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 language | English |
|---|---|
| Pages (from-to) | 1559-1563 |
| Number of pages | 5 |
| Journal | Bulletin of the Korean Chemical Society |
| Volume | 25 |
| Issue number | 10 |
| DOIs | |
| Publication status | Published - 2004 Oct 20 |
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All Science Journal Classification (ASJC) codes
- Chemistry(all)
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Spectroscopic studies on interaction of protoberberines with the deoxyoligonucleotide d(GCCGTCGTTTTACA)2. / Park, Hye Seo; Kim, Eun Hee; Kang, Mi Ran; Chung, In Kwon; Cheong, Chaejoon; Lee, Weon Tae.
In: Bulletin of the Korean Chemical Society, Vol. 25, No. 10, 20.10.2004, p. 1559-1563.Research output: Contribution to journal › Article
TY - JOUR
T1 - Spectroscopic studies on interaction of protoberberines with the deoxyoligonucleotide d(GCCGTCGTTTTACA)2
AU - Park, Hye Seo
AU - Kim, Eun Hee
AU - Kang, Mi Ran
AU - Chung, In Kwon
AU - Cheong, Chaejoon
AU - Lee, Weon Tae
PY - 2004/10/20
Y1 - 2004/10/20
N2 - 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.
AB - 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.
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U2 - 10.5012/bkcs.2004.25.10.1559
DO - 10.5012/bkcs.2004.25.10.1559
M3 - Article
VL - 25
SP - 1559
EP - 1563
JO - Bulletin of the Korean Chemical Society
JF - Bulletin of the Korean Chemical Society
SN - 0253-2964
IS - 10
ER -