Abstract:
The phosphine ligand (Ph2 PCH2 N(CH3 )(CH2 )2 Ph, PNMPEA) obtained by the reaction of the (hydroxymethyl)diphenylphosphine with naturally occurring alkaloid N-methylphenethylamine, was used to synthesize the half-sandwich iridium(III) (Ir(η5 -Cp*)Cl2 Ph2 PCH2 N(CH3 )(CH2 )2 Ph, IrPNMPEA) and ruthenium(II) (Ru(η6 -p-cymene)Cl2 Ph2 PCH2 N(CH3 )(CH2 )2 Ph, RuPNMPEA) complexes. They were characterized using a vast array of methods, including 1D and 2D NMR, ESI(+)MS spectrometry, elemental analysis, cyclic voltammetry (CV), electron spectroscopy in the UV-Vis range (absorption, fluorescence) and density functional theory (DFT). The initial antimicrobial activity in vitro toward Gram-positive and Gram-negative bacterial strains was examined, indicating that both complexes are selective towards Gram-positive bacteria, e. g., Staphylococcus aureus, where the IrPNMPEA has been more bactericidal compared to RuPNMPEA. Additionally, the interactions of these compounds with various biomolecules, such as DNA (ctDNA, plasmid DNA, 9-ethylguanine (9-EtG), and 9-methyladenine (9-MeA)), nicotinamide adenine dinucleotide (NADH), glutathione (GSH), and ascorbic acid (Asc) were described. The results showed that both Ir(III) and Ru(II) complexes accelerate the oxidation process of NADH, GSH and Asc that appeared to occur by an electron transfer mechanism. Interestingly, only IrPNMPEA leads to the formation of various biomolecule adducts, which can explain its higher activity. Furthermore, RuPNMPEA and IrPNMPEA have been interacting with the DNA through weak noncovalent interactions.
摘要:
膦配体(Ph2PCH2N(CH3)(CH2)2Ph,PNMPEA)通过(羟甲基)二苯基膦与天然存在的生物碱N-甲基苯乙胺的反应获得,用于合成半夹心铱(III)(Ir(η5-Cp*)Cl2Ph2PCH2N(CH3)(CH2)2Ph,IrPNMPEA)和钌(II)(Ru(η6-对-异丙苯)Cl2Ph2PCH2N(CH3)(CH2)2Ph,RuPNMPEA)复合物。它们的特征是使用各种各样的方法,包括1D和2DNMR,ESI(+)质谱,元素分析,循环伏安法(CV),紫外-可见范围内的电子能谱(吸收,荧光)和密度泛函理论(DFT)。检查了体外对革兰氏阳性和革兰氏阴性细菌菌株的初始抗菌活性,表明两种复合物对革兰氏阳性细菌具有选择性,例如,金黄色葡萄球菌,与RuPNMPEA相比,IrPNMPEA更具杀菌性。此外,这些化合物与各种生物分子的相互作用,如DNA(ctDNA,质粒DNA,9-乙基鸟嘌呤(9-EtG),和9-甲基腺嘌呤(9-MeA)),烟酰胺腺嘌呤二核苷酸(NADH),谷胱甘肽(GSH),和抗坏血酸(Asc)进行了描述。结果表明,Ir(III)和Ru(II)配合物加速了NADH的氧化过程,GSH和Asc似乎是通过电子转移机制发生的。有趣的是,只有IrPNMPEA导致各种生物分子加合物的形成,这可以解释其更高的活性。此外,RuPNMPEA和IrPNMPEA通过弱的非共价相互作用与DNA相互作用。