Phenothiazinium-fluoroquinolone drug conjugates.
Synthesis and antibacterial screening of a homologous series of 3-dialkylaminophenothiazinium-7-norfloxacin conjugates was carried out alongside a corresponding series of symmetrical methylene blue derivatives. The norfloxacin conjugates maintained typical methylene blue derivative photoproperties, such as long wavelength absorption, but produced no measurable singlet oxygen in the standard assay and provided no significant increase in the magnitude of photoantibacterial action, this being similar to the methylene blue homologues, although both the conjugates and homologues were considerably more active than methylene blue itself both against Staphylococcus aureus and Escherichia coli. DNA binding via intercalation was considerably greater for the series of norfloxacin conjugates than for the methylene blue homologues.
Wainwright
Mark
M
School of Pharmacy and Biomolecular Sciences, Liverpool John Moores University, Byrom Street, Liverpool L3 3AF, UK. mark_wainwright@hotmail.com
Shah
Ami
A
Meegan
Katie
K
Loughran
Ciara
C
Smith
Andy
A
Valli
Nasima
N
Dempster
Nicola
N
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D004353:Drug Evaluation, Preclinical; D004926:Escherichia coli / Q000187:drug effects; D024841:Fluoroquinolones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D006801:Humans; D008826:Microbial Sensitivity Tests; D050296:Microbial Viability / Q000187:drug effects; D015394:Molecular Structure; D010640:Phenothiazines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013211:Staphylococcus aureus / Q000187:drug effects
D000900:Anti-Bacterial Agents; D024841:Fluoroquinolones; D010640:Phenothiazines