N-Aroyloxylthioxo-naphthalimides as DNA photocleavers of aroyloxyl oxygen radicals: Synthesis, evaluation, and substituents' effect

Yufang Xu; Xiayu Huang; Xuhong Qian; Wei Yao

doi:10.1016/j.bmc.2004.02.013

N-Aroyloxylthioxo-naphthalimides as DNA photocleavers of aroyloxyl oxygen radicals: Synthesis, evaluation, and substituents' effect

Yufang Xu
, Xiayu Huang
, Xuhong Qian^*
, Wei Yao

^*Corresponding author for this work

East China University of Science and Technology
Dalian University of Technology

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

11 Scopus citations

Abstract

Novel N-Aroyloxylthioxo-naphthalimides as highly efficient 'time-resolved' DNA photocleavers of aroyloxyl radicals type were designed and synthesized. The substituents at the aroyloxyl moiety have an important and unusual influence on the DNA photocleavage, and DNA photodamages of the compounds were unusually not depended on the electronic effects of substituents on the corresponding oxygen-centered radicals. With AM1 semi-empirical quantum calculation, it was found that their photocleaving activities were correlated with the densities of electron clouds on the N-O bonds in the triplet state. N-(m-Dichloro-benzoyloxy) -thioxo-naphthalimide could photodamage DNA effectively at less than the concentration of 2μM.

Original language	English
Pages (from-to)	2335-2341
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	12
Issue number	9
DOIs	https://doi.org/10.1016/j.bmc.2004.02.013
State	Published - 1 May 2004
Externally published	Yes

Keywords

Aroyloxylthioxonaphthalimides
DNA photocleaver
Oxygen centered radical
Substituent effect

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10.1016/j.bmc.2004.02.013

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title = "N-Aroyloxylthioxo-naphthalimides as DNA photocleavers of aroyloxyl oxygen radicals: Synthesis, evaluation, and substituents' effect",

abstract = "Novel N-Aroyloxylthioxo-naphthalimides as highly efficient 'time-resolved' DNA photocleavers of aroyloxyl radicals type were designed and synthesized. The substituents at the aroyloxyl moiety have an important and unusual influence on the DNA photocleavage, and DNA photodamages of the compounds were unusually not depended on the electronic effects of substituents on the corresponding oxygen-centered radicals. With AM1 semi-empirical quantum calculation, it was found that their photocleaving activities were correlated with the densities of electron clouds on the N-O bonds in the triplet state. N-(m-Dichloro-benzoyloxy) -thioxo-naphthalimide could photodamage DNA effectively at less than the concentration of 2μM.",

keywords = "Aroyloxylthioxonaphthalimides, DNA photocleaver, Oxygen centered radical, Substituent effect",

author = "Yufang Xu and Xiayu Huang and Xuhong Qian and Wei Yao",

year = "2004",

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doi = "10.1016/j.bmc.2004.02.013",

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TY - JOUR

T1 - N-Aroyloxylthioxo-naphthalimides as DNA photocleavers of aroyloxyl oxygen radicals

T2 - Synthesis, evaluation, and substituents' effect

AU - Xu, Yufang

AU - Huang, Xiayu

AU - Qian, Xuhong

AU - Yao, Wei

PY - 2004/5/1

Y1 - 2004/5/1

N2 - Novel N-Aroyloxylthioxo-naphthalimides as highly efficient 'time-resolved' DNA photocleavers of aroyloxyl radicals type were designed and synthesized. The substituents at the aroyloxyl moiety have an important and unusual influence on the DNA photocleavage, and DNA photodamages of the compounds were unusually not depended on the electronic effects of substituents on the corresponding oxygen-centered radicals. With AM1 semi-empirical quantum calculation, it was found that their photocleaving activities were correlated with the densities of electron clouds on the N-O bonds in the triplet state. N-(m-Dichloro-benzoyloxy) -thioxo-naphthalimide could photodamage DNA effectively at less than the concentration of 2μM.

AB - Novel N-Aroyloxylthioxo-naphthalimides as highly efficient 'time-resolved' DNA photocleavers of aroyloxyl radicals type were designed and synthesized. The substituents at the aroyloxyl moiety have an important and unusual influence on the DNA photocleavage, and DNA photodamages of the compounds were unusually not depended on the electronic effects of substituents on the corresponding oxygen-centered radicals. With AM1 semi-empirical quantum calculation, it was found that their photocleaving activities were correlated with the densities of electron clouds on the N-O bonds in the triplet state. N-(m-Dichloro-benzoyloxy) -thioxo-naphthalimide could photodamage DNA effectively at less than the concentration of 2μM.

KW - Aroyloxylthioxonaphthalimides

KW - DNA photocleaver

KW - Oxygen centered radical

KW - Substituent effect

UR - https://www.scopus.com/pages/publications/1842636191

U2 - 10.1016/j.bmc.2004.02.013

DO - 10.1016/j.bmc.2004.02.013

M3 - 文章

C2 - 15080930

AN - SCOPUS:1842636191

SN - 0968-0896

VL - 12

SP - 2335

EP - 2341

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 9

ER -

N-Aroyloxylthioxo-naphthalimides as DNA photocleavers of aroyloxyl oxygen radicals: Synthesis, evaluation, and substituents' effect

Abstract

Keywords

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