Bulletin of the Korean Chemical Society

  • 제34권3호
  • /
  • Pages.749-752
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  • 2013
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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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)
  • 투고 : 2012.11.13
  • 심사 : 2012.12.05
  • 발행 : 2013.03.20
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초록

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.

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