Synthesis and properties of acrylamide-substituted base pair specific dyes for deoxyribonucleic acid template mediated synthesis of dye polymers

Abstract

We have tried to construct synthetic polymers for sequence-specific recognition and complexation of longer deoxynucleotide sequences. For this purpose, we developed a method of template-directed polymerization of basic pair specific DNA ligands such as basic dyes. The template-directed polymerization consists in a copolymerization of various dyes of different specificities staying simultaneously in a binding equilibrium with DNA. In the present paper, we describe the synthesis and the properties of base pair specific monomers especially designed for performance of radical chain polymerization reactions in aqueous medium at room temperature. Different acrylamide derivatives of well-known dyes, such as AT-specific malachite green and GC-specific phenyl neutral red, were synthesized and studied for their ability of base pair specific complex formation with DNA of different base composition. Partition equilibrium dialysis and dye titration agarose gel electrophoresis were used to ensure for several dyes that they may be incorporated into different polymers via copolymerization of their acrylamido derivatives with various small base-unspecific monomers without substantial change of their binding parameters. Furthermore, we demonstrate that acrylamide and other small acrylamide derivatives can be used as building blocks for the synthesis of polymeric links between base pair specific monomers. The results and their consequences for template polymerization reactions are discussed.

pH- and Metal Ion- Sensitive Hydrogels based on N-[2-(dimethylaminoethyl)acrylamide]

“…Acrylic acid (AA) (Fluka) and N,N -dimethylacrylamide (DMAAm) (Fluka) were distilled under vacuum and stored at a low temperature. N -[2-(Dimethylaminoethyl)acrylamide] (DMAEAAm) monomer was synthesized according to the procedure discussed below [26].…”

Development of a sensitive and group‐specific polyclonal antibody‐based enzyme‐linked immunosorbent assay (ELISA) for detection of malachite green and leucomalachite green in water and fish samples

“…1 according to the procedures described in Ref. 30 with some modification. First, nitro‐leucomalachite green (NO 2 ‐LMG) was synthesised by reacting p ‐nitrobenzaldehyde (7.5 g) and N , N ‐dimethylaniline (14 mL) with zinc chloride (6.8 g) as catalyst at 100 °C for 5 h. The product was cooled to room temperature and dissolved in 150 mL of acetone.…”

A New Thermo-, pH-, and CO2-Responsive Homopolymer of Poly[N-[2-(diethylamino)ethyl]acrylamide]: Is the Diethylamino Group Underestimated?

“…The monomer of N -[2-(diethyl­amino)­ethyl]­acrylamide (DEAEAM) was synthesized as shown in Scheme . Typically, into a flask with a magnetic stir, N , N -diethyl­ethylene­diamine (150 mmol, 17.43 g) and CHCl 3 (150 mL) were added under a nitrogen atmosphere, and then the flask was put in an ice–water bath.…”