Studies on the binding mechanism of fluoroquinolones to melanin.

In order to elucidate the binding mechanism of melanin and fluoroquinolones (ofloxacin, norfloxacin, ciprofloxacin, lomefloxacin, levofloxacin), we investigated the interaction of fluoroquinolones with compounds such as l-beta-(3,4-dihydroxyphenyl) alanine (l-DOPA), l-tyrosine, 5-hydroxy-l-tryptophan, l-tryptophan, and l-phenylalanine, which possess the kind of functional groups that melanin does and are closely related to melanin. The recovery of drugs from the melanin-drug complexes by metal ions of Li, Na, Ka, Mg, Ca, Ba, Cu, Ni, and Fe was demonstrated. Smaller and highly charged cations were found to be more effective for this recovery, and magnesium ions were the most effective of all the ions investigated.