C-glyco"RGD" as αIIb β3 and αv β integrin ligands for imaging applications: Synthesis, in vitro evaluation and molecular modeling

Bioorganic & Medicinal Chemistry
Timothé VuckoSandrine Lamandé-Langle

Abstract

The design of conjugates displaying simultaneously high selectivity and high affinity for different subtypes of integrins is a current challenge. The arginine-glycine-aspartic acid amino acid sequence (RGD) is one of the most efficient short peptides targeting these receptors. We report herein the development of linear and cyclic fluoro-C-glycoside"RGD" conjugates, taking advantage of the robustness and hydrophilicity of C-glycosides. As attested by in vitro evaluation, the design of these C-glyco"RGD" with a flexible three-carbon triazolyl linker allows distinct profiles towards αIIbβ3 and αvβ3 integrins. Molecular-dynamics simulations confirm the suitability of cyclic C-glyco-c(RGDfC) to target αvβ3 integrin. These C-glyco"RGD" could become promising biological tools in particular for Positron Emission Tomography imaging.

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