Synthesis of osteotropic hydroxybisphosphonate derivatives of fluoroquinolone antibacterials

James C McPherson 3rd; Royce Runner; Thomas B Buxton; John F Hartmann; Dan Farcasiu; Ilona Bereczki; Erzsébet Roth; Szilvia Tollas; Eszter Ostorházi; Ferenc Rozgonyi; Pál Herczegh

doi:10.1016/j.ejmech.2011.10.049

Synthesis of osteotropic hydroxybisphosphonate derivatives of fluoroquinolone antibacterials

Eur J Med Chem. 2012 Jan;47(1):615-8. doi: 10.1016/j.ejmech.2011.10.049. Epub 2011 Nov 4.

Authors

James C McPherson 3rd¹, Royce Runner, Thomas B Buxton, John F Hartmann, Dan Farcasiu, Ilona Bereczki, Erzsébet Roth, Szilvia Tollas, Eszter Ostorházi, Ferenc Rozgonyi, Pál Herczegh

Affiliation

¹ Department of Clinical Investigation, Eisenhower Army Medical Center, Fort Gordon, GA, USA.

PMID: 22093760
DOI: 10.1016/j.ejmech.2011.10.049

Abstract

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.

MeSH terms

Adsorption
Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / chemistry
Anti-Bacterial Agents / metabolism
Anti-Bacterial Agents / pharmacology*
Bacteria / drug effects
Bone and Bones / drug effects
Bone and Bones / metabolism
Durapatite / chemistry
Durapatite / metabolism
Fluoroquinolones / chemical synthesis*
Fluoroquinolones / chemistry
Fluoroquinolones / metabolism
Fluoroquinolones / pharmacology*
Nanostructures
Organophosphonates / chemistry*

Substances

Anti-Bacterial Agents
Fluoroquinolones
Organophosphonates
Durapatite