Display options
Cite
Lewandowski EM, Szczupak Ł, Wong S, et al. Antibacterial Properties of Metallocenyl-7-ADCA Derivatives and Structure in Complex with CTX-M . Organometallics. 2017;36(9):1673-1676doi: 10.1021/acs.organomet.6b00888.
Lewandowski, E. M., Szczupak, �. �., Wong, S., Skiba, J., Guśpiel, A., Solecka, J., Vrček, V., Kowalski, K., & Chen, Y. (2017). Antibacterial Properties of Metallocenyl-7-ADCA Derivatives and Structure in Complex with CTX-M . Organometallics, 36(9), 1673-1676. https://doi.org/10.1021/acs.organomet.6b00888
Lewandowski, Eric M, et al. "Antibacterial Properties of Metallocenyl-7-ADCA Derivatives and Structure in Complex with CTX-M ." Organometallics vol. 36,9 (2017): 1673-1676. doi: https://doi.org/10.1021/acs.organomet.6b00888
Lewandowski EM, Szczupak Ł, Wong S, Skiba J, Guśpiel A, Solecka J, Vrček V, Kowalski K, Chen Y. Antibacterial Properties of Metallocenyl-7-ADCA Derivatives and Structure in Complex with CTX-M . Organometallics. 2017 May 08;36(9):1673-1676. doi: 10.1021/acs.organomet.6b00888. Epub 2017 Feb 01. PMID: 29051683; PMCID: PMC5642929.
Copy Download .nbib Format: NLM
Share it on

Organometallics. 2017 May 08;36(9):1673-1676. doi: 10.1021/acs.organomet.6b00888. Epub 2017 Feb 01.

Antibacterial Properties of Metallocenyl-7-ADCA Derivatives and Structure in Complex with CTX-M .

Organometallics

Eric M Lewandowski, Łukasz Szczupak, Stephanie Wong, Joanna Skiba, Adam Guśpiel, Jolanta Solecka, Valerije Vrček, Konrad Kowalski, Yu Chen

Affiliations

  1. Department of Molecular Medicine, University of South Florida Morsani College of Medicine, 12901 Bruce B. Downs Blvd., Tampa, Florida 33612, United States.
  2. Department of Organic Chemistry, Faculty of Chemistry, University of ?ód?, Tamka 12, PL-91403 ?ód?, Poland.
  3. National Institute of Public Health-National Institute of Hygiene, Chocimska 24, PL-00791, Warsaw, Poland.
  4. Faculty of Pharmacy and Biochemistry, University of Zagreb, Ante Kova?i?a 1, Zagreb, Croatia.

PMID: 29051683 PMCID: PMC5642929 DOI: 10.1021/acs.organomet.6b00888

Abstract

A series of six novel metallocenyl-7-ADCA (metallocenyl = ferrocenyl or ruthenocenyl; 7-ADCA = 7-aminodesacetoxycephalosporanic acid) conjugates were synthesized and their antibacterial properties evaluated by biochemical and microbiological assays. The ruthenocene derivatives showed a higher level of inhibition of DD-carboxypeptidase 64-575, a Penicillin Binding Protein (PBP), than the ferrocene derivatives and the reference compound penicillin G. Protein X-ray crystallographic analysis revealed a covalent acyl-enzyme complex of a ruthenocenyl compound with CTX-M β-lactamase E166A mutant, corresponding to a similar complex with PBPs responsible for the bactericidal activities of these compounds. Most interestingly, an intact compound was captured at the crystal-packing interface, elucidating for the first time the structure of a metallocenyl β-lactam compound that previously eluded small molecule crystallography. We propose that protein crystals, even from biologically unrelated molecules, can be utilized to determine structures of small molecules.

Conflict of interest statement

Notes The coordinates and structure factors have been deposited in the Protein Data Bank (PDB), www.rcsb.org, with the accession code PDB ID: 5UJO. The authors declare no competing financial interest.

References

  1. Chem Soc Rev. 2015 Dec 21;44(24):8802-17 - PubMed
  2. Science. 2008 Jul 18;321(5887):356-61 - PubMed
  3. Biochem J. 1974 Oct;143(1):115-27 - PubMed
  4. ACS Chem Biol. 2013 Jul 19;8(7):1442-50 - PubMed
  5. Antimicrob Agents Chemother. 1995 Jun;39(6):1211-33 - PubMed
  6. FEMS Microbiol Rev. 2008 Mar;32(2):234-58 - PubMed
  7. J Am Chem Soc. 2007 May 2;129(17):5378-80 - PubMed
  8. Eur J Med Chem. 2010 Mar;45(3):1181-8 - PubMed
  9. Dalton Trans. 2012 Jun 7;41(21):6350-8 - PubMed
  10. Ann N Y Acad Sci. 2013 Jan;1277:91-104 - PubMed
  11. J Mol Biol. 2005 Apr 29;348(2):349-62 - PubMed
  12. Biochem Pharmacol. 2007 Dec 15;74(12):1686-701 - PubMed
  13. Antimicrob Agents Chemother. 2013 Jul;57(7):3137-46 - PubMed
  14. Clin Microbiol Rev. 1995 Oct;8(4):557-84 - PubMed
  15. Annu Rev Microbiol. 2011;65:455-78 - PubMed
  16. Eur J Med Chem. 2012 Nov;57:234-9 - PubMed
  17. Proteins. 1999 Dec 1;37(4):628-40 - PubMed
  18. Nature. 2013 Mar 28;495(7442):461-6 - PubMed
  19. Protein Sci. 2014 Mar;23(3):243-59 - PubMed
  20. Chem Commun (Camb). 2015 Apr 11;51(28):6186-9 - PubMed
  21. FEMS Microbiol Rev. 2006 Sep;30(5):673-91 - PubMed
  22. Mol Cell. 2012 Dec 14;48(5):705-12 - PubMed
  23. Clin Microbiol Rev. 2010 Jan;23(1):160-201 - PubMed
  24. Proc Natl Acad Sci U S A. 1993 Sep 15;90(18):8653-7 - PubMed
  25. Proc Natl Acad Sci U S A. 1964 Sep;52:833-9 - PubMed
  26. Clin Microbiol Rev. 2001 Oct;14(4):933-51, table of contents - PubMed
  27. Biochemistry. 2015 Jan 20;54(2):447-57 - PubMed
  28. Antimicrob Agents Chemother. 1998 Jan;42(1):1-17 - PubMed
  29. J Med Chem. 2011 Jan 13;54(1):3-25 - PubMed
  30. Antimicrob Agents Chemother. 2004 Jan;48(1):1-14 - PubMed
  31. J Am Chem Soc. 2005 Apr 20;127(15):5423-34 - PubMed
  32. J Mol Biol. 2006 Apr 14;357(5):1471-82 - PubMed
  33. J Mol Biol. 2010 Jul 2;400(1):108-20 - PubMed
  34. FEMS Microbiol Rev. 2000 Jul;24(3):251-62 - PubMed
  35. Curr Opin Microbiol. 2010 Oct;13(5):551-7 - PubMed
  36. Biochem J. 1966 Jan;98(1):11C-3C - PubMed

Publication Types

Grant support