{"title":"作为潜在的管蛋白聚合抑制剂的双(苯甲酰丙酮)铜(II)配合物:合成、晶体结构、光谱特性、HSA、DFT、分子对接研究和抗氧化活性","authors":"Abdenour Guerraoui, Meriem Goudjil, Amel Djedouani, Amani Direm, Abdelhalim Boussaa, Douniazed Hannachi, Elvira Fantechi, Giampiero Ruani, Abdecharif Boumaza","doi":"10.1007/s11224-024-02354-w","DOIUrl":null,"url":null,"abstract":"<p>The reaction of 1-phenyl-1,3-butanedione, also known as benzoylacetone (bzac), with adequate copper salts (sulfate/acetate) at a molar ratio of 2:1 in methanol led to two mononuclear complexes, <i>trans</i>-[Cu(bzac)<sub>2</sub>] (<b>I</b>) and <i>cis</i>-[Cu(bzac)<sub>2</sub>(CH<sub>3</sub>OH)] (<b>II</b>). Both complexes crystallize in the monoclinic <i>P2</i><sub><i>1</i></sub><i>/c</i> symmetry. The copper is four- and five-coordinate, exhibiting a square planar geometry and a distorted square-based pyramid in <b>I</b> and <b>II</b>, respectively. Their crystal structures form discrete supramolecular packing. Indeed, <i>Hirshfeld</i> surface analysis (HSA) with 2D fingerprint plots revealed short-range intermolecular contacts involving O—H···Ο hydrogen bonds and C—H<i>···π</i> interactions in both complexes, in addition to <i>π···π</i> interactions in <b>I</b>. The complexes were characterized by IR and UV‒Vis spectroscopic methods. Moreover, a thorough examination of <b>I</b> and <b>II</b> was conducted, focusing on their structural attributes, electronic characteristics, and both linear and nonlinear optical (NLO) responses through density functional theory (DFT) and time-dependent density functional theory (TD-DFT) calculations. These quantum calculations were executed utilizing uωwb97xd/6-311G**/SDD. The results revealed that the <i>β</i><sub>0</sub> value for <b>II</b> was approximately 23 times greater than that of urea. On the other hand, the static and dynamic second hyperpolarizabilities (<i>γ</i>(0; 0,0,0), <i>γ</i>(− 2<i>ω</i>; <i>ω</i>,0,0), and <i>γ</i>(− 2<i>ω</i>; <i>ω</i>,<i>ω</i>,0)) of <b>I</b> are approximately 33% higher than those of <b>II</b>. From this, we infer that the complexes under investigation have potential as outstanding materials for second- and third-order NLO applications. The interactions of <b>I</b> and <b>II</b> with tubulin (PDB ID: 4O2B) were evaluated by molecular docking studies. The results showed that both complexes can bind to many sites on the target and may inhibit its polymerization process. Furthermore, the antioxidant activity of both complexes was also determined and fully discussed.</p>","PeriodicalId":780,"journal":{"name":"Structural Chemistry","volume":"172 1","pages":""},"PeriodicalIF":2.1000,"publicationDate":"2024-06-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Cu(II)-bis(benzoylacetonate) complexes as potential inhibitors for tubulin polymerization: synthesis, crystal structure, spectral characterization, HSA, DFT, molecular docking studies, and antioxidant activity\",\"authors\":\"Abdenour Guerraoui, Meriem Goudjil, Amel Djedouani, Amani Direm, Abdelhalim Boussaa, Douniazed Hannachi, Elvira Fantechi, Giampiero Ruani, Abdecharif Boumaza\",\"doi\":\"10.1007/s11224-024-02354-w\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>The reaction of 1-phenyl-1,3-butanedione, also known as benzoylacetone (bzac), with adequate copper salts (sulfate/acetate) at a molar ratio of 2:1 in methanol led to two mononuclear complexes, <i>trans</i>-[Cu(bzac)<sub>2</sub>] (<b>I</b>) and <i>cis</i>-[Cu(bzac)<sub>2</sub>(CH<sub>3</sub>OH)] (<b>II</b>). Both complexes crystallize in the monoclinic <i>P2</i><sub><i>1</i></sub><i>/c</i> symmetry. The copper is four- and five-coordinate, exhibiting a square planar geometry and a distorted square-based pyramid in <b>I</b> and <b>II</b>, respectively. Their crystal structures form discrete supramolecular packing. Indeed, <i>Hirshfeld</i> surface analysis (HSA) with 2D fingerprint plots revealed short-range intermolecular contacts involving O—H···Ο hydrogen bonds and C—H<i>···π</i> interactions in both complexes, in addition to <i>π···π</i> interactions in <b>I</b>. The complexes were characterized by IR and UV‒Vis spectroscopic methods. Moreover, a thorough examination of <b>I</b> and <b>II</b> was conducted, focusing on their structural attributes, electronic characteristics, and both linear and nonlinear optical (NLO) responses through density functional theory (DFT) and time-dependent density functional theory (TD-DFT) calculations. These quantum calculations were executed utilizing uωwb97xd/6-311G**/SDD. The results revealed that the <i>β</i><sub>0</sub> value for <b>II</b> was approximately 23 times greater than that of urea. On the other hand, the static and dynamic second hyperpolarizabilities (<i>γ</i>(0; 0,0,0), <i>γ</i>(− 2<i>ω</i>; <i>ω</i>,0,0), and <i>γ</i>(− 2<i>ω</i>; <i>ω</i>,<i>ω</i>,0)) of <b>I</b> are approximately 33% higher than those of <b>II</b>. From this, we infer that the complexes under investigation have potential as outstanding materials for second- and third-order NLO applications. The interactions of <b>I</b> and <b>II</b> with tubulin (PDB ID: 4O2B) were evaluated by molecular docking studies. The results showed that both complexes can bind to many sites on the target and may inhibit its polymerization process. Furthermore, the antioxidant activity of both complexes was also determined and fully discussed.</p>\",\"PeriodicalId\":780,\"journal\":{\"name\":\"Structural Chemistry\",\"volume\":\"172 1\",\"pages\":\"\"},\"PeriodicalIF\":2.1000,\"publicationDate\":\"2024-06-27\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Structural Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1007/s11224-024-02354-w\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Structural Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1007/s11224-024-02354-w","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
摘要
在甲醇中,1-苯基-1,3-丁二酮(又称苯甲酰丙酮(bzac))与适当的铜盐(硫酸盐/醋酸盐)以 2:1 的摩尔比发生反应,生成了两种单核络合物,即反式-[Cu(bzac)2] (I) 和顺式-[Cu(bzac)2(CH3OH)] (II)。这两种配合物均以单斜 P21/c 对称性结晶。在 I 和 II 中,铜分别为四配位和五配位,呈现出正方形平面几何和扭曲的正方形金字塔形。它们的晶体结构形成了离散的超分子堆积。事实上,利用二维指纹图谱进行的希尔斯菲尔德表面分析(HSA)显示,除了 I 中的π---π相互作用外,这两种配合物中还存在涉及 O-H---Ο 氢键和 C-H---π 相互作用的短程分子间接触。此外,还通过密度泛函理论(DFT)和时变密度泛函理论(TD-DFT)计算,对 I 和 II 进行了深入研究,重点关注它们的结构属性、电子特性以及线性和非线性光学(NLO)响应。这些量子计算是利用 uωwb97xd/6-311G**/SDD 进行的。结果显示,II 的 β0 值约为尿素的 23 倍。另一方面,I 的静态和动态第二超极化率(γ(0; 0,0,0)、γ(- 2ω; ω,0,0)和 γ(- 2ω; ω,ω,0))比 II 高约 33%。由此,我们推断所研究的配合物有可能成为二阶和三阶 NLO 应用的杰出材料。分子对接研究评估了 I 和 II 与小管蛋白(PDB ID:4O2B)的相互作用。结果表明,这两种复合物都能与目标物上的许多位点结合,并可能抑制其聚合过程。此外,还测定并充分讨论了这两种复合物的抗氧化活性。
Cu(II)-bis(benzoylacetonate) complexes as potential inhibitors for tubulin polymerization: synthesis, crystal structure, spectral characterization, HSA, DFT, molecular docking studies, and antioxidant activity
The reaction of 1-phenyl-1,3-butanedione, also known as benzoylacetone (bzac), with adequate copper salts (sulfate/acetate) at a molar ratio of 2:1 in methanol led to two mononuclear complexes, trans-[Cu(bzac)2] (I) and cis-[Cu(bzac)2(CH3OH)] (II). Both complexes crystallize in the monoclinic P21/c symmetry. The copper is four- and five-coordinate, exhibiting a square planar geometry and a distorted square-based pyramid in I and II, respectively. Their crystal structures form discrete supramolecular packing. Indeed, Hirshfeld surface analysis (HSA) with 2D fingerprint plots revealed short-range intermolecular contacts involving O—H···Ο hydrogen bonds and C—H···π interactions in both complexes, in addition to π···π interactions in I. The complexes were characterized by IR and UV‒Vis spectroscopic methods. Moreover, a thorough examination of I and II was conducted, focusing on their structural attributes, electronic characteristics, and both linear and nonlinear optical (NLO) responses through density functional theory (DFT) and time-dependent density functional theory (TD-DFT) calculations. These quantum calculations were executed utilizing uωwb97xd/6-311G**/SDD. The results revealed that the β0 value for II was approximately 23 times greater than that of urea. On the other hand, the static and dynamic second hyperpolarizabilities (γ(0; 0,0,0), γ(− 2ω; ω,0,0), and γ(− 2ω; ω,ω,0)) of I are approximately 33% higher than those of II. From this, we infer that the complexes under investigation have potential as outstanding materials for second- and third-order NLO applications. The interactions of I and II with tubulin (PDB ID: 4O2B) were evaluated by molecular docking studies. The results showed that both complexes can bind to many sites on the target and may inhibit its polymerization process. Furthermore, the antioxidant activity of both complexes was also determined and fully discussed.
期刊介绍:
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