Oxoisoaporphine alkaloid derivatives: Synthesis, DNA binding affinity and cytotoxicity

Huang Tang; Xiao Dong Wang; Yong Biao Wei; Shi Liang Huang; Zhi Shu Huang; Jia Heng Tan; Lin Kun An; Jianyong Wu; Albert Sun-Chi Chan; Lian Quan Gu

doi:10.1016/j.ejmech.2007.07.004

Oxoisoaporphine alkaloid derivatives: Synthesis, DNA binding affinity and cytotoxicity

Huang Tang
, Xiao Dong Wang
, Yong Biao Wei
, Shi Liang Huang
, Zhi Shu Huang
, Jia Heng Tan
, Lin Kun An
, Jianyong Wu
, Albert Sun-Chi Chan
, Lian Quan Gu

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

39 Citations (Scopus)

Abstract

A series of novel oxoisoaporphine alkaloid derivatives, 9-aminoalkanamido-1-azabenzanthrone (general formula Ar-NHCO(CH2)nNR2, Ar = 1-azabenzanthrone, n = 1, 2 or 3), had been synthesized. Compared with 1-azabenzanthrone, the derivatives had significantly higher DNA binding affinity with calf thymus DNA, and higher potent cytotoxicity against different tumor cell lines. The cytotoxicity and the structure-activity relationship of the prepared compounds were studied. The derivatives with two methylene groups (n = 2), and piperidine or ethanolamine functional group in the side chain exhibited highest DNA binding affinity and cytotoxicity.

Original language	English
Pages (from-to)	973-980
Number of pages	8
Journal	European Journal of Medicinal Chemistry
Volume	43
Issue number	5
DOIs	https://doi.org/10.1016/j.ejmech.2007.07.004
Publication status	Published - 1 May 2008

Keywords

Cytotoxicity
DNA binding
Oxoisoaporphine alkaloid derivatives
Synthesis

ASJC Scopus subject areas

Molecular Medicine
Organic Chemistry
Drug Discovery
Pharmaceutical Science

More information

10.1016/j.ejmech.2007.07.004

Cite this

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title = "Oxoisoaporphine alkaloid derivatives: Synthesis, DNA binding affinity and cytotoxicity",

abstract = "A series of novel oxoisoaporphine alkaloid derivatives, 9-aminoalkanamido-1-azabenzanthrone (general formula Ar-NHCO(CH2)nNR2, Ar = 1-azabenzanthrone, n = 1, 2 or 3), had been synthesized. Compared with 1-azabenzanthrone, the derivatives had significantly higher DNA binding affinity with calf thymus DNA, and higher potent cytotoxicity against different tumor cell lines. The cytotoxicity and the structure-activity relationship of the prepared compounds were studied. The derivatives with two methylene groups (n = 2), and piperidine or ethanolamine functional group in the side chain exhibited highest DNA binding affinity and cytotoxicity.",

keywords = "Cytotoxicity, DNA binding, Oxoisoaporphine alkaloid derivatives, Synthesis",

author = "Huang Tang and Wang, \{Xiao Dong\} and Wei, \{Yong Biao\} and Huang, \{Shi Liang\} and Huang, \{Zhi Shu\} and Tan, \{Jia Heng\} and An, \{Lin Kun\} and Jianyong Wu and \{Sun-Chi Chan\}, Albert and Gu, \{Lian Quan\}",

year = "2008",

month = may,

day = "1",

doi = "10.1016/j.ejmech.2007.07.004",

language = "English",

volume = "43",

pages = "973--980",

journal = "European Journal of Medicinal Chemistry",

issn = "0223-5234",

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}

TY - JOUR

T1 - Oxoisoaporphine alkaloid derivatives: Synthesis, DNA binding affinity and cytotoxicity

AU - Tang, Huang

AU - Wang, Xiao Dong

AU - Wei, Yong Biao

AU - Huang, Shi Liang

AU - Huang, Zhi Shu

AU - Tan, Jia Heng

AU - An, Lin Kun

AU - Wu, Jianyong

AU - Sun-Chi Chan, Albert

AU - Gu, Lian Quan

PY - 2008/5/1

Y1 - 2008/5/1

N2 - A series of novel oxoisoaporphine alkaloid derivatives, 9-aminoalkanamido-1-azabenzanthrone (general formula Ar-NHCO(CH2)nNR2, Ar = 1-azabenzanthrone, n = 1, 2 or 3), had been synthesized. Compared with 1-azabenzanthrone, the derivatives had significantly higher DNA binding affinity with calf thymus DNA, and higher potent cytotoxicity against different tumor cell lines. The cytotoxicity and the structure-activity relationship of the prepared compounds were studied. The derivatives with two methylene groups (n = 2), and piperidine or ethanolamine functional group in the side chain exhibited highest DNA binding affinity and cytotoxicity.

AB - A series of novel oxoisoaporphine alkaloid derivatives, 9-aminoalkanamido-1-azabenzanthrone (general formula Ar-NHCO(CH2)nNR2, Ar = 1-azabenzanthrone, n = 1, 2 or 3), had been synthesized. Compared with 1-azabenzanthrone, the derivatives had significantly higher DNA binding affinity with calf thymus DNA, and higher potent cytotoxicity against different tumor cell lines. The cytotoxicity and the structure-activity relationship of the prepared compounds were studied. The derivatives with two methylene groups (n = 2), and piperidine or ethanolamine functional group in the side chain exhibited highest DNA binding affinity and cytotoxicity.

KW - Cytotoxicity

KW - DNA binding

KW - Oxoisoaporphine alkaloid derivatives

KW - Synthesis

UR - https://www.scopus.com/pages/publications/42949117372

U2 - 10.1016/j.ejmech.2007.07.004

DO - 10.1016/j.ejmech.2007.07.004

M3 - Journal article

C2 - 17720282

SN - 0223-5234

VL - 43

SP - 973

EP - 980

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

IS - 5

ER -

Oxoisoaporphine alkaloid derivatives: Synthesis, DNA binding affinity and cytotoxicity

Abstract

Keywords

ASJC Scopus subject areas

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