首页|8-羟基喹啉衍生物锌(Ⅱ)配合物的合成、结构及抗肿瘤活性

8-羟基喹啉衍生物锌(Ⅱ)配合物的合成、结构及抗肿瘤活性

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锌是生物体内必需的第二大微量元素,参与一系列的生理过程.以锌元素合成的金属配合物展示了抗肿瘤、抗菌、抗病毒和抗氧化等多种生理活性,对机体的维持和运转具有重要的调控功能.以8-羟基喹啉-2-甲醛(8-HQ)和2-肼基4,6-二甲基嘧啶(H2L)为起始原料,经缩合反应获得配体8-羟基喹啉衍生物希夫碱(8HQL).以8HQL为活性配体,与ZnCl2通过水热法合成8-羟基喹啉衍生物希夫碱-锌(Ⅱ)配合物(8HQL-Zn).X-单晶衍射结果表明:8HQL-Zn属斜方晶系,空间群为Pbca.运用密度泛函B3LYP方法对配合物8HQL-Zn进行量子化学计算,得到8HQL-Zn的前线轨道能量分布及能带间隙.运用MTT法对化合物进行抗肿瘤活性测试,结果表明:配合物8HQL-Zn对肿瘤细胞SW480和SY5Y的增殖具有明显抑制作用,其中,对SY5Y的抑制作用最强,IC50=6.38±0.28 μmol/L;对正常细胞LO2增殖的抑制作用相对较弱,IC50=14.35±0.39 μmol/L.肿瘤细胞选择性指数(SI)分析表明:配合物8HQL-Zn对癌细胞具有较好的选择性(SI=1.57~2.25).
Synthesis,Structure and Anticancer Activity of 8-Hydroxyquinoline Derivative's Zinc(Ⅱ)Complex
Zinc plays a crucial role in a multitude of physiological processes as the second essential trace element in living organisms.The zinc-synthesized metal complexes exhibit diverse physiological activities and possess significant regulatory functions for maintaining and optimizing bodily functions,including antitumor,antibacterial,antiviral and antioxidant properties.In this study,the 8-hydroxyquinolinederivative(8HQL)was synthesized through a Schiff base condensation reaction u-sing 8-hydroxyquinoline-2-carbaldehyde(8-HQ)and 2-hydrazino-4,6-dimethylpyrimidine(H2 L)as starting materials.By mixing the synthesized 8HQL with ZnCl2 and employing a hydrothermal method,a unique zinc(Ⅱ)complex of the Schiff base derivative of 8-hydroxyquinoline,referred to as 8HQL-Zn,was successfully prepared.The structure of this Zn(Ⅱ)complex was accurately character-ized by X-ray single crystal diffraction analysis,revealing its belonging to the rhombic crystal system with a spatial group of Pbca.Using the B3LYP calculation method in density functional theory,quan-tum chemical calculations were performed on 8HQL-Zn complex to determine the frontier orbital ener-gy distribution and band gap of 8HQL-Zn.MTT assay results demonstrated that 8HQL-Zn significant-ly inhibits the proliferation of SW480 and SY5Y tumor cells,particularly SY5Y,with an IC50 value of(6.38±0.28)μmol/L.This effect was more pronounced compared to normal LO2 cells which exhibi-ted an IC50 value of(14.35±0.39)µmol/L.Furthermore,tumor cell selectivity index(SI)analysis revealed that 8HQL-Zn exhibits favorable selectivity towards cancer cells with a selectivity index ran-ging from 1.57 to 2.25.

8-hydroxyquinolineZinc(Ⅱ)complexeSchiff baseanticancer activitysynthesis

张树琳、覃荣祝、黄燕珊、林啟福、韦祖壮

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北部湾大学海洋学院,广西钦州 535011

8-羟基喹啉 锌(Ⅱ)配合物 希夫碱 抗肿瘤活性 合成

2024

合成化学
四川省化学化工学会 中国科学院成都有机化学研究所

合成化学

CSTPCD
影响因子:0.42
ISSN:1005-1511
年,卷(期):2024.32(12)