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Synthesis, DNA/BSA binding and DNA photocleavage properties of water soluble BODIPY dyes
Dyes and Pigments ( IF 4.1 ) Pub Date : 2017-09-21 , DOI: 10.1016/j.dyepig.2017.09.051
Zekeriya Biyiklioglu , Burak Barut , Arzu Özel

In this study, new BODIPY dyes (2, 3) and their water soluble derivatives (2a, 3a) were synthesized for the first time. The identity of BODIPY dyes 2-3a were confirmed by 1H NMR, 13C NMR, FT-IR, UV–Vis and mass spectrometry. The binding properties of 2a and 3a with CT-DNA have been investigated absorption titration, competitive ethidium bromide, viscosity and electrophoresis experiments. These binding studies claimed that 2a and 3a intercalate with CT-DNA. The Kb values of 2a and 3a calculated as 3.58 ± (0.08) × 105 M−1 and 1.27 ± (0.10) × 105 M−1, indicating that the compounds have strong binding affinities to CT-DNA. The DNA-photocleavage activities of 2a and 3a were investigated using supercoiled pBR322 plasmid DNA on agarose gel electrophoresis. 2a and 3a have remarkable photocleavage activities in the presence of irradiation at 650 ± 20 nm via hydroxyl radical and singlet oxygen pathways. To determine to quenching mechanism of BSA with compounds were performed using UV–Vis absorption spectroscopy. The results demonstrated that the compounds might bind to BSA via static quenching mechanism. The results suggested that synthesized new water soluble BODIPY compounds have strong affinity to CT-DNA and BSA and can effectively cleavage activities by irradiation.



中文翻译:

水溶性BODIPY染料的合成,DNA / BSA结合和DNA光裂解性能

在这项研究中,首次合成了新的BODIPY染料(2,3)及其水溶性衍生物(2a,3a)。通过1 H NMR,13 C NMR,FT-IR,UV-Vis和质谱法确认了BODIPY染料2-3a的身份。研究了2a3a与CT-DNA的结合特性,吸收滴定,竞争性溴化乙锭,粘度和电泳实验。这些结合研究声称2a3a插入CT-DNA。2a3aKb值计算为3.58±(0.08)×10 5 M -1和1.27±(0.10)×10 5  M -1,表明该化合物对CT-DNA具有很强的结合亲和力。使用超螺旋pBR322质粒DNA在琼脂糖凝胶电泳上研究了2a3a的DNA光解活性。2a3a在通过羟基自由基和单线态氧途径在650±20 nm的辐射下,具有显着的光裂解活性。为了确定化合物对BSA的淬灭机理,使用了UV-Vis吸收光谱法。结果表明这些化合物可能通过静态猝灭机理与BSA结合。结果表明,合成的新型水溶性BODIPY化合物对CT-DNA和BSA具有很强的亲和力,并且可以通过辐射有效地裂解活性。

更新日期:2017-09-21
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