First Description of a Guanidine-embedded Pillar[5]arene: Opening New Avenues for Biological Applications

Abstract

<jats:p>Guanidine functionality embedded in macrocyclic framework provides intriguing and tunable chemical and physical characteristics to molecular structures. We describe in this paper the first example of guanidine-containing pillar[5]arene and their potential applications in biology and material science. The reaction of O-alkylated p-aminopillar[5]arene with guanylating reagent, amidinopyrazole hydrochloride, gives first ever synthesis of a new generation of guanidine-embedded pillararene 2 under mild reaction conditions.</jats:p>

Synthesis and Bioactivity of Guanidinium‐Functionalized Pillar[5]arene as a Biofilm Disruptor

“…[10][11][12] Therefore, we hypothesized that perfunctionalization of pillar [5]arene with guanidinium would endow the novel molecular structure with potential bioactivity against bacteria and bacterial biofilms. Although mono-guanidine-functionalized pillar [5]arene was previously synthesized, [14] the pillar scaffold was not leveraged to preorganize multiple groups. Herein, we designed and synthesized the first guanidinium perfunctionalized pillar [5]arene (GP5) (Scheme 1), which not only exhibited antibacterial potency against Gram-negative Escherichia coli and Gram-positive Staphylococcus aureus bacterial strains, but also effectively disrupted preformed E. coli biofilms via efficient penetration of biofilm barriers and destruction of biofilmenclosed bacteria.…”