Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis and DNA-binding Properties of Trehalose-tethered Monomeric and Dimeric Berberines

  • Wang, Yong-Min (School of Pharmaceutical Sciences, Southern Medical University) ;
  • Zhou, Chun-Qiong (School of Pharmaceutical Sciences, Southern Medical University) ;
  • Chen, Jin-Xiang (School of Pharmaceutical Sciences, Southern Medical University) ;
  • Chen, Wen-Hua (School of Pharmaceutical Sciences, Southern Medical University)
  • Received : 2012.11.13
  • Accepted : 2012.12.05
  • Published : 2013.03.20
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Abstract

Trehalose-tethered monomeric and dimeric berberines were synthesized in 50% and 30% from the reaction of berberrubine with 6-tosyl-${\alpha}$,${\alpha}^{\prime}$-trehalose and 6,6'-ditosyl-${\alpha}$,${\alpha}^{\prime}$-trehalose, respectively, and fully characterized by MS (HR and ESI) and NMR ($^1H$, $^{13}C$, COSY and HSQC). Spectrophotometric and spectrofluorimetric titrations indicated that compared with berberine, trehalose-tethered monomeric berberine had comparable DNA-binding affinity toward calf-thymus DNA, whereas trehalose-spaced dimeric berberine exhibited higher DNA-binding affinity. The potential application of these conjugates is also briefly discussed.

Keywords

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