The Synthesis of the Amphiphilic Block Copolymer Based on o-Nitrobenzyl Phototrigger and the Research of Photo-responsive Properties

doi:10.7517/j.issn.1674-0475.2015.06.494

Imaging Science and Photochemistry ›› 2015, Vol. 33 ›› Issue (6): 494-502.DOI: 10.7517/j.issn.1674-0475.2015.06.494

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The Synthesis of the Amphiphilic Block Copolymer Based on o-Nitrobenzyl Phototrigger and the Research of Photo-responsive Properties

ZHANG Yeye¹, LIN Qiuning², LU Guangzhao¹, ZHU Linyong², ZHONG yanqiang¹, ZOU Hao¹

1. Department of Pharmaceutics, School of Pharmacy, Second Military Medical University, Shanghai 200433, P.R. China;
2. Key Laboratory for Advanced Materials, School of Chemistry and Molecular Engineering, East China University of Science and Technology, Shanghai 200237, P.R. China

Received:2015-09-17 Revised:2015-10-21 Online:2015-11-16 Published:2015-11-16

Abstract

Abstract:

A photo-responsive amphiphilic block copolymer—Polyethylene glycol-S-(o-nitro-m-methoxy-p-dodecone alkoxy benzyl ester) (PEG-VND) was for the first time designed, and synthesized based on o-Nitrobenzyl phototrigger (VND) and polymer PEG₁₀₀₀-NH₂. And the related phototrigger S-(o-nitro-m-methoxy-p-dodecone alkoxy benzyl alcohol) (VND) was synthesized from vanilin and 1-bromododecane as raw materials. The molecular structure was characterized by infrared spectroscope(FT-IR) and nuclear magnetic resonance(¹HNMR). Their physical properties, self-assembly, and model drug release of PEG-VND were thoroughly investigated. The sizes and images of PEG-VND micelles were determined by malvern Zetasizer Nano ZS and transmission electron microscopy (TEM). The characteristic absorption spectrums of these copolymers changed along with the UV irradiation and then leveled off, indicating that the o-nitrobenzyl groups were gradually photocleaved from copolymers until the completion of photocleavage. The PEG-VND copolymers self assembled into micelles in aqueous solution. Model drug nile red can be loaded inside the micelles and can be released in a controlled manner by changing the irradiation time, which was induced by gradually photocleaving the PEG-VND. This work provides a facile strategy not only for the photoresponsive o-nitrobenzyl-based block copolymers but also for the fabrication of photoresponsive nanomedicine potential.

Key words: photo-responsive, o-nitrobenzyl phototrigger, amphiphilic block copolymer

ZHANG Yeye, LIN Qiuning, LU Guangzhao, ZHU Linyong, ZHONG yanqiang, ZOU Hao. The Synthesis of the Amphiphilic Block Copolymer Based on o-Nitrobenzyl Phototrigger and the Research of Photo-responsive Properties[J]. Imaging Science and Photochemistry, 2015, 33(6): 494-502.

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The Synthesis of the Amphiphilic Block Copolymer Based on o-Nitrobenzyl Phototrigger and the Research of Photo-responsive Properties

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