On the photophysicochemical properties of selected fluoroquinolones: Solvatochromic and fluorescence spectroscopy study

Abdulilah Dawoud Bani-Yaseen*, Fawaz Hammad, Bader Ghanem, Elham G. Mohammad

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

13 Scopus citations

Abstract

The photophysicochemical properties of selected fluoroquinolones in different solvents of various physical properties, including polarity and hydrogen bonding ability, were investigated using steady state fluorescence spectroscopy. The solvent-dependant fluorescence emission spectra of selected fluoroquinolones, namely ciprofloxacin (CIPR) and enrofloxacin (ENRO), were employed to gain insights concerning its photophysicochemical properties of interests. Interestingly, fluorescence spectra of the selected drugs exhibited structured emission spectra in nonpolar solvents such as hexane, whereas unstructured spectra were observed in more polar solvents such as alcohols and water. Also, a notable bathochromic shift in λmaxem was observed in fluorescence spectra of both drugs with increasing solvent polarity that resulted in biphasic behavior upon applying the Lippert-Mataga correlation that correspond to general and specific solvent effects. Applying the Lippert-Mataga correlation to the fluorescence spectra of CIPR and ENRO in various solvents was employed to estimate the dipole moment difference between the ground and excited states of them, Δμ(μe- μg), where obtained results revealed the values of 9.4 and 16.2 Debye for the LE and ICT states of ENRO, respectively, and 8.0 and 16.2 Debye for the LE and ICT states of CIPR, respectively. Multiple linear regression analysis (MLRA) based on Kamlet-Taft equating was applied against absorption frequency (νabs), emission frequency (νem), Stokes shift (â̂†ν), and fluorescence quantum yield (Φf), where obtained results revealed excellent correlation (R: 0.916-0.966) that are consistent with other results considering the effect of solvent polarizability, hydrogen bonding ability, and viscosity on the photophysicochemical properties of the studied fluoroquinolones.

Original languageEnglish (US)
Pages (from-to)93-101
Number of pages9
JournalJournal of Fluorescence
Volume23
Issue number1
DOIs
StatePublished - Jan 1 2013

Keywords

  • Fluorescence
  • Fluoroquinolones
  • Kamlet-Taft equation
  • Lippert-Mataga correlation
  • Multiple linear regression analysis
  • Solvatochromism

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Psychology
  • Social Sciences (miscellaneous)
  • Sociology and Political Science
  • Spectroscopy
  • Clinical Biochemistry
  • Law

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