Orthogonal Design of a Water-Soluble meso-Tetraphenylethene-Functionalized Pillar[5]arene with Aggregation-Induced Emission Property and Its Therapeutic Application

An orthogonal strategy was utilized for synthesizing a novel water-soluble pillar[5]­arene ( m-TPEWP5) with tetraphenylethene-functionalized on the bridged methylene group (meso-position) of the pillararene skeleton. The obtained macrocycle exhibit both the aggregation-induced emission (AIE) effect...

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Bibliographic Details
Published in:ACS applied materials & interfaces 2021-08, Vol.13 (31), p.37466-37474
Main Authors: Tian, Xueqi, Zuo, Minzan, Niu, Pengbo, Velmurugan, Krishnasamy, Wang, Kaiya, Zhao, Yue, Wang, Leyong, Hu, Xiao-Yu
Format: Article
Language:English
Subjects:
Animals
Benzylidene Compounds - chemical synthesis
Benzylidene Compounds - chemistry
Calixarenes - chemical synthesis
Calixarenes - chemistry
Camptothecin - analogs & derivatives
Camptothecin - pharmacology
Cell Line, Tumor
Drug Carriers - chemical synthesis
Drug Carriers - chemistry
Drug Design
Drug Liberation
Female
Fluorescent Dyes - chemical synthesis
Fluorescent Dyes - chemistry
Fluorometry
Functional Nanostructured Materials (including low-D carbon)
Humans
Mice
Mice, Inbred BALB C
Mice, Nude
Nanoparticles - chemistry
Neoplasms - diagnosis
Prodrugs - chemistry
Prodrugs - pharmacology
Quaternary Ammonium Compounds - chemical synthesis
Quaternary Ammonium Compounds - chemistry
Solubility
Water - chemistry
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Summary:An orthogonal strategy was utilized for synthesizing a novel water-soluble pillar[5]­arene ( m-TPEWP5) with tetraphenylethene-functionalized on the bridged methylene group (meso-position) of the pillararene skeleton. The obtained macrocycle exhibit both the aggregation-induced emission (AIE) effect and interesting host–guest property. Moreover, it can be made to bind with a tailor-made camptothecin-based prodrug guest (DNS-G) to form AIE-nanoparticles based on host–guest interaction and the fluorescence resonance energy transfer process for fabricating a drug delivery system. This novel type of water-soluble AIE-active macrocycle can serve as a potential fluorescent material for cancer diagnosis and therapy. In addition, the present orthogonal strategy for designing meso-functionalized aromatic macrocycles may pave a new avenue for creating novel supramolecular structures and functional materials.
ISSN:1944-8244
1944-8252
DOI:10.1021/acsami.1c07106