NDLI: A pillar[5]arene-based [2]rotaxane lights up mitochondria

Content Provider	Royal Society of Chemistry (RSC)
Author	Zhou, Jiong Shao, Li Hu, Qinglian Yu, Guocan Li, Yang Tang, Guping Zhang, Zhihua Huang, Feihe Wu, Dan
Copyright Year	2016
Abstract	Subcellular organelle-specific reagents for simultaneous targeting, imaging and treatment are highly desirable for cancer therapy. However, it remains a challenge to fabricate a single molecular platform containing a targeting group, imaging and therapeutic agents through traditional synthesis. Due to their superior sensitivity and photostability, fluorescent probes with aggregation-induced emission (AIE) characteristics have attracted more and more attention in studying the process of translocation, drug release, and excretion of nanomedicines in vitro or in vivo. We construct a pillar[5]arene-based [2]rotaxane (R1) by employing tetraphenylethene (TPE) and triphenylphosphonium (TPP) moieties as stoppers; the TPE unit retains the aggregation-induced emission (AIE) attribute and the TPP group is used as a mitochondria-targeting agent. R1 exhibits enhanced AIE, high specificity to mitochondria, and superior photostability. By introducing doxorubicin (DOX) into R1, prodrug R2 is constructed as a dual-fluorescence-quenched Förster resonance energy transfer (FRET) system, in which the TPE-based axle acts as a donor fluorophore and the DOX unit acts as the acceptor. Upon hydrolysis of R2 in endo/lysosomes, the fluorescences of the carrier and the drug recover. R1 is further utilized as a drug delivery platform to conjugate other anticancer drugs containing amine groups through imine formation to prepare prodrugs. The anticancer drugs are released from these prodrugs in the cells upon hydrolysis of the pH-responsive imine bonds.
Starting Page	3017
Ending Page	3024
Page Count	8
File Format	HTM / HTML PDF
ISSN	20416520
Volume Number	7
Issue Number	5
Journal	Chemical Science
DOI	10.1039/c6sc00036c
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Subscribed
Subject Keyword	Förster resonance energy transfer TPE Drug delivery Prodrug Imine DOX Doxorubicin Mitochondrion Hydrolysis Fluorophore Fluorescences AIE Cancer Rotaxane
Content Type	Text
Resource Type	Article
Subject	Chemistry

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