Synthesis of linked berberine dimers and their remarkably enhanced DNA-binding affinities

Wen Hua Chen; Ji Yan Pang; Yong Qin; Qian Peng; Zongwei CAI; Zhi Hong JIANG

doi:10.1016/j.bmcl.2004.10.098

Synthesis of linked berberine dimers and their remarkably enhanced DNA-binding affinities

Wen Hua Chen^*, Ji Yan Pang, Yong Qin, Qian Peng, Zongwei CAI, Zhi Hong JIANG

^*Corresponding author for this work

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

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Abstract

This communication describes the facile synthesis of five novel berberine dimers and their strong affinities toward double-stranded DNA. These berberine dimers were synthesized in 37-84% yields from the reaction of berberrubine with dihaloalkanes of varying lengths, and fully characterized by HRMS and ¹H NMR. Compared with the monomeric parent berberine, these dimers showed greatly enhanced binding affinities up to approximately 100-fold, with two double helical oligodeoxynucleotides, d(AAGAATTCTT)₂ and d(TAAGAATTCTTA)₂, which was investigated by means of fluorescence spectrometry.

Original language	English
Pages (from-to)	2689-2692
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	15
Issue number	10
DOIs	https://doi.org/10.1016/j.bmcl.2004.10.098
Publication status	Published - 16 May 2005

Scopus Subject Areas

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

User-Defined Keywords

Berberine dimer
DNA
Fluorescence spectrometry
Noncovalent interaction

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10.1016/j.bmcl.2004.10.098

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title = "Synthesis of linked berberine dimers and their remarkably enhanced DNA-binding affinities",

abstract = "This communication describes the facile synthesis of five novel berberine dimers and their strong affinities toward double-stranded DNA. These berberine dimers were synthesized in 37-84% yields from the reaction of berberrubine with dihaloalkanes of varying lengths, and fully characterized by HRMS and 1H NMR. Compared with the monomeric parent berberine, these dimers showed greatly enhanced binding affinities up to approximately 100-fold, with two double helical oligodeoxynucleotides, d(AAGAATTCTT)2 and d(TAAGAATTCTTA)2, which was investigated by means of fluorescence spectrometry.",

keywords = "Berberine dimer, DNA, Fluorescence spectrometry, Noncovalent interaction",

author = "Chen, {Wen Hua} and Pang, {Ji Yan} and Yong Qin and Qian Peng and Zongwei CAI and JIANG, {Zhi Hong}",

note = "Funding Information: The authors are grateful to Professor Irving H. Goldberg, Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, for his critical reading of the manuscript. 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.",

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doi = "10.1016/j.bmcl.2004.10.098",

language = "English",

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journal = "Bioorganic and Medicinal Chemistry Letters",

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AU - Chen, Wen Hua

AU - Pang, Ji Yan

AU - Qin, Yong

AU - Peng, Qian

AU - CAI, Zongwei

AU - JIANG, Zhi Hong

N1 - Funding Information: The authors are grateful to Professor Irving H. Goldberg, Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, for his critical reading of the manuscript. 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 - 2005/5/16

Y1 - 2005/5/16

N2 - This communication describes the facile synthesis of five novel berberine dimers and their strong affinities toward double-stranded DNA. These berberine dimers were synthesized in 37-84% yields from the reaction of berberrubine with dihaloalkanes of varying lengths, and fully characterized by HRMS and 1H NMR. Compared with the monomeric parent berberine, these dimers showed greatly enhanced binding affinities up to approximately 100-fold, with two double helical oligodeoxynucleotides, d(AAGAATTCTT)2 and d(TAAGAATTCTTA)2, which was investigated by means of fluorescence spectrometry.

AB - This communication describes the facile synthesis of five novel berberine dimers and their strong affinities toward double-stranded DNA. These berberine dimers were synthesized in 37-84% yields from the reaction of berberrubine with dihaloalkanes of varying lengths, and fully characterized by HRMS and 1H NMR. Compared with the monomeric parent berberine, these dimers showed greatly enhanced binding affinities up to approximately 100-fold, with two double helical oligodeoxynucleotides, d(AAGAATTCTT)2 and d(TAAGAATTCTTA)2, which was investigated by means of fluorescence spectrometry.

KW - Berberine dimer

KW - DNA

KW - Fluorescence spectrometry

KW - Noncovalent interaction

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SN - 0960-894X

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EP - 2692

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 10

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Synthesis of linked berberine dimers and their remarkably enhanced DNA-binding affinities

Abstract

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