Directed adenine functionalization for creating complex architectures for material and biological applications

Abstract

In this feature article, targeted design strategies are outlined for modified adenine nucleobase derivatives in order to construct metal-mediated discrete complexes, ring-expanded purine skeletons, linear and catenated coordination polymers, shape-selective MOFs, and purine-capped nanoparticles, with a wide range of applications from gas and solvent adsorption to bioimaging agents and anticancer metallodrugs. The success of such design strategies could be ascribed to the rich chemistry of purine and pyrimidine derivatives, versatile coordination behavior, ability to bind a host of metal ions, which could be further tuned by the introduction of additional functionalities, and their inherent propensity to hydrogen bond and exhibit π-π interactions. These noncovalent interactions produce stable frameworks and network solids that are useful as advanced materials, and the biocompatibility of these ligand complexes provides an impetus for assessing novel biological applications.

Unusual gas‐phase hydration efficiency of magnesium–adenosine complex

“…This may be easy rationalized by the lack of oxygen atoms in the adenine molecule. Therefore, in a number of review papers devoted to metal complexes with adenine and its conjugates, the Mg 2+ complexes have not been even mentioned 12–15 . On the other hand, there are strong suggestions that in the Mg–ATP complex an interaction between the adenine N7 atom and Mg 2+ is possible, since in the adenine molecule the N7 atom seems to be the most prone to interact with metal cations 16–20 .…”

Supramolecular architectures in metal(II) (Cd/Zn) halide/nitrate complexes of cytosine/5-fluorocytosine

“…The interplay of metal coordination and base pairing in nuleobases has become an important area of study. Supramolecular hydrogen-bonding patterns of nucleobase metal complexes have been reported in the literature ISSN 2053ISSN -2296 # 2018 International Union of Crystallography (Thomas-Gipson et al, 2017;Mohapatra et al, 2017;Marino et al, 2016;Lippert et al, 2016;Karthikeyan et al, 2010;Stanley et al, 2006;Muthiah et al, 2001). The synergy between these interactions in nucleobases has led to the development and construction of novel DNA materials in various fields (Amo-Ochoa & Zamora, 2014).…”

Purine‐Based Fluorescent Sensors for Imaging Zinc Ions in HeLa Cells

“…This metal‐chelating ability of the nucleobases can be tuned by the introduction of additional functionalities and give different metal‐chelated frameworks, which have various material and biological applications. [32a] These metal nucleobase interactions also provide a biomodel for studying the biological effects of metal ions on nucleic acids. [32b] On the basis of these, we prepared three new modified‐purine‐based imine‐methoxyphenol Schiff bases, HL1 , HL2 , and HL3 , which selectively exhibit fluorescence enhancement in the presence of zinc ions.…”

“…[32a] These metal nucleobase interactions also provide a biomodel for studying the biological effects of metal ions on nucleic acids. [32b] On the basis of these, we prepared three new modified‐purine‐based imine‐methoxyphenol Schiff bases, HL1 , HL2 , and HL3 , which selectively exhibit fluorescence enhancement in the presence of zinc ions. But HL1 and HL3 exhibit larger enhancement with Zn 2+ ions.…”