Supramolecular gels made from nucleobase, nucleoside and nucleotide analogs

Abstract

Supramolecular or molecular gels are attractive for various applications, including diagnostics, tissue scaffolding and targeted drug release. Gelators derived from natural products are of particular interest for biomedical purposes, as they are generally biocompatible and stimuli-responsive. The building blocks of nucleic acids (i.e. nucleobases, nucleosides, and nucleotides) are desirable candidates for supramolecular gelation as they readily engage in reversible, noncovalent interactions. In this review, we describe a number of organo- and hydrogels formed through the assembly of nucleosides, nucleotides, and their derivatives. While natural nucleosides and nucleotides generally require derivatization to induce gelation, guanosine and its corresponding nucleotides are well known gelators. This unique gelating ability is due to propensity of the guanine nucleobase to self-associate into stable higher-order assemblies, such as G-ribbons, G4-quartets, and G-quadruplexes.

Hydrogels Based on Ag+‐Modulated Assembly of 5′‐Adenosine Monophosphate for Enriching Biomolecules

“…In addition, when metal ions are present, metal–nucleobase coordination plays a critical role in the interaction of nucleotides or DNA with metal ions because the nucleobase has a nitrogen‐containing heterocycle with a number of metal‐binding sites . By studying the metal–nucleobase interactions, one can further understand and speculate on the mechanism of action between metal ions and some important biomolecules, such as DNA and RNA . Metal–nucleobase interactions extensively exist in systems formed by various metal ions and four nucleobases (adenine, thymine, guanine, and cytosine) and their derivatives.…”

Developing a Self‐Healing Supramolecular Nucleoside Hydrogel Based on Guanosine and Isoguanosine

“…However, so far, only few studies have been conducted on self‐healing supramolecular nucleoside hydrogels compared to self‐healing polymer hydrogels . Nucleosides and nucleotides are widely utilized as building blocks of supramolecular assembly materials due to their unique Watson–Crick base pairing and biocompatibility properties . It is well‐known that guanosine (G) can form three‐dimensional hydrogels with a G 4 ‐quadruplex molecular structure (Figure ), and certain metal ions are required to bind in the central cavity to template and stabilize the structure .…”

Luminescent Ultralong Microfibers Prepared through Supramolecular Self‐Assembly of Lanthanide Ions and Thymidine in Water

“…Typically, as compared with the traditional synthetic organic chemistry, in which covalent bonds dominate, SSA is based on noncovalent interactions, such as hydrogen‐bonding, π–π stacking, and hydrophilic/hydrophobic interactions . Nucleosides and their derivatives, which are the building blocks of nucleic acids and consist of a nucleobase and a pentose, have been proven desirable building units for SSA in water . Nucleosides contain nitrogen heterocycles, which provide multiple active sites for hydrogen‐bonding, π–π and metal–ion‐bonding interactions; in addition, the pentose offers more active sites for hydrogen bonds .…”