Sophistication of foldamer form and function in vitro and in vivo

Abstract

SummaryAdvances in the foldamer field in recent years are as diverse as the backbones of which they are composed. Applications have ranged from cellular penetration and membrane disruption to discrete molecular recognition, while efforts to control the complex geometric shape of foldamers has entered the realm of tertiary and quaternary structure. This review will provide recent examples of progress in the foldamer field, highlighting the significance of this class of compounds and the advances that have been made towards exploiting their full potential.

The Urea Renaissance

“…[28,29] Those foldamers are unique scaffolds for potential use in a range of biological and biomedical applications. [30] Glycoluril and formaldehyde condense under acidic conditions to deliver the cucurbit[n]urils 14 (Figure 4), which consist of n glycoluril units that are joined to the next one by two methylene bridges to form a closed band in which the urea oxygen atoms are tilted inwards, thus forming a partly enclosed cavity. These compounds are particularly interesting because they are capable of binding other molecules within these cavities.…”

Van Der Waals Interactions and the Hydrophobic Effect

“…There is an expansive list of foldamers designed for a wide range of applications, including cell permeation, membrane disruption, discrete molecular recognition, and selective reaction with encapsulated guests [58][59][60][61][62][63]. Likewise, a wide variety of subunits have been used to build foldamers, including steroids [64][65][66], aromatic oligoamides [67], β-peptides [58,61,62], and m-phenylene ethynylenes [63,[68][69][70]. There are many examples of foldamers that are water soluble [62,[71][72][73][74], but in terms of hosts designed to bind guest molecules, they are relatively few.…”

“…Likewise, a wide variety of subunits have been used to build foldamers, including steroids [64][65][66], aromatic oligoamides [67], β-peptides [58,61,62], and m-phenylene ethynylenes [63,[68][69][70]. There are many examples of foldamers that are water soluble [62,[71][72][73][74], but in terms of hosts designed to bind guest molecules, they are relatively few. Indeed recent efforts in this area have focused on the reverse: that is, the encapsulation of polar molecules for solubilization in organic solvents or transport across bilayers [64,67,75,76].…”

Die Harnstoff‐Renaissance

“…[28,29] Solche Foldamere sind einzigartige Gerüste für eine Reihe von biologischen und biomedizinischen Anwendungen. [30] Glycoluril und Formaldehyd kondensieren unter sauren Bedingungen zu den Cucurbit[n]urilen (14; Abbildung 4), die (14) und Cucurbit [7]uril (14a).…”