Hoogsteen triplexes stabilized through ethynyl-linked pyrene-indole synthesized by high-temperature Sonogashira coupling

Autor:	Imrich Géci, Maha I. Fatthalla, Maike Heintz, Per T. Jørgensen, Erik B. Pedersen
Rok vydání:	2022
Předmět:	Pyrenes Indoles Nucleic Acids Organic Chemistry Temperature Oligonucleotides Nucleic Acid Conformation DNA Physical and Theoretical Chemistry Nucleic Acid Denaturation Biochemistry Intercalating Agents
Zdroj:	Organic & Biomolecular Chemistry. 20:8873-8884
ISSN:	1477-0539 1477-0520
DOI:	10.1039/d2ob01466a
Popis:	The low binding affinity of unmodified triplex-forming oligonucleotides (TFO) is the main drawback to their promising utilization in gene therapy. In the present study, we have synthesized DNA intercalator 5-(pyren-1-ylethynyl)indole Y, known as twisted intercalating nucleic acid (TINA), by a Cu-mediated Sonogashira palladium-catalyzed coupling reaction of 1-ethynylpyrene with 5-iodoindole at a high temperature under anaerobic conditions. Coupling with indole C-5 was far more preferable in obtaining stable TINA-indole than enamine site C-3, as neither hydration of the triple bond to ketones nor competitive Glaser-type homocoupling of acetylenes was observed. The insertion of the new TINA monomer Y as a bulge in the middle or at the 5'-end of the oligodeoxynucleotide sequence
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::c988566bdf0fc72b59d999ab9572b3c8 https://doi.org/10.1039/d2ob01466a Zobrazit plný text záznamu