798567-32-5

Upstream product

• 83948-53-2 3-bromopropylamine tert-butylcarbamate 
• 432515-23-6 t-butyl (S)-3-(4-hydroxy-3-nitrophenyl)-2-(3-trifluoromethyl-1-benzenesulfonylamino)-propionate 
• 58885-58-8 N-tert-butoxycarbonyl-3-aminopropanol 
• 432515-20-3 (S)-t-butyl 3-(4-hydroxyphenyl)-2-(3-trifluoromethylbenzenesulfonylamino)propionate 
• 777-44-6 3-(Trifluoromethyl)benzenesulfonyl chloride 
• 16874-12-7 Tyr(tBu) 

Downstream Products

• 798567-33-6 (S)-t-butyl 3-(4-(3-t-butoxycarbonylaminopropoxy)-3-aminophenyl)-2-(3-(trifluoromethyl)phenylsulfonamido)propionate 

Relevant academic research and scientific papers

αvβ3 integrin-targeting Arg-Gly-Asp (RGD) peptidomimetics containing oligoethylene glycol (OEG) spacers

RGD peptides are used in biomaterials science for surface modifications with a view to elicit selective cellular responses. Our objective is to replace peptides by small peptidomimetics acting similarly. We designed novel molecules targeting αvβ3 integrin and featuring spacer-arms (for surface grafting), which do not disturb the biological activity, from (L) N-(3-(trifluoromethyl)benzenesulfonyl) tyrosine used as scaffold. Various Arg-mimics were fixed on the phenol function, and the ortho position was used for the coupling of OEG spacers. All peptidomimetics were active in the nM range in a binding test toward human αvβ 3 integrin (IC50 = 0.1 to 1.7 nM) and selective versus platelet integrin αIIbβ3. Selected compounds revealed excellent ability to inhibit bone cells adhesion on vitronectin. Modeling and docking studies were performed for comparing the most active RGD peptidomimetic to cilengitide, i.e., cyclo-[RGDfN(Me)V]-. Lastly, the adhesion of endothelial cells on a cultivation support grafted with RGD peptidomimetics was significantly improved. 2009 American Chemical Society.

Novel RGD-like molecules based on the tyrosine template: Design, synthesis, and biological evaluation on isolated integrins αVβ 3/αIIbβ3 and in cellular adhesion tests

RGD (Arg-Gly-Asp) peptidomimetics have been designed for covalent anchorage on biomaterials. The tyrosine template was thus equipped with (i) a basic side chain of various flexibility, (ii) an acidic side chain, which incorporated the XPS fluorine tag, and (iii) a spacer-arm terminated by a primary amine for surface grafting. The most active compounds showed IC50 values in the nanomolar range versus isolated human integrins αVβ 3 and αIIbβ3. Preincubation of CaCo2 cells with soluble peptidomimetics (2 and 19a) prevented cellular adhesion on culture plates coated with vitronectin. On the other hand, peptidomimetics (19a and 19b) immobilized on a poly(ethylene)terephthalate membrane (PET) promoted CaCo2 cells adhesion. A modeling study at the ab initio level in MINI-1′ basis allowed to compare the various synthetic ligands of integrins and to propose novel pharmacophore structures.