title: Antibacterial Derivatives of Ciprofloxacin to Inhibit Growth of Necrotizing Fasciitis Associated Penicillin Resistant Escherichia coli.
abstract: Escherichia coli (E. coli) is associated with necrotizing fasciitis (type I) and can induce enough damage to tissue causing hypoxia. Three ester derivatives of the broad-spectrum antibiotic ciprofloxacin were placed into bacteria culture simultaneously with the parent ciprofloxacin (drug 1) to ascertain the level of antibacterial activity. The n-propyl (drug 2), n-pentyl (drug 3), and n-octyl (drug 4) esters of ciprofloxacin were synthesized under mixed phase conditions and by microwave excitation. The formation of ester derivatives of ciprofloxacin modified important molecular properties such as Log P and polar surface area which improves tissue penetration, yet preserved strong antibacterial activity. The Log P values for drugs 1, 2, 3, and 4 became -0.701, 0.437, 1.50, and 3.02, respectively. The polar surface areas for drugs 1, 2, 3, and 4 were determined to be 74.6 Angstroms(2), 63.6 Angstroms(2), 63.6 Angstroms(2), and 63.6 Angstroms(2), respectively. These values of Log P and polar surface area improved tissue penetration, as indicated by the determination of dermal permeability coefficient (K p ) and subsequently into the superficial fascial layer. All drugs induced greater than 60% bacterial cell death at concentrations less than 1.0 micrograms/milliliter. The ester derivatives of ciprofloxacin showed strong antibacterial activity toward penicillin resistant E. coli.
authors.affiliation: University of Nebraska, College of Arts & Sciences, Durham Science Center, Department of Chemistry, Omaha, NE 68182, USA.
authors.forename: Ronald
authors.initials: R
authors.lastname: Bartzatt
authors.affiliation: Texas A & M Health Science Center, Department of Microbial and Molecular Pathogenesis, Bryan, TX 77807, USA.
authors.forename: Suat L G
authors.initials: SL
authors.lastname: Cirillo
authors.affiliation: Texas A & M Health Science Center, Department of Microbial and Molecular Pathogenesis, Bryan, TX 77807, USA.
authors.forename: Jeffrey D
authors.initials: JD
authors.lastname: Cirillo