Mostafa Gamal A E, Yousef Tarek A, ElGamal Ali A, Homoda Atef M A, AlRabiah Haitham
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia; Applied Organic Chemistry Department, National Research Center, Dokki, Cairo 12622, Egypt.
College of Science, Chemistry Department, Imam Mohammad Ibn Saud Islamic University (IMSIU), Riyadh 11623, Saudi Arabia; Department of Toxic and Narcotic Drug, Forensic Medicine, Mansoura Laboratory, Medicolegal Organization, Ministry of Justice, Egypt.
Bioorg Chem. 2022 Mar;120:105603. doi: 10.1016/j.bioorg.2022.105603. Epub 2022 Jan 11.
To understand bioactive molecule-receptor interactions it is important to understand the molecular complexation and structural recognition properties of the materials in question. To this aim, the electron donating bioactive molecule tamoxifen (TAM) was combined with the electron accepting molecules 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and 7,7,8,8-tetracyanoquinodimethane (TCNQ) to form TAM-DDQ and TAM-TCNQ charge transfer (CT) complexes. The properties of the complexes in solution and solid, their donor-acceptor interactions were investigated, and their stability was assessed in acetonitrile. Solid complexes of TAM-DDQ and TAM-TCNQ were characterized using nuclear magnetic resonance (NMR) and Fourier transform infrared (FTIR) spectroscopies to confirm their formation. Job's and modified Benesi-Hildebrand methods were used to study the stoichiometries and association constants of TAM-DDQ and TAM-TCNQ, from which their stoichiometries were found to be 1:1. The physical parameters of the CT complexes in terms of their molar extension constants, dipole moments, and formation constants were determined to study their stability in solution. The results obtained in this study indicate that the complexes are suitable for assessing TAM in pharmaceutical preparations. The experimental results were complemented by density functional theory (geometry optimization, energy transition, and molecular electrostatic potential maps) at DFT/B3LYPlevel of theory.
为了理解生物活性分子与受体的相互作用，了解相关材料的分子络合和结构识别特性非常重要。为此，将供电子生物活性分子他莫昔芬（TAM）与受电子分子2,3 - 二氯 - 5,6 - 二氰基 - 1,4 - 苯醌（DDQ）和7,7,8,8 - 四氰基对苯二醌二甲烷（TCNQ）结合，形成TAM - DDQ和TAM - TCNQ电荷转移（CT）络合物。研究了络合物在溶液和固体中的性质、供体 - 受体相互作用，并在乙腈中评估了它们的稳定性。使用核磁共振（NMR）和傅里叶变换红外（FTIR）光谱对TAM - DDQ和TAM - TCNQ的固体络合物进行了表征，以确认它们的形成。采用乔布法和改进的贝内西 - 希尔德布兰德方法研究了TAM - DDQ和TAM - TCNQ的化学计量比和缔合常数，发现它们的化学计量比为1:1。测定了CT络合物的摩尔延伸常数、偶极矩和形成常数等物理参数，以研究它们在溶液中的稳定性。本研究获得的数据表明，这些络合物适用于评估药物制剂中的他莫昔芬。在DFT/B3LYP理论水平上，通过密度泛函理论（几何优化、能量跃迁和分子静电势图）对实验结果进行了补充。
