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Volumn 67, Issue 7, 2012, Pages 1683-1696

Antistaphylococcal activity of DNA-interactive pyrrolobenzodiazepine (PBD) dimers and PBD-biaryl conjugates

Author keywords

DNA adduct formation; MRSA; Pyrrolobenzodiazepine dimers; Pyrrolobenzodiazepine biaryl conjugates

Indexed keywords

BENZODIAZEPINE DERIVATIVE; DEOXYRIBONUCLEASE I; DIMER; DOUBLE STRANDED DNA; PYRROLOBENZODIAZEPINE; UNCLASSIFIED DRUG;

EID: 84862690637     PISSN: 03057453     EISSN: 14602091     Source Type: Journal    
DOI: 10.1093/jac/dks127     Document Type: Article
Times cited : (23)

References (42)
  • 2
    • 0013852032 scopus 로고
    • Isolation and characterization of anthramycin, a new antitumor antibiotic
    • Leimgruber W, Stefanovic V, Schenker F et al. Isolation and characterization of anthramycin, a new antitumor antibiotic. J Amer Chem Soc 1965; 87: 5791-3.
    • (1965) J Amer Chem Soc , vol.87 , pp. 5791-5793
    • Leimgruber, W.1    Stefanovic, V.2    Schenker, F.3
  • 3
    • 0015377787 scopus 로고
    • Studies on tomaymycin, a new antibiotic. I. Isolation and properties of tomaymycin
    • Arima K, Kosaka M, Tamura G et al. Studies on tomaymycin, a new antibiotic. I. Isolation and properties of tomaymycin. J Antibiot (Tokyo) 1972; 25: 437-44.
    • (1972) J Antibiot (Tokyo) , vol.25 , pp. 437-444
    • Arima, K.1    Kosaka, M.2    Tamura, G.3
  • 5
    • 10944272743 scopus 로고    scopus 로고
    • Antibacterial resistance worldwide: causes, challenges and responses
    • Levy SB, Marshall B. Antibacterial resistance worldwide: causes, challenges and responses. Nat Med 2004; 10 Suppl 12: S122-9.
    • (2004) Nat Med , vol.10 , Issue.SUPPL. 12
    • Levy, S.B.1    Marshall, B.2
  • 6
    • 77957980707 scopus 로고    scopus 로고
    • Origins and evolution of antibiotic resistance
    • Davies J, Davies G. Origins and evolution of antibiotic resistance. Microbiol Mol Biol Rev 2010; 74: 417-33.
    • (2010) Microbiol Mol Biol Rev , vol.74 , pp. 417-433
    • Davies, J.1    Davies, G.2
  • 7
    • 33747362870 scopus 로고    scopus 로고
    • Colistin: the re-emerging antibiotic for multidrug-resistant Gram-negative bacterial infections
    • Li J, Nation RL, Turnidge JD et al. Colistin: the re-emerging antibiotic for multidrug-resistant Gram-negative bacterial infections. Lancet Infect Dis 2006; 6: 589-601.
    • (2006) Lancet Infect Dis , vol.6 , pp. 589-601
    • Li, J.1    Nation, R.L.2    Turnidge, J.D.3
  • 8
    • 24644491729 scopus 로고    scopus 로고
    • Pyrrolobenzodiazepine dimers: novel sequence-selective, DNA-interactive, cross-linking agents with activity against Gram-positive bacteria
    • Hadjivassileva T, Thurston DE, Taylor PW. Pyrrolobenzodiazepine dimers: novel sequence-selective, DNA-interactive, cross-linking agents with activity against Gram-positive bacteria. J Antimicrob Chemother 2005; 56: 513-8.
    • (2005) J Antimicrob Chemother , vol.56 , pp. 513-518
    • Hadjivassileva, T.1    Thurston, D.E.2    Taylor, P.W.3
  • 9
    • 34248184551 scopus 로고    scopus 로고
    • Interactions of pyrrolobenzodiazepine dimers and duplex DNA from methicillinresistant Staphylococcus aureus
    • Hadjivassileva T, Stapleton PD, Thurston DE et al. Interactions of pyrrolobenzodiazepine dimers and duplex DNA from methicillinresistant Staphylococcus aureus. Int J Antimicrob Agents 2007; 290: 672-8.
    • (2007) Int J Antimicrob Agents , vol.290 , pp. 672-678
    • Hadjivassileva, T.1    Stapleton, P.D.2    Thurston, D.E.3
  • 10
    • 73949111108 scopus 로고    scopus 로고
    • Response of Staphylococcus aureus to subinhibitory concentrations of a sequence-selective. DNA minor groove cross-linking pyrrolobenzodiazepine dimer
    • Doyle M, Feuerbaum E-A, Fox KR et al. Response of Staphylococcus aureus to subinhibitory concentrations of a sequence-selective, DNA minor groove cross-linking pyrrolobenzodiazepine dimer. J Antimicrob Chemother 2009; 64: 949-59.
    • (2009) J Antimicrob Chemother , vol.64 , pp. 949-959
    • Doyle, M.1    Feuerbaum, E.-A.2    Fox, K.R.3
  • 11
    • 0031017942 scopus 로고    scopus 로고
    • Inhibition of bacteriophage T7 RNA polymerase in vitro transcription by DNA-binding pyrrolo[2,1-c][1,4]-benzodiazepines
    • Puvvada MS, Forrow SA, Hartley JA et al. Inhibition of bacteriophage T7 RNA polymerase in vitro transcription by DNA-binding pyrrolo[2,1-c][1,4]-benzodiazepines. Biochemistry 1997; 36: 2478-84.
    • (1997) Biochemistry , vol.36 , pp. 2478-2484
    • Puvvada, M.S.1    Forrow, S.A.2    Hartley, J.A.3
  • 12
    • 0037489428 scopus 로고    scopus 로고
    • Sequence-selective recognition of duplex DNA through covalent interstrand cross-linking: kinetic and molecular modeling studies with pyrrolobenzodiazepine dimers
    • Smellie M, Bose DS, Thompson AS et al. Sequence-selective recognition of duplex DNA through covalent interstrand cross-linking: kinetic and molecular modeling studies with pyrrolobenzodiazepine dimers. Biochemistry 2003; 42: 8232-9.
    • (2003) Biochemistry , vol.42 , pp. 8232-8239
    • Smellie, M.1    Bose, D.S.2    Thompson, A.S.3
  • 13
    • 15544389177 scopus 로고    scopus 로고
    • Sequence-selective interaction of the minor-groove interstrand cross-linking agent SJG-136 with naked and cellular DNA: footprinting and enzyme inhibition studies
    • Martin C, Ellis T, McGurk CJ et al. Sequence-selective interaction of the minor-groove interstrand cross-linking agent SJG-136 with naked and cellular DNA: footprinting and enzyme inhibition studies. Biochemistry 2005; 44: 4135-47.
    • (2005) Biochemistry , vol.44 , pp. 4135-4147
    • Martin, C.1    Ellis, T.2    McGurk, C.J.3
  • 14
    • 79954619907 scopus 로고    scopus 로고
    • The minor groove-binding agent ELB-21 forms multiple interstrand and intrastrand covalent cross-links with duplex DNA and displays potent bactericidal activity against methicillin-resistant Staphylococcus aureus
    • Rosado H, Rahman K, Feuerbaum E-A et al. The minor groove-binding agent ELB-21 forms multiple interstrand and intrastrand covalent cross-links with duplex DNA and displays potent bactericidal activity against methicillin-resistant Staphylococcus aureus. J Antimicrob Chemother 2011; 66: 985-96.
    • (2011) J Antimicrob Chemother , vol.66 , pp. 985-996
    • Rosado, H.1    Rahman, K.2    Feuerbaum, E.-A.3
  • 15
    • 4644248593 scopus 로고    scopus 로고
    • The novel sequence-specific DNA cross-linking agent SJG-136 (NSC 694501) has potent and selective in vitro cytotoxicity in human B-cell chronic lymphocytic leukemia cells with evidence of a p53-independent mechanism of cell kill
    • Pepper CJ, Hambly RM, Fegan CD et al. The novel sequence-specific DNA cross-linking agent SJG-136 (NSC 694501) has potent and selective in vitro cytotoxicity in human B-cell chronic lymphocytic leukemia cells with evidence of a p53-independent mechanism of cell kill. Cancer Res 2004; 64: 6750-5.
    • (2004) Cancer Res , vol.64 , pp. 6750-6755
    • Pepper, C.J.1    Hambly, R.M.2    Fegan, C.D.3
  • 16
    • 33746033381 scopus 로고    scopus 로고
    • Time-dependent cytotoxicity induced by SJG-136 (NSC 694501): influence of the rate of interstrand cross-link formation on DNA damage signaling
    • Arnould S, Spanswick VJ, Macpherson JS et al. Time-dependent cytotoxicity induced by SJG-136 (NSC 694501): influence of the rate of interstrand cross-link formation on DNA damage signaling. Mol Cancer Ther 2006; 5: 1602-9.
    • (2006) Mol Cancer Ther , vol.5 , pp. 1602-1609
    • Arnould, S.1    Spanswick, V.J.2    Macpherson, J.S.3
  • 17
    • 70349743960 scopus 로고    scopus 로고
    • The pyrrolobenzodiazepine dimer SJG-136 forms sequence-dependent intrastrand DNA cross-links and monoalkylated adducts in addition to interstrand cross-links
    • Rahman KM, Thompson AS, James CH et al. The pyrrolobenzodiazepine dimer SJG-136 forms sequence-dependent intrastrand DNA cross-links and monoalkylated adducts in addition to interstrand cross-links. J Amer Chem Soc 2009; 131: 13756-66.
    • (2009) J Amer Chem Soc , vol.131 , pp. 13756-13766
    • Rahman, K.M.1    Thompson, A.S.2    James, C.H.3
  • 18
    • 0042287719 scopus 로고    scopus 로고
    • The evolution of genomic base composition in bacteria
    • Haywood-Farmer E, Otto SP. The evolution of genomic base composition in bacteria. Evolution 2003; 57: 1783-92.
    • (2003) Evolution , vol.57 , pp. 1783-1792
    • Haywood-Farmer, E.1    Otto, S.P.2
  • 19
    • 33748537069 scopus 로고    scopus 로고
    • Design, synthesis, and biophysical and biological evaluation of a series of pyrrolobenzodiazepinepoly(N-methylpyrrole) conjugates
    • Wells G, Martin CRH, Howard PW et al. Design, synthesis, and biophysical and biological evaluation of a series of pyrrolobenzodiazepinepoly(N-methylpyrrole) conjugates. J Med Chem 2006; 49: 5442-61.
    • (2006) J Med Chem , vol.49 , pp. 5442-5461
    • Wells, G.1    Martin, C.R.H.2    Howard, P.W.3
  • 20
    • 2342644094 scopus 로고    scopus 로고
    • Modulation of β-lactam resistance in Staphylococcus aureus by catechins and gallates
    • Stapleton PD, Shah S, Anderson JC et al. Modulation of β-lactam resistance in Staphylococcus aureus by catechins and gallates. Int J Antimicrob Agents 2004; 23: 462-7.
    • (2004) Int J Antimicrob Agents , vol.23 , pp. 462-467
    • Stapleton, P.D.1    Shah, S.2    Anderson, J.C.3
  • 21
    • 0025341331 scopus 로고
    • New colorimetric cytotoxicity assay for anticancer drug screening
    • Skehan P, Storeng R, Scudiero DA et al. New colorimetric cytotoxicity assay for anticancer drug screening. J Natl Cancer Inst 1990; 82: 1107-12.
    • (1990) J Natl Cancer Inst , vol.82 , pp. 1107-1112
    • Skehan, P.1    Storeng, R.2    Scudiero, D.A.3
  • 22
    • 10744225213 scopus 로고    scopus 로고
    • Linker length modulates DNA cross-linking reactivity and cytotoxic potency of C8/C8' ether-linked C2-exo-unsaturated pyrrolo[2,1-c][1,4]benzodiazepine (PBD) dimers
    • Gregson SJ, Howard PW, Gullick DR et al. Linker length modulates DNA cross-linking reactivity and cytotoxic potency of C8/C8' ether-linked C2-exo-unsaturated pyrrolo[2,1-c][1,4]benzodiazepine (PBD) dimers. J Med Chem 2004; 47: 1161-74.
    • (2004) J Med Chem , vol.47 , pp. 1161-1174
    • Gregson, S.J.1    Howard, P.W.2    Gullick, D.R.3
  • 23
    • 0033519732 scopus 로고    scopus 로고
    • Effect of A-ring modifications on the DNA-binding behavior and cytotoxicity of pyrrolo[2,1-c] [1,4]benzodiazepines
    • Thurston DE, Bose DS, Howard PW et al. Effect of A-ring modifications on the DNA-binding behavior and cytotoxicity of pyrrolo[2,1-c] [1,4]benzodiazepines. J Med Chem 1999; 42: 1951-64.
    • (1999) J Med Chem , vol.42 , pp. 1951-1964
    • Thurston, D.E.1    Bose, D.S.2    Howard, P.W.3
  • 24
    • 79954467838 scopus 로고    scopus 로고
    • Synthesis of DNA-interactive pyrrolo[2,1-c] [1,4]benzodiazepines (PBDs)
    • Antonow D, Thurston DE. Synthesis of DNA-interactive pyrrolo[2,1-c] [1,4]benzodiazepines (PBDs). Chem Rev 2011; 111: 2815-64.
    • (2011) Chem Rev , vol.111 , pp. 2815-2864
    • Antonow, D.1    Thurston, D.E.2
  • 25
    • 40749083920 scopus 로고    scopus 로고
    • An asymmetric C8/C8'-tripyrrole-linked sequence-selective pyrrolo[2,1-c][1,4] benzodiazepine (PBD) dimer DNA interstrand cross-linking agent spanning 11 DNA base pairs
    • Tiberghien AC, Evans DA, Kiakos K et al. An asymmetric C8/C8'-tripyrrole-linked sequence-selective pyrrolo[2,1-c][1,4] benzodiazepine (PBD) dimer DNA interstrand cross-linking agent spanning 11 DNA base pairs. Bioorg Med Chem Lett 2008; 18: 2073-7.
    • (2008) Bioorg Med Chem Lett , vol.18 , pp. 2073-2077
    • Tiberghien, A.C.1    Evans, D.A.2    Kiakos, K.3
  • 26
    • 71049132318 scopus 로고    scopus 로고
    • Synthesis of a novel C2/ C2'-aryl-substituted pyrrolo[2,1-c][1,4]benzodiazepine dimer prodrug with improved water solubility and reduced reaction rate
    • Howard PW, Chen Z, Gregson SJ et al. Synthesis of a novel C2/ C2'-aryl-substituted pyrrolo[2,1-c][1,4]benzodiazepine dimer prodrug with improved water solubility and reduced reaction rate. Bioorg Med Chem Lett 2009; 19: 6463-6.
    • (2009) Bioorg Med Chem Lett , vol.19 , pp. 6463-6466
    • Howard, P.W.1    Chen, Z.2    Gregson, S.J.3
  • 27
    • 77950584653 scopus 로고    scopus 로고
    • Structure-activity relationships of monomeric C2-aryl pyrrolo[2,1-c][1,4]benzodiazepine (PBD) antitumor agents
    • Antonow D, Kaliszczak M, Kang GD et al. Structure-activity relationships of monomeric C2-aryl pyrrolo[2,1-c][1,4]benzodiazepine (PBD) antitumor agents. J Med Chem 2010; 53: 2927-41.
    • (2010) J Med Chem , vol.53 , pp. 2927-2941
    • Antonow, D.1    Kaliszczak, M.2    Kang, G.D.3
  • 28
    • 34247492103 scopus 로고    scopus 로고
    • Footprinting: a method for determining the sequence selectivity, affinity and kinetics of DNA-binding ligands
    • Hampshire AJ, Rusling DA, Broughton-Head VJ et al. Footprinting: a method for determining the sequence selectivity, affinity and kinetics of DNA-binding ligands. Methods 2007; 42: 128-40.
    • (2007) Methods , vol.42 , pp. 128-140
    • Hampshire, A.J.1    Rusling, D.A.2    Broughton-Head, V.J.3
  • 29
    • 38949129801 scopus 로고    scopus 로고
    • Preferred binding sites for the bifunctional intercalator TANDEM determined using DNA fragments that contain every symmetrical hexanucleotide sequence
    • Hampshire AJ, Fox KR. Preferred binding sites for the bifunctional intercalator TANDEM determined using DNA fragments that contain every symmetrical hexanucleotide sequence. Anal Biochem 2008; 374: 298-303.
    • (2008) Anal Biochem , vol.374 , pp. 298-303
    • Hampshire, A.J.1    Fox, K.R.2
  • 30
    • 30744464935 scopus 로고    scopus 로고
    • Design, validation, and application of a seven-strain Staphylococcus aureus PCR product microarray for comparative genomics
    • Witney AA, Marsden GL, Holden MT et al. Design, validation, and application of a seven-strain Staphylococcus aureus PCR product microarray for comparative genomics. Appl Environ Microbiol 2005; 71: 7504-14.
    • (2005) Appl Environ Microbiol , vol.71 , pp. 7504-7514
    • Witney, A.A.1    Marsden, G.L.2    Holden, M.T.3
  • 33
    • 4444221565 scopus 로고    scopus 로고
    • UCSF Chimera - a visualization system for exploratory research and analysis
    • Pettersen EF, Goddard TD, Huang CC et al. UCSF Chimera - a visualization system for exploratory research and analysis. J Comput Chem 2004; 25: 1605-12.
    • (2004) J Comput Chem , vol.25 , pp. 1605-1612
    • Pettersen, E.F.1    Goddard, T.D.2    Huang, C.C.3
  • 34
    • 31444441667 scopus 로고    scopus 로고
    • Dual role of MutS glutamate 38 in mismatch discrimination and in the authorization of repair
    • Lebbink JHG, Georgijevic D, Natrajan G et al. Dual role of MutS glutamate 38 in mismatch discrimination and in the authorization of repair. EMBO J 2006; 25: 409-19.
    • (2006) EMBO J , vol.25 , pp. 409-419
    • Lebbink, J.H.G.1    Georgijevic, D.2    Natrajan, G.3
  • 35
    • 33750344433 scopus 로고    scopus 로고
    • Environmental stress and lesion-bypass DNA polymerases
    • Nohmi T. Environmental stress and lesion-bypass DNA polymerases. Ann Rev Microbiol 2006; 60: 231-53.
    • (2006) Ann Rev Microbiol , vol.60 , pp. 231-253
    • Nohmi, T.1
  • 36
    • 77956271552 scopus 로고    scopus 로고
    • SG2285, a novel C2-aryl-substituted pyrrolobenzodiazepine dimer prodrug that cross-links DNA and exerts highly potent antitumor activity
    • Hartley JA, Hamaguchi A, Coffils M et al. SG2285, a novel C2-aryl-substituted pyrrolobenzodiazepine dimer prodrug that cross-links DNA and exerts highly potent antitumor activity. Cancer Res 2010; 70: 6849-58.
    • (2010) Cancer Res , vol.70 , pp. 6849-6858
    • Hartley, J.A.1    Hamaguchi, A.2    Coffils, M.3
  • 37
    • 0037172403 scopus 로고    scopus 로고
    • Genome and virulence determinants of high virulence community-acquired MRSA
    • Baba T, Takeuchi F, Kuroda M et al. Genome and virulence determinants of high virulence community-acquired MRSA. Lancet 2002; 359: 1819-27.
    • (2002) Lancet , vol.359 , pp. 1819-1827
    • Baba, T.1    Takeuchi, F.2    Kuroda, M.3
  • 38
    • 80052225565 scopus 로고    scopus 로고
    • Effect of base sequence on the DNA cross-linking properties of pyrrolobenzodiazepine (PBD) dimers
    • Rahman KM, James CH, Thurston DE. Effect of base sequence on the DNA cross-linking properties of pyrrolobenzodiazepine (PBD) dimers. Nucl Acids Res 2011; 39: 5800-12.
    • (2011) Nucl Acids Res , vol.39 , pp. 5800-5812
    • Rahman, K.M.1    James, C.H.2    Thurston, D.E.3
  • 39
    • 4644353500 scopus 로고    scopus 로고
    • SJG-136 (NSC 694501), a novel rationally designed DNA minor groove interstrand cross-linking agent with potent and broad spectrum antitumour activity: part 1: cellular pharmacology, in vitro and initial in vivo antitumour activity
    • Hartley JA, Spanswick VJ, Brooks N et al. SJG-136 (NSC 694501), a novel rationally designed DNA minor groove interstrand cross-linking agent with potent and broad spectrum antitumour activity: part 1: cellular pharmacology, in vitro and initial in vivo antitumour activity. Cancer Res 2004; 64: 6693-9.
    • (2004) Cancer Res , vol.64 , pp. 6693-6699
    • Hartley, J.A.1    Spanswick, V.J.2    Brooks, N.3
  • 40
    • 4644316457 scopus 로고    scopus 로고
    • SJG-136 (NSC 694501), a novel rationally designed DNA minor groove interstrand cross-linking agent with potent and broad spectrum antitumour activity: part 2: efficacy evaluations
    • Alley MC, Hollingshead MG, Pacula-Cox CM et al. SJG-136 (NSC 694501), a novel rationally designed DNA minor groove interstrand cross-linking agent with potent and broad spectrum antitumour activity: part 2: efficacy evaluations. Cancer Res 2004; 64: 6700-6.
    • (2004) Cancer Res , vol.64 , pp. 6700-6706
    • Alley, M.C.1    Hollingshead, M.G.2    Pacula-Cox, C.M.3
  • 41
    • 77956686608 scopus 로고    scopus 로고
    • Histone yH2AX and poly(ADP-ribose) as clinical pharmacodynamic biomarkers
    • Redon CE, Nakamura AJ, Zhang YW et al. Histone yH2AX and poly(ADP-ribose) as clinical pharmacodynamic biomarkers. Clin Cancer Res 2010; 16: 4532-42.
    • (2010) Clin Cancer Res , vol.16 , pp. 4532-4542
    • Redon, C.E.1    Nakamura, A.J.2    Zhang, Y.W.3
  • 42
    • 77649192721 scopus 로고    scopus 로고
    • A phase I trial of SJG-136 (NSC#694501) in advanced solid tumors
    • Janjigian Y, Lee W, Kris M et al. A phase I trial of SJG-136 (NSC#694501) in advanced solid tumors. Cancer Chemother Pharmacol 2010; 65: 833-8.
    • (2010) Cancer Chemother Pharmacol , vol.65 , pp. 833-838
    • Janjigian, Y.1    Lee, W.2    Kris, M.3


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