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Issue 5, 2016
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A pillar[5]arene-based [2]rotaxane lights up mitochondria

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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.

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

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Supplementary files

Article information


Submitted
05 Jan 2016
Accepted
20 Jan 2016
First published
21 Jan 2016

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2016,7, 3017-3024
Article type
Edge Article

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

G. Yu, D. Wu, Y. Li, Z. Zhang, L. Shao, J. Zhou, Q. Hu, G. Tang and F. Huang, Chem. Sci., 2016, 7, 3017 DOI: 10.1039/C6SC00036C

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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