Impact of positive charge and ring-size on the interactions of calixarenes with DNA, RNA and nucleotides

Abstract

Comparison of various calix[6]arene and calix[4]arene derivatives revealed that only analogues bearing permanent positive charge non-covalently bind to ds-DNA and ds-RNA, by insertion into DNA minor groove or RNA major...

Novel pyrene-calix[4]arene derivatives as highly sensitive sensors for nucleotides, DNA and RNA

“…aThe best fit of experimental data was obtained for 1 : 1 stoichiometry of dye/NMP complex or for DNA/RNA by processing of titration data by means of Scatchard equation gave values of ratio n [bound dye]/[DNA/RNA] = 0.1 and 0.2, for easier comparison all log K values were re-calculated for fixed n = 0.2.bΔInt = Int(100% complex)/Int 0 .cPublished data. 9 For DNA/RNA log K values estimated from competition experiments.…”

“…[5][6][7][8] Some of these systems were recently studied by us as possible candidates for DNA/RNA binding in a frame of a wider project oriented towards the research of DNA/RNA recognition by specially designed calixarene derivatives. 9,10 Development of new biomimetic systems capable of selective DNA/RNA binding is a subject of utmost importance for the development of new drugs, biosensors or tools for basic biochemical and biological studies. [11][12][13] The covalently linked pyrene functional group, belonging to a group of polycyclic aromatic hydrocarbons (PAH), is especially interesting to us due to its unique properties like intense blue emission, high uorescence quantum yield, long-lived singlet excited state, long emission lifetime (>100 ns), as well as its pronounced hydrophobicity.…”

“…Only recently we partially addressed that issue by studying interactions of neutral and cationic calixarenes with nucleotides and DNA, revealing the importance of positive charge for efficient binding to DNA. 9 In this paper, we report on the synthesis, photochemical and photophysical characterization of pyrene-calixarene conjugates 2 and 3 (Scheme 1), including quantum yield and uorescence lifetime measurements, as well as the binding affinity of these compounds towards mononucleotides and DNA/RNA chains (ctDNA, p(dAdT) 2 , pApU, p(dGdC) 2 ). The stability constants of the formed complexes were determined from UV-Vis and/or uorescence titration data.…”

“…5–8 Some of these systems were recently studied by us as possible candidates for DNA/RNA binding in a frame of a wider project oriented towards the research of DNA/RNA recognition by specially designed calixarene derivatives. 9,10 Development of new biomimetic systems capable of selective DNA/RNA binding is a subject of utmost importance for the development of new drugs, biosensors or tools for basic biochemical and biological studies. 11–13…”

Calix[4]arene Polyamine Triazoles: Synthesis, Aggregation and DNA Binding

“…There are many successful examples in the literature of using cationic calixarenes for DNA binding, compaction and even storage. For this can be used calixarene-amines [ 19 ], multicalixarene-amines [ 20 ], calixdendrimer-amines [ 21 ], calixarenes bearing guanidinium [ 22 , 23 , 24 ] or arginine [ 25 ] groups as well as calixarene-ammonium derivatives [ 26 , 27 , 28 ]. We have previously demonstrated that thiacalixarene derivatives in the 1,3-alternate configuration carrying two [ 29 ] or four [ 30 ] diethylenetriamine fragments in combination with triazole fragments effectively bind and compact DNA.…”