Interactions of ciprofloxacin with DPPC and DPPG: Fluorescence anisotropy, ATR-FTIR and 31P NMR spectroscopies and conformational analysis

Hayet Bensikaddour, Karim Snoussi, Laurence Lins, Françoise Van Bambeke, Paul M. Tulkens, Robert Brasseur, Erik Goormaghtigh, Marie Paule Mingeot-Leclercq

Research output: Contribution to journalArticle

Abstract

The interactions between a drug and lipids may be critical for the pharmacological activity. We previously showed that the ability of a fluoroquinolone antibiotic, ciprofloxacin, to induce disorder and modify the orientation of the acyl chains is related to its propensity to be expelled from a monolayer upon compression [1]. Here, we compared the binding of ciprofloxacin on DPPC and DPPG liposomes (or mixtures of phospholipids [DOPC:DPPC], and [DOPC:DPPG]) using quasi-elastic light scattering and steady-state fluorescence anisotropy. We also investigated ciprofloxacin effects on the transition temperature (Tm) of lipids and on the mobility of phosphate head groups using Attenuated Total Reflection Fourier Transform Infrared-Red Spectroscopy (ATR-FTIR) and 31P Nuclear Magnetic Resonance (NMR) respectively. In the presence of ciprofloxacin we observed a dose-dependent increase of the size of the DPPG liposomes whereas no effect was evidenced for DPPC liposomes. The binding constants Kapp were in the order of 105 M- 1 and the affinity appeared dependent on the negative charge of liposomes: DPPG > DOPC:DPPG (1:1; M:M) > DPPC > DOPC:DPPC (1:1; M:M). As compared to the control samples, the chemical shift anisotropy (Δσ) values determined by 31P NMR showed an increase of 5 and 9 ppm for DPPC:CIP (1:1; M:M) and DPPG:CIP (1:1; M:M) respectively. ATR-FTIR experiments showed that ciprofloxacin had no effect on the Tm of DPPC but increased the order of the acyl chains both below and above this temperature. In contrast, with DPPG, ciprofloxacin induced a marked broadening effect on the transition with a decrease of the acyl chain order below its Tm and an increase above this temperature. Altogether with the results from the conformational analysis, these data demonstrated that the interactions of ciprofloxacin with lipids depend markedly on the nature of their phosphate head groups and that ciprofloxacin interacts preferentially with anionic lipid compounds, like phosphatidylglycerol, present at a high content in these membranes.

Original languageEnglish (US)
Pages (from-to)2535-2543
Number of pages9
JournalBBA - Biomembranes
Volume1778
Issue number11
DOIs
StatePublished - Nov 2008
Externally publishedYes

Fingerprint

Fluorescence Polarization
Fourier Transform Infrared Spectroscopy
Ciprofloxacin
Nuclear magnetic resonance spectroscopy
Fourier transforms
Anisotropy
Magnetic Resonance Spectroscopy
Fluorescence
Spectroscopy
Infrared radiation
Liposomes
Lipids
Temperature
Phosphates
Nuclear magnetic resonance
Phosphatidylglycerols
Elastic scattering
1,2-dipalmitoylphosphatidylglycerol
Transition Temperature
Fluoroquinolones

Keywords

  • P NMR
  • ATR-FTIR
  • Ciprofloxacin
  • Conformational analysis
  • DPPC
  • DPPG
  • Melting temperature
  • Steady-state fluorescence anisotropy

ASJC Scopus subject areas

  • Biochemistry
  • Cell Biology
  • Biophysics

Cite this

Bensikaddour, H., Snoussi, K., Lins, L., Van Bambeke, F., Tulkens, P. M., Brasseur, R., ... Mingeot-Leclercq, M. P. (2008). Interactions of ciprofloxacin with DPPC and DPPG: Fluorescence anisotropy, ATR-FTIR and 31P NMR spectroscopies and conformational analysis. BBA - Biomembranes, 1778(11), 2535-2543. https://doi.org/10.1016/j.bbamem.2008.08.015

Interactions of ciprofloxacin with DPPC and DPPG : Fluorescence anisotropy, ATR-FTIR and 31P NMR spectroscopies and conformational analysis. / Bensikaddour, Hayet; Snoussi, Karim; Lins, Laurence; Van Bambeke, Françoise; Tulkens, Paul M.; Brasseur, Robert; Goormaghtigh, Erik; Mingeot-Leclercq, Marie Paule.

In: BBA - Biomembranes, Vol. 1778, No. 11, 11.2008, p. 2535-2543.

Research output: Contribution to journalArticle

Bensikaddour, H, Snoussi, K, Lins, L, Van Bambeke, F, Tulkens, PM, Brasseur, R, Goormaghtigh, E & Mingeot-Leclercq, MP 2008, 'Interactions of ciprofloxacin with DPPC and DPPG: Fluorescence anisotropy, ATR-FTIR and 31P NMR spectroscopies and conformational analysis', BBA - Biomembranes, vol. 1778, no. 11, pp. 2535-2543. https://doi.org/10.1016/j.bbamem.2008.08.015
Bensikaddour, Hayet ; Snoussi, Karim ; Lins, Laurence ; Van Bambeke, Françoise ; Tulkens, Paul M. ; Brasseur, Robert ; Goormaghtigh, Erik ; Mingeot-Leclercq, Marie Paule. / Interactions of ciprofloxacin with DPPC and DPPG : Fluorescence anisotropy, ATR-FTIR and 31P NMR spectroscopies and conformational analysis. In: BBA - Biomembranes. 2008 ; Vol. 1778, No. 11. pp. 2535-2543.
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abstract = "The interactions between a drug and lipids may be critical for the pharmacological activity. We previously showed that the ability of a fluoroquinolone antibiotic, ciprofloxacin, to induce disorder and modify the orientation of the acyl chains is related to its propensity to be expelled from a monolayer upon compression [1]. Here, we compared the binding of ciprofloxacin on DPPC and DPPG liposomes (or mixtures of phospholipids [DOPC:DPPC], and [DOPC:DPPG]) using quasi-elastic light scattering and steady-state fluorescence anisotropy. We also investigated ciprofloxacin effects on the transition temperature (Tm) of lipids and on the mobility of phosphate head groups using Attenuated Total Reflection Fourier Transform Infrared-Red Spectroscopy (ATR-FTIR) and 31P Nuclear Magnetic Resonance (NMR) respectively. In the presence of ciprofloxacin we observed a dose-dependent increase of the size of the DPPG liposomes whereas no effect was evidenced for DPPC liposomes. The binding constants Kapp were in the order of 105 M- 1 and the affinity appeared dependent on the negative charge of liposomes: DPPG > DOPC:DPPG (1:1; M:M) > DPPC > DOPC:DPPC (1:1; M:M). As compared to the control samples, the chemical shift anisotropy (Δσ) values determined by 31P NMR showed an increase of 5 and 9 ppm for DPPC:CIP (1:1; M:M) and DPPG:CIP (1:1; M:M) respectively. ATR-FTIR experiments showed that ciprofloxacin had no effect on the Tm of DPPC but increased the order of the acyl chains both below and above this temperature. In contrast, with DPPG, ciprofloxacin induced a marked broadening effect on the transition with a decrease of the acyl chain order below its Tm and an increase above this temperature. Altogether with the results from the conformational analysis, these data demonstrated that the interactions of ciprofloxacin with lipids depend markedly on the nature of their phosphate head groups and that ciprofloxacin interacts preferentially with anionic lipid compounds, like phosphatidylglycerol, present at a high content in these membranes.",
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