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基于1,8-萘二甲酰亚胺的多功能化合物作为铜探针、溶酶体染色剂和非病毒载体。

1,8-Naphthalimide-Based Multifunctional Compounds as Cu Probes, Lysosome Staining Agents, and Non-viral Vectors.

作者信息

Gao Yong-Guang, Liu Fen-Li, Patil Suryaji, Li Di-Jie, Qadir Abdul, Lin Xiao, Tian Ye, Li Yu, Qian Ai-Rong

机构信息

Lab for Bone Metabolism, Key Lab for Space Biosciences and Biotechnology, School of Life Sciences, Northwestern Polytechnical University, Xi'an, China.

Research Center for Special Medicine and Health Systems Engineering, School of Life Sciences, Northwestern Polytechnical University, Xi'an, China.

出版信息

Front Chem. 2019 Sep 10;7:616. doi: 10.3389/fchem.2019.00616. eCollection 2019.

DOI:10.3389/fchem.2019.00616
PMID:31552230
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6747039/
Abstract

A series of multifunctional compounds (MFCs) - based on 1,8-naphthalimide moiety were designed and synthesized. Due to the good fluorescence property and nucleic acid binding ability of 1,8-naphthalimide, these MFCs were applied in Cu ion recognition, lysosome staining as well as RNA delivery. It was found that these MFCs exhibited highly selective fluorescence turn-off for Cu in aqueous solution. The fluorescence emission of was quenched by a factor of 116-, 20-, 12-, and 14-fold in the presence of Cu ions, respectively. Most importantly, -Cu and -Cu could be used as imaging reagents for detection of lysosome in live human cervical cancer cells (HeLa) using fluorescence microscopy. Furthermore, in order to evaluate the RNA delivery ability of , cellular uptake experiments were performed in HeLa, HepG2, U2Os, and MC3T3-E1 cell lines. The results showed that all the materials could deliver Cy5-labled RNA into the targeted cells. Among them, compound modified with long hydrophobic chain exhibited the best RNA delivery efficiency in the four tested cell lines, and the performance was far better than lipofectamine 2000 and 25 kDa PEI, indicating the potential application in non-viral vectors.

摘要

设计并合成了一系列基于1,8-萘二甲酰亚胺部分的多功能化合物（MFCs）。由于1,8-萘二甲酰亚胺具有良好的荧光性质和核酸结合能力，这些MFCs被应用于铜离子识别、溶酶体染色以及RNA递送。研究发现，这些MFCs在水溶液中对铜离子表现出高度选择性的荧光猝灭。在铜离子存在下，[具体化合物名称]的荧光发射分别被猝灭了116倍、20倍、12倍和14倍。最重要的是，[具体化合物名称]-铜和[具体化合物名称]-铜可作为成像试剂，使用荧光显微镜检测活的人宫颈癌细胞（HeLa）中的溶酶体。此外，为了评估[具体化合物名称]的RNA递送能力，在HeLa、HepG2、U2Os和MC3T3-E1细胞系中进行了细胞摄取实验。结果表明，所有材料都能将Cy5标记的RNA递送至靶细胞。其中，用长疏水链修饰的化合物在四种测试细胞系中表现出最佳的RNA递送效率，其性能远优于脂质体2000和25 kDa聚乙烯亚胺，表明其在非病毒载体中的潜在应用价值。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/62da3ac86f70/fchem-07-00616-g0013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/f259d7b095e4/fchem-07-00616-g0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/21ed81349212/fchem-07-00616-g0014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/ac4e162659ef/fchem-07-00616-g0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/e61e5a43b768/fchem-07-00616-g0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/a03f937faa7f/fchem-07-00616-g0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/0b83a1b9d74a/fchem-07-00616-g0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/4839f8de782e/fchem-07-00616-g0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/c0f4b5428b01/fchem-07-00616-g0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/50d3b3b677c4/fchem-07-00616-g0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/dd9cead05034/fchem-07-00616-g0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/f32b8b524a39/fchem-07-00616-g0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/cffdf7455223/fchem-07-00616-g0011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/9d92fd6acc7a/fchem-07-00616-g0012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/62da3ac86f70/fchem-07-00616-g0013.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/f259d7b095e4/fchem-07-00616-g0001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/21ed81349212/fchem-07-00616-g0014.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/ac4e162659ef/fchem-07-00616-g0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/e61e5a43b768/fchem-07-00616-g0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/a03f937faa7f/fchem-07-00616-g0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/0b83a1b9d74a/fchem-07-00616-g0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/4839f8de782e/fchem-07-00616-g0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/c0f4b5428b01/fchem-07-00616-g0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/50d3b3b677c4/fchem-07-00616-g0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/dd9cead05034/fchem-07-00616-g0009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/f32b8b524a39/fchem-07-00616-g0010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/cffdf7455223/fchem-07-00616-g0011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/9d92fd6acc7a/fchem-07-00616-g0012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfc3/6747039/62da3ac86f70/fchem-07-00616-g0013.jpg

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