title: Conjugation of hemin to G-quadruplex forming oligonucleotide using click chemistry.
abstract: Peroxidase-mimicking DNAzyme is one of the systems that recently gained a great interest. It has been successfully applied for designing numerous bioassays. The success of this system is connected to its advantages over a protein enzyme, horseradish peroxidase. Promising strategy for further improvement of performance of DNAzyme with peroxidase-like activity was proposed recently. It was based on the covalent attachment of hemin moiety to the G-quadruplex scaffold. We report here the first attempt of conjugating hemin to the G-quadruplex DNA using click chemistry approach. We modified hemin molecule through attachment of an azide-terminated linker to the porphyrin carboxylic group. Two click chemistry approaches were examined to conjugate the azide-modified hemin to a G-quadruplex oligonucleotide: copper-catalyzed and Cu-free cycloaddition reactions. Using Cu-free click reaction, we successfully synthesized G-quadruplex-hemin conjugate that exhibited promising peroxidase activity.
authors.affiliation: Laboratory of Bioanalytical Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Umultowska 89b, 61-614 Poznan, Poland. Electronic address: kosman@amu.edu.pl.
authors.forename: J
authors.initials: J
authors.lastname: Kosman
authors.affiliation: Laboratory of Bioanalytical Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Umultowska 89b, 61-614 Poznan, Poland.
authors.forename: A
authors.initials: A
authors.lastname: Stanislawska
authors.affiliation: Laboratory of Bioanalytical Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Umultowska 89b, 61-614 Poznan, Poland.
authors.forename: A
authors.initials: A
authors.lastname: Gluszynska
authors.affiliation: Laboratory of Bioanalytical Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Umultowska 89b, 61-614 Poznan, Poland. Electronic address: juskowia@amu.edu.pl.
authors.forename: B
authors.initials: B
authors.lastname: Juskowiak
mesh_terms: D000480:Alkynes / Q000737:chemistry; D017151:Antibodies, Catalytic; D001386:Azides / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry; D002384:Catalysis; D057930:Click Chemistry; D003300:Copper / Q000737:chemistry; D021881:DNA, Catalytic / Q000737:chemistry*; D054856:G-Quadruplexes; D006427:Hemin / Q000737:chemistry*; D011166:Porphyrins / Q000737:chemistry
chemical_list: D000480:Alkynes; D017151:Antibodies, Catalytic; D001386:Azides; D002264:Carboxylic Acids; D021881:DNA, Catalytic; D011166:Porphyrins; D006427:Hemin; D003300:Copper
keywords: Click chemistry; DNAzyme; G-quadruplex; Hemin