Toward Light-Controlled Supramolecular Peptide Dimerization

Abstract

The selective photodeprotection of the NVoc-modified FGG tripeptide yields the transformation of its 1:1 receptor–ligand complex with cucurbit[8]uril into a homoternary FGG 2 @CB8 assembly. The resulting light-induced dimerization of the model peptide provides a tool for the implementation of stimuli-responsive supramolecular chemistry in biologically relevant contexts.

Preparation and In Vitro Validation of a Cucurbit[7]uril-Peptide Conjugate Targeting the LDL Receptor

“…Besides its constricted hydrophobic cavity prone to welcome a plethora of neutral or/and cationic guests with high or ultrahigh binding affinity, , CB[7] is endowed with a good water solubility, and its low toxicity is compatible with its use in biology . Early work established the possibility to complex platinum drugs in CB[7], which was followed by numerous complexation studies , including bioactive compounds (e.g., amantadine, camptothecin, nitidine, clofazimine, sorafenib, fasudil, arecoline), peptides, and proteins, but also to enable monitoring of enzymatic activities . However, beside their proven ability to efficiently complex such bioactive compounds, cucurbiturils suffer from low tissue specificity.…”

A study of the supramolecular assembly formed by cucurbit[7]uril and 4-cyanophenol

“…Remarkable aqueous host-guest chemistry is possible because of their selectivity and excellent capacity to include specific guests in solution [16][17][18][19] . The Q[n]s hydrophobic cavities contribute to their host-guest complexation, which can bond positively charged guest molecules to form host-guest complexes via non-covalent interactions [20][21][22] . There are macrocyclic confinement effects due to differing degrees of polymerization having cavities of different confined sizes.…”

Inclusion-Activated Reversible E/Z Isomerization of a Cyanostilbene Derivative Based on Cucurbit[8]uril under 365 nm Ultraviolet Irradiation

“…On the other hand, one possible additional strategy for accomplishing this task is to take advantage of supramolecular macrocyclic compounds, − especially cucurbit­[ n ]­uril (CB­[ n ]). − CB­[ n ] can bond positively charged guest molecules to form host–guest complexes in a process of dynamic equilibrium through non-covalent interactions . In the previous reports, supramolecular macrocyclic host molecules were mostly used to research dimerization of double bonds to accelerate the reaction speed. , …”