Interactions of pyrrolobenzodiazepine dimers and duplex DNA from methicillin-resistant Staphylococcus aureus

International Journal of Antimicrobial Agents

Volumn 29, Issue 6, 2007, Pages 672-678

  Hadjivassileva, Tsveta ^a   Stapleton, Paul D ^a   Thurston, David E ^a   Taylor, Peter W ^a  

^a UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

DNA cross linking; MRSA; Pyrrolobenzodiazepine dimers; Staphylococcus aureus

Indexed keywords

ANTIINFECTIVE AGENT; DNA 16S; DOUBLE STRANDED DNA; ELB 21; GENOMIC DNA; PYRROLOBENZODIAZEPINE DIMER; SJG 136; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ARTICLE; DNA BINDING; DNA CROSS LINKING; DNA EXTRACTION; DRUG POTENCY; DRUG STRUCTURE; FREQUENCY ANALYSIS; INCUBATION TIME; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; PRIORITY JOURNAL; STAPHYLOCOCCUS AUREUS;

ANTI-BACTERIAL AGENTS; BENZODIAZEPINES; CROSS-LINKING REAGENTS; DIMERIZATION; DNA, BACTERIAL; METHICILLIN RESISTANCE; MOLECULAR STRUCTURE; PYRROLES; STAPHYLOCOCCUS AUREUS;

EID: 34248184551     PISSN: 09248579     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijantimicag.2007.01.005     Document Type: Article

References (24)

1. Public Health Laboratory Service. Staphylococcus aureus bacteraemia: England, Wales and Northern Ireland, January to December 2002. Commun Dis Rep CDR Wkly 2003;13(12):www.hpa.org.uk/cdr/archives/2003/cdr1203.pdf.
2. Firth N. Evolution of antimicrobial multi-resistance in Gram-positive bacteria. In: Amábile-Cuevas C.F. (Ed). Multiple drug resistant bacteria (2003), Horizon Scientific, Wymondham, UK 33-60
3. Rubin R.J., Harrington C.A., Poon A., Dietrich K., Green J.A., and Moiduddin A. The economic impact of Staphylococcus aureus infection in New York City hospitals. Emerg Infect Dis 5 (1999) 9-17
4. Hadjivassileva T., Thurston D.E., and Taylor P.W. Pyrrolobenzodiazepine dimers: novel sequence-selective, DNA-interactive, cross-linking agents with activity against Gram-positive bacteria. J Antimicrob Chemother 56 (2005) 513-518
5. Thurston D.E. Advances in the study of pyrrolo[2,1-c][1,4]-benzodiazepine antitumour antibiotics. In: Waring M.J., and Neidle S. (Eds). Molecular aspects of anticancer drug-DNA interactions (1993), Macmillan, London, UK 54-88
6. Puvvada M.S., Forrow S.A., Hartley J.A., et al. Inhibition of bacteriophage T7 RNA polymerase in vitro transcription by DNA-binding pyrrolo[2,1-c][1,4]-benzodiazepines. Biochemistry 36 (1997) 2478-2484
7. Smellie M., Bose D.S., Thompson A.S., Jenkins T.C., Hartley J.A., and Thurston D.E. Sequence-selective recognition of duplex DNA through covalent interstrand cross-linking: kinetic and molecular modeling studies with pyrrolobenzodiazepine dimers. Biochemistry 42 (2003) 8232-8239
8. Gregson S.J., Howard P.W., Hartley J.A., et al. Design, synthesis, and evaluation of a novel pyrrolobenzodiazepine DNA-interactive agent with highly efficient cross-linking ability and potent cytotoxicity. J Med Chem 44 (2001) 737-748
9. Baraldi P.G., Balboni G., Cacciari B., et al. Synthesis, in vitro antiproliferative activity, and DNA-binding properties of hybrid molecules containing pyrrolo[2,1-c][1,4]benzodiazepine and minor-groove-binding oligopyrrole carriers. J Med Chem 42 (1999) 5131-5141
10. Gregson S.J., Howard P.W., Gullick D.R., 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) dimmers. J Med Chem 47 (2004) 1161-1174
11. Holden M.T., Feil E.J., Lindsay J.A., et al. Complete genomes of two clinical Staphylococcus aureus strains: evidence for the rapid evolution of virulence and drug resistance. Proc Natl Acad Sci USA 101 (2004) 9786-9791
12. Pitcher D.G., Saunders N.A., and Owen R.J. Rapid extraction of bacterial genomic DNA with guanidium thiocyanate. Lett Appl Microbiol 8 (1989) 151-156
13. Jones G.B., Davey C.L., Jenkins T.C., et al. The non-covalent interaction of pyrrolo[2,1-c][1,4]benzodiazepine-5,11-diones with DNA. Anticancer Drug Des 5 (1990) 249-264
14. Futscher B.W., Pieper R.O., Dalton W.S., and Erickson L.C. Gene-specific DNA interstrand cross-links produced by nitrogen mustard in the human tumor cell line Colo320HSR. Cell Growth Differ 3 (1992) 217-223
15. Kohner P., Uhl J., Kolbert C., Persing D., and Cockerill F. Comparison of susceptibility testing methods with mecA gene analysis for determining oxacillin (methicillin) resistance in clinical isolates of Staphylococcus aureus and coagulase-negative Staphylococcus spp. J Clin Microbiol 37 (1999) 2952-2961
16. James P.L., Le Strat L., Ellervik U., et al. Effects of a hairpin polyamide on DNA melting: comparison with distamycin and Hoechst 33258. Biophys Chem 111 (2004) 205-212
17. Dervan P.B. Molecular recognition of DNA by small molecules. Bioorg Med Chem 9 (2001) 2215-2235
18. Overbye K.M., and Barrett J.F. Antibiotics: where did we go wrong?. Drug Discov Today 10 (2005) 45-52
19. Neidle S., and Thurston D.E. Chemical approaches to the discovery and development of cancer therapies. Nat Rev Cancer 5 (2005) 285-296
20. Ge Y., Difuntorum S., Touami S., et al. In vitro antimicrobial activity of GSQ1530, a new heteroaromatic polycyclic compound. Antimicrob Agents Chemother 46 (2002) 3168-3174
21. Gross M., Burli R., Jones P., et al. Pharmacology of novel heteroaromatic polycycle antibacterials. Antimicrob Agents Chemother 47 (2003) 3448-3457
22. Kaizerman J.A., Gross M.I., Ge Y., et al. DNA binding ligands targeting drug-resistant bacteria: structure, activity, and pharmacology. J Med Chem 46 (2003) 3914-3929
23. Brli R., Kaizerman J.A., Duan J.-X., et al. DNA binding ligands with in vivo efficacy in murine models of bacterial infection: optimization of internal aromatic amino acids. Bioorg Med Chem Lett 14 (2004) 2067-2072
24. Martin C., Ellis T., McGurk C.J., 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 44 (2005) 4135-4147