Nucleotide‐Bearing Benzylidene‐Tetrahydroxanthylium Near‐IR Fluorophore for Sensing DNA Replication, Secondary Structures and Interactions

0532176 - ÚOCHB 2021 RIV DE eng J - Journal Article
Kuba, Miroslav - Kraus, Tomáš - Pohl, Radek - Hocek, Michal
Nucleotide‐Bearing Benzylidene‐Tetrahydroxanthylium Near‐IR Fluorophore for Sensing DNA Replication, Secondary Structures and Interactions.
Chemistry - A European Journal. Roč. 26, č. 52 (2020), s. 11950-11954. ISSN 0947-6539. E-ISSN 1521-3765
R&D Projects: GA ČR(CZ) GA17-14791S; GA MŠMT(CZ) EF16_019/0000729
Grant - others:AV ČR(CZ) AP1501
Program: Akademická prémie - Praemium Academiae
Institutional support: RVO:61388963
Keywords : DNA * fluorescence * nucleotides * real-time PCR
OECD category: Organic chemistry
Impact factor: 5.236, year: 2020
Method of publishing: Open access
https://doi.org/10.1002/chem.202003192

Thymidine triphosphate bearing benzylidene‐tetrahydroxanthylium near‐IR fluorophore linked to the 5‐methyl group via triazole was synthesized through the CuAAC reaction and was used for polymerase synthesis of labelled DNA probes. The fluorophore lights up upon incorporation to DNA (up to 348‐times) presumably due to interactions in major groove and the fluorescence further increases in the single‐stranded oligonucleotide. The labelled dsDNA senses binding of small molecules and proteins by a strong decrease of fluorescence. The nucleotide was used as a light‐up building block in real‐time PCR for detection of SARS‐CoV‐2 virus.
Permanent Link: http://hdl.handle.net/11104/0310762