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氧化还原活性氨基脲衍生菲咯啉及其银配合物的合成、表征与抗应用

Synthesis, Characterization, and Anti- Application of Redox-Active Ethyl Carbazate-Derivatized Phenanthroline and Its Silver Complexes.

作者信息

Aluri Ravallika, Natarajan Aishwarya, Kumari Jyothi, Sriram Dharmarajan, Samanta Pralok K, Gangopadhyay Aditi, Rangan Krishnan

机构信息

Department of Chemistry, Birla Institute of Technology and Science, Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad 500 078, Telangana, India.

Department of Pharmacy, Birla Institute of Technology and Science, Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad 500 078, Telangana, India.

出版信息

ACS Omega. 2025 Jun 13;10(27):28993-29013. doi: 10.1021/acsomega.5c00871. eCollection 2025 Jul 15.

DOI:10.1021/acsomega.5c00871
PMID:40687003
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12273601/
Abstract

Exploring the design and synthesis of new antibiotic compounds is important to treat multidrug-resistant bacterial infections for the already exposed drug molecules. In this work, a phenanthroline derivative, namely, 6-[2-(ethoxycarbonyl)-diazen-1-yl]-1,10-phenanthroline-5-one (ECDPO), and its mono- and bis-ligand silver complexes [Ag-(ECDPO)-(NO)] and [Ag-(ECDPO)]-(NO) were synthesized. Single-crystal X-ray diffraction (XRD) structure of methanol-solvated ECDPO was studied, which crystallized in a monoclinic system, 2/ space group. ECDPO is a planar molecule, and supramolecular arrays are stabilized by various hydrogen bonding, namely, O-H···N, N-H···O, and C-H···O, and π-π interactions. The spectroscopic features of ECDPO and its silver complexes were thoroughly studied by high-resolution mass spectrometry (HRMS), IR, H NMR, C NMR, UV-visible spectroscopy, and X-ray photoelectron spectroscopy (XPS). Electrochemical redox features were studied by cyclic voltammetry. The ECDPO molecule and its silver complexes were studied for antibacterial activity against bacteria and (). ECDPO shows a minimum inhibitory concentration (MIC) of 1.56 μg/mL against , which is comparable to that of one of the clinically used drug candidates, namely, ethambutol. Silver complexes [Ag-(ECDPO)-(NO)] and [Ag-(ECDPO)]-(NO) showed enhanced anti activities and MICs of 0.78 and 0.39 μg/mL, respectively.

摘要

探索新型抗生素化合物的设计与合成对于治疗已暴露的耐药性细菌感染的药物分子至关重要。在这项工作中，合成了一种菲咯啉衍生物，即6-[2-(乙氧基羰基)-重氮-1-基]-1,10-菲咯啉-5-酮（ECDPO）及其单配体和双配体银配合物[Ag-(ECDPO)-(NO)]和[Ag-(ECDPO)]-(NO)。研究了甲醇溶剂化的ECDPO的单晶X射线衍射（XRD）结构，其结晶于单斜晶系，空间群为2/。ECDPO是一个平面分子，超分子阵列通过各种氢键，即O-H···N、N-H···O和C-H···O以及π-π相互作用得以稳定。通过高分辨率质谱（HRMS）、红外光谱（IR）、氢核磁共振（H NMR）、碳核磁共振（C NMR）、紫外可见光谱和X射线光电子能谱（XPS）对ECDPO及其银配合物的光谱特征进行了深入研究。通过循环伏安法研究了电化学氧化还原特征。研究了ECDPO分子及其银配合物对细菌和（此处原文缺失具体细菌名称）的抗菌活性。ECDPO对（此处原文缺失具体细菌名称）的最低抑菌浓度（MIC）为1.56μg/mL，与临床使用的候选药物之一乙胺丁醇相当。银配合物[Ag-(ECDPO)-(NO)]和[Ag-(ECDPO)]-(NO)表现出增强的抗菌活性，MIC分别为0.78和0.39μg/mL。

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