Acta Chimica Sinica ›› 2013, Vol. 71 ›› Issue (08): 1136-1140.DOI: 10.6023/A13030275 Previous Articles     Next Articles



顾晓瑜, 王朝阳, 童真   

  1. 华南理工大学材料科学研究所 广州 510640
  • 投稿日期:2013-03-14 发布日期:2013-05-17
  • 通讯作者: 王朝阳, E-mail:
  • 基金资助:

    项目受国家自然科学基金(No. 21274046)和广东省自然科学基金(No. S2012020011057)资助

Preparation of Amphiphilic Diselenide Copolymer and Formation of Its Aggregates

Gu Xiaoyu, Wang Chaoyang, Tong Zhen   

  1. Research Institute of Materials Science, South China University of Technology, Guangzhou 510640
  • Received:2013-03-14 Published:2013-05-17
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21274046) and the Natural Science Foundation of Guangdong Province (No. S2012020011057).

Selenium has several unique biological effects in many aspects, making use of bioactive components and inorganic selenium to prepare antitumor organic selenium compounds will have a great significant impact on cancer therapy and patient wellbeing. It was well-known that Se—Se bond is very reactive and sensitive to the dual redox environment, therefore, we can take advantage of such feature to prepare diselenide-containing polymers which can be applied in the area of drug controlled release. In this paper, we prepared amphiphilic diselenide copolymers with diselenide-containing diols (HO-SeSe-OH), isophorone diisocyanate (IPDI), and water soluble low-molecular chitosan (LW-CS). The synthetic copolymers were characterized by means of gel permeation chromatography (GPC), 1H NMR and FTIR spectroscopy. The molecular weight of CS-PUSeSe-CS copolymer was 4.42×104 g/mol which calculated according to the integral ratio of the peaks at δ 4.00 and 4.42 which related to CH2O groups of chitosan and NHCOOCH2 groups of IPDI, respectively. The size distribution of aggregates measured by dynamic light scattering (DLS) measurements, which gave a result of about 130 nm in average diameter. The critical aggregate concentration (CAC) of aggregates was measured by the fluorescent probe method and the result was 0.01 mg/mL. The dual redox responsive of aggregates was studied both in VC and H2O2 solution, the results showed that amphiphilic diselenide copolymer would cause Se—Se chain scission in no matter weak oxidative or reductive ambient environment. Although negative charged drug-rhodamine B (RB) could not release out from aggregates due to electrostatic attraction. However, positive charged drug-doxorubicin hydrochloride (Doxo) can easily release from aggregates in reductive VC solution by analyzing UV-spectra at the wavelength of 500 nm, indicating aggregates assembled from diselenide-containing copolymers may act as powerful and efficient bionano reactors and realize controllable drug delivery by breaking Se—Se bonds.

Key words: diselenide, amphiphilic copolymer, dual redox, Doxo, drug release