Study on noncovalent complexes of cytotoxic protoberberine alkaloids with double-stranded DNA by using electrospray ionization mass spectrometry

Wen Hua Chen; Chi Leung Chan; Zongwei CAI; Guo An Luo; Zhi Hong JIANG

doi:10.1016/j.bmcl.2004.07.037

Study on noncovalent complexes of cytotoxic protoberberine alkaloids with double-stranded DNA by using electrospray ionization mass spectrometry

Wen Hua Chen, Chi Leung Chan, Zongwei CAI, Guo An Luo, Zhi Hong JIANG

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

51 Citations (Scopus)

Abstract

The first ESI-MS spectrometric investigation of the noncovalent complexes of four protoberberine alkaloids 1-4 with three double-stranded DNA sequences was described. The noncovalent complexes of four cytotoxic protoberberine alkaloids that is, berberine, palmatine, jatrorrhizine, and coptisine with double-stranded oligodeoxynucleotides d(AAGAATTCTT) ₂ were investigated by electrospray ionization mass spectrometry. These four active components from Chinese herbal medicines showed both 1:1 and 1:2 binding stoichiometries, independent on the alkaloid-to-DNA ratios. Binding affinities in the order of palmatine ≥ jatrorrhizine > coptisine > berberine with d(AAGAATTCTT) ₂ were obtained. Additionally, the preliminary results indicated that berberine had some sequence selectivities.

Original language	English
Pages (from-to)	4955-4959
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	14
Issue number	19
DOIs	https://doi.org/10.1016/j.bmcl.2004.07.037
Publication status	Published - 4 Oct 2004

Scopus Subject Areas

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

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10.1016/j.bmcl.2004.07.037

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title = "Study on noncovalent complexes of cytotoxic protoberberine alkaloids with double-stranded DNA by using electrospray ionization mass spectrometry",

abstract = "The first ESI-MS spectrometric investigation of the noncovalent complexes of four protoberberine alkaloids 1-4 with three double-stranded DNA sequences was described. The noncovalent complexes of four cytotoxic protoberberine alkaloids that is, berberine, palmatine, jatrorrhizine, and coptisine with double-stranded oligodeoxynucleotides d(AAGAATTCTT) 2 were investigated by electrospray ionization mass spectrometry. These four active components from Chinese herbal medicines showed both 1:1 and 1:2 binding stoichiometries, independent on the alkaloid-to-DNA ratios. Binding affinities in the order of palmatine ≥ jatrorrhizine > coptisine > berberine with d(AAGAATTCTT) 2 were obtained. Additionally, the preliminary results indicated that berberine had some sequence selectivities.",

author = "Chen, {Wen Hua} and Chan, {Chi Leung} and Zongwei CAI and Luo, {Guo An} and JIANG, {Zhi Hong}",

note = "Funding Information: The authors are grateful to Prof. Irving H. Goldberg, Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, for his critical reading of the manuscript. This project was financially supported by the Faculty Research Grant of Hong Kong Baptist University and Research Grants Council, University Grants Committee of Hong Kong.",

year = "2004",

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doi = "10.1016/j.bmcl.2004.07.037",

language = "English",

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journal = "Bioorganic and Medicinal Chemistry Letters",

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AU - Chen, Wen Hua

AU - Chan, Chi Leung

AU - CAI, Zongwei

AU - Luo, Guo An

AU - JIANG, Zhi Hong

N1 - Funding Information: The authors are grateful to Prof. Irving H. Goldberg, Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, for his critical reading of the manuscript. This project was financially supported by the Faculty Research Grant of Hong Kong Baptist University and Research Grants Council, University Grants Committee of Hong Kong.

PY - 2004/10/4

Y1 - 2004/10/4

N2 - The first ESI-MS spectrometric investigation of the noncovalent complexes of four protoberberine alkaloids 1-4 with three double-stranded DNA sequences was described. The noncovalent complexes of four cytotoxic protoberberine alkaloids that is, berberine, palmatine, jatrorrhizine, and coptisine with double-stranded oligodeoxynucleotides d(AAGAATTCTT) 2 were investigated by electrospray ionization mass spectrometry. These four active components from Chinese herbal medicines showed both 1:1 and 1:2 binding stoichiometries, independent on the alkaloid-to-DNA ratios. Binding affinities in the order of palmatine ≥ jatrorrhizine > coptisine > berberine with d(AAGAATTCTT) 2 were obtained. Additionally, the preliminary results indicated that berberine had some sequence selectivities.

AB - The first ESI-MS spectrometric investigation of the noncovalent complexes of four protoberberine alkaloids 1-4 with three double-stranded DNA sequences was described. The noncovalent complexes of four cytotoxic protoberberine alkaloids that is, berberine, palmatine, jatrorrhizine, and coptisine with double-stranded oligodeoxynucleotides d(AAGAATTCTT) 2 were investigated by electrospray ionization mass spectrometry. These four active components from Chinese herbal medicines showed both 1:1 and 1:2 binding stoichiometries, independent on the alkaloid-to-DNA ratios. Binding affinities in the order of palmatine ≥ jatrorrhizine > coptisine > berberine with d(AAGAATTCTT) 2 were obtained. Additionally, the preliminary results indicated that berberine had some sequence selectivities.

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AN - SCOPUS:4444255843

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VL - 14

SP - 4955

EP - 4959

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 19

ER -

Study on noncovalent complexes of cytotoxic protoberberine alkaloids with double-stranded DNA by using electrospray ionization mass spectrometry

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