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 t...

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Bibliographic Details
Published in:European journal of medicinal chemistry 2012, Vol.47 (1), p.615-618
Main Authors: McPherson, James C., Runner, Royce, Buxton, Thomas B., Hartmann, John F., Farcasiu, Dan, Bereczki, Ilona, Rőth, Erzsébet, Tollas, Szilvia, Ostorházi, Eszter, Rozgonyi, Ferenc, Herczegh, Pál
Format: Article
Language:English
Subjects:
1-Hydroxybisphosphonate
Adsorption
Anti-Bacterial Agents - chemical synthesis
Anti-Bacterial Agents - chemistry
Anti-Bacterial Agents - metabolism
Anti-Bacterial Agents - pharmacology
Antibacterial agents
Antibiotic
Antibiotics. Antiinfectious agents. Antiparasitic agents
Bacteria - drug effects
Biological and medical sciences
Bone and Bones - drug effects
Bone and Bones - metabolism
Bone model
Durapatite - chemistry
Durapatite - metabolism
Fluoroquinolone
Fluoroquinolones - chemical synthesis
Fluoroquinolones - chemistry
Fluoroquinolones - metabolism
Fluoroquinolones - pharmacology
Medical sciences
Nanostructures
Organophosphonates - chemistry
Osteotropic
Pharmacology. Drug treatments
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Summary: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. [Display omitted] ► 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.
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2011.10.049