Novel DNA bis-intercalators of isoquinolino[4,5-bc]acridines: Design, synthesis and evaluation of cytotoxic activity

Peng Yang; Qing Yang; Xuhong Qian

doi:10.1016/j.tet.2005.09.065

Novel DNA bis-intercalators of isoquinolino[4,5-bc]acridines: Design, synthesis and evaluation of cytotoxic activity

Peng Yang
, Qing Yang
, Xuhong Qian^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

42 Scopus citations

Abstract

Mono- and dinuclear isoquinolino[4,5-bc]acridine derivatives were designed and facilely synthesized, their DNA-binding affinities and cytotoxic activities were evaluated. A4 induced unwinding of supercoiled plasmid pBR 322 DNA by (36±2)°while A6 induced that by (41±1)°, both of which were higher than the mono-analogue A1 ((19±2)°). A6 exhibited the highest in vitro antitumor activity against human lung cancer cell (A549) and A4 was the most active one against murine leukemia cell (P388). DNA binding constant and molecular model indicated that both the length of linker chain and the distance of interchromophore were key impact factors for DNA binding affinity and biological activity.

Original language	English
Pages (from-to)	11895-11901
Number of pages	7
Journal	Tetrahedron
Volume	61
Issue number	50
DOIs	https://doi.org/10.1016/j.tet.2005.09.065
State	Published - 12 Dec 2005
Externally published	Yes

Keywords

Acridine
Cytotoxicity
DNA-intercalation

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.tet.2005.09.065

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title = "Novel DNA bis-intercalators of isoquinolino[4,5-bc]acridines: Design, synthesis and evaluation of cytotoxic activity",

abstract = "Mono- and dinuclear isoquinolino[4,5-bc]acridine derivatives were designed and facilely synthesized, their DNA-binding affinities and cytotoxic activities were evaluated. A4 induced unwinding of supercoiled plasmid pBR 322 DNA by (36±2)°while A6 induced that by (41±1)°, both of which were higher than the mono-analogue A1 ((19±2)°). A6 exhibited the highest in vitro antitumor activity against human lung cancer cell (A549) and A4 was the most active one against murine leukemia cell (P388). DNA binding constant and molecular model indicated that both the length of linker chain and the distance of interchromophore were key impact factors for DNA binding affinity and biological activity.",

keywords = "Acridine, Cytotoxicity, DNA-intercalation",

author = "Peng Yang and Qing Yang and Xuhong Qian",

year = "2005",

month = dec,

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doi = "10.1016/j.tet.2005.09.065",

language = "英语",

volume = "61",

pages = "11895--11901",

journal = "Tetrahedron",

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}

TY - JOUR

T1 - Novel DNA bis-intercalators of isoquinolino[4,5-bc]acridines

T2 - Design, synthesis and evaluation of cytotoxic activity

AU - Yang, Peng

AU - Yang, Qing

AU - Qian, Xuhong

PY - 2005/12/12

Y1 - 2005/12/12

N2 - Mono- and dinuclear isoquinolino[4,5-bc]acridine derivatives were designed and facilely synthesized, their DNA-binding affinities and cytotoxic activities were evaluated. A4 induced unwinding of supercoiled plasmid pBR 322 DNA by (36±2)°while A6 induced that by (41±1)°, both of which were higher than the mono-analogue A1 ((19±2)°). A6 exhibited the highest in vitro antitumor activity against human lung cancer cell (A549) and A4 was the most active one against murine leukemia cell (P388). DNA binding constant and molecular model indicated that both the length of linker chain and the distance of interchromophore were key impact factors for DNA binding affinity and biological activity.

AB - Mono- and dinuclear isoquinolino[4,5-bc]acridine derivatives were designed and facilely synthesized, their DNA-binding affinities and cytotoxic activities were evaluated. A4 induced unwinding of supercoiled plasmid pBR 322 DNA by (36±2)°while A6 induced that by (41±1)°, both of which were higher than the mono-analogue A1 ((19±2)°). A6 exhibited the highest in vitro antitumor activity against human lung cancer cell (A549) and A4 was the most active one against murine leukemia cell (P388). DNA binding constant and molecular model indicated that both the length of linker chain and the distance of interchromophore were key impact factors for DNA binding affinity and biological activity.

KW - Acridine

KW - Cytotoxicity

KW - DNA-intercalation

UR - https://www.scopus.com/pages/publications/27744451528

U2 - 10.1016/j.tet.2005.09.065

DO - 10.1016/j.tet.2005.09.065

M3 - 文章

AN - SCOPUS:27744451528

SN - 0040-4020

VL - 61

SP - 11895

EP - 11901

JO - Tetrahedron

JF - Tetrahedron

IS - 50

ER -

Novel DNA bis-intercalators of isoquinolino[4,5-bc]acridines: Design, synthesis and evaluation of cytotoxic activity

Abstract

Keywords

UN SDGs

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