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, Weon Tae 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

Fingerprint

Berberine
Protons
DNA
Chemical shift
Intercalation
Bioactivity
Ultraviolet spectroscopy
Alkaloids
Nuclear magnetic resonance spectroscopy
Substitution reactions
berberrubine
protoberberine

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

@article{519c594351cd488f8a80790488978def,
title = "Spectroscopic studies on interaction of protoberberines with the deoxyoligonucleotide d(GCCGTCGTTTTACA)2",
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.",
author = "Park, {Hye Seo} and Kim, {Eun Hee} and Kang, {Mi Ran} and Chung, {In Kwon} and Chaejoon Cheong and Lee, {Weon Tae}",
year = "2004",
month = "10",
day = "20",
doi = "10.5012/bkcs.2004.25.10.1559",
language = "English",
volume = "25",
pages = "1559--1563",
journal = "Bulletin of the Korean Chemical Society",
issn = "0253-2964",
publisher = "Korean Chemical Society",
number = "10",

}

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 journalArticle

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.

UR - http://www.scopus.com/inward/record.url?scp=10644231735&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=10644231735&partnerID=8YFLogxK

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 -