Spacer length and attaching position-dependent binding of synthesized protoberberine dimers to double-stranded DNA

Yu Hua Long; Li Ping Bai; Yong Qin; Ji Yan Pang; Wen Hua Chen; Zongwei CAI; Zun Le Xu; Zhi Hong JIANG

doi:10.1016/j.bmc.2006.03.004

Spacer length and attaching position-dependent binding of synthesized protoberberine dimers to double-stranded DNA

Yu Hua Long, Li Ping Bai, Yong Qin, Ji Yan Pang, Wen Hua Chen^*, Zongwei CAI, Zun Le Xu, Zhi Hong JIANG

^*Corresponding author for this work

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

28 Citations (Scopus)

Abstract

Six jatrorrhizine homodimers and berberine-jatrorrhizine heterodimers have been synthesized in moderate to good yields from the reaction of jatrorrhizine with α,ω-dibromoalkanes and 9-O-(ω-bromoalkyl)berberines, respectively. Their binding activities toward calf thymus (CT) DNA and three double-stranded oligodeoxynucleotides, d(AAGAATTCTT)₂, d(TAAGAATTCTTA)₂, and d(TTAAGAATTCTTAA)₂, were investigated by means of spectrofluorimetric and spectrophotometric titrations. The results indicate that these dimers exhibit enhanced DNA-binding affinities due to the cooperative interaction of the two protoberberine subunits. A comparative study of the DNA-binding behaviors of berberine homodimers, jatrorrhizine homodimers, and berberine-jatrorrhizine heterodimers suggests that spacer length and attaching position are of great importance in modulating their DNA-binding affinities.

Original language	English
Pages (from-to)	4670-4676
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	14
Issue number	13
DOIs	https://doi.org/10.1016/j.bmc.2006.03.004
Publication status	Published - 1 Jul 2006

Scopus Subject Areas

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

User-Defined Keywords

Dimerization
DNA binding
Jatrorrhizine
Protoberberine
Synthesis

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10.1016/j.bmc.2006.03.004

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title = "Spacer length and attaching position-dependent binding of synthesized protoberberine dimers to double-stranded DNA",

abstract = "Six jatrorrhizine homodimers and berberine-jatrorrhizine heterodimers have been synthesized in moderate to good yields from the reaction of jatrorrhizine with α,ω-dibromoalkanes and 9-O-(ω-bromoalkyl)berberines, respectively. Their binding activities toward calf thymus (CT) DNA and three double-stranded oligodeoxynucleotides, d(AAGAATTCTT)2, d(TAAGAATTCTTA)2, and d(TTAAGAATTCTTAA)2, were investigated by means of spectrofluorimetric and spectrophotometric titrations. The results indicate that these dimers exhibit enhanced DNA-binding affinities due to the cooperative interaction of the two protoberberine subunits. A comparative study of the DNA-binding behaviors of berberine homodimers, jatrorrhizine homodimers, and berberine-jatrorrhizine heterodimers suggests that spacer length and attaching position are of great importance in modulating their DNA-binding affinities.",

keywords = "Dimerization, DNA binding, Jatrorrhizine, Protoberberine, Synthesis",

author = "Long, {Yu Hua} and Bai, {Li Ping} and Yong Qin and Pang, {Ji Yan} and Chen, {Wen Hua} and Zongwei CAI and Xu, {Zun Le} and JIANG, {Zhi Hong}",

note = "Funding Information: Financial support from Hong Kong Baptist University, Research Grants Council, University Grants Committee of Hong Kong and Guangdong NSF (5300905) is gratefully acknowledged. ",

year = "2006",

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doi = "10.1016/j.bmc.2006.03.004",

language = "English",

volume = "14",

pages = "4670--4676",

journal = "Bioorganic and Medicinal Chemistry",

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TY - JOUR

T1 - Spacer length and attaching position-dependent binding of synthesized protoberberine dimers to double-stranded DNA

AU - Long, Yu Hua

AU - Bai, Li Ping

AU - Qin, Yong

AU - Pang, Ji Yan

AU - Chen, Wen Hua

AU - CAI, Zongwei

AU - Xu, Zun Le

AU - JIANG, Zhi Hong

N1 - Funding Information: Financial support from Hong Kong Baptist University, Research Grants Council, University Grants Committee of Hong Kong and Guangdong NSF (5300905) is gratefully acknowledged.

PY - 2006/7/1

Y1 - 2006/7/1

N2 - Six jatrorrhizine homodimers and berberine-jatrorrhizine heterodimers have been synthesized in moderate to good yields from the reaction of jatrorrhizine with α,ω-dibromoalkanes and 9-O-(ω-bromoalkyl)berberines, respectively. Their binding activities toward calf thymus (CT) DNA and three double-stranded oligodeoxynucleotides, d(AAGAATTCTT)2, d(TAAGAATTCTTA)2, and d(TTAAGAATTCTTAA)2, were investigated by means of spectrofluorimetric and spectrophotometric titrations. The results indicate that these dimers exhibit enhanced DNA-binding affinities due to the cooperative interaction of the two protoberberine subunits. A comparative study of the DNA-binding behaviors of berberine homodimers, jatrorrhizine homodimers, and berberine-jatrorrhizine heterodimers suggests that spacer length and attaching position are of great importance in modulating their DNA-binding affinities.

AB - Six jatrorrhizine homodimers and berberine-jatrorrhizine heterodimers have been synthesized in moderate to good yields from the reaction of jatrorrhizine with α,ω-dibromoalkanes and 9-O-(ω-bromoalkyl)berberines, respectively. Their binding activities toward calf thymus (CT) DNA and three double-stranded oligodeoxynucleotides, d(AAGAATTCTT)2, d(TAAGAATTCTTA)2, and d(TTAAGAATTCTTAA)2, were investigated by means of spectrofluorimetric and spectrophotometric titrations. The results indicate that these dimers exhibit enhanced DNA-binding affinities due to the cooperative interaction of the two protoberberine subunits. A comparative study of the DNA-binding behaviors of berberine homodimers, jatrorrhizine homodimers, and berberine-jatrorrhizine heterodimers suggests that spacer length and attaching position are of great importance in modulating their DNA-binding affinities.

KW - Dimerization

KW - DNA binding

KW - Jatrorrhizine

KW - Protoberberine

KW - Synthesis

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DO - 10.1016/j.bmc.2006.03.004

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ER -

Spacer length and attaching position-dependent binding of synthesized protoberberine dimers to double-stranded DNA

Abstract

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