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One-pot Synthesis of Water-Soluble, β-cyclodextrin-based Polyrotaxanes in a Homogeneous Water System and Its Use in Bio-Applications

One-pot Synthesis of Water-Soluble, β-cyclodextrin-based Polyrotaxanes in a Homogeneous Water System and Its Use in Bio-Applications

Shuling Yu, Jintao Yuan, Jiahua Shi, Xiaojiao Ruan, Yali Wang, Shufang Gao, Yu Du

J Mater Chem B. 2015 Jul 14;3(26):5277-5283.

PMID: 32262603

Abstract:

A small, nano-sized, water-soluble polyrotaxane (PR) was synthesized using a highly efficient one-pot synthesis strategy in a homogeneous water system, formed from β-cyclodextrin-(COOH)2, poly(propylene glycol)bis(2-aminopropyl ether) (PPG, 2 kDa) and a mono-(6-azido-6-desoxy)-β-cyclodextrin stopper via room temperature click chemistry. β-cyclodextrin-(COOH)2 and PR were characterized by one- and two-dimensional NMR as well as by high resolution transmission electron microscopy (HR-TEM). The number of carboxyl groups in one PR was determined by 1H NMR. Two-dimensional diffusion-ordered NMR spectroscopy (2D DOSY) and nuclear Overhauser enhancement spectroscopy (2D NOESY) show that β-cyclodextrin-(COOH)2 and PPG successfully formed an inclusion complex. HR-TEM revealed the morphology of water-soluble PR as a spherical nanoparticle with a size of approximately 3.5 nm ± 1.5 nm. PR was labeled with rhodamine to assess its biocompatibility and cell membrane penetrability in vitro. The in vivo real-time fluorescent imaging biodistribution experiments indicated that water-soluble PR can actively target tumor sites using an enhanced permeability and retention (EPR) effect, with a significantly prolonged blood circulation time in tumor-bearing mice.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP9046100	Poly(propylene glycol) bis(2-aminopropyl ether)		9046-10-0	Price

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