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^*

^*Corresponding author for this work

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

48 Scopus citations

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.

Original language	English
Pages (from-to)	3149-3155
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	13
Issue number	9
DOIs	https://doi.org/10.1016/j.bmc.2005.02.045
State	Published - 1 May 2005
Externally published	Yes

Keywords

Antitumor
Cytotoxicity
DNA cleavage
Phenyl naphthothiazole carboxamides
Photocleavage
Synthesis

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10.1016/j.bmc.2005.02.045

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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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doi = "10.1016/j.bmc.2005.02.045",

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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

Y1 - 2005/5/1

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

UR - https://www.scopus.com/pages/publications/16244367779

U2 - 10.1016/j.bmc.2005.02.045

DO - 10.1016/j.bmc.2005.02.045

M3 - 文章

C2 - 15809150

AN - SCOPUS:16244367779

SN - 0968-0896

VL - 13

SP - 3149

EP - 3155

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

Abstract

Keywords

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