Non-peptidic inhibitors of Matrix-Metalloproteinases (MMPIs) gained an important position in recent years, both for pharmacological applications and for molecular imaging purposes after appropriate labeling. We synthesized a library of partially fluorinated arylsulfonamides bearing different zinc binding groups (ZBG) such as α-amino hydroxamates 1, α-amino phosphonates 2a,b, and α-amino acids 3. The influences of fluorine substituents, the nature of the ZBG and the absolute configuration of the compounds on the inhibitory potencies against gelatinases (MMP-2 and MMP-9) and collagenases (MMP-8 and MMP-13) were investigated. Finally, selected highly potent inhibitors were 18F-radiolabeled and tested as radiotracers for molecular imaging of active MMPs with Positron Emission Tomography (PET).

Fluorine-containing matrix-metalloproteinase inhibitors: The role of Fluorine substituents and Zinc binding groups on activity

255th National Meeting (2018)

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