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Design, Synthesis and Evaluation of a Series of Zinc(II) Complexes of Anthracene-Affixed Multifunctional Organic Assembly as Potential Antibacterial and Antibiofilm Agents against Methicillin-Resistant Staphylococcus aureus
ACS Applied Materials & Interfaces ( IF 8.3 ) Pub Date : 2023-05-02 , DOI: 10.1021/acsami.2c21899 Avishek Majumder 1 , Chandan Sarkar 1 , Indrajit Das 2 , Sujan Sk 1 , Shrabasti Bandyopadhyay 2 , Supratim Mandal 2 , Manindranath Bera 1
ACS Applied Materials & Interfaces ( IF 8.3 ) Pub Date : 2023-05-02 , DOI: 10.1021/acsami.2c21899 Avishek Majumder 1 , Chandan Sarkar 1 , Indrajit Das 2 , Sujan Sk 1 , Shrabasti Bandyopadhyay 2 , Supratim Mandal 2 , Manindranath Bera 1
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A novel class of zinc(II)-based metal complexes, i.e., [Zn2(acdp)(μ-Cl)]·2H2O (1), [Zn2(acdp)(μ-NO3)]·2H2O (2), and [Zn2(acdp)(μ-O2CCF3)]·2H2O (3) (Cl– = chloride; NO3– = nitrate; CF3CO2– = trifluoroacetate) of anthracene-affixed multifunctional organic assembly, H3acdp (H3acdp = N,N′-bis[anthracene-2-ylmethyl]-N,N′-bis[carboxymethyl]-1,3-diaminopropan-2-ol), have emerged as promising antibacterial and antibiofilm agents in the domain of medicinal chemistry. Accordingly, complexes 1–3 were synthesized by utilizing H3acdp in combination with ZnCl2, Zn(NO3)2·6H2O, and Zn(CF3CO2)2·H2O respectively, in the presence of NaOH at ambient temperature. The complexation between H3acdp and Zn2+ was delineated by a combined approach of spectrophotometric and spectrofluorometric titration studies. The stoichiometry of acdp3–/Zn2+ in all three complexes is observed to be 1:2, as confirmed by spectrophotometric/spectrofluorometric titration data. Elemental analysis (C, H, N, Zn), molar conductance, FTIR, UV–vis, and thermoanalytical (TGA/DTA) data were effectively used to characterize these complexes. Besides, the structures of 1–3 were established by density functional theory (DFT) calculation using B3LYP/6-311G, specifying a self-assembled compact geometry with average Zn···Zn separation of 3.4629 Å. All three zinc complexes exhibited significantly high antibacterial and antibiofilm activity against methicillin-resistant Staphylococcus aureus (MRSA BAA1717). However, complex 1 showed a more recognizable activity than 2 and 3, with minimum inhibitory concentration (MIC) values of 200, 350, and 450 μg/mL, respectively. The antimicrobial activity was tested by employing the minimum inhibitory concentration (MIC) and time-kill assay. The crystal violet (CV) assay and microscopic study were performed to examine the antibiofilm activity. As observed, complexes 1–3 had an effect on the production of extracellular polymeric substance (EPS), biofilm cell-viability, and other virulence factors such as staphyloxanthin and hemolysin production, autoaggregation ability, and microbial cell-surface hydrophobicity. Reactive oxygen species (ROS) generated due to inhibition of staphyloxanthin production in response to 1–3 were also analyzed. Moreover, complexes 1–3 showed an ability to damage the bacterial cell membrane due to accumulation of ROS resulting in DNA leakage. In addition, complexes 1–3 displayed a synergistic/additive activity with a commercially available antibiotic drug, vancomycin, with enhanced antibacterial activity. On the whole, our investigation disclosed that complex 1 could be a promising drug lead and attract much attention to medicinal chemists compared to 2 and 3 from therapeutic aspects.
中文翻译：
蒽附加多功能有机组装的一系列锌 (II) 配合物的设计、合成和评价作为潜在的抗甲氧西林金黄色葡萄球菌抗菌和抗生物膜剂
一类新的基于锌 (II) 的金属配合物，即 [Zn 2 (acdp)(μ-Cl)]·2H 2 O ( 1 ), [Zn 2 (acdp)(μ-NO 3 )]·2H 2 O ( 2 ) 和 [Zn 2 (acdp)(μ-O 2 CCF 3 )]·2H 2 O ( 3 ) (Cl – = 氯化物；NO 3 – = 硝酸盐；CF 3 CO 2 – = 三氟乙酸盐)蒽固定的多功能有机组装体，H 3 acdp (H 3 acdp = N , N'-bis[anthracene-2-ylmethyl]- N , N' -bis[carboxymethyl]-1,3-diaminopropan-2-ol), 已成为药物化学领域有前途的抗菌剂和抗生物膜剂。因此，在 NaOH 存在下，分别使用 H 3 acdp 与 ZnCl 2、Zn(NO 3 ) 2 ·6H 2 O 和 Zn(CF 3 CO 2 ) 2 ·H 2 O合成配合物1 – 3在环境温度下。H 3 acdp与Zn 2+的络合由分光光度法和分光光度计滴定研究的组合方法描绘。acdp 3– /Zn 2+在所有三种复合物中的化学计量比均为 1:2，这已通过分光光度法/荧光分光光度法滴定数据得到证实。元素分析（C、H、N、Zn）、摩尔电导、FTIR、UV-vis 和热分析 (TGA/DTA) 数据被有效地用于表征这些配合物。此外， 1-3的结构是使用 B3LYP/6-311G 通过密度泛函理论 (DFT) 计算建立的，指定了具有 3.4629 Å 平均 Zn···Zn 分离度的自组装紧凑几何结构。所有三种锌配合物都对耐甲氧西林表现出显着高的抗菌和抗生物膜活性金黄色葡萄球菌(MRSA BAA1717)。然而，复合物1显示出比2和3更可识别的活性，最小抑菌浓度 (MIC) 值分别为 200、350 和 450 μg/mL。通过使用最小抑菌浓度 (MIC) 和时间杀灭测定法测试抗菌活性。进行结晶紫 (CV) 测定和显微镜研究以检查抗生物膜活性。据观察，复合物1 – 3对细胞外聚合物 (EPS) 的产生、生物膜细胞活力和其他毒力因子如葡萄黄素和溶血素产生、自聚集能力和微生物细胞表面疏水性有影响。还分析了由于响应1 – 3抑制葡萄黄素产生而产生的活性氧 (ROS)。此外，复合物1-3显示出由于 ROS积累导致 DNA 泄漏而破坏细菌细胞膜的能力。此外，配合物1 – 3显示出与市售抗生素药物万古霉素的协同/加和活性，具有增强的抗菌活性。总的来说，我们的调查表明，与2和3相比，复合物1可能是一种有前途的药物先导药物，并且从治疗方面吸引了很多药物化学家的关注。
更新日期：2023-05-02
中文翻译：
蒽附加多功能有机组装的一系列锌 (II) 配合物的设计、合成和评价作为潜在的抗甲氧西林金黄色葡萄球菌抗菌和抗生物膜剂
一类新的基于锌 (II) 的金属配合物，即 [Zn 2 (acdp)(μ-Cl)]·2H 2 O ( 1 ), [Zn 2 (acdp)(μ-NO 3 )]·2H 2 O ( 2 ) 和 [Zn 2 (acdp)(μ-O 2 CCF 3 )]·2H 2 O ( 3 ) (Cl – = 氯化物；NO 3 – = 硝酸盐；CF 3 CO 2 – = 三氟乙酸盐)蒽固定的多功能有机组装体，H 3 acdp (H 3 acdp = N , N'-bis[anthracene-2-ylmethyl]- N , N' -bis[carboxymethyl]-1,3-diaminopropan-2-ol), 已成为药物化学领域有前途的抗菌剂和抗生物膜剂。因此，在 NaOH 存在下，分别使用 H 3 acdp 与 ZnCl 2、Zn(NO 3 ) 2 ·6H 2 O 和 Zn(CF 3 CO 2 ) 2 ·H 2 O合成配合物1 – 3在环境温度下。H 3 acdp与Zn 2+的络合由分光光度法和分光光度计滴定研究的组合方法描绘。acdp 3– /Zn 2+在所有三种复合物中的化学计量比均为 1:2，这已通过分光光度法/荧光分光光度法滴定数据得到证实。元素分析（C、H、N、Zn）、摩尔电导、FTIR、UV-vis 和热分析 (TGA/DTA) 数据被有效地用于表征这些配合物。此外， 1-3的结构是使用 B3LYP/6-311G 通过密度泛函理论 (DFT) 计算建立的，指定了具有 3.4629 Å 平均 Zn···Zn 分离度的自组装紧凑几何结构。所有三种锌配合物都对耐甲氧西林表现出显着高的抗菌和抗生物膜活性金黄色葡萄球菌(MRSA BAA1717)。然而，复合物1显示出比2和3更可识别的活性，最小抑菌浓度 (MIC) 值分别为 200、350 和 450 μg/mL。通过使用最小抑菌浓度 (MIC) 和时间杀灭测定法测试抗菌活性。进行结晶紫 (CV) 测定和显微镜研究以检查抗生物膜活性。据观察，复合物1 – 3对细胞外聚合物 (EPS) 的产生、生物膜细胞活力和其他毒力因子如葡萄黄素和溶血素产生、自聚集能力和微生物细胞表面疏水性有影响。还分析了由于响应1 – 3抑制葡萄黄素产生而产生的活性氧 (ROS)。此外，复合物1-3显示出由于 ROS积累导致 DNA 泄漏而破坏细菌细胞膜的能力。此外，配合物1 – 3显示出与市售抗生素药物万古霉素的协同/加和活性，具有增强的抗菌活性。总的来说，我们的调查表明，与2和3相比，复合物1可能是一种有前途的药物先导药物，并且从治疗方面吸引了很多药物化学家的关注。
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