Department of Chemistry (Biochemistry Division), Faculty of Science, Cairo University, Giza, 12613, Egypt.
Department of Chemistry, Faculty of Science, Cairo University, Giza, 12613, Egypt.
Chem Biodivers. 2022 Sep;19(9):e202100958. doi: 10.1002/cbdv.202100958. Epub 2022 Aug 31.
The cyclocondensation reaction of aldehydes with dimedone and bis(6-aminopyrimidin-4-one) in acetic acid led to the formation of the corresponding bis(pyrimido[4,5-b]quinoline-4,6-diones) which are known as bis(sulfanediyl)bis(tetrahydro-5-deazaflavin) analogs in a single step. Also, bis(pyrimido[4,5-b]quinoline-4,6-diones) which are linked to naphthyl core via phenoxymethyl linkage is prepared. The interactions of the synthesized compounds with DNA and bovine serum albumin (BSA) were studied. Gel electrophoresis assay was used to show the capability of the compounds to photocleave the supercoiled pBR322 plasmid DNA in UV-A (365 nm). Besides, the most photocleavable compound, bis(tetrahydropyrimido[4,5-b]quinoline-4,6-dione) linked to pyridin-3-yl at position-5 exhibits good binding affinities toward CT-DNA and BSA as supported by UV/VIS spectral studies. In addition to the experimental findings, a molecular docking simulation was performed to collect detailed binding data for this compound to both biomolecules.
醛与二亚甲基丙酮和双(6-氨基嘧啶-4-酮)在乙酸中的环缩合反应一步生成相应的双(嘧啶并[4,5-b]喹啉-4,6-二酮)，这些化合物被称为双(亚磺酰基)双(四氢-5-氮杂黄素)类似物。此外，还通过苯氧甲基键将双(嘧啶并[4,5-b]喹啉-4,6-二酮)连接到萘核上。研究了合成化合物与 DNA 和牛血清白蛋白 (BSA) 的相互作用。凝胶电泳试验用于证明这些化合物在 UV-A（365nm）下具有光解超螺旋 pBR322 质粒 DNA 的能力。此外，最具光解活性的化合物是 5 位连接吡啶-3-基的四氢嘧啶并[4,5-b]喹啉-4,6-二酮，它与 CT-DNA 和 BSA 具有良好的结合亲和力，这得到了紫外可见光谱研究的支持。除了实验结果外，还进行了分子对接模拟，以收集该化合物与这两种生物分子的详细结合数据。
