Acrylamide-dT: a polymerisable nucleoside for DNA incorporation

Abstract

Nucleoside derivative Acrylamide-dT can be readily synthesised and incorporated multiple times into DNA sequences at any position via automated synthesis.

Hybrid Aptamer‐Molecularly Imprinted Polymer (aptaMIP) Nanoparticles from Protein Recognition—A Trypsin Model

“…This multiple-linker strategy has also been employed by Allabush who used it to incorporate an aptamer into a gel for protein electrophoresis. [21] Incorporation of an aptamer into a hybrid system in this manner also has shown to increase stability, [22] and counter any thermal or enzymatic (nuclease) degradation that is often seen with aptamers on their own. [23,24] The aim of this study is to further explore the development of hybrid-MIP nanoparticles (aptaMIP NP) for a protein target (trypsin).…”

Application of thymine-based nucleobase-modified acrylamide as a functional co-monomer in electropolymerised thin-film molecularly imprinted polymer (MIP) for selective protein (haemoglobin) binding

“…Partially following the synthesis of Allabush et al [36], 5-Iodo-2'-deoxyuridine (1.00 g, 2.82 mmol) and palladium acetate (60 mg, 0.28 mmol) were dissolved in DMF (3 mL) in a 10 mL microwave vial, equipped with a small magnetic stirrer bar. Tributylamine (0.67 mL, 2.82 mmol) and N,N'methylenebisacrylamide (1.09 g, 7.06 mmol), were then added.…”

“…Partially following the method of Allabush et al the synthesis of the target Acrylamide-dT involved using the commercially available 5-iodo-2'deoxyuridine and substituting the iodine at C5 with an acrylamide group via the Heck reaction with N,N'-methylenebisacrylamide (Figure 1) [36]. A microwave-assisted procedure was used, which was adapted from Fujimoto and allowed the two entities to be coupled together to form Acrylamide-dT in a good yield (75%) [37].…”

Interaction of Acrylamide, Acrolein, and 5-Hydroxymethylfurfural with Amino Acids and DNA

“…In an in vitro test, Allabush et al found that the acryl­amide group can react with a DNA sequence (5′-GGTTG­GTGTG­GTTGG-3′) to form adducts with bases in different positions, including 5′ end and 7, 9 positions. Adduct formation increased the thermal melting ( T m ) of the DNA sequence from 62.7 °C for unmodified DNA to 66.7 °C for three incorporated acrylamide-dT’s …”

“…Adduct formation increased the thermal melting (T m ) of the DNA sequence from 62.7 °C for unmodified DNA to 66.7 °C for three incorporated acrylamide-dT's. 25 Glycidamide is more reactive than acrylamide according to an in vivo study. Glycidamide−DNA adducts were detected in lung, liver, spleen, and bone marrow tissues of B6C3F1/Tk mice intraperitoneally administered with 0.70 mmol/kg bw/ day acrylamide or glycidamide for 16 days.…”