Naphthalimide intercalators with chiral amino side chains: Effects of chirality on DNA binding, photodamage and antitumor cytotoxicity

Qing Yang; Peng Yang; Xuhong Qian; Lianpeng Tong

doi:10.1016/j.bmcl.2008.09.104

Naphthalimide intercalators with chiral amino side chains: Effects of chirality on DNA binding, photodamage and antitumor cytotoxicity

Qing Yang, Peng Yang, Xuhong Qian, Lianpeng Tong

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

49 Scopus citations

Abstract

Several novel heterocyclic-fused naphthalimides intercalators with chiral amino side chains were investigated. Their side chains' chiral configuration determines DNA binding activities in the order: S-enantiomers > R-enantiomers. And their DNA photodamaging activities were in good agreement with their DNA binding constants, the S-enantiomers could photocleave circular supercoiled pBR322 DNA more efficiently than their R-enantiomers. S-enantiomer B³ could photodamage DNA at 0.2 μM and cleave supercoiled plasmid DNA from form I to form II completely at 50 μM. Almost all of these intercalators showed effective cytoxicities against human lung cancer cells and murine leukemia cells. S-enantiomers showed different antitumor cytotoxicity by comparison with R-enantiomers. This work may provide additional information for the role of amino side chains on intercalators as antitumor agents.

Original language	English
Pages (from-to)	6210-6213
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	18
Issue number	23
DOIs	https://doi.org/10.1016/j.bmcl.2008.09.104
State	Published - 1 Dec 2008
Externally published	Yes

Keywords

Antitumor agents
Chirality
DNA intercalation
DNA photodamage
Naphthalimide

UN SDGs

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

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10.1016/j.bmcl.2008.09.104

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title = "Naphthalimide intercalators with chiral amino side chains: Effects of chirality on DNA binding, photodamage and antitumor cytotoxicity",

abstract = "Several novel heterocyclic-fused naphthalimides intercalators with chiral amino side chains were investigated. Their side chains' chiral configuration determines DNA binding activities in the order: S-enantiomers > R-enantiomers. And their DNA photodamaging activities were in good agreement with their DNA binding constants, the S-enantiomers could photocleave circular supercoiled pBR322 DNA more efficiently than their R-enantiomers. S-enantiomer B3 could photodamage DNA at 0.2 μM and cleave supercoiled plasmid DNA from form I to form II completely at 50 μM. Almost all of these intercalators showed effective cytoxicities against human lung cancer cells and murine leukemia cells. S-enantiomers showed different antitumor cytotoxicity by comparison with R-enantiomers. This work may provide additional information for the role of amino side chains on intercalators as antitumor agents.",

keywords = "Antitumor agents, Chirality, DNA intercalation, DNA photodamage, Naphthalimide",

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

year = "2008",

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day = "1",

doi = "10.1016/j.bmcl.2008.09.104",

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volume = "18",

pages = "6210--6213",

journal = "Bioorganic and Medicinal Chemistry Letters",

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T1 - Naphthalimide intercalators with chiral amino side chains

T2 - Effects of chirality on DNA binding, photodamage and antitumor cytotoxicity

AU - Yang, Qing

AU - Yang, Peng

AU - Qian, Xuhong

AU - Tong, Lianpeng

PY - 2008/12/1

Y1 - 2008/12/1

N2 - Several novel heterocyclic-fused naphthalimides intercalators with chiral amino side chains were investigated. Their side chains' chiral configuration determines DNA binding activities in the order: S-enantiomers > R-enantiomers. And their DNA photodamaging activities were in good agreement with their DNA binding constants, the S-enantiomers could photocleave circular supercoiled pBR322 DNA more efficiently than their R-enantiomers. S-enantiomer B3 could photodamage DNA at 0.2 μM and cleave supercoiled plasmid DNA from form I to form II completely at 50 μM. Almost all of these intercalators showed effective cytoxicities against human lung cancer cells and murine leukemia cells. S-enantiomers showed different antitumor cytotoxicity by comparison with R-enantiomers. This work may provide additional information for the role of amino side chains on intercalators as antitumor agents.

AB - Several novel heterocyclic-fused naphthalimides intercalators with chiral amino side chains were investigated. Their side chains' chiral configuration determines DNA binding activities in the order: S-enantiomers > R-enantiomers. And their DNA photodamaging activities were in good agreement with their DNA binding constants, the S-enantiomers could photocleave circular supercoiled pBR322 DNA more efficiently than their R-enantiomers. S-enantiomer B3 could photodamage DNA at 0.2 μM and cleave supercoiled plasmid DNA from form I to form II completely at 50 μM. Almost all of these intercalators showed effective cytoxicities against human lung cancer cells and murine leukemia cells. S-enantiomers showed different antitumor cytotoxicity by comparison with R-enantiomers. This work may provide additional information for the role of amino side chains on intercalators as antitumor agents.

KW - Antitumor agents

KW - Chirality

KW - DNA intercalation

KW - DNA photodamage

KW - Naphthalimide

UR - https://www.scopus.com/pages/publications/55649085266

U2 - 10.1016/j.bmcl.2008.09.104

DO - 10.1016/j.bmcl.2008.09.104

M3 - 文章

C2 - 18930399

AN - SCOPUS:55649085266

SN - 0960-894X

VL - 18

SP - 6210

EP - 6213

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 23

ER -

Naphthalimide intercalators with chiral amino side chains: Effects of chirality on DNA binding, photodamage and antitumor cytotoxicity

Abstract

Keywords

UN SDGs

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