DNA-binding affinities and sequence selectivity of quaternary benzophenanthridine alkaloids sanguinarine, chelerythrine, and nitidine

Li Ping Bai; Zhongzhen ZHAO; Zongwei CAI; Zhi Hong JIANG

doi:10.1016/j.bmc.2006.05.012

DNA-binding affinities and sequence selectivity of quaternary benzophenanthridine alkaloids sanguinarine, chelerythrine, and nitidine

Li Ping Bai, Zhongzhen ZHAO, Zongwei CAI, Zhi Hong JIANG^*

^*Corresponding author for this work

Research output: Contribution to journal › Journal article › peer-review

99 Citations (Scopus)

Abstract

A comparative study on the intercalating binding of sanguinarine, chelerythrine, and nitidine with CT DNA, poly(dG-dC)·poly(dG-dC), poly(dA-dT)·poly(dA-dT), and seven sequence-designed double-stranded oligodeoxynucleotides has been performed using fluorometric and spectrophotometric techniques, aiming at providing insights into their sequence selectivity for DNA-binding. The results show that both sanguinarine and nitidine bind preferentially to DNA containing alternating GC base pairs [d(TGCGCA)₂], while chelerythrine exhibits quite distinct sequence selectivity from sanguinarine, which shows a high specificity for DNA containing contiguous GC base pairs [5′-TGGGGA-3′/3′-ACCCCT-5′].

Original language	English
Pages (from-to)	5439-5445
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	14
Issue number	16
DOIs	https://doi.org/10.1016/j.bmc.2006.05.012
Publication status	Published - 15 Aug 2006

Scopus Subject Areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

User-Defined Keywords

Alkaloid
DNA-binding
Fluorescence spectrometry
Intercalations
Sequence selectivity

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10.1016/j.bmc.2006.05.012

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title = "DNA-binding affinities and sequence selectivity of quaternary benzophenanthridine alkaloids sanguinarine, chelerythrine, and nitidine",

abstract = "A comparative study on the intercalating binding of sanguinarine, chelerythrine, and nitidine with CT DNA, poly(dG-dC)·poly(dG-dC), poly(dA-dT)·poly(dA-dT), and seven sequence-designed double-stranded oligodeoxynucleotides has been performed using fluorometric and spectrophotometric techniques, aiming at providing insights into their sequence selectivity for DNA-binding. The results show that both sanguinarine and nitidine bind preferentially to DNA containing alternating GC base pairs [d(TGCGCA)2], while chelerythrine exhibits quite distinct sequence selectivity from sanguinarine, which shows a high specificity for DNA containing contiguous GC base pairs [5′-TGGGGA-3′/3′-ACCCCT-5′].",

keywords = "Alkaloid, DNA-binding, Fluorescence spectrometry, Intercalations, Sequence selectivity",

author = "Bai, {Li Ping} and Zhongzhen ZHAO and Zongwei CAI and JIANG, {Zhi Hong}",

note = "Funding Information: This work was financially supported by the Faculty Research Grants from Hong Kong Baptist University and Research Grants Council, University Grants Committee of Hong Kong.",

year = "2006",

month = aug,

day = "15",

doi = "10.1016/j.bmc.2006.05.012",

language = "English",

volume = "14",

pages = "5439--5445",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

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TY - JOUR

T1 - DNA-binding affinities and sequence selectivity of quaternary benzophenanthridine alkaloids sanguinarine, chelerythrine, and nitidine

AU - Bai, Li Ping

AU - ZHAO, Zhongzhen

AU - CAI, Zongwei

AU - JIANG, Zhi Hong

N1 - Funding Information: This work was financially supported by the Faculty Research Grants from Hong Kong Baptist University and Research Grants Council, University Grants Committee of Hong Kong.

PY - 2006/8/15

Y1 - 2006/8/15

N2 - A comparative study on the intercalating binding of sanguinarine, chelerythrine, and nitidine with CT DNA, poly(dG-dC)·poly(dG-dC), poly(dA-dT)·poly(dA-dT), and seven sequence-designed double-stranded oligodeoxynucleotides has been performed using fluorometric and spectrophotometric techniques, aiming at providing insights into their sequence selectivity for DNA-binding. The results show that both sanguinarine and nitidine bind preferentially to DNA containing alternating GC base pairs [d(TGCGCA)2], while chelerythrine exhibits quite distinct sequence selectivity from sanguinarine, which shows a high specificity for DNA containing contiguous GC base pairs [5′-TGGGGA-3′/3′-ACCCCT-5′].

AB - A comparative study on the intercalating binding of sanguinarine, chelerythrine, and nitidine with CT DNA, poly(dG-dC)·poly(dG-dC), poly(dA-dT)·poly(dA-dT), and seven sequence-designed double-stranded oligodeoxynucleotides has been performed using fluorometric and spectrophotometric techniques, aiming at providing insights into their sequence selectivity for DNA-binding. The results show that both sanguinarine and nitidine bind preferentially to DNA containing alternating GC base pairs [d(TGCGCA)2], while chelerythrine exhibits quite distinct sequence selectivity from sanguinarine, which shows a high specificity for DNA containing contiguous GC base pairs [5′-TGGGGA-3′/3′-ACCCCT-5′].

KW - Alkaloid

KW - DNA-binding

KW - Fluorescence spectrometry

KW - Intercalations

KW - Sequence selectivity

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U2 - 10.1016/j.bmc.2006.05.012

DO - 10.1016/j.bmc.2006.05.012

M3 - Journal article

C2 - 16730995

AN - SCOPUS:33745631235

SN - 0968-0896

VL - 14

SP - 5439

EP - 5445

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 16

ER -

DNA-binding affinities and sequence selectivity of quaternary benzophenanthridine alkaloids sanguinarine, chelerythrine, and nitidine

Abstract

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