Benzothiazole-based cyanines as fluorescent “light-up” probes for duplex and quadruplex DNA
Turaev A. V., Tsvetkov V. B., Tankevich M. V., Smirnov I. P., Aralov A. V., Pozmogova G. E., Varizhuk A. M.
Biochimie
Vol.162, P. 216-228
Опубликовано: 2019
Тип ресурса: Статья
DOI:10.1016/j.biochi.2019.04.018
Аннотация:
Analogs of benzothiazole orange (BO)with one, two or three methylbenzothiazolylmethylidene substituents in the 1-methylpyridinium ring were obtained from the respective picolinium, lutidinium or collidinium salts. Fluorescence parameters of the known and new dyes in complexes with various DNA structures, including G-quadruplexes (G4s)and i-motifs (IMs), were analyzed. All dyes efficiently distinguished G4s and ss-DNA. The bi- and tri-substituted derivatives had basically similar distributions of relative fluorescence intensities. The mono-substituted derivatives exhibited enhanced sensitivity to parallel G4s. All dyes were particularly sensitive to a G4 structure with an additional duplex module (the thrombin-binding aptamer TBA31), presumably due to a distinctive binding mode (interaction with the junction between the two modules). In particular, BO showed a strong (160-fold)enhancement in fluorescence quantum yield in complex with TBA31 compared to the free dye. The fluorescence quan
Ключевые слова:
Cyanine dyes; G-quadruplex; I-motif; Light-up probe
aptamer; benzothiazole derivative; fluorescent dye; guanine quadruplex; pyridinium derivative; single stranded DNA; thrombin; benzothiazole derivative; DNA; fluorescent dye; absorption; Article; chemical structure; circular dichroism; DNA structure; fluorescence analysis; fluorescent lighting; melting point; molecular dynamics; molecular model; nucleotide sequence; oncogene; promoter region; quantum yield; chemistry; fluorescence; molecular docking; nucleotide motif; procedures; spectrofluorometry; Benzothiazoles; Circular Dichroism; DNA; Fluorescence; Fluorescent Dyes; G-Quadruplexes; Molecular Docking Simulation; Molecular Dynamics Simulation; Nucleotide Motifs; Spectrometry, Fluorescence
Язык текста: Английский
ISSN: 1638-6183
Turaev A. V.
Tsvetkov V. B. Vladimir Borisovich 1964-
Tankevich M. V.
Smirnov I. P.
Aralov A. V.
Pozmogova G. E.
Varizhuk A. M.
Тюраев А. В.
Цветков В. Б. Владимир Борисович 1964-
Танкевич М. В.
Смирнов И. П.
Аралов А. В.
Позмогова Г. Е.
Варижук А. М.
Benzothiazole-based cyanines as fluorescent “light-up” probes for duplex and quadruplex DNA
Текст визуальный непосредственный
Biochimie
Elsevier Science Publisher B.V.
Vol.162 P. 216-228
2019
Статья
Cyanine dyes G-quadruplex I-motif Light-up probe
aptamer benzothiazole derivative fluorescent dye guanine quadruplex pyridinium derivative single stranded DNA thrombin benzothiazole derivative DNA fluorescent dye absorption Article chemical structure circular dichroism DNA structure fluorescence analysis fluorescent lighting melting point molecular dynamics molecular model nucleotide sequence oncogene promoter region quantum yield chemistry fluorescence molecular docking nucleotide motif procedures spectrofluorometry Benzothiazoles Circular Dichroism DNA Fluorescence Fluorescent Dyes G-Quadruplexes Molecular Docking Simulation Molecular Dynamics Simulation Nucleotide Motifs Spectrometry, Fluorescence
Analogs of benzothiazole orange (BO)with one, two or three methylbenzothiazolylmethylidene substituents in the 1-methylpyridinium ring were obtained from the respective picolinium, lutidinium or collidinium salts. Fluorescence parameters of the known and new dyes in complexes with various DNA structures, including G-quadruplexes (G4s)and i-motifs (IMs), were analyzed. All dyes efficiently distinguished G4s and ss-DNA. The bi- and tri-substituted derivatives had basically similar distributions of relative fluorescence intensities. The mono-substituted derivatives exhibited enhanced sensitivity to parallel G4s. All dyes were particularly sensitive to a G4 structure with an additional duplex module (the thrombin-binding aptamer TBA31), presumably due to a distinctive binding mode (interaction with the junction between the two modules). In particular, BO showed a strong (160-fold)enhancement in fluorescence quantum yield in complex with TBA31 compared to the free dye. The fluorescence quan