Skip to main content
SpringerLink
Log in

Factor analysis of microbiological activity data and structural parameters of antibacterial quinolones

  • Original Paper
  • Published:
Journal of Molecular Modeling Aims and scope Submit manuscript

Abstract

Factor analysis (FA) was performed on quinolone derivatives with antibacterial activity to model relationships between molecular descriptors and microbiological activities determined on five bacterial cell lines (Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Staphylococcus aureus and Streptococcus pneumoniae). Molecular modeling studies were performed with the use of HyperChem software and MM+ molecular mechanics with the semi-empirical AM1 method. Factor analysis led to the extraction of two main factors, with the share of factor 1 amounting to about 76% and factor 2 to about 24% for all the parameters used in the statistical analysis. Moreover, FA results indicated that energy of orbitals lowest unoccupied molecular orbital, energy of ionization, electron affinity, electronegativity, maximum electron density, refraction and polarizability appeared to be descriptors important for the antibacterial activity of quinolones.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2

Similar content being viewed by others

References

  1. Domagala JM, Hanna LD, Heifetz CL, Hutt MP, Mich TF, Sanchez JP, Solomon M (1986) New structure-activity relationships of the quinolone antibacterials using the target enzyme. The development and application of a DNA gyrase assay. J Med Chem 29:394–404

    Article  CAS  Google Scholar 

  2. Remuson P, Bouzard D, Di Cesare P, Essiz M, Jacquet JP, Kiechel JR, Ledoussal B, Kessler RE, Fung-Tomc J (1991) Fluoronaphthyridines and -quinolones as antibacterial agents. 3. Synthesis and structure-activity relationships of new 1-(1, 1-dimethyl-2-fluoroethyl), 1-[1-methyl-1-(fluoromethyl)-2-fluoroethyl], and 1-[1, 1-(difluoromethyl)-2-fluoroethyl] substituted derivatives. J Med Chem 34:29–37

    Article  Google Scholar 

  3. Ball P (2000) Quinolone generations: natural history or natural selection? J Antimicrob Chemother 46:17–24

    CAS  Google Scholar 

  4. Bearden DT, Danziger LH (2001) Mechanism of action of and resistance to quinolones. Pharmacotherapy 21:224–232

    Article  Google Scholar 

  5. Oliphant CM, Green GM (2002) Quinolones: a comprehensive review. Am Fam Physician 65:455–464

    Google Scholar 

  6. Brighty KE, Gootz TD (1997) The chemistry and biological profile of trovafloxacin. J Antimicrob Chemother 39:1–14

    Article  CAS  Google Scholar 

  7. Smith HJ, Nichol KA, Hoban DJ, Zhanel GG (2002) Dual activity of fluoroquinolones against Streptococcus pneumoniae: the facts behind the claims. J Antimicrob Chemother 49:893–895

    Article  CAS  Google Scholar 

  8. Hoogkamp-Korstanje JAA (1997) In-vitro activities of ciprofloxacin, levofloxacin, lomefloxacin, ofloxacin, pefloxacin, sparfloxacin and trovafloxacin against gram-positive and gram-negative pathogens from respiratory tract infections. J Antimicrob Chemother 40:427–431

    Article  CAS  Google Scholar 

  9. King A, May J, French G, Phillips L (2000) Comparative in vitro activity of gemifloxacin. J Antimicrob Chemother 45:1–12

    Article  CAS  Google Scholar 

  10. Milatovic D, Schmitz FJ, Brisse S, Verhoef J, Fluit AC (2000) In vitro activities of sitafloxacin (DU-6859a) and six other fluoroquinolones against 8, 796 clinical bacterial isolates. Antimicrob Agents Chemother 44:1102–1107

    Article  CAS  Google Scholar 

  11. Piddock LJV, Jin YF, Griegs DJ (2001) Effect of hydrophobicity and molecular mass on the accumulation of fluoroquinolones by Staphylococcus aureus. J Antimicrob Chemother 47:261–270

    Article  CAS  Google Scholar 

  12. Weller TMA, Andrews JM, Jevons G, Wise R (2002) The in vitro activity of BMS-284756, a new des-fluorinated quinolone. J Antimicrob Chemother 49:177–184

    Article  CAS  Google Scholar 

  13. Yun HJ, Min YH, Lim JA, Kang JW, Kim SY, Kim MJ, Jeong JH, Choi YJ, Kwon HJ, Jung YH, Shim MJ, Choi EC (2002) In vitro and in vivo antibacterial activities of DW286, a new fluoronaphthyridone antibiotic. Antimicrob Agents Chemother 46:3071–3074

    Article  CAS  Google Scholar 

  14. Parr RG, Pearson RG (1983) Absolute hardness: companion parameter to absolute electronegativity. J Am Chem Soc 105:7512–7516

    Article  CAS  Google Scholar 

  15. Robles J, Bartolotti LJ (1984) Electronegativities, electron affinities, ionization potentials, and hardnesses of elements within spin polarized density functional theory. J Am Chem Soc 106:3723–3727

    Article  CAS  Google Scholar 

  16. Kaliszan R, Ośmiałowski K (1990) Correlation between chemical structure of non-congeneric solutes and their retention on polybutadiene-coated alumina. J Chromatogr 506:3–16

    Article  CAS  Google Scholar 

  17. Gami-Yilinkou R, Kaliszan R (1991) Chromatographic data for pharmacological classification of imidazol(in)e drugs. J Chromatogr 550:573–584

    Article  CAS  Google Scholar 

  18. Gami-Yilinkou R, Nasal A, Kaliszan R (1993) Application of chemometrically processed chromatographic data for pharmacologically relevant classification of antihistamine drugs. J Chromatogr 633:57–63

    Article  CAS  Google Scholar 

  19. Nasal A, Buciński A, Bober L, Kaliszan R (1997) Prediction of pharmacological classification by means of chromatographic parameters processed by principal component analysis. Int J Pharm 153:43–55

    Article  Google Scholar 

  20. Bober L, Nasal A, Kuchta A, Kaliszan R (1998) Chemometric analysis of retention data from high-performance liquid chromatography-structural parameters and biological activity of sulphonamides. Acta Chromatogr 8:48–69

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Medicinal Chemistry, Faculty of Pharmacy, Collegium Medicum, Nicolaus Copernicus University, Bydgoszcz, Poland

    Marcin Koba, Tomasz Bączek, Danuta Rystok-Grabska, Jolanta Stasiak & Katarzyna Koba

  2. Department of Biopharmaceutics and Pharmacodynamics, Medical University of Gdańsk, Al. Gen. J. Hallera 107, 80-416, Gdańsk, Poland

    Tomasz Bączek, Katarzyna Macur & Teresa Frąckowiak

  3. POLPHARMA SA Pharmaceutical Works, Starogard Gdański, Poland

    Leszek Bober

  4. Department of Biopharmacy, Faculty of Pharmacy, Collegium Medicum, Nicolaus Copernicus University, Bydgoszcz, Poland

    Adam Buciński

Authors
  1. Marcin Koba
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Tomasz Bączek
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Katarzyna Macur
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Leszek Bober
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Teresa Frąckowiak
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Adam Buciński
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Danuta Rystok-Grabska
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Jolanta Stasiak
    View author publications

    You can also search for this author in PubMed Google Scholar

  9. Katarzyna Koba
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Tomasz Bączek.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Koba, M., Bączek, T., Macur, K. et al. Factor analysis of microbiological activity data and structural parameters of antibacterial quinolones. J Mol Model 16, 327–335 (2010). https://doi.org/10.1007/s00894-009-0549-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00894-009-0549-3

Keywords

Search

Navigation