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Carbazole ligands as c-myc G-quadruplex binders. 2018

Agata Głuszyńska, and Bernard Juskowiak, and Martyna Kuta-Siejkowska, and Marcin Hoffmann, and Shozeb Haider
Laboratory of Bioanalytical Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Poznań 61-614, Umultowska Street 89b, Poland. Electronic address: aglusz@amu.edu.pl.

The interactions of c-myc G-quadruplex with three carbazole derivatives were investigated by UV-Vis spectrophotometry, fluorescence, CD spectroscopy, and molecular modeling. The results showed that a combination of carbazole scaffold functionalized with ethyl, triazole and imidazole groups resulted in stabilization of the intramolecular G-quadruplex formed by the DNA sequence derived from the NHE III1 region of c-myc oncogene (Pu22). Binding to the G-quadruplex Pu22 resulted in the significant increase in fluorescence intensity of complexed ligands 1-3. All ligands were capable of interacting with G4 DNA with binding stoichiometry indicating that two ligand molecules bind to G-quadruplex with comparable affinity, which agrees with binding model of end-stacking on terminal G-tetrads.

UI MeSH Term Description Entries
D008024 Ligands A molecule that binds to another molecule, used especially to refer to a small molecule that binds specifically to a larger molecule, e.g., an antigen binding to an antibody, a hormone or neurotransmitter binding to a receptor, or a substrate or allosteric effector binding to an enzyme. Ligands are also molecules that donate or accept a pair of electrons to form a coordinate covalent bond with the central metal atom of a coordination complex. (From Dorland, 27th ed) Ligand
D002227 Carbazoles Benzo-indoles similar to CARBOLINES which are pyrido-indoles. In plants, carbazoles are derived from indole and form some of the INDOLE ALKALOIDS.
D006801 Humans Members of the species Homo sapiens. Homo sapiens,Man (Taxonomy),Human,Man, Modern,Modern Man
D016259 Genes, myc Family of retrovirus-associated DNA sequences (myc) originally isolated from an avian myelocytomatosis virus. The proto-oncogene myc (c-myc) codes for a nuclear protein which is involved in nucleic acid metabolism and in mediating the cellular response to growth factors. Truncation of the first exon, which appears to regulate c-myc expression, is crucial for tumorigenicity. The human c-myc gene is located at 8q24 on the long arm of chromosome 8. L-myc Genes,N-myc Genes,c-myc Genes,myc Genes,v-myc Genes,L-myc Proto-Oncogenes,N-myc Proto-Oncogenes,c-myc Proto-Oncogenes,myc Oncogene,v-myc Oncogenes,Gene, L-myc,Gene, N-myc,Gene, c-myc,Gene, myc,Gene, v-myc,Genes, L-myc,Genes, N-myc,Genes, c-myc,Genes, v-myc,L myc Genes,L myc Proto Oncogenes,L-myc Gene,L-myc Proto-Oncogene,N myc Genes,N myc Proto Oncogenes,N-myc Gene,N-myc Proto-Oncogene,Oncogene, myc,Oncogene, v-myc,Oncogenes, myc,Oncogenes, v-myc,Proto-Oncogene, L-myc,Proto-Oncogene, N-myc,Proto-Oncogene, c-myc,Proto-Oncogenes, L-myc,Proto-Oncogenes, N-myc,Proto-Oncogenes, c-myc,c myc Genes,c myc Proto Oncogenes,c-myc Gene,c-myc Proto-Oncogene,myc Gene,myc Oncogenes,v myc Genes,v myc Oncogenes,v-myc Gene,v-myc Oncogene
D054856 G-Quadruplexes Higher-order DNA and RNA structures formed from guanine-rich sequences. They are formed around a core of at least 2 stacked tetrads of hydrogen-bonded GUANINE bases. They can be formed from one two or four separate strands of DNA (or RNA) and can display a wide variety of topologies, which are a consequence of various combinations of strand direction, length, and sequence. (From Nucleic Acids Res. 2006;34(19):5402-15) DNA G-Quadruplexes,DNA, Quadruplex,G-Quadruplexes, DNA,G-Quadruplexes, RNA,Guanine-Quadruplexes,Guanine-Quartets,Guanine-Tetrads,Quadruplex DNA,RNA, G-Quadruplexes,Tetraplex DNA,DNA G Quadruplexes,DNA, Tetraplex,G Quadruplexes,G Quadruplexes, DNA,G Quadruplexes, RNA,G-Quadruplexes RNA,G-Quadruplexes RNAs,Guanine Quadruplexes,Guanine Quartets,Guanine Tetrads,Guanine-Quartet,Guanine-Tetrad,RNA G-Quadruplexes,RNA, G Quadruplexes,RNAs, G-Quadruplexes

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