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首页> 美国卫生研究院文献>Molecules >Synthesis Crystal Structure and Biological Activity of a Multidentate Calix4arene Ligand Doubly Functionalized by 2-Hydroxybenzeledene-Thiosemicarbazone
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Synthesis Crystal Structure and Biological Activity of a Multidentate Calix4arene Ligand Doubly Functionalized by 2-Hydroxybenzeledene-Thiosemicarbazone

机译：2-羟基苯并二氮杂-硫杂氨基脲双官能化的多齿杯4芳烃配体的合成晶体结构和生物活性

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摘要

The design and synthesis of a novel tert-butyl-calix[4]arene functionalized at 1, 3 positions of the lower rim with two terminal 2-hydroxybenzeledene-thiosemicarbazone moieties is reported. The new ligand with multi-dentate chelating properties was fully characterized by several techniques: ESI-Mass spectroscopy, FT-IR, 1H-NMR, and single crystal X-ray diffraction. The solid state structure confirms that the calix[4]arene macrocycle has the expected open cone conformation, with two opposite phenyl rings inclined outwards with large angles. The conformation of the two alkoxythiosemicarbazone arms produces a molecule with a C2 point group symmetry. An interesting chiral helicity is observed, with the two thiosemicarbazone groups oriented in opposite directions like a two-blade propeller. A water molecule is encapsulated in the center of the two-blade propeller through multiple H-bond coordinations. The antibacterial, antifungal, anticancer, and cytotoxic activities of the calix[4]arene-thiosemicarbazone ligand and its metal derivatives (Co2+, Ni2+, Cu2+, and Zn2+) were investigated. A considerable antibacterial activity (in particular against , MIC, and MBC = 31.25 μg/mL) was observed for the ligand and its metal derivatives. Significant antifungal activities against yeast ( ) were also observed for the ligand (MIC = 31.25 μg/mL and MBC = 125 μg/mL) and for its Co derivative (MIC = 62.5 μg/mL). All compounds show cytotoxicity against the tested cancerous cells. For the Saos-2 cell line, the promising anticancer activity of ligand L (IC < 25 μg/mL) is higher than its metal derivatives. The microscopic analysis of DAPI-stained cells shows that the treated cells change in morphology, with deformation and fragmentation of the nuclei. The hemo-compatibility study demonstrated that this class of compounds are suitable candidates for further in vivo investigations.
机译：报道了一种新型的叔丁基杯[4]芳烃的设计与合成，该芳烃在下边缘的1、3位具有两个末端2-羟基苯二烯-硫代半碳酰胺基团官能化。具有多齿螯合特性的新配体已通过多种技术进行了充分表征：ESI-质谱，FT-IR，1H-NMR和单晶X射线衍射。固态结构证实了杯[4]芳烃大环具有预期的开锥构象，两个相对的苯环以大角度向外倾斜。两个烷氧基硫半脲键的构象产生具有C2点基对称性的分子。观察到一个有趣的手性螺旋，两个硫代半碳环基团的方向相反，就像一个两叶螺旋桨。水分子通过多个H键配位而封装在两叶螺旋桨的中心。研究了杯[4]芳烃-硫代半碳酰胺配体及其金属衍生物（Co2 +，Ni2 +，Cu2 +和Zn2 +）的抗菌，抗真菌，抗癌和细胞毒性活性。对于配体及其金属衍生物，观察到了相当大的抗菌活性（特别是对MIC和MBC = 31.25μg/ mL）。对于配体（MIC = 31.25μg/ mL和MBC = 125μg/ mL）及其辅酶衍生物（MIC = 62.5μg/ mL），也观察到了针对酵母的显着抗真菌活性。所有化合物对被测癌细胞均显示出细胞毒性。对于Saos-2细胞系，配体L（IC <25μg/ mL）的有希望的抗癌活性高于其金属衍生物。 DAPI染色细胞的显微镜分析表明，处理过的细胞的形态发生了变化，并发生了核的变形和断裂。血液相容性研究表明，这类化合物适合用于进一步的体内研究。

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