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基于异核锰(I)的氨基醌桥联酯/酰胺功能化双核金属镫的单锅自组装:潜在的抗癌和可见光触发的一氧化碳释放分子

Single-Pot Self-Assembly of Heteroleptic Mn(I)-Based Aminoquinonato-Bridged Ester/Amide-Functionalized Dinuclear Metallastirrups: Potential Anticancer and Visible-Light-Triggered CORMs.

作者信息

Divya Dhanaraj, Nagarajaprakash Ramamurthy, Vidhyapriya Pitchavel, Sakthivel Natarajan, Manimaran Bala

机构信息

Department of Chemistry and Department of Biotechnology, Pondicherry University, Puducherry 605014, India.

Chemical Sciences Research Group, Division of Research & Development, Lovely Professional University, Phagwara 144411, Punjab, India.

出版信息

ACS Omega. 2019 Jul 26;4(7):12790-12802. doi: 10.1021/acsomega.9b01438. eCollection 2019 Jul 31.

Abstract

Multicomponent self-assembly of Mn(CO), a bis-chelating aminoquinonato (ON∩ON) bridge (L), and an ester/amide-functionalized flexible neutral ditopic linker (L') has resulted into the formation of MLL'-type manganese(I)-based dinuclear metallastirrups of general formula [{(CO)Mn(μ-η-L)Mn(CO)}(μ-L')] (-). Compounds - were accomplished via orthogonal bonding of the aminoquinone ligand (2,5-bis(-butylamino)-1,4-benzoquinone/2,5-bis(phenethylamino)-1,4-benzoquinone) and ditopic pyridyl ligand to manganese carbonyl. The resultant metallastirrups were characterized using elemental analyses and IR, UV-vis, H NMR, and electrospray ionization-mass spectroscopic techniques. The molecular structure of was confirmed by single-crystal X-ray diffraction methods. Furthermore, molecular recognition capabilities of , , , and were evaluated with aromatic compounds containing hydroxy/amine functionalities. Anticancer activities of compounds -, -, , and were investigated against three cancer cell lines, that is, lung (A549), colon (HCT-15), and cervical (HeLa) as well as on normal cells (HEK 293). Compound showed a broad-spectrum inhibition toward these cancer cells upon exposure to visible light. The myoglobin assay was performed using UV-vis absorption spectroscopy to investigate the visible-light-triggered CO release from and that could be related to their ability to effectively inhibit cancer cells. In addition, morphological studies confirmed the induction of autophagy due to the treatment of cancer cells using compound .

摘要

锰(CO)、双螯合氨基醌(ON∩ON)桥(L)和酯/酰胺功能化柔性中性双齿连接体(L')的多组分自组装形成了通式为[{(CO)Mn(μ-η-L)Mn(CO)}(μ-L')] (-)的MLL'-型锰(I)基双核金属镫形物。化合物 - 通过氨基醌配体(2,5-双(-丁基氨基)-1,4-苯醌/2,5-双(苯乙氨基)-1,4-苯醌)和双齿吡啶配体与锰羰基的正交键合来实现。使用元素分析以及红外、紫外-可见、氢核磁共振和电喷雾电离-质谱技术对所得的金属镫形物进行了表征。通过单晶X射线衍射方法确定了 的分子结构。此外,评估了 、 、 和 对含有羟基/胺官能团的芳香化合物的分子识别能力。研究了化合物 - 、 - 、 和 对三种癌细胞系即肺癌(A549)、结肠癌(HCT-15)和宫颈癌(HeLa)以及正常细胞(HEK 293)的抗癌活性。化合物 在暴露于可见光时对这些癌细胞表现出广谱抑制作用。使用紫外-可见吸收光谱进行肌红蛋白测定,以研究从 和 可见光触发的CO释放,这可能与其有效抑制癌细胞的能力有关。此外,形态学研究证实了使用化合物 处理癌细胞会诱导自噬。

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