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Related Concept Videos

Inhibitors of Bacterial DNA Synthesis01:28

Inhibitors of Bacterial DNA Synthesis

Bacterial pathogens depend on precise and efficient DNA replication to sustain infection. Two type II topoisomerases—DNA gyrase and topoisomerase IV—are critical to this process, as they resolve DNA supercoiling and unlink chromosomes during replication. Fluoroquinolones, synthetic derivatives of quinolones, exploit this mechanism by stabilizing the transient DNA–enzyme cleavage complex, preventing strand religation, and causing lethal double-strand breaks. These antibiotics are selectively...
Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic acid...
Carboxylic Acids to Acid Chlorides01:18

Carboxylic Acids to Acid Chlorides

Carboxylic acids react with SOCl2 or PCl5 to form acid chlorides. Amongst the carboxylic acid derivatives, acid chlorides are the most reactive and synthetically important derivatives. They are useful reagents for Friedel–Crafts acylation of some aromatic compounds.
α-Halogenation of Carboxylic Acid Derivatives: Overview01:14

α-Halogenation of Carboxylic Acid Derivatives: Overview

Unlike aldehydes and ketones, carboxylic acids do not readily participate in α halogenation reactions via enols or enolate intermediates. However, α-halogenated acids are obtained through other methods. One of the approaches is the Hell–Volhard–Zelinsky (HVZ) reaction, wherein the carboxylic acid is treated with halogen in the presence of PBr3. It involves the conversion of acid to acid halide, which exists in equilibrium with its enol form. The enol attacks the electrophilic halogen to produce...
Reactions of Carboxylic Acids: Introduction01:41

Reactions of Carboxylic Acids: Introduction

Carboxylic acids possess an acidic –COOH functional group. The acidity can be attributed to the resonance stabilization of their conjugate base, wherein the negative charge is delocalized over both oxygen atoms.
Substituent Effects on Acidity of Carboxylic Acids01:31

Substituent Effects on Acidity of Carboxylic Acids

The acidity of carboxylic acids is influenced by the nature of the substituents bounded to the functional group. The acid strength is determined by the stability of the carboxylate anion—the conjugate base formed by dissociating the corresponding carboxylic acid.

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Visualization of Bacterial Resistance using Fluorescent Antibiotic Probes
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Published on: March 2, 2020

Fluoroquinolone salts with carboxylic acids.

J Satyanarayana Reddy1, Saraswatula Viswanadha Ganesh1, Ravikumar Nagalapalli1

  • 1Centre for Research on Drug Repurposing, Institute of Life Sciences, University of Hyderabad, Hyderabad 500 046, India.

Journal of Pharmaceutical Sciences
|March 12, 2011
PubMed
Summary

New fluoroquinolone antibiotic salts with carboxylic acids show improved solubility and dissolution rates in neutral conditions, offering potential advantages over existing drugs.

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Area of Science:

  • Pharmaceutical Chemistry
  • Materials Science
  • Drug Delivery

Background:

  • Fluoroquinolone antibiotics, such as norfloxacin and ciprofloxacin, are crucial antibacterial agents.
  • Optimizing the physicochemical properties of these drugs can enhance their therapeutic efficacy.
  • Salt formation is a common strategy to modify drug solubility and dissolution characteristics.

Purpose of the Study:

  • To synthesize and characterize novel fluoroquinolone antibiotic salts with various carboxylic acids.
  • To investigate the impact of counterions and hydration on the solubility and dissolution profiles of these new salts.
  • To evaluate the chemical stability of the novel salts under different pH conditions.

Main Methods:

  • Crystallization of norfloxacin and ciprofloxacin with carboxylic acids (oxalate, tartarate, benzoate, malonate, citrate).
  • Characterization using infrared spectroscopy, differential scanning calorimetry, X-ray powder diffraction, and single crystal X-ray diffraction.
  • Solubility and dissolution studies in pure water, 0.1 N HCl, and phosphate buffer solution (pH 6.8).

Main Results:

  • Six new fluoroquinolone salts were successfully synthesized; five were hydrates.
  • Crystal structures confirmed molecular composition, stoichiometry, and proton transfer.
  • The new salts exhibited higher solubility and faster dissolution in neutral/alkaline media compared to reference drugs, with reversed performance in acidic media.
  • Novel salts demonstrated superior chemical stability over norfloxacin under dissolution conditions.

Conclusions:

  • Novel fluoroquinolone salts with carboxylic acids offer improved solubility and dissolution profiles in physiologically relevant pH ranges.
  • The choice of counterion and hydration state significantly influences the salt's physicochemical properties.
  • These findings suggest potential for developing enhanced fluoroquinolone formulations with improved bioavailability.