Jump to ContentJump to Main Navigation
Show Summary Details
More options …

Acta Pharmaceutica

The Journal of Croatian Pharmaceutical Society

4 Issues per year

IMPACT FACTOR 2016: 1.288
5-year IMPACT FACTOR: 1.600

CiteScore 2016: 1.55

SCImago Journal Rank (SJR) 2016: 0.353
Source Normalized Impact per Paper (SNIP) 2016: 0.854

Open Access
See all formats and pricing
More options …
Volume 59, Issue 3 (Sep 2009)


Metalloantibiotics: Synthesis, characterization and antimicrobial evaluation of bismuth-fluoroquinolone complexes against Helicobacter pylori

Anwar Shaikh
  • Pharmacy Department, Faculty of Technology and Engineering, The M. S. University of Baroda, Vadodara-390001, India
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Rajani Giridhar
  • Pharmacy Department, Faculty of Technology and Engineering, The M. S. University of Baroda, Vadodara-390001, India
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Francis Megraud
  • Laboratoire de Bacteriologie, Université Victor Segalen Bordeaux 2 and Hôpital Pellegrin, Place Amélie Raba-Léon 33076 Bordeaux cedex France
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Mange Yadav
  • Pharmacy Department, Faculty of Technology and Engineering, The M. S. University of Baroda, Vadodara-390001, India
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2009-10-09 | DOI: https://doi.org/10.2478/v10007-009-0027-6

Metalloantibiotics: Synthesis, characterization and antimicrobial evaluation of bismuth-fluoroquinolone complexes against Helicobacter pylori

Novel organometallic compounds have been prepared by complexing the fluoroquinolones, norfloxacin, ofloxacin, ciprofloxacin, sparfloxacin, lomefloxacin, pefloxacin and gatifloxacin, with bismuth. The complexes were characterized by UV, IR, atomic absorption spectroscopy, elemental analysis, differential scanning calorimetry, thermogravimetric analysis and mass spectrometry. Their antibacterial potential against Helicobacter pylori and other microorganisms was investigated. These compounds were found to possess strong activity against Helicobacter pylori with a minimum inhibitory concentration of 0.5 mg L-1. They also exhibited moderate activity against Escherichia coli, Staphylococcus aureus, Bacillus pumilus and Staphylococcus epidermidis. These bismuth-fluoroquinolone complexes have the potential to be developed as drugs against H. pylori related ailments.

Metaloantibiotici: Sinteza, karakterizacija i antimikrobno djelovanje kompleksa fluorokinolona s bizmutom na Helicobacter pylori

Komplesacijom fluorokinolona, norfloksacina, ofloksacina, ciprofloksacina, sparfloksacina, lomefloksacina, pefloksacina i gatifloksacina s bizmutom pripravljeni su novi organometalni spojevi. Dobiveni kompleksi karakterizirani su UV, IR i atomskom apsorpcijskom spektroskopijom, elementarnom analizom, diferencijalnom pretražnom kalorimetrijom, termogravimetrijskom analizom i spektrometrijom masa. Nadalje, ispitivan je njihov učinak na Helicobacter pylori i druge mikroorganizme. Ispitivani spojevi pokazuju snažno djelovanje na Helicobacter pylori u koncentraciji 0,5 mg L-1 te umjereno djelovanje na Escherichia coli, Staphylococcus aureus, Bacillus pumilus i Staphylococcus epidermidis. Kompleksi fluorokinolona s bizmutom potencijalni su lijekovi za infekcije uzrokovane H. pylori.

Keywords: fluoroquinolone; bismuth; complex; antimicrobial activity; Helicobacter pylori

Keywords: fluorokinolon; bizmut; kompleks; antimikrobno djelovanje; Helicobacter pylory

  • R. Nagarajan, S. N. Mehta, S. R. Naik and W. Fabry, Preparation and activity of some novel organo-metallic complexes against Helicobacter pylori, Arzneim. Forsch/Drug Res. 49 (1999) 951-954.Google Scholar

  • I. Muhammad, I. Javed, I. Shahid and I. Nazia, In vitro antibacterial studies of ciprofloxacin-imines and their complexes with Cu (II), Ni (II), Co (II) and Zn (II), Turk. J. Biol. 31 (2007) 67-72.Google Scholar

  • S. Nakajima, D. Y. Graham, T. Hattori and T. Bamba, Strategy for treatment of Helicobacter pylori infection in adults II. Practical Policy in 2000, Curr. Pharm. Design 15 (2000) 1515-1529; DOI: 10.2174/1381612003399013.CrossrefGoogle Scholar

  • L. J. Ming, Structure and function of »metalloantibiotics«, Med. Res. Rev. 23 (2003) 697-762; DOI: 10.1002/med.10052.CrossrefPubMedGoogle Scholar

  • Z. H. Chohan, C. T. Supuran and A. Scozzafava, Metal binding and antibacterial activity of ciprofloxacin complexes, J. Enz. Inhib. Med. Chem. 20 (2005) 303-307; DOI: 10.1080/14756360310001624948.CrossrefGoogle Scholar

  • A. J. Schaeffer, The expanding role of fluoroquinolones, Dis. Mon. 49 (2003) 129-147; DOI: 10.1016/S0011-5029(03)90005-8.CrossrefPubMedGoogle Scholar

  • J. Strahilevitz, A. Robicsek and D. C. Hooper, Role of the extended alpha4 domain of Staphylococcus aureus gyrase A protein in determining low sensitivity to quinolones, Antimicrob. Agents Chemother. 50 (2006) 600-606; DOI: 10.1128/AAC.50.2.600-606.2006.CrossrefGoogle Scholar

  • Y. Dinh, Bacterial topoisomerase I as a target for discovery of antibacterial compounds, Nucl. Acids Res. 37 (2009) 731-737; DOI: 10.1093/nar/gkn936.Web of ScienceCrossrefGoogle Scholar

  • A. Foroumadi, M. Safavi, S. Emami, F. Siavoshi, S. Najjari, F. A. Safari and A. Shafiee, Structure-activity relationship study of a series of N-substituted piperazinyl-fluoroquinolones as anti-Helicobacter pylori agents, Med. Chem. 4 (2008) 498-502; DOI: 10.2174/157340608785700162.Web of ScienceCrossrefPubMedGoogle Scholar

  • M. Zupancic, I. Turel, P. Bukovec, A. White and D. J. Williams, Synthesis and characterization of two novel zinc(II) complexes with ciprofloxacin. Crystal structure of [C17H19N3O3F]2 · [ZnCl4] · 2H2O, Croat. Chem. Acta 74 (2001) 61-74.Google Scholar

  • T. Mach, P. Neves, E. Spiga, H. Weingart, M. Winterhalter, P. Ruggerone, M. Ceccarelli and P. Gameiro, Facilitated permeation of antibiotics across membrane channels - Interaction of the quinolone moxifloxacin with the Omp F channel, J. Am. Chem. Soc. 40 (2008) 13301-13309.Web of ScienceCrossrefGoogle Scholar

  • J. Clitherow, Preparation of Ranitidine Salts and Oral Compositions Containing them, U.K. Pat. GB 2,220,937, Jan 24, 1990; ref. Chem. Abstr. 113 (1990) 65266n.Google Scholar

  • L. Vertesy, M. Astrid and K. Michael, Bismuth Salts of Moenomycin-Like Antibiotic Preparation, Use and Pharmaceuticals Containing Such Salts for Treatment of Stomach Disorders, Eur. Pat. 864,579, Sep 16, 1998; ref. Chem. Abstr. 129 (1998) 216854m.Google Scholar

  • M. Guo, I. Harvey, W. Yang, L. Coghill, A. John, T. A. Ross and P. J. Sadler, Synergistic anion and metal binding to the ferric ion-binding protein from Neisseria gonorrhoeae, J. Biol. Chem. 278 (2003) 2490-2502.Google Scholar

  • A. R. Shaikh, R. Giridhar and M. R. Yadav, Bismuth-norfloxacin complex: Synthesis, physicochemical and antimicrobial evaluation, Int. J. Pharm. 332 (2007) 24-30; DOI: 10.1016/j.ijpharm.2006.11.037.CrossrefWeb of ScienceGoogle Scholar

  • National Committee for Clinical Laboratory Standards, Methods for Antimicrobial Testing of Anaerobic Bacteria, Approved standard M11-A3, 2nd ed., Villanova (PA): National Committee for Clinical Laboratory Standards 1993.Google Scholar

  • I. Turel, I. Leban and N. Bukovec, Synthesis, characterization, and crystal structure of a copper(II) complex with quinolone family member (ciprofloxacin); bis (1)-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-piperazin-1-yl-quinoline-3-carboxylate copper(II) chloride hexahydrate, J. Inorg. Biochem. 56 (1994) 273-282.Google Scholar

About the article

Published Online: 2009-10-09

Published in Print: 2009-09-01

Citation Information: Acta Pharmaceutica, ISSN (Online) 1846-9558, ISSN (Print) 1330-0075, DOI: https://doi.org/10.2478/v10007-009-0027-6.

Export Citation

This content is open access.

Citing Articles

Here you can find all Crossref-listed publications in which this article is cited. If you would like to receive automatic email messages as soon as this article is cited in other publications, simply activate the “Citation Alert” on the top of this page.

Mohammed T. Alghamdi, A.A. Alsibaai, M.S. El-Shahawi, and Moamen S. Refat
Journal of Molecular Structure, 2017, Volume 1130, Page 264
Donal Keogan and Darren Griffith
Molecules, 2014, Volume 19, Number 9, Page 15258
Aysegul Golcu
Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 2014, Volume 44, Number 10, Page 1509
Jorge AR Salvador, Sandra AC Figueiredo, Rui MA Pinto, and Samuel M Silvestre
Future Medicinal Chemistry, 2012, Volume 4, Number 11, Page 1495
Harun Muslu, Aysegul Golcu, Mehmet Tumer, and Mehmet Ozsoz
Journal of Coordination Chemistry, 2011, Volume 64, Number 19, Page 3393
György Miklós Buzás
Orvosi Hetilap, 2010, Volume 151, Number 49, Page 2003

Comments (0)

Please log in or register to comment.
Log in