Abstract
Hydroxy-substituted tetrachlorodibenzo[b,e][1,4]dioxin and tetrachlorodibenzo[b,d]furans have been synthesized using 3,4-dichloroanisole, 2,3,6-trichlorophenol and 4,5-dichlorocatechol as starting materials and electrophilic and/or nucleophilic aromatic substitution reactions for the assembly of the dibenzo[b,e][1,4]dioxin and dibenzo[b,d]furan systems. The thus-obtained phenolic compounds were then alkylated with N-1-(4,4-dimethyl-2,6-dioxocyclohexylidene)ethyl (Dde)-protected 3-bromopropan-1-amine to give the corresponding N-Dde protected 3-aminopropoxy-substituted tetrachlorodibenzo[b,e][1,4]dioxin and tetrachlorodibenzo[b,d]furans, respectively. Hydrazinolysis-mediated Dde removal from the former compound provided the corresponding amino-substituted dioxin, which was coupled to carboxy-substituted magnetic beads affording magnetic beads coated by the amino-substituted dioxin. The latter is an attractive intermediate for the development of selective single-standard DNA (ssDNA) aptamers, which constitute molecular recognition elements in photonic biosensors with potential application to the monitoring of the dangerous environmental pollutants, dioxins having serious implications in human health.
Highlights
Photonic biosensors are simple, portable, robust, and cost-effective analytical devices for the rapid and specific screening and sensitive monitoring of environmental pollutants, water, foods and beverages contaminants
Photonic biosensors combine molecular recognition elements (MREs) with optical transducer systems, which convert light rays into electronic signals, so that the specific binding of a target molecule to the MRE to be translated into a measurable electrical signal [1,2,3]
PCDDs have been synthesized through the condensation of chlorinated catechols or their corresponding dipotassium salts and chlorinated aromatics, bearing two chlorine atoms in adjacent positions, at the refluxing point (189 ◦ C) of dimethyl sulfoxide (DMSO) [18,19]
Summary
Portable, robust, and cost-effective analytical devices for the rapid and specific screening and sensitive monitoring of environmental pollutants, water, foods and beverages contaminants. Photonic biosensors combine molecular recognition elements (MREs) with optical transducer systems, which convert light rays into electronic signals, so that the specific binding of a target molecule to the MRE to be translated into a measurable electrical signal [1,2,3]. Target specific, single-stranded synthetic oligonucleotides (ssDNA, RNA) or peptide sequences, which fold into three-dimensional shapes capable of binding non-covalently and with high affinity to a target molecule. They are readily generated through an in vitro process called Systematic Evolution of Ligands by EXponential Enrichment (SELEX). Aptamers for a variety of environmental pollutants with serious implications in human aptamers for a variety of environmental pollutants with serious implic health, including the dioxin-like polychlorinated biphenyls (PCBs), have veloped, aptamers for polychlorinated dibenzofurans (PCDFs)
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