Tahirli Shahla, Aliyeva Fargana, Şenol Halil, Demukhamedova Svetlana, Akverdieva Gulnara, Aliyeva Irada, Veysova Sitara, Sadeghian Nastaran, Günay Sevilay, Erden Yavuz, Taslimi Parham, Sujayev Afsun, Chiragov Famil
Baku State University, Baku, Azerbaijan.
Institute of Chemistry of Additives named after acad. A. M. Guliyev, Baku, Azerbaijan.
J Biomol Struct Dyn. 2025 Jul;43(11):5552-5576. doi: 10.1080/07391102.2024.2309646. Epub 2024 Jan 31.
A synthesized azo compound based on 4-amino antipyrine and its complexes with Ni(II) in solution and solid phase is reported. The structures of these compounds have been testified by IR and NMR spectroscopy. The combined experimental and theoretical approach was used. To study the structure and properties of the synthesized compound, as well as its possible complex formation with the Ni(II), ab initio quantum-chemical calculations were carried out using the Hartree-Fock (HF) method with the 6-31 G basis set and the electron density functional theory (DFT) method with hybrid three-parameter potential B3LYP and extended basis set 6-311++G(d,p) taking into account polarization and diffuse functions for all atoms. The geometric, energy, and electronic parameters were calculated and analyzed. The HOMO-LUMO energy gap has been calculated to determine chemical activity. Both complexes had effective inhibition against butyrylcholinesterase and acetylcholinesterase. IC50 values were found as 19.43 and 27.08 µM for AChE, 2.37 and 7.40 µM for BChE, respectively. For the anticancer outcome, high doses of compound E1 inhibited viability by about 40-45%, while this rate was around 65-70% for compound E2 at the same doses. Anticholinesterase and anticancer potential of compounds E1 and E2 also evaluated by in silico techniques. Both compounds show strong binding to VEGFR1, with E2 exhibiting superior inhibitory activity in hAChE and hBChE through shorter and stronger interactions. MD simulations suggest that E2 forms more stable complexes with hAChE and hBChE compared to E1, making it a promising candidate for further exploration in anticancer and anticholinesterase therapies.
报道了一种基于4-氨基安替比林的合成偶氮化合物及其在溶液和固相中与Ni(II)形成的配合物。这些化合物的结构已通过红外光谱和核磁共振光谱得到证实。采用了实验与理论相结合的方法。为了研究合成化合物的结构和性质，以及它与Ni(II)可能形成的配合物，使用了哈特里-福克（HF）方法和6-31G基组进行从头算量子化学计算，并使用混合三参数势B3LYP和扩展基组6-311++G(d,p)的电子密度泛函理论（DFT）方法，同时考虑了所有原子的极化和弥散函数。计算并分析了几何、能量和电子参数。计算了最高已占分子轨道（HOMO）-最低未占分子轨道（LUMO）能隙以确定化学活性。两种配合物对丁酰胆碱酯酶和乙酰胆碱酯酶均有有效抑制作用。乙酰胆碱酯酶（AChE）的半数抑制浓度（IC50）值分别为19.43和27.08μM，丁酰胆碱酯酶（BChE）的IC50值分别为2.37和7.40μM。在抗癌效果方面，高剂量的化合物E1使细胞活力抑制约40-45%，而相同剂量下化合物E2的这一比例约为65-70%。还通过计算机模拟技术评估了化合物E1和E2的抗胆碱酯酶和抗癌潜力。两种化合物均与血管内皮生长因子受体1（VEGFR1）有强烈结合，其中E2通过更短更强的相互作用在人乙酰胆碱酯酶（hAChE）和人丁酰胆碱酯酶（hBChE）中表现出更强的抑制活性。分子动力学（MD）模拟表明，与E1相比，E2与hAChE和hBChE形成的配合物更稳定，这使其成为抗癌和抗胆碱酯酶治疗中进一步探索的有前景的候选物。
