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Chinese Journal of Organic Chemistry >

2018 , Vol. 38 >Issue 1: 148 - 155

DOI: https://doi.org/10.6023/cjoc201708042

Articles

Design, Synthesis and Properties of the Antibacterial Peptides Based on Tat(49-57)

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  • a College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou 450001;
    b School of Material and Chemical Engineering, Henan University of Engineering, Zhengzhou 450007;
    c School of Chemical Engineering and Food Science, Zhengzhou Institute of Technology, Zhengzhou 450044

Received date: 2017-08-21

  Revised date: 2017-10-23

  Online published: 2017-10-31

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 21572046, 21172054).

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Abstract

Four novel cationic antibacterial peptide analogs were modified at the N-terminus of the cell-penetrating peptide transacting activator of transcription TAT(49-57) by attaching dipeptides. Peptides were synthesized through standard Fmoc solid-phase peptide synthesis procedures, purified by reversed-phase high performance liquid chromatography (RP-HPLC), and characterized by 1H NMR, ESI-MS and elemental analysis. Tat(YY), Tat(FF), Tat(FF) and Tat(YY), Tat(FF) demonstrated better antibacterial activities against E. coli, S. typhimurium, B. subtilis and S. aureus with low hemolysis. respectively, but had no inhibitory effect on fungus growth. The Tat(49-57) analogs inhibited the bacteria more effectively than Tat(49-57). The interactions between peptides and calf thymus DNA (ct-DNA) were investigated with multi-spectroscopic techniques. The results showed that both peptides could interact with DNA via the groove binding mode. Compared to TAT(49-57), antibacterial peptide analogs combined with DNA much closer via binding constants, which has the value to become an excellent antibacterial agent with further improved and designed.

Key words： cell-penetrating peptide; solid-phase synthesis; antibacterial activity; non-covalent binding

Cite this article

Lü Mingxiu, Mai Wenpeng, Lu Kui, Duan Bingchao, Zhao Yufen . Design, Synthesis and Properties of the Antibacterial Peptides Based on Tat(49-57)[J]. Chinese Journal of Organic Chemistry, 2018 , 38(1) : 148 -155 . DOI: 10.6023/cjoc201708042

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