Bright and sensitive ratiometric fluorescent probe enabling endogenous FA imaging and mechanistic exploration of indirect oxidative damage due to FA in various living systems
Dou, Kun1; Chen, Guang1,2,3; Yu, Fabiao2; Liu, Yuxia1; Chen, Lingxin2; Cao, Ziping1; Chen, Tao3; Li, Yulin3; You, Jinmao1,2; Chen, Guang(Qufu Normal Univ, Coll Chem & Chem Engn, Key Lab Life Organ Anal, Key Lab Pharmaceut Intermediates & Anal Nat Med, Qufu 273165, Peoples R China); You, Jinmao(Qufu Normal Univ, Coll Chem & Chem Engn, Key Lab Life Organ Anal, Key Lab Pharmaceut Intermediates & Anal Nat Med, Qufu 273165, Peoples R China)
2017-11-01
发表期刊CHEMICAL SCIENCE
ISSN2041-6520
卷号8期号:11页码:7851-7861
产权排序第2完成单位
摘要As a notorious toxin, formaldehyde (FA) poses an immense threat to human health. Aberrantly elevated FA levels lead to serious pathologies, including organ damage, neurodegeneration, and cancer. Unfortunately, current techniques limit FA imaging to general comparative studies, instead of a mechanistic exploration of its biological role, and this is presumably due to the lack of robust molecular tools for reporting FA in living systems. More importantly, despite being reductive, FA, however, can induce oxidative damage to organisms, thus providing a challenge to the mechanistic study of FA using fluorescence imaging. Herein, we presented the design and multi-application of a bright sensitive ratiometric fluorescent probe 1-(4-(1H-phenanthro[9,10-d] imidazol-2-yl) phenyl) but-3-en-1-amine (PIPBA). With a p-extended phenylphenanthroimidazole fluorophore and an allylamine group, PIPBA exhibited high quantum yield (phi = 0.62) in blue fluorescent emission and selective reactivity toward FA. When sensing FA, PIPBA transformed to PIBE, which is a product capable of releasing bright green fluorescence (phi = 0.51) with its enhanced intramolecular charge transfer (ICT). Transformation of PIPBA to PIBE contributed to 80 nm of red shift in emission wavelength and a highly sensitive ratiometric response (92.2-fold), as well as a quite low detection limit (0.84 mu M). PIPBA was successfully applied to various living systems, realizing, for the first time, ratiometric quantification (in cells), in vivo imaging (zebrafish), and living tissue imaging (vivisectional mouse under anaesthetic) of endogenous FA that was spontaneously generated by biological systems. Furthermore, with the aid of PIPBA, we obtained visual evidence for the oxidative damage of FA in both HeLa cells and renal tissue of a living mouse. The results demonstrated that FA exerted indirect oxidative damage by interacting with free radicals, thus producing more oxidizing species, which eventually caused aggravated oxidative damage to the organism. The indirect oxidative damage due to FA could be alleviated by an exogenous or endogenous antioxidant. The excellent behaviors of PIPBA demonstrate that a chemical probe can detect endogenous FA in cells/tissue/vivo, promising to be an effective tool for further exploration of the biological mechanism of FA in living systems.
DOI10.1039/c7sc03719h
项目资助者National Natural Science Foundation of China(21475074, 21403123, 21375075, 1301595, 21402106, 21475075, 21275089, 21405093, 21405094, 81303179, 21305076) ; Shandong Province Key Laboratory of Detection Technology for Tumor Markers(KLDTTM2015-6, KLDTTM2015-9)
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收录类别SCI
关键词[WOS]AZA-COPE REACTION ; SELECTIVE DETECTION ; MASS-SPECTROMETRY ; FREE-RADICALS ; FATTY-ACIDS ; VITAMIN-E ; FORMALDEHYDE ; CELLS ; DNA ; STRESS
文章类型Article
语种英语
WOS研究方向Chemistry
WOS记录号WOS:000413532800066
引用统计
被引频次:9[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.yic.ac.cn/handle/133337/23461
专题中科院海岸带环境过程与生态修复重点实验室
通讯作者Chen, Guang; You, Jinmao; Chen, Guang(Qufu Normal Univ, Coll Chem & Chem Engn, Key Lab Life Organ Anal, Key Lab Pharmaceut Intermediates & Anal Nat Med, Qufu 273165, Peoples R China); You, Jinmao(Qufu Normal Univ, Coll Chem & Chem Engn, Key Lab Life Organ Anal, Key Lab Pharmaceut Intermediates & Anal Nat Med, Qufu 273165, Peoples R China)
作者单位1.Qufu Normal Univ, Coll Chem & Chem Engn, Key Lab Life Organ Anal, Key Lab Pharmaceut Intermediates & Anal Nat Med, Qufu 273165, Peoples R China
2.Chinese Acad Sci, Yantai Inst Coastal Zone Res, Key Lab Coastal Environm Proc & Ecol Remediat, Yantai 264003, Peoples R China
3.Chinese Acad Sci, Northwest Inst Plateau Biol, Key Lab Tibetan Med Res, Qinghai Key Lab Qinghai Tibet Plateau Biol Resour, Xining 810001, Qinghai, Peoples R China
通讯作者单位中国科学院烟台海岸带研究所
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Dou, Kun,Chen, Guang,Yu, Fabiao,et al. Bright and sensitive ratiometric fluorescent probe enabling endogenous FA imaging and mechanistic exploration of indirect oxidative damage due to FA in various living systems[J]. CHEMICAL SCIENCE,2017,8(11):7851-7861.
APA Dou, Kun.,Chen, Guang.,Yu, Fabiao.,Liu, Yuxia.,Chen, Lingxin.,...&You, Jinmao.(2017).Bright and sensitive ratiometric fluorescent probe enabling endogenous FA imaging and mechanistic exploration of indirect oxidative damage due to FA in various living systems.CHEMICAL SCIENCE,8(11),7851-7861.
MLA Dou, Kun,et al."Bright and sensitive ratiometric fluorescent probe enabling endogenous FA imaging and mechanistic exploration of indirect oxidative damage due to FA in various living systems".CHEMICAL SCIENCE 8.11(2017):7851-7861.
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