Design, Synthesis, and Characterization of 1-(Anthracen-9-ylmethyl)-1,5,9-triazacyclododecane (Ant-[12]aneN3) and Its DNA Photocleavage Activity.

IF 1.5 4区 医学 Q4 CHEMISTRY, MEDICINAL
Yoshimi Ichimaru, Koichi Kato, Yoshihiro Yamaguchi, Takayuki Sakamoto, Wanchun Jin, Masaaki Kurihara, Mikako Fujita, Masami Otsuka, Hiromasa Kurosaki
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Abstract

Here, a DNA cleavage reagent (1-(anthracen-9-ylmethyl)-1,5,9-triazacyclododecane = Ant-[12]aneN3) was designed and synthesized, and its DNA photocleavage activity under UV irradiation at λ = 365 nm was evaluated. Ant-[12]aneN3 is a molecule containing anthracene as the photosensitizer and [12]aneN3 ( = 1,5,9-triazacyclododecane) as the DNA-interacting component. The cyclic polyamine [12]aneN3 could coordinate with zinc ions (ZnII) and affect DNA cleavage activity. Therefore, when Ant-[12]aneN3 reacted with Zn(NO3)‧6H2O, the product was not a ZnII complex but an N-protonated form of Ant-[12]aneN3. In DNA cleavage experiments with the pUC19 plasmid, Ant-[12]aneN3 also showed DNA photocleavage activity in a ZnII-independent manner. That is, [12]aneN3 enhances the DNA photocleavage activity of anthracene in a ZnII-independent manner, unlike bpa (bis(2-picolyl)amine), which was previously reported to enhance DNA cleavage activity by chelating ZnII. Under physiological conditions, the nitrogen atoms of [12]aneN3 appear protonated without the addition of ZnII salts and showed an affinity for the negatively charged DNA. The results of this study may facilitate the design of effective DNA cleavage reagents.

1-(蒽-9-甲基)-1,5,9-三氮杂环十二烷(Ant-[12]aneN3)的设计、合成、表征及其DNA光裂解活性
本文设计并合成了1-(蒽-9-甲基)-1,5,9-三氮杂环十二烷= Ant-[12]aneN3) DNA裂解试剂,并对其在λ = 365 nm紫外辐照下的DNA光裂解活性进行了评价。Ant-[12]aneN3是一种以蒽为光敏剂,[12]aneN3(= 1,5,9-三氮杂环十二烷)为dna相互作用组分的分子。环状多胺[12]aneN3可以与锌离子(zni)配位,影响DNA的裂解活性。因此,当Ant-[12]aneN3与Zn(NO3)·6H2O反应时,产物不是一个ni配合物,而是一个n -质子化形式的Ant-[12]aneN3。在pUC19质粒的DNA切割实验中,Ant-[12]aneN3也显示出与ni无关的DNA光切割活性。也就是说,[12]aneN3以不依赖于ni的方式增强蒽的DNA光裂解活性,而不像以前报道的双酚a(双(2-吡啶)胺)通过螯合ni来增强DNA裂解活性。在生理条件下,[12]aneN3的氮原子在没有添加ni盐的情况下出现质子化,并对带负电荷的DNA表现出亲和力。本研究结果可为设计有效的DNA切割试剂提供参考。
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来源期刊
CiteScore
3.20
自引率
5.90%
发文量
132
审稿时长
1.7 months
期刊介绍: The CPB covers various chemical topics in the pharmaceutical and health sciences fields dealing with biologically active compounds, natural products, and medicines, while BPB deals with a wide range of biological topics in the pharmaceutical and health sciences fields including scientific research from basic to clinical studies. For details of their respective scopes, please refer to the submission topic categories below. Topics: Organic chemistry In silico science Inorganic chemistry Pharmacognosy Health statistics Forensic science Biochemistry Pharmacology Pharmaceutical care and science Medicinal chemistry Analytical chemistry Physical pharmacy Natural product chemistry Toxicology Environmental science Molecular and cellular biology Biopharmacy and pharmacokinetics Pharmaceutical education Chemical biology Physical chemistry Pharmaceutical engineering Epidemiology Hygiene Regulatory science Immunology and microbiology Clinical pharmacy Miscellaneous.
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