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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 34, Number 3
BKCSDE 34(3)
March 20, 2013 

Synthesis and DNA-binding Properties of Trehalose-tethered Monomeric and Dimeric Berberines
Yong-Min Wang, Chun-Qiong Zhou, Jin-Xiang Chen, Wen-Hua Chen*
Protoberberine, Trehalose, DNA binder, Non-covalent interaction
Trehalose-tethered monomeric and dimeric berberines were synthesized in 50% and 30% from the reaction of berberrubine with 6-tosyl-α,α'-trehalose and 6,6'-ditosyl-α,α'-trehalose, respectively, and fully characterized by MS (HR and ESI) and NMR (1H, 13C, 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.
749 - 752
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