Journal of Molecular Structure ( IF 4.0 ) Pub Date : 2023-12-03 , DOI: 10.1016/j.molstruc.2023.137234 Thaeny Costa Amaral , Nícolas Glanzmann , Adilson D. da Silva , Gabriele de M. Pereira , Pedro P. Corbi , Christian S.C. Canales , Fernando R. Pavan , Kaíque A.D Oliveira , Alexandre Cuin
Sulfonamides (sulfas) are a specific class of organic compounds that possesses antibacterial, anti-inflammatory, antiviral and antitumor activities. This class of molecules is also used in the synthesis of silver(I) complexes, which usually present significant biological activity as antimicrobial agents. In this context, the present work describes the synthesis, structural characterization and antibacterial assays of two silver(I) complexes with the sulfa drugs sulfapyridine (SPY) and sulfamerazine (SM). Chemical analyses and high-resolution mass spectrometric studies led to 1:1 metal/ligand compositions, suggesting the minimal formulas C11H10N3O2SAg·2H2O for AgSPY and C11H11N4O2SAg·2H2O for AgSM. Spectroscopic techniques such as 1H, 13C and {1H–15N} nuclear magnetic resonance (NMR), and also infrared measurements (IR) suggest the coordination of the ligands to silver(I) ions by the nitrogen atom of the SO2N moiety for both complexes. Crystal structures of AgSPY and AgSM were solved and refined by X-ray powder diffraction studies, where dimeric structures with Ag(I) ions bridging between two ligand molecules by the usual eight membered ring [AgNCN]2 and strong argentophilic interactions were observed. Minimum Inhibitory Concentration (MIC90) assays showed the promising activities of the free sulfonamides and the respective complexes against Mycobacterium tuberculosis H37Rv. MIC90 values, in µmol L–1, were 2.47, 3.60, 1.33 and 1.61 for SPY, AgSPY, SM and AgSM, respectively. The obtained MIC90 values were lower than those found for silver sulfadiazine and silver nitrate in the same experimental conditions.
中文翻译:
银(I)与磺胺吡啶(SPY)和磺胺嘧啶(SM)配合物的合成、光谱和结构表征以及体外抗分枝杆菌活性
磺酰胺(磺胺)是一类特殊的有机化合物,具有抗菌、抗炎、抗病毒和抗肿瘤活性。此类分子还用于合成银(I)络合物,该络合物通常作为抗菌剂具有显着的生物活性。在此背景下,本工作描述了两种银(I)与磺胺药物磺胺吡啶(SPY)和磺胺嘧啶(SM)配合物的合成、结构表征和抗菌测定。化学分析和高分辨率质谱研究得出 1:1 的金属/配体组成,表明最小分子式为 C 11 H 10 N 3 O 2 SAg·2H 2 O 代表 AgSPY 和 C 11 H 11 N 4 O 2 SAg·2H 2 O 表示 AgSM。光谱技术,例如 1 H、 13 C 和 { 1 H– 15 N} 核磁共振 (NMR),以及红外测量 (IR) 表明两种配合物的 SO 2 N 部分的氮原子使配体与银 (I) 离子配位。 AgSPY 和 AgSM 的晶体结构通过 X 射线粉末衍射研究得到解决和细化,其中 Ag(I) 离子通过通常的八元环 [AgNCN] 2 在两个配体分子之间桥联的二聚体结构,并且强观察到亲银相互作用。最低抑制浓度(MIC 90 )测定显示游离磺酰胺和各自的复合物对结核分枝杆菌H37Rv具有良好的活性。 SPY、AgSPY、SM 和 AgSM 的 MIC 90 值(以 µmol L –1 为单位)分别为 2.47、3.60、1.33 和 1.61。 在相同实验条件下,所得的 MIC 90 值低于磺胺嘧啶银和硝酸银的 MIC 90 值。