANTHRACEN 9 YLMETHOXY) 4,8 DIMETHYL 2 OXO 2H CHROMEN 3 YL]PROPANOIC ACID; 3 [7 (BENZYLOXY) 4, 8 DIMETHYL 2 OXO 2H CHROMEN 3 YL]PROPANOIC ACID; 3 [7 (BIPHENYL 2 YLMETHOXY) 4 METHYL 2 OXO 2H CHROMEN 3 YL]PROPANOIC ACID; 3 [7 (BIPHENYL 2 YLMETHOXY) 4,8 DIMETHYL 2 OXO 2H CHROMEN 3 YL]PROPANOIC ACID; 3 [7 (BIPHENYL 3 YLMETHOXY) 4 METHYL 2 OXO 2H CHROMEN 3 YL]PROPANOIC ACID; 3 [7 (BIPHENYL 3 YLMETHOXY) 4,8 DIMETHYL 2 OXO 2H CHROMEN 3 YL]PROPANOIC ACID; 3 [7 (BIPHENYL 4 YLMETHOXY) 4 METHYL 2 OXO 2H CHROMEN 3 YL]PROPANOIC ACID; 3 [7 (BIPHENYL 4 YLMETHOXY) 4,8 DIMETHYL 2 OXO 2H CHROMEN 3 YL]PROPANOIC ACID; 3 [7 (ISOQUINOLIN 1 YLMETHOXY) 4 METHYL 2 OXO 2H CHROMEN 3 YL]PROPANOIC ACID; 3 [7 (ISOQUINOLIN 1 YLMETHOXY) 4,8 DIMETHYL 2 OXO 2H CHROMEN 3 YL]PROPANOIC ACID; 3 [7 [(2' CYANOBIPHENYL 4 YL)METHOXY] 4,8 DIMETHYL 2 OXO 2H CHROMEN 3 YL]PROPANOIC ACID; 3 [7 [(3',4' DICHLOROBIPHENYL 4 YL)METHOXY] 4,8 DIMETHYL 2 OXO 2H CHROMEN 3 YL]PROPANOIC ACID; 3 [7 [(4' CHLOROBIPHENYL 4 YL)METHOXY] 4,8 DIMETHYL 2 OXO 2H CHROMEN 3 YL]PROPANOIC ACID; 3 [7 [(4' FLUOROBIPHENYL 4 YL)METHOXY] 4,8 DIMETHYL 2 OXO 2H CHROMEN 3 YL]PROPANOIC ACID; 3 [7 [(7 CHLOROQUINOLIN 2 YL)METHOXY] 4 METHYL 2 OXO 2H CHROMEN 3 YL]PROPANOIC ACID; 3 [7 [(7 CHLOROQUINOLIN 2 YL)METHOXY] 4,8 DIMETHYL 2 OXO 2H CHROMEN 3 YL]PROPANOIC ACID; 7 [(2',4' DIFLUOROBIPHENYL 4 YL)METHOXY] 4,8 DIMETHYL 3 (3 CARBOXYPROPYL) 2 OXO 2H CHROMENE; ANTIBIOTIC AGENT; CIPROFLOXACIN; COUMARIN DERIVATIVE; DOUBLE STRANDED DNA; ETHYL 3 [7 [(4 BROMOBENZYL)OXY] 4,8 DIMETHYL 2 OXO 2H CHROMEN 3 YL]PROPANOATE; HELICASE; SINGLE STRANDED DNA; UNCLASSIFIED DRUG; UNINDEXED DRUG;

EID: 84871648732     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm300922h     Document Type: Article
Times cited : (63)

References (38)
  • 1
    • 0035969492 scopus 로고    scopus 로고
    • Index case of fatal inhalational anthrax due to bioterrorism in the United States
    • DOI 10.1056/NEJMoa012948
    • Bush, L. M.; Abrams, B. H.; Beall, A.; Johnson, C. C. Index case of fatal inhalational anthrax due to bioterrorism in the United States N. Engl. J. Med. 2001, 345, 1607-1610 (Pubitemid 33126840)
    • (2001) New England Journal of Medicine , vol.345 , Issue.22 , pp. 1607-1610
    • Bush, L.M.1    Abrams, B.H.2    Beall, A.3    Johnson, C.C.4
  • 3
    • 2942679433 scopus 로고    scopus 로고
    • DnaG interacts with a linker region that joins the N- and C-domains of DnaB and induces the formation of 3-fold symmetric rings
    • DOI 10.1093/nar/gkh628
    • Thirlway, J.; Turner, I. J.; Gibson, C. T.; Gardiner, L.; Brady, K.; Allen, S.; Roberts, C. J.; Soultanas, P. DnaG interacts with a linker region that joins the N- and C-domains of DnaB and induces the formation of 3-fold symmetric rings Nucleic Acids Res. 2004, 32, 2977-2986 (Pubitemid 39022988)
    • (2004) Nucleic Acids Research , vol.32 , Issue.10 , pp. 2977-2986
    • Thirlway, J.1    Turner, I.J.2    Gibson, C.T.3    Gardiner, L.4    Brady, K.5    Allen, S.6    Roberts, C.J.7    Soultanas, P.8
  • 4
    • 0842331838 scopus 로고    scopus 로고
    • Expression, purification, crystallization, and NMR studies of the helicase interaction domain of Escherichia coli DnaG primase
    • DOI 10.1016/j.pep.2003.10.001
    • Loscha, K.; Oakley, A. J.; Bancia, B.; Schaeffer, P. M.; Prosselkov, P.; Otting, G.; Wilce, M. C.; Dixon, N. E. Expression, purification, crystallization, and NMR studies of the helicase interaction domain of Escherichia coli DnaG primase Protein Expression Purif. 2004, 33, 304-310 (Pubitemid 38161997)
    • (2004) Protein Expression and Purification , vol.33 , Issue.2 , pp. 304-310
    • Loscha, K.1    Oakley, A.J.2    Bancia, B.3    Schaeffer, P.M.4    Prosselkov, P.5    Otting, G.6    Wilce, M.C.J.7    Dixon, N.E.8
  • 5
    • 0034714241 scopus 로고    scopus 로고
    • Identification of a region of Escherichia coli DnaB required for functional interaction with DnaG at the replication fork
    • Chang, P.; Marians, K. J. Identification of a region of Escherichia coli DnaB required for functional interaction with DnaG at the replication fork J. Biol. Chem. 2000, 275, 26187-26195
    • (2000) J. Biol. Chem. , vol.275 , pp. 26187-26195
    • Chang, P.1    Marians, K.J.2
  • 6
    • 0034635137 scopus 로고    scopus 로고
    • Mapping protein-protein interactions within a stable complex of DNA primase and DnaB helicase from Bacillus stearothermophilus
    • DOI 10.1021/bi9918801
    • Bird, L. E.; Pan, H.; Soultanas, P.; Wigley, D. B. Mapping protein-protein interactions within a stable complex of DNA primase and DnaB helicase from Bacillus stearothermophilus Biochemistry 2000, 39, 171-182 (Pubitemid 30033332)
    • (2000) Biochemistry , vol.39 , Issue.1 , pp. 171-182
    • Bird, L.E.1    Pan, H.2    Soultanas, P.3    Wigley, D.B.4
  • 7
    • 0347993077 scopus 로고    scopus 로고
    • Mechanism and Stoichiometry of Interaction of DnaG Primase with DnaB Helicase of Escherichia coli in RNA Primer Synthesis
    • DOI 10.1074/jbc.M308956200
    • Mitkova, A. V.; Khopde, S. M.; Biswas, S. B. Mechanism and stoichiometry of interaction of DnaG primase with DnaB helicase of Escherichia coli in RNA primer synthesis J. Biol. Chem. 2003, 278, 52253-52261 (Pubitemid 38035813)
    • (2003) Journal of Biological Chemistry , vol.278 , Issue.52 , pp. 52253-52261
    • Mitkova, A.V.1    Khopde, S.M.2    Biswas, S.B.3
  • 8
    • 0033600551 scopus 로고    scopus 로고
    • Mechanism of DnaB helicase of Escherichia coli: Structural domains involved in ATP hydrolysis, DNA binding, and oligomerization
    • Biswas, E. E.; Biswas, S. B. Mechanism of DnaB helicase of Escherichia coli: structural domains involved in ATP hydrolysis, DNA binding, and oligomerization Biochemistry 1999, 38, 10919-10928
    • (1999) Biochemistry , vol.38 , pp. 10919-10928
    • Biswas, E.E.1    Biswas, S.B.2
  • 9
    • 0037106446 scopus 로고    scopus 로고
    • Site-directed mutagenesis reveals roles for conserved amino acid residues in the hexameric DNA helicase DnaB from Bacillus stearothermophilus
    • Soultanas, P.; Wigley, D. B. Site-directed mutagenesis reveals roles for conserved amino acid residues in the hexameric DNA helicase DnaB from Bacillus stearothermophilus Nucleic Acids Res. 2002, 30, 4051-4060
    • (2002) Nucleic Acids Res. , vol.30 , pp. 4051-4060
    • Soultanas, P.1    Wigley, D.B.2
  • 12
    • 0035929121 scopus 로고    scopus 로고
    • Identification of critical staphylococcal genes using conditional phenotypes generated by antisense RNA
    • DOI 10.1126/science.1063566
    • Ji, Y.; Zhang, B.; Van, S. F.; Horn; Warren, P.; Woodnutt, G.; Burnham, M. K.; Rosenberg, M. Identification of critical staphylococcal genes using conditional phenotypes generated by antisense RNA Science 2001, 293, 2266-2269 (Pubitemid 32900238)
    • (2001) Science , vol.293 , Issue.5538 , pp. 2266-2269
    • Ji, Y.1    Zhang, B.2    Van Horn, S.F.3    Warren, P.4    Woodnutt, G.5    Burnham, M.K.R.6    Rosenberg, M.7
  • 14
    • 0033786801 scopus 로고    scopus 로고
    • Structure and Function of Hexameric Helicases
    • Patel, S. S.; Picha, K. M. Structure and Function of Hexameric Helicases Annu. Rev. Biochem. 2000, 69, 651-697
    • (2000) Annu. Rev. Biochem. , vol.69 , pp. 651-697
    • Patel, S.S.1    Picha, K.M.2
  • 15
    • 0037180395 scopus 로고    scopus 로고
    • Synthesis of nucleotide analogues that potently and selectively inhibit human DNA primase
    • DOI 10.1021/bi026468r
    • Moore, C. L.; Chiaramonte, M.; Higgins, T.; Kuchta, R. D. Synthesis of nucleotide analogues that potently and selectively inhibit human DNA primase Biochemistry 2002, 41, 14066-14075 (Pubitemid 35364879)
    • (2002) Biochemistry , vol.41 , Issue.47 , pp. 14066-14075
    • Moore, C.L.1    Chiaramonte, M.2    Higgins, T.3    Kuchta, R.D.4
  • 17
    • 22744445013 scopus 로고    scopus 로고
    • Pumps, paradoxes and ploughshares: Mechanism of the MCM2-7 DNA helicase
    • DOI 10.1016/j.tibs.2005.06.007, PII S0968000405001866
    • Takahashi, T. S.; Wigley, D. B.; Walter, J. C. Pumps, paradoxes and ploughshares: mechanism of the MCM2-7 DNA helicase Trends Biochem. Sci. 2005, 30, 437-444 (Pubitemid 41033239)
    • (2005) Trends in Biochemical Sciences , vol.30 , Issue.8 , pp. 437-444
    • Takahashi, T.S.1    Wigley, D.B.2    Walter, J.C.3
  • 18
    • 0035369593 scopus 로고    scopus 로고
    • Development of a novel helicase assay using electrochemiluminescence
    • DOI 10.1006/abio.2001.5093
    • Zhang, L.; Schwartz, G.; O'Donnell, M.; Harrison, R. K. Development of a novel helicase assay using electrochemiluminescence Anal. Biochem. 2001, 293, 31-37 (Pubitemid 32500502)
    • (2001) Analytical Biochemistry , vol.293 , Issue.1 , pp. 31-37
    • Zhang, L.1    Schwartz, G.2    O'Donnell, M.3    Harrison, R.K.4
  • 21
    • 0037092968 scopus 로고    scopus 로고
    • Homogenous assays for Escherichia coli DnaB-stimulated DnaG primase and DnaB helicase and their use in screening for chemical inhibitors
    • DOI 10.1006/abio.2002.5627
    • Zhang, Y.; Yang, F.; Kao, Y. C.; Kurilla, M. G.; Pompliano, D. L.; Dicker, I. B. Homogenous assays for Escherichia coli DnaB-stimulated DnaG primase and DnaB helicase and their use in screening for chemical inhibitors Anal. Biochem. 2002, 304, 174-179 (Pubitemid 34522960)
    • (2002) Analytical Biochemistry , vol.304 , Issue.2 , pp. 174-179
    • Zhang, Y.1    Yang, F.2    Kao, Y.-C.3    Kurilla, M.G.4    Pompliano, D.L.5    Dicker, I.B.6
  • 24
    • 0035114683 scopus 로고    scopus 로고
    • FlashPlate scintillation proximity assays for characterization of screening of DNA polymerase, primase, and helicase activities
    • DOI 10.1089/108705701750067015
    • Earnshaw, D. L.; Pope, A. J. FlashPlate scintillation proximity assays for characterization and screening of DNA polymerase, primase, and helicase activities J. Biomol. Screening 2001, 6, 39-46 (Pubitemid 32172443)
    • (2001) Journal of Biomolecular Screening , vol.6 , Issue.1 , pp. 39-46
    • Earnshaw, D.L.1    Pope, A.J.2
  • 26
    • 33845903833 scopus 로고    scopus 로고
    • Drugs for bad bugs: Confronting the challenges of antibacterial discovery
    • DOI 10.1038/nrd2201, PII NRD2201
    • Payne, D. J.; Gwynn, M. N.; Holmes, D. J.; Pompliano, D. L. Drugs for bad bugs: confronting the challenges of antibacterial discovery Nature Rev. Drug Discovery 2007, 6, 29-40 (Pubitemid 46020284)
    • (2007) Nature Reviews Drug Discovery , vol.6 , Issue.1 , pp. 29-40
    • Payne, D.J.1    Gwynn, M.N.2    Holmes, D.J.3    Pompliano, D.L.4
  • 27
    • 34548844459 scopus 로고    scopus 로고
    • Myricetin inhibits Escherichia coli DnaB helicase but not primase
    • DOI 10.1016/j.bmc.2007.07.057, PII S0968089607006293
    • Griep, M. A.; Blood, S.; Larson, M. A.; Koepsell, S. A.; Hinrichs, S. H. Myricetin inhibits Escherichia coli DnaB helicase but not primase Bioorg. Med. Chem. 2007, 15, 7203-7208 (Pubitemid 47451782)
    • (2007) Bioorganic and Medicinal Chemistry , vol.15 , Issue.22 , pp. 7203-7208
    • Griep, M.A.1    Blood, S.2    Larson, M.A.3    Koepsell, S.A.4    Hinrichs, S.H.5
  • 29
    • 46349105758 scopus 로고    scopus 로고
    • Inhibition of DNA helicase, ATPase and DNA-binding activities of E. coli RecQ helicase by chemotherapeutic agents
    • DOI 10.1093/jb/mvn026
    • Zhang, B.; Zhang, A. H.; Chen, L.; Xi, X. G. Inhibition of DNA Helicase, ATPase and DNA-Binding Activities of E. coli RecQ Helicase by Chemotherapeutic Agents J. Biochem. 2008, 143, 773-779 (Pubitemid 351918936)
    • (2008) Journal of Biochemistry , vol.143 , Issue.6 , pp. 773-779
    • Zhang, B.1    Zhang, A.-H.2    Chen, L.3    Xi, X.G.4
  • 30
    • 66449129371 scopus 로고    scopus 로고
    • Discovery, characterization and comparison of inhibitors of Bacillus anthracis and Staphylococcus aureus replicative DNA helicases
    • Aiello, D.; Barnes, M. H.; Biswas, E. E.; Biswas, S. B.; Gu, S.; Williams, J. D.; Bowlin, T. L.; Moir, D. T. Discovery, characterization and comparison of inhibitors of Bacillus anthracis and Staphylococcus aureus replicative DNA helicases Bioorg. Med. Chem. 2009, 17, 4466-4476
    • (2009) Bioorg. Med. Chem. , vol.17 , pp. 4466-4476
    • Aiello, D.1    Barnes, M.H.2    Biswas, E.E.3    Biswas, S.B.4    Gu, S.5    Williams, J.D.6    Bowlin, T.L.7    Moir, D.T.8
  • 31
    • 24644445060 scopus 로고    scopus 로고
    • Neoflavones. 2. Methods for synthesizing and modifying 4-arylcoumarins
    • DOI 10.1007/s10600-005-0126-7
    • Garazd, M. M.; Garazd, Y. L.; Khilya, V. P. Neoflavaones. 2. Methods for synthesizing and modifying 4-arylcoumarins Chem. Nat. Compd. 2005, 41, 245-271 (Pubitemid 41264863)
    • (2005) Chemistry of Natural Compounds , vol.41 , Issue.3 , pp. 245-271
    • Garazd, M.M.1    Garazd, Ya.L.2    Khilya, V.P.3
  • 32
    • 78649643920 scopus 로고    scopus 로고
    • Ethidium bromide MIC screening for enhanced efflux pump gene expression or efflux activity in Staphylococcus aureus
    • Patel, D.; Kosmidis, C.; Seo, S. M.; Kaatz, G. W. Ethidium bromide MIC screening for enhanced efflux pump gene expression or efflux activity in Staphylococcus aureus Antimicrob. Agents Chemother. 2010, 54, 5070-5073
    • (2010) Antimicrob. Agents Chemother. , vol.54 , pp. 5070-5073
    • Patel, D.1    Kosmidis, C.2    Seo, S.M.3    Kaatz, G.W.4
  • 34
    • 0023917654 scopus 로고
    • A malachite green procedure for orthophosphate determination and its use in alkaline phosphatase-based enzyme immunoassay
    • Baykov, A. A.; Evtushenko, O. A.; Avaeva, S. M. A malachite green procedure for orthophosphate determination and its use in alkaline phosphatase-based enzyme immunoassay Anal. Biochem. 1988, 171, 266-270
    • (1988) Anal. Biochem. , vol.171 , pp. 266-270
    • Baykov, A.A.1    Evtushenko, O.A.2    Avaeva, S.M.3
  • 36
    • 0003922953 scopus 로고    scopus 로고
    • Approved Guideline (M26-A); National Committee for Clinical Laboratory Standards: Wayne, PA.
    • Methods for Determining Bactericidal Activity of Antimicrobial Agents; Approved Guideline (M26-A); National Committee for Clinical Laboratory Standards: Wayne, PA, 1999.
    • (1999) Methods for Determining Bactericidal Activity of Antimicrobial Agents
  • 37
    • 0035889749 scopus 로고    scopus 로고
    • Higher production of rabies virus in serum-free medium cell cultures on microcarriers
    • DOI 10.1016/S0168-1656(01)00362-5, PII S0168165601003625
    • Frazzati-Gallina, N. M.; Paoli, R. L.; Mourao-Fuches, R. M.; Jorge, S. A.; Pereira, C. A. Higher production of rabies virus in serum-free medium cell cultures on microcarriers J. Biotechnol. 2001, 92, 67-72 (Pubitemid 32972104)
    • (2001) Journal of Biotechnology , vol.92 , Issue.1 , pp. 67-72
    • Frazzati-Gallina, N.M.1    Paoli, R.L.2    Mourao-Fuches, R.M.3    Jorge, S.A.C.4    Pereira, C.A.5
  • 38
    • 0029076753 scopus 로고
    • A critical assessment of the use of microculture tetrazolium assays to measure cell growth and function
    • Marshall, N. J.; Goodwin, C. J.; Holt, S. J. A critical assessment of the use of microculture tetrazolium assays to measure cell growth and function Growth Regul. 1995, 5, 69-84
    • (1995) Growth Regul. , vol.5 , pp. 69-84
    • Marshall, N.J.1    Goodwin, C.J.2    Holt, S.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.