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新型 6-甲基-2-氧代-1,2-二氢喹啉-3-甲酰基-4n-取代缩氨基硫脲席夫碱铜(II)配合物的合成、表征及生物活性

Synthesis, Characterization and Biological Activity of Novel Cu(II) Complexes of 6-Methyl-2-Oxo-1,2-Dihydroquinoline-3-Carbaldehyde-4n-Substituted Thiosemicarbazones.

机构信息

Department of Industrial Engineering, University of Padova, 35131 Padova, Italy.

Chemistry Research Center, National Engineering College, K. R. Nagar, Kovilpatti, Tamilnadu 628503, India.

出版信息

Molecules. 2020 Apr 17;25(8):1868. doi: 10.3390/molecules25081868.

DOI:10.3390/molecules25081868
PMID:32316698
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7221752/
Abstract

Three new 6-methyl-2-oxo-1,2-dihydroquinoline-3-carbaldehyde-thiosemicarbazones-N-4-substituted pro-ligands and their Cu(II) complexes (, -NH; , -NHMe; , -NHEt) have been prepared and characterized. In both the X-ray structures of and , two crystallographically independent complex molecules were found that differ either in the nature of weakly metal-binding species (water in and nitrate in ) or in the co-ligand (water in and methanol in ). Electron Paramagnetic Resonance (EPR) measurements carried out on complexes and confirmed the presence of such different species in the solution. The electrochemical behavior of the pro-ligands and of the complexes was investigated, as well as their biological activity. Complexes and exhibited a high cytotoxicity against human tumor cells and 3D spheroids derived from solid tumors, related to the high cellular uptake. Complexes and also showed a high selectivity towards cancerous cell lines with respect to non-cancerous cell lines and were able to circumvent cisplatin resistance. Via the Transmission Electron Microscopy (TEM) imaging technique, preliminary insights into the biological activity of copper complexes were obtained.

摘要

三种新的 6-甲基-2-氧代-1,2-二氢喹啉-3-甲酰基缩氨基硫脲-N-4-取代前配体及其 Cu(II) 配合物（，-NH；，-NHMe；，-NHEt）已经制备并进行了表征。在 和 的 X 射线结构中，发现了两个结晶学上独立的配合物分子，它们要么在弱金属结合物种（水中的 和硝酸盐中的 ）的性质上有所不同，要么在共配体（水中的 和甲醇中的 ）的性质上有所不同。电子顺磁共振（EPR）测量证实了溶液中存在这种不同的物种。研究了前配体和配合物的电化学行为及其生物活性。配合物 和 对人肿瘤细胞和源自实体瘤的 3D 球体表现出高细胞毒性，这与高细胞摄取有关。与非癌细胞系相比，配合物 和 对癌细胞系也具有高选择性，并且能够克服顺铂耐药性。通过透射电子显微镜（TEM）成像技术，初步了解了铜配合物的生物活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/80ce1e5339d6/molecules-25-01868-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/ae2a66505a78/molecules-25-01868-ch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/7a60ab292e57/molecules-25-01868-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/941810ecd405/molecules-25-01868-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/71e8edbef202/molecules-25-01868-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/423842d24e60/molecules-25-01868-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/18194241418f/molecules-25-01868-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/ef3c0771ecba/molecules-25-01868-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/44d2c261cddb/molecules-25-01868-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/9452c891134c/molecules-25-01868-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/76573e03d9f6/molecules-25-01868-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/49cd96fa21d1/molecules-25-01868-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/954207bf1cb8/molecules-25-01868-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/83823d1ea728/molecules-25-01868-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/80ce1e5339d6/molecules-25-01868-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/ae2a66505a78/molecules-25-01868-ch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/7a60ab292e57/molecules-25-01868-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/941810ecd405/molecules-25-01868-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/71e8edbef202/molecules-25-01868-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/423842d24e60/molecules-25-01868-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/18194241418f/molecules-25-01868-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/ef3c0771ecba/molecules-25-01868-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/44d2c261cddb/molecules-25-01868-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/9452c891134c/molecules-25-01868-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/76573e03d9f6/molecules-25-01868-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/49cd96fa21d1/molecules-25-01868-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/954207bf1cb8/molecules-25-01868-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/83823d1ea728/molecules-25-01868-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/260b/7221752/80ce1e5339d6/molecules-25-01868-g012.jpg

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