Citation: Geng-Hui LIAO, Xiang-Rong LIU, Shun-Sheng ZHAO, Zai-Wen YANG, Zheng YANG. Crystal Structures, ct-DNA/BSA Binding Properties and Antibacterial Activities of Halogenated Pyridyl Hydrazones[J]. Chinese Journal of Structural Chemistry, ;2020, 39(3): 467-484. doi: 10.14102/j.cnki.0254-5861.2011-2506 shu

Crystal Structures, ct-DNA/BSA Binding Properties and Antibacterial Activities of Halogenated Pyridyl Hydrazones

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 June 2019
Accepted Date: 22 October 2019

Fund Project: the 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(11)

Three new halogenated pyridyl hydrazones, namely 4-chlorobenzaldehyde-4-chlo-ropyridine-2-formyl acylhydrazone (C₁₃H₉Cl₂N₃O, 3a), 4-bromobenzaldehyde-4-chloropyridine-2-formyl acylhydrazone (C₁₃H₉BrClN₃O, 3b) and 4-iodobenzaldehyde-4-chloropyridine-2-formyl acylhydrazone (C₁₃H₉ClIN₃O, 3c), have been synthesized and characterized by elemental analysis, IR, ¹H NMR, and single-crystal X-ray diffraction. The X-ray diffraction analysis revealed that 3a~3c crystallize in monoclinic with space group Cc. The units of 3a~3c were linked by intermolecular N–H···X (X = Cl, Br, I) hydrogen bonds into 2D layered structures, which were further extended into 3D networks by a series of π-π stacking interactions. Thermogravimetric analysis showed that all of them possessed higher thermal stabilities. The reactivities toward calf thymus DNA (ct-DNA) and bovine serum albumin (BSA) of 3a~3c were investigated by UV-vis and fluorescent spectroscopy as well as molecular docking simulation. Both theoretical and experimental results indicated that 3a~3c bound to ct-DNA in the mode of minor groove binding, and interacted with BSA through the hydrophobic cavity near TRP213. Besides, the orders of binding affinities of 3a~3c to ct-DNA and BSA were both 3c > 3b > 3a, which were the same as that of antibacterial activities. Thus, the interactions of iodinated acylhydrazone with biological targets were stronger than that of chlorinated and brominated acylhydrazones, which provided a representative case for halogenation of lead compounds in rational drug design.
- acylhydrazone,
- crystal structure,
- thermal stability,
- ct-DNA,
- BSA,
- antibacterial activity
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