Synthetic mimics of biotin/(strept)avidin

Abstract

Biotin/(strept)avidin self-assembly is a powerful platform for nanoscale fabrication and capture with many different applications in science, medicine, and nanotechnology. However, biotin/(strept)avidin self-assembly has several well-recognized drawbacks that limit performance in certain technical areas and there is a need for synthetic mimics that can either become superior replacements or operational partners with bio-orthogonal recognition properties. The goal of this tutorial review is to describe the recent progress in making high affinity synthetic association partners that operate in water or biological media. The review starts with a background summary of biotin/(strept)avidin self-assembly and the current design rules for creating synthetic mimics. A series of case studies are presented that describe recent success using synthetic derivatives of cyclodextrins, cucurbiturils, and various organic cyclophanes such as calixarenes, deep cavitands, pillararenes, and tetralactams. In some cases, two complementary partners associate to produce a nanoscale complex and in other cases a ditopic host molecule is used to link two partners. The article concludes with a short discussion of future directions and likely challenges.

A Visible–Near‐Infrared Light‐Responsive Host–Guest Pair with Nanomolar Affinity in Water

“…CBn can be employed in numerous applications that are based on the extraordinary high affinity displayed by these macrocycles. Examples include recognition, self‐assembly and isolation of biomolecules, noncovalent functionalization of biopharmaceuticals, bioimaging and supramolecular materials such as polymers, microcapsules, and supramolecular organic frameworks …”

“…Examples include recognition, self-assembly andi solationo fb iomolecules, noncovalent functionalization of biopharmaceuticals, bioimaging and supramolecular materials such as polymers, microcapsules, and supramolecular organic frameworks. [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30][31] Akey feature of supramolecular systems relies on the reversible nature of noncovalent bonds,a llowing control of association processes using externals timuli. Light is recognized as a superior stimulusf or many applications because it allows for remote spatiotemporal control, it is orthogonal to other stimuli, and additional reagents are not required.…”

Recognition of Different Metal Cations by a trans‐4‐[4‐(Dimethylamino)styryl]‐1‐methylpyridinium Iodide@Tetramethylcucurbit[6]uril Probe

“…Cucurbit[n]urils (Q[n]s) [1][2][3][4][5][6] are generally characterized by a nearly neutral electro-potential cavity and two negative electro-potential carbonyl-fringed portals, in addition to a positive electro-potential outer surface: the cavities of Q[n]s can accommodate various guest molecules through hydrophobic interactions, resulting in characteristic cucurbit[n]uril chemistry known as Q[n]-based host-guest chemistry; [7][8][9][10][11][12][13][14][15][16][17] Additionally, carbonyl groups on the rims of the portals of Q[n]s can interact with metal ions through direct coordination, resulting in distinct Q[n]-based coordination chemistry; [18][19][20][21] Furthermore, the positive electro-potential outer surface of Q[n]s can induce the formation of various novel supramolecular assemblies thorough the outer surface interaction of cucurbit[n]urils, which is another emerging research field in cucurbit[n]uril chemistry. [22] To date, Q[n]-based host-guest chemistry and Q[n]based coordination chemistry have received most attention in Q[n] research, including molecular machines or switches, [23] materials science, supramolecular materials and polymers, [15,24] life science, [25] catalysis, [13,14] sensors and other applications.…”

Supramolecular Interactions of Bambus[6]urils with Quinoline and 6‐Hydroxyisoquinoline Hydrochloride Salts

“…Molecular recognition has always been an integral part of supramolecular chemistry. As Lehn said upon receipt of the Nobel Prize, recognition, reactivity, and transport represent the three basic functional features of supramolecular species, therefore, molecular recognition of macrocyclic compounds has also been greatly developed recently . Molecular recognition refers to the interaction of two or more molecules through noncovalent bond interactions, which may be hydrogen bonds, metal coupling, hydrophobic interactions, van der Waals forces, and so on.…”

“…As Lehn said upon receipt of the Nobel Prize, recognition, reactivity, and transport represent the three basic functional features of supramolecular species, therefore, molecular recognition of macrocyclic compounds has also been greatly developed recently. [1][2][3] Molecular recognition refers to the interaction of two or more molecules through noncovalent bond interactions, which may be hydrogen bonds, metal coupling, hydrophobic interactions, van der Waals forces, and so on. Molecular recognition was first considered in terms of the lock-and-key relationship between an enzyme and its substrate, but emphasis has now shifted towards identifying the main guest among a range of structures through a combination of specific interactions.…”