Synthesis and Properties of A Mitochondria-targeted Coumarin-based pH Fluorescent Probe

Jun CHEN; Yan FENG; Xiang-ming MENG

doi:10.37188/CJL.20200363

您当前的位置：

首页 >

文章列表页 >

Synthesis and Properties of A Mitochondria-targeted Coumarin-based pH Fluorescent Probe

Synthesis and Properties of Materials | 更新时间：2021-04-23

- Synthesis and Properties of A Mitochondria-targeted Coumarin-based pH Fluorescent Probe
- Chinese Journal of Luminescence Vol. 42, Issue 4, Pages: 462-469(2021)
- 作者机构：
  
  安徽大学化学化工学院，安徽　合肥　 230601
- 作者简介：
- 基金信息：
  
  the National Natural Science Foundation of China(21778001;21672001)
- DOI：10.37188/CJL.20200363
  CLC： O482.31
- Received：29 November 2020，
  
  Revised：2020-12-31，
  
  Published：01 April 2021
- 稿件说明：
移动端阅览
Jun CHEN, Yan FENG, Xiang-ming MENG. Synthesis and Properties of A Mitochondria-targeted Coumarin-based pH Fluorescent Probe[J]. Chinese Journal of Luminescence, 2021, 42(4): 462-469.
DOI：

Jun CHEN, Yan FENG, Xiang-ming MENG. Synthesis and Properties of A Mitochondria-targeted Coumarin-based pH Fluorescent Probe[J]. Chinese Journal of Luminescence, 2021, 42(4): 462-469. DOI： 10.37188/CJL.20200363.

摘要

线粒体作为一种重要的细胞器，其功能包括能量供应、信号传导、细胞分化以及控制细胞生理周期和细胞生长等。线粒体的任何损伤及随后的功能障碍都可能导致一系列人类疾病。其中线粒体pH直接影响着其生化过程，正常的pH水平是线粒体功能正常运作的基础。本文以7-羟基香豆素为原料，合成了一种对线粒体特异性标记的pH荧光探针(CMPH)。并对该探针的光学性质、细胞毒性和线粒体靶向能力进行了研究。结果表明，探针CMPH具有较大的斯托克斯位移，能对pH特异性荧光响应。pH在6.58.2范围内时，探针的荧光强度和pH值具有良好的线性关系。细胞毒性测试表明探针CMPH细胞毒性低。共聚焦荧光成像结果证明，该探针能有效靶向线粒体并能监测线粒体pH的变化。我们的目的是为线粒体pH变化的监测提供一种新的成像工具。

Abstract

Mitochondrion is an important organelle whose functions include energy supply

signal transduction

cell differentiation

cell death

and the control of cell physiological cycle and cell growth. Any damage to mitochondria and subsequent dysfunction could lead to a range of human diseases. Mitochondrial pH directly affects its biochemical process

and the normal pH level is the basis for the normal operation of mitochondrial function. In this paper

a mitochondria-targeted pH fluorescent probe(CMPH) was synthesized by choosing 7-hydroxycoumarin as the raw material. Its optical properties

cytotoxicity and mitochondria-targeted ability were studied. The results showed that probe CMPH had a large Stokes shift

can specifically give a fluorescent response to pH

and its fluorescent intensities had a good linear relationship to pH values in the range of pH=6.5-8.2. Cytotoxicity testing indicated that probe CMPH had low cytotoxicity. Confocal fluorescence imaging demonstrated that CMPH can efficiently target mitochondria and monitor the change of mitochondrial pH. Our purpose is to provide a new imaging tool for monitoring the change of mitochondrial pH.

关键词

Keywords

references

ZHONG W X , RABINOWITZ J D , WHITE E . Mitochondria and cancer [J]. Mol. Cell , 2016 , 61 ( 5 ): 667 - 676 .

HAJNÓCZKY G , CSORDÁS G , YI M . Old players in a new role:mitochondria-associated membranes, VDAC, and ryanodine receptors as contributors to calcium signal propagation from endoplasmic reticulum to the mitochondria [J]. Cell Calcium , 2002 , 32 ( 5-6 ): 363 - 377 .

WANG H , LIU C , ZHAO Y X , et al . Mitochondria regulation in ferroptosis [J]. Eur. J. Cell Biol. , 2020 , 99 ( 1 ): 151058 .

赵梓圳，付爱玲 . 线粒体治疗:一种新型的线粒体相关疾病的生物疗法 [J]. 生物工程学报， 2021 ， doi: 10.13345/j.cjb.200383 http://doi.org/10.13345/j.cjb.200383 .

ZHAO Z Z , FU A L . Mitochondrial therapy:a new strategy for treating mitochondrion-associated diseases [J]. Chin. J. Biotech. , 2021 , doi: 10.13345/j.cjb.200383 http://doi.org/10.13345/j.cjb.200383 . (in Chinese)

CHAKRABARTY S , KABEKKODU S P , SINGH R P , et al . Mitochondria in health and disease [J]. Mitochondrion , 2018 , 43 : 25 - 29 .

DING W X , YIN X M . Mitophagy:mechanisms, pathophysiological roles, and analysis [J]. Biol. Chem. , 2012 , 393 ( 7 ): 547 - 564 .

KHAN N A , GOVINDARAJ P , SOUMITTRA N , et al . Leber’s hereditary optic neuropathy-specific mutation m. 11778G>A exists on diverse mitochondrial haplogroups in India [J]. Invest. Ophthalmol. Vis. Sci. , 2017 , 58 ( 10 ): 3923 - 3930 .

WU M Y , LI K , LIU Y H , et al . Mitochondria-targeted ratiometric fluorescent probe for real time monitoring of pH in living cells [J]. Biomaterials , 2015 , 53 : 669 - 678 .

LI X L , ZHENG J Z , LIU W J , et al . Long-term super-resolution imaging of mitochondrial dynamics [J]. Chin. Chem. Lett. , 2020 , 31 ( 11 ): 2937 - 2940 .

FANG Z J , SU Z , QIN W J , et al . Two-photon dual-channel fluorogenic probe for in situ imaging the mitochondrial H2S/viscosity in the brain of drosophila Parkinson's disease model [J]. Chin. Chem. Lett. , 2020 , 31 ( 11 ): 2903 - 2908 .

SZAKACS Z , HAGELE G , TYKA R . 1H/31P NMR pH indicator series to eliminate the glass electrode in NMR spectroscopic pKa determinations [J]. Anal. Chim. Acta , 2004 , 522 ( 2 ): 247 - 258 .

WONG L S , BRADLEY M . Immobilisation and assessment of aniline dyes for non-fluorescent pH sensing applications [J]. Tetrahedron Lett. , 2005 , 46 ( 34 ): 5731 - 5734 .

ROTH I , JBARAH A A , HOLZE R . 2-nitro-1, 4-diaminobenzene-functionalized poly(vinyl amine)s as water-soluble UV-Vis-sensitive pH sensors [J]. Macromol. Rapid Commun. , 2006 , 27 ( 3 ): 193 - 199 .

BI L Y , WANG Y Q , YANG Y , et al . Highly sensitive and reproducible SERS sensor for biological pH detection based on a uniform gold nanorod array platform [J]. ACS Appl. Mater. Interfaces , 2018 , 10 ( 18 ): 15381 - 15387 .

GÜHLKE M , HEINER Z , KNEIPP J . Combined near-infrared excited SEHRS and SERS spectra of pH sensors using silver nanostructures [J]. Phys. Chem. Chem. Phys. , 2015 , 17 ( 39 ): 26093 - 26100 .

彭洪尚，黄世华 . 比率荧光纳米水凝胶的制备以及在pH探测中的应用 [J]. 发光学报， 2010 ， 31 ( 3 ): 395 - 399 .

PENG H S , HUANG S H . A ratiometric fluorescense nanogel for pH sensor [J]. Chin. J. Lumin. , 2010 , 31 ( 3 ): 395 - 399 . (in Chinese)

PAN W , WANG H H , YANG L M , et al . Ratiometric fluorescence nanoprobes for subcellular pH imaging with a single-wavelength excitation in living cells [J]. Anal. Chem. , 2016 , 88 ( 13 ): 6743 - 6748 .

URANO Y . Novel live imaging techniques of cellular functions and in vivo tumors based on precise design of small molecule-based ‘Activatable’ fluorescence probes [J]. Curr. Opin. Chem. Biol. , 2012 , 16 ( 5-6 ): 602 - 608 .

NING P , HOU L L , FENG Y , et al . Real-time visualization of autophagy by monitoring the fluctuation of lysosomal pH with a ratiometric two-photon fluorescent probe [J]. Chem. Commun. , 2019 , 55 ( 12 ): 1782 - 1785 .

HUANG Y L , ZHOU Q , FENG Y , et al . Rational design of a ratiometric two-photon fluorescent probe for real-time visualization of apoptosis [J]. Chem. Commun. , 2018 , 54 ( 74 ): 10495 - 10498 .

JIANG J C , TIAN X H , XU C Z , et al . A two-photon fluorescent probe for real-time monitoring of autophagy by ultrasensitive detection of the change in lysosomal polarity [J]. Chem. Commun. , 2017 , 53 ( 26 ): 3645 - 3648 .

JIANG C K , LI L C , JIANG J C , et al . A bright two-photon fluorescent probe for real-time monitoring autophagy in living cells [J]. Chin. Chem. Lett. , 2020 , 31 ( 2 ): 447 - 450 .

YANG J J , YU Y W , WANG B X , et al . A sensitive fluorescent probe based on coumarin for detection of cysteine in living cells [J]. J. Photochem. Photobiol. A, Chem. , 2017 , 338 : 178 - 182 .

程晓红，阮志军，钟志成，等 . 基于香豆素的荧光传感器及其对次氯酸根的快速检测 [J]. 发光学报， 2018 ， 39 ( 8 ): 1182 - 1191 .

CHENG X H , RUAN Z J , ZHONG Z C , et al . Rapid-responsive fluorescent probes based on coumarin dye for sensitive detection of hypochlorite [J]. Chin. J. Lumin. , 2018 , 39 ( 8 ): 1182 - 1191 . (in English)

解丽娟，李建民 . 7-二乙胺基-3-(2'-吡啶)香豆素的新用途:溶酶体荧光探针 [J]. 发光学报， 2013 ， 34 ( 11 ): 1538 - 1543 .

XIE L J , LI J M . A new use of 7-(diethylamino)-3-(pyridin-2-yl)coumarin:as lysosome fluorescence probe [J]. Chin. J. Lumin. , 2013 , 34 ( 11 ): 1538 - 1543 . (in Chinese)

JIANG N , FAN J L , XU F , et al . Ratiometric fluorescence imaging of cellular polarity:decrease in mitochondrial polarity in cancer cells [J]. Angew. Chem. , 2015 , 127 ( 8 ): 2540 - 2544 .

XIE Y H , ZHANG C Y , WANG Z H , et al . Fluorogenic assay for acetohydroxyacid synthase:design and applications [J]. Anal. Chem. , 2019 , 91 ( 21 ): 13582 - 13590 .

YE S C , LIANG Q , LI Z Y , et al . A highly sensitive and selective naked-eye probe for detection of Fe3+ based on a 2, 5-bis[3-benzyl-2-methylbenzothiazole]-croconaine [J]. Tetrahedron , 2017 , 73 ( 10 ): 1350 - 1357 .

YAO D F , LIN Z , WU J C . Near-infrared fluorogenic probes with polarity-sensitive emission for in vivo imaging of an ovarian cancer biomarker [J]. ACS Appl. Mater. Interfaces , 2016 , 8 ( 9 ): 5847 - 5856 .

唐倩，但飞君，曾晓燕，等 . 含吡啶环香豆素酸性pH荧光探针的合成及应用 [J]. 分析试验室， 2019 ， 38 ( 2 ): 202 - 206 .

TANG Q , DAN F J , ZENG X Y , et al . Synthesis and application of acid pH fluorescent probes containing pyridine ring coumarin [J]. Chin. J. Anal. Lab. , 2019 , 38 ( 2 ): 202 - 206 . (in Chinese)

SHEN S L , ZHANG X F , BAI S Y , et al . A novel ratiometric pH probe for extreme acidity based on FRET and PET [J]. RSC Adv. , 2015 , 5 ( 18 ): 13341 - 13346 .

YANG S H , YANG W G , GUO Q R , et al . A highly selective and ratiometric fluorescence probe for the detection of Hg2+ and pH change based on coumarin in aqueous solution [J]. Tetrahedron , 2014 , 70 ( 46 ): 8914 - 8918 .

LIU M Q , HU M S , JIANG Q , et al . A novel coumarin derivative as a sensitive probe for tracing intracellular pH changes [J]. RSC Adv. , 2015 , 5 ( 21 ): 15778 - 15783 .

SALEH N , AL-SOUD Y A , NAU W M . Novel fluorescent pH sensor based on coumarin with piperazine and imidazole substituents [J]. Spectrochim. Acta A: Mol. Biomol. Spectrosc. , 2008 , 71 ( 3 ): 818 - 822 .

LIU X J , WANG L L , BING T , et al . A mitochondria-targeted ratiometric fluorescent pH probe [J]. ACS Appl. Bio. Mater. , 2019 , 2 ( 3 ): 1368 - 1375 .

Views

528

下载量

CSCD

Alert me when the article has been cited

提交

Tools

Publicity Resources

Construction and Application of A Cu²⁺ Fluorescent Probe Based on Coumarin-Cd²⁺ Complex

Construction and Application of Zn²⁺ Fluorescent Probe Based on Coumarin

Synthesis of Coumarin Fluorescent Probe Based on Schiff Base Structure and Identification to Mg²⁺

Highly Sensitive Fluorescent Coumarin-based Probes for Selective Detection of Copper Ion

Related Author

Jun Chen

Yan Feng

Xiangming Meng

XIAO Jiayang

ZHU Xinyue

GUO Xiaoyun

YANG Fan

YANG Tairan

Related Institution

School of Chemistry and Chemical Engineering， Anhui University

Yingkou Food and Drug Testing Center

College of Chemical Engineering， University of Science and Technology Liaoning

School of Chemistry and Chemical Engineering, Yulin University

State Key Laboratory of Fine Chemicals, Department of Chemistry, Dalian University of Technology

AI问答

Address：No.3888 Dong Nanhu Road, Changchun, Jilin, China Postal code：130033
Tel：0431-86176862 Email：fgxbt@126.com
Technical support is provided by Beijing Founder electronics co., LTD 吉ICP备11002662号-17 京公网安备11010802024621
It is recommended to read the content of this site in Chrome&IE9+. Please switch to extreme mode in browser 360.
Cookies We use cookies to help provide and enhance our service and tailor content. By continuing, you agree to the use of cookies.

⁰