Spectroscopic studies on interaction of protoberberines with the deoxyoligonucleotide d(GCCGTCGTTTTACA)2

Hye Seo Park, Eun Hee Kim, Mi Ran Kang, In Kwon Chung, Chaejoon Cheong, Weontae Lee

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

The topoisomerase 11 poisoning effect of certain protoberberine alkaloids is associated with anti-cancer activity. Structure-activity relationships of protoberberine analogues substituted on the ring protons reveal that substitution at the C19 position is an important determinant of biological activity. In this study, the effects of substituent modification at the C19 position on the interaction of protoberberines with DNA are determined using UV and NMR spectroscopy. The line broadening effect on aliphatic resonances, chemical shift changes of the imino protons of HP14 upon berberine and berberrubine binding to HP14, and the rate of the exchange process between protoberberine analogs bound indicate that berberrubine binds HP14 more specifically than berberine. In addition, the free HP14 is altered by the substituent at the 19-position. UV spectra of berberrubine have shown a hypochromic effect together with a slight red shift, which are usually regarded as characteristics of DNA intercalation. These results are consistent with our previous report that the berberrubine is partially intercalated with HP14 with molar ratio 1:1, whereas a non-specific interaction is predominant between the berberine and HP 14.

Original languageEnglish
Pages (from-to)1559-1563
Number of pages5
JournalBulletin of the Korean Chemical Society
Volume25
Issue number10
DOIs
Publication statusPublished - 2004 Oct 20

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

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