Synthesis, DNA binding and cytotoxicity of new pyrazole emodin derivatives

J. H. Tan; Q. X. Zhang; Z. S. Huang; Y. Chen; X. D. Wang; L. Q. Gu; Jianyong Wu

doi:10.1016/j.ejmech.2006.04.006

Synthesis, DNA binding and cytotoxicity of new pyrazole emodin derivatives

J. H. Tan, Q. X. Zhang, Z. S. Huang, Y. Chen, X. D. Wang, L. Q. Gu, Jianyong Wu

Research output: Journal article publication › Journal article › Academic research › peer-review

52 Citations (Scopus)

Abstract

A series of new anthrapyrazoles were derived from emodin by attaching various cationic alkyl amino side chains onto a pyrazole ring which had been incorporated into the anthraquinone chromophore. Compared with emodin, the derivatives had significantly higher DNA binding affinity based on interaction with calf thymus DNA, and much more potent cytotoxicity against different tumor cells. The derivatives with a mono-cationic alkyl side chain exhibited the highest DNA binding affinity and cytotoxicity.

Original language	English
Pages (from-to)	1041-1047
Number of pages	7
Journal	European Journal of Medicinal Chemistry
Volume	41
Issue number	9
DOIs	https://doi.org/10.1016/j.ejmech.2006.04.006
Publication status	Published - 1 Sept 2006

Keywords

Amino side chain
Anthrapyrazole
Cytotoxicity
DNA binding
Emodin derivatives
Tumor cells

ASJC Scopus subject areas

Pharmacology
Drug Discovery
Organic Chemistry

More information

10.1016/j.ejmech.2006.04.006

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title = "Synthesis, DNA binding and cytotoxicity of new pyrazole emodin derivatives",

abstract = "A series of new anthrapyrazoles were derived from emodin by attaching various cationic alkyl amino side chains onto a pyrazole ring which had been incorporated into the anthraquinone chromophore. Compared with emodin, the derivatives had significantly higher DNA binding affinity based on interaction with calf thymus DNA, and much more potent cytotoxicity against different tumor cells. The derivatives with a mono-cationic alkyl side chain exhibited the highest DNA binding affinity and cytotoxicity.",

keywords = "Amino side chain, Anthrapyrazole, Cytotoxicity, DNA binding, Emodin derivatives, Tumor cells",

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AU - Tan, J. H.

AU - Zhang, Q. X.

AU - Huang, Z. S.

AU - Chen, Y.

AU - Wang, X. D.

AU - Gu, L. Q.

AU - Wu, Jianyong

PY - 2006/9/1

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N2 - A series of new anthrapyrazoles were derived from emodin by attaching various cationic alkyl amino side chains onto a pyrazole ring which had been incorporated into the anthraquinone chromophore. Compared with emodin, the derivatives had significantly higher DNA binding affinity based on interaction with calf thymus DNA, and much more potent cytotoxicity against different tumor cells. The derivatives with a mono-cationic alkyl side chain exhibited the highest DNA binding affinity and cytotoxicity.

AB - A series of new anthrapyrazoles were derived from emodin by attaching various cationic alkyl amino side chains onto a pyrazole ring which had been incorporated into the anthraquinone chromophore. Compared with emodin, the derivatives had significantly higher DNA binding affinity based on interaction with calf thymus DNA, and much more potent cytotoxicity against different tumor cells. The derivatives with a mono-cationic alkyl side chain exhibited the highest DNA binding affinity and cytotoxicity.

KW - Amino side chain

KW - Anthrapyrazole

KW - Cytotoxicity

KW - DNA binding

KW - Emodin derivatives

KW - Tumor cells

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U2 - 10.1016/j.ejmech.2006.04.006

DO - 10.1016/j.ejmech.2006.04.006

M3 - Journal article

C2 - 16716458

SN - 0223-5234

VL - 41

SP - 1041

EP - 1047

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

IS - 9

ER -

Synthesis, DNA binding and cytotoxicity of new pyrazole emodin derivatives

Abstract

Keywords

ASJC Scopus subject areas

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