{"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":null,"pages":null},"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}
引用次数: 0
Abstract
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:
Structural Chemistry is an international forum for the publication of peer-reviewed original research papers that cover the condensed and gaseous states of matter and involve numerous techniques for the determination of structure and energetics, their results, and the conclusions derived from these studies. The journal overcomes the unnatural separation in the current literature among the areas of structure determination, energetics, and applications, as well as builds a bridge to other chemical disciplines. Ist comprehensive coverage encompasses broad discussion of results, observation of relationships among various properties, and the description and application of structure and energy information in all domains of chemistry.
We welcome the broadest range of accounts of research in structural chemistry involving the discussion of methodologies and structures,experimental, theoretical, and computational, and their combinations. We encourage discussions of structural information collected for their chemicaland biological significance.