Synthesis of osteotropic hydroxybisphosphonate derivatives of fluoroquinolone antibacterials

1-Hydroxybisphosphonate derivatives of ciprofloxacin, gatifloxacin and moxifloxacin have been synthesized using Cu(I) catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction. The 1,2,3-triazol linked hydroxybisphosphonate derivative of ciprofloxacin exhibited antibacterial activity comparable to the parent antibiotic and all fluoroquinolone-bisphosphonates displayed osteotropic properties in a bone model.

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► Bisphosphonate derivatives of antibiotics are osteotropic compounds.
► New hydroxibisphosphonate derivatives of fluoroquinolone antibacterials were synthesized.
► The fluoroquinolone-bisphosphonate conjugates strongly adsorb on hydroxyapatite bone model.
► The conjugates have antibacterial activity.
► The new compounds will be evaluated for treatment of osteomyelitis.