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Guanidinium-rich transporters are promising agents to deliver a wide range of molecules through cell membranes. This article reports the synthesis of a modular, conformationally restricted guanidinium display scaffold, designed with the goal to study the impact of conformational restrictions on the resulting properties of the transporters and ultimately probe the anionic chemical space of the cellular membrane. The scaffold was assembled on solid phase as a peptoid, and its subsequent biological evaluation showed very good cellular penetration and low cytotoxicity.

Modular sub-monomeric cell-penetrating guanidine-rich peptoids – synthesis, assembly and biological evaluation