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http://dx.doi.org/10.5012/bkcs.2013.34.3.749

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)
Publication Information
Bulletin of the Korean Chemical Society / v.34, no.3, 2013 , pp. 749-752 More about this Journal
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
Protoberberine; Trehalose; DNA binder; Non-covalent interaction;
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