Citation: Jie YANG, Xiang-Rong LIU, Geng-Hui LIAO, Ming-Kun YU, Zai-Wen YANG, Shun-Sheng ZHAO. Synthesis, Crystal Structures, and Binding Behaviors with CT-DNA/BSA, Antimicrobial and Cytotoxic Activities of Three New Pyrazine Acylhydrazones[J]. Chinese Journal of Structural Chemistry, ;2020, 39(9): 1639-1654. doi: 10.14102/j.cnki.0254-5861.2011-2770 shu

Synthesis, Crystal Structures, and Binding Behaviors with CT-DNA/BSA, Antimicrobial and Cytotoxic Activities of Three New Pyrazine Acylhydrazones

College of Chemistry and Chemical Engineering, Xi'an University of Science and Technology, Xi'an 710054, China

Corresponding author: Xiang-Rong LIU, liuxiangrongxk@163.com
Received Date: 19 February 2020
Accepted Date: 19 June 2020

Fund Project: the National Natural Science Foundation of China U1903033the National Natural Science Foundation of China 21073139the National Natural Science Foundation of China 21373158Science and Technology on Combustion and Explosion Laboratory Foundation of Shaanxi 6142603010301

Figures(23)

Three new acylhydrazones containing pyrazine ring (C₁₂H₁₁N₅O₂·CH₃COOH, 1; C₁₃H₁₃N₅O·2CH₃COOH, 2; C₁₃H₁₃N₅O₃·C₁₃H₁₃N₅O₃, 3) were synthesized and fully characterized. The single-crystal XRD indicated that both 1 and 2 crystallized in monoclinic, P2₁/c space group but 3 belonged to monoclinic, C2/c space group. The temperature of the maximum thermal decomposition peaks measured by thermogravimetry for 1~3 is 284, 289 and 276 ℃ respectively, all showing better thermal stabilities. The interactions of 1~3 with calf thymus DNA (CT-DNA) and bovine serum albumin (BSA) were studied by UV-Vis absorption spectroscopy and fluorescence spectroscopy, respectively, presenting that 1~3 could bind to CT-DNA via groove binding mode and quench the fluorescence of BSA through static process. Moreover, molecular docking studies of the interactions between 1~3 with DNA/BSA were in good agreement with experimental results. From antimicrobial activities of 1~3 and gentamycin sulfate against Staphylococcus aureus, Escherichia coli and Salmonella typhimurium, it was inferred that 3 had generally stronger antibacterial activity than 1 and 2 and is more active against Staphylococcus aureus than gentamycin sulfate. The cytotoxic tests of 1~3 and etoposide on human lung cancer cells (A549) were carried out by using the MTT method.
- acylhydrazone,
- crystal structure,
- CT-DNA/BSA binding,
- antimicrobial activity,
- cytotoxic activity
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