Novel heterocyclic family of phenyl naphthothiazole carboxamides derived from naphthalimides: Synthesis, antitumor evaluation, and DNA photocleavage

Zhigang Li; Qing Yang; Xuhong Qian

doi:10.1016/j.bmc.2005.02.045

Novel heterocyclic family of phenyl naphthothiazole carboxamides derived from naphthalimides: Synthesis, antitumor evaluation, and DNA photocleavage

Zhigang Li
, Qing Yang
, Xuhong Qian^*

^*此作品的通讯作者

Dalian University of Technology
East China University of Science and Technology

科研成果: 期刊稿件 › 文章 › 同行评审

48 引用（Scopus）

摘要

A new heterocyclic family of (2-(dimethylamino)ethyl)-2-substituted phenylnaphtho[2,1-d]thiazole-5-carboxamides modified from naphthalimides was designed, synthesized, and quantitatively evaluated as antitumor agents and photonucleases. All these compounds were found to be more cytotoxic against P388 than against A549. B₃ (m-NO₂) was found to be the strongest inhibitor for P388 with IC₅₀ of 1.49 μM, while B ₂ was the most cytotoxic compound against A549 with IC₅₀ of 12 μM. B₄ (p-CH₃), the most efficient DNA photocleaver, showed detectable DNA cleavage at 0.5 μM and total cleavage from form I to 100% form II at 50 μM. The photocleaving mechanism was changed with the modification to be via superoxide anion and radical.

源语言	英语
页（从-至）	3149-3155
页数	7
期刊	Bioorganic and Medicinal Chemistry
卷	13
期	9
DOI	https://doi.org/10.1016/j.bmc.2005.02.045
出版状态	已出版 - 1 5月 2005
已对外发布	是

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title = "Novel heterocyclic family of phenyl naphthothiazole carboxamides derived from naphthalimides: Synthesis, antitumor evaluation, and DNA photocleavage",

abstract = "A new heterocyclic family of (2-(dimethylamino)ethyl)-2-substituted phenylnaphtho[2,1-d]thiazole-5-carboxamides modified from naphthalimides was designed, synthesized, and quantitatively evaluated as antitumor agents and photonucleases. All these compounds were found to be more cytotoxic against P388 than against A549. B3 (m-NO2) was found to be the strongest inhibitor for P388 with IC50 of 1.49 μM, while B 2 was the most cytotoxic compound against A549 with IC50 of 12 μM. B4 (p-CH3), the most efficient DNA photocleaver, showed detectable DNA cleavage at 0.5 μM and total cleavage from form I to 100\% form II at 50 μM. The photocleaving mechanism was changed with the modification to be via superoxide anion and radical.",

keywords = "Antitumor, Cytotoxicity, DNA cleavage, Phenyl naphthothiazole carboxamides, Photocleavage, Synthesis",

author = "Zhigang Li and Qing Yang and Xuhong Qian",

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T1 - Novel heterocyclic family of phenyl naphthothiazole carboxamides derived from naphthalimides

T2 - Synthesis, antitumor evaluation, and DNA photocleavage

AU - Li, Zhigang

AU - Yang, Qing

AU - Qian, Xuhong

PY - 2005/5/1

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N2 - A new heterocyclic family of (2-(dimethylamino)ethyl)-2-substituted phenylnaphtho[2,1-d]thiazole-5-carboxamides modified from naphthalimides was designed, synthesized, and quantitatively evaluated as antitumor agents and photonucleases. All these compounds were found to be more cytotoxic against P388 than against A549. B3 (m-NO2) was found to be the strongest inhibitor for P388 with IC50 of 1.49 μM, while B 2 was the most cytotoxic compound against A549 with IC50 of 12 μM. B4 (p-CH3), the most efficient DNA photocleaver, showed detectable DNA cleavage at 0.5 μM and total cleavage from form I to 100% form II at 50 μM. The photocleaving mechanism was changed with the modification to be via superoxide anion and radical.

AB - A new heterocyclic family of (2-(dimethylamino)ethyl)-2-substituted phenylnaphtho[2,1-d]thiazole-5-carboxamides modified from naphthalimides was designed, synthesized, and quantitatively evaluated as antitumor agents and photonucleases. All these compounds were found to be more cytotoxic against P388 than against A549. B3 (m-NO2) was found to be the strongest inhibitor for P388 with IC50 of 1.49 μM, while B 2 was the most cytotoxic compound against A549 with IC50 of 12 μM. B4 (p-CH3), the most efficient DNA photocleaver, showed detectable DNA cleavage at 0.5 μM and total cleavage from form I to 100% form II at 50 μM. The photocleaving mechanism was changed with the modification to be via superoxide anion and radical.

KW - Antitumor

KW - Cytotoxicity

KW - DNA cleavage

KW - Phenyl naphthothiazole carboxamides

KW - Photocleavage

KW - Synthesis

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DO - 10.1016/j.bmc.2005.02.045

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SN - 0968-0896

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SP - 3149

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JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 9

ER -

Novel heterocyclic family of phenyl naphthothiazole carboxamides derived from naphthalimides: Synthesis, antitumor evaluation, and DNA photocleavage

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