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Journal of Chinese Pharmaceutical Sciences ›› 2018, Vol. 27 ›› Issue (12): 817-823.DOI: 10.5246/jcps.2018.12.082

• Original articles •     Next Articles

The relationship between structural parameters and antibacterial biofilm activity for alkyl rhamnoside as a novel amphiphilic material

Guanghua Peng1, Wenxi Zhang1, Maoyuan Song1, Mengya Yin1, Jiaxing Wang1, Jiajia Li1, Yajie Liu1, Yuanyuan Zhang1, Xinru Li1*, Guiling Li2*   

  1. 1. Beijing Key Laboratory of Molecular Pharmaceutics and New Drug System; School of Pharmaceutical Sciences, Pekig University Health Science Center, Beijing 100191, China
    2. Institute of Medicinal Biotechnology, Chinese Academy of Medical Science & Peking Union Medical College, Beijing 100050, China
  • Received:2018-05-24 Revised:2018-10-23 Online:2018-12-30 Published:2018-11-05
  • Contact: Tel.: +86-010-82805360, E-mail: ll@bjmu.edu.cn; liguiling99@gmail.com
  • Supported by:

    National Natural Science Foundation of China (Grant No. 81573381), and CAMS Initiative for Innovative Medicine (Grant No. CAMS-I2M-1-012).

Abstract:

In the present study, we aimed to explore the structure-activity relationship for the new amphiphilic material rhamnoside with antibacterial biofilm activity, and provide the basis for selecting rhamnoside with the optimum antibacterial biofilm activity. A series of alkyl rhamnosides with different carbon chain lengths were obtained by a simple and effective synthesis method. The structure was characterized by 1H NMR spectrum, and their critical micelle concentration (CMC) was measured by fluorescence probe method. The hydrophilic and lipophilic balance (HLB) value was obtained by calculation. The minimal inhibitory concentration (MIC) of Staphylococcus aureus was determined by the broth double dilution method. The effect of biofilm inhibition and biofilm disruption was assayed by crystal violet method. The results showed that with the increase of carbon chain length, the CMC and HLB of alkyl rhamnosides displayed a linear downward trend, indicating that the lipophilicity and surface activityof the alkyl rhamnoside were increased. At the same time, the antibacterial activity in vitro produced the maximum, ie, 12-hydroxydecanoyl rhamnoside had the strongest antibacterial activity in vitro. Similarly, this material also exhibited the strongest antibacterial biofilm activity in vitro. The results of this study demonstrated that the most potent active material was obtained through the structure-activity relationship and it could be applied antibacterial biofilms in clinical practice.

Key words: Biofilm, Alkyl rhamnoside, Amphiphilic material, Structure-activity relationship

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