A Novel Curcumin Derivatives Fluorescent Probe for Selective Recognition of Cysteine

Fan LUO; Dong-bin ZHENG; Zhi-qiang YANG; Yun DENG

doi:10.37188/CJL.20210211

您当前的位置：

首页 >

文章列表页 >

A Novel Curcumin Derivatives Fluorescent Probe for Selective Recognition of Cysteine

Luminescence Applications and Interdisciplinary Fields | 更新时间：2021-11-23

- A Novel Curcumin Derivatives Fluorescent Probe for Selective Recognition of Cysteine
  增强出版
- Chinese Journal of Luminescence Vol. 42, Issue 11, Pages: 1810-1817(2021)
- 作者机构：
  
  成都中医药大学药学院　西南特色中药资源国家重点实验室，四川　成都　611137
- 作者简介：
- 基金信息：
  
  National Natural Science Foundation of China(U19A2011);Project First-Class Disciplines Development supported by Chengdu University of TCM(CZYJC1905)
- DOI：10.37188/CJL.20210211
  CLC： O482.31
- Published：01 November 2021，
  
  Received：18 June 2021，
  
  Revised：28 June 2021，
- 稿件说明：
移动端阅览
FAN LUO, DONG-BIN ZHENG, ZHI-QIANG YANG, et al. A Novel Curcumin Derivatives Fluorescent Probe for Selective Recognition of Cysteine. [J]. Chinese journal of luminescence, 2021, 42(11): 1810-1817.
DOI：

FAN LUO, DONG-BIN ZHENG, ZHI-QIANG YANG, et al. A Novel Curcumin Derivatives Fluorescent Probe for Selective Recognition of Cysteine. [J]. Chinese journal of luminescence, 2021, 42(11): 1810-1817. DOI： 10.37188/CJL.20210211.

摘要

半胱氨酸(Cysteine

Cys)作为生物体内一种重要的含巯基氨基酸，与细胞代谢、氧化还原稳态密切相关，然而过量的半胱氨酸可能会导致类风湿性关节炎、阿尔兹海默病等。因此，开发一种能选择性识别半胱氨酸的荧光探针具有重要的研究意义。本文设计合成了一种以姜黄素-二氟硼为基本骨架，2-氯-5-硝基苯甲酰基为识别位点的荧光探针分子1，并将其用于半胱氨酸的识别。结果表明，探针能高选择性识别Cys，荧光强度与Cys浓度在10~70 μmol·L

-1

范围内呈良好的线性关系，检出限为2.9 μmol·L

-1

。同时，Cys的加入会引起探针溶液颜色肉眼可见的显著变化，由黄色变为无色。此外，该探针能模拟检测水样中添加的半胱氨酸，在自来水、河水样品中的半胱氨酸的回收率为98%~109%。

Abstract

As an important sulfhydryl amino acid in organism

cysteine(Cys) is closely related to cell metabolism and redox homeostasis. However

excess amount of Cys is associated with diseases including rheumatoid arthritis

Alzheimer's disease. Thus

it is of great significance to develop a fluorescent probe for selective recognition of cysteine. In this paper

a fluorescence probe based on curcumin-difluoride and modified with 2-chloro-5-nitrobenzoyl was synthesized for the determination of cysteine. The results showed that the probe could selectively recognize Cys. A good linear relationship between the fluorescence intensity of the probe and Cys concentration in the range of 10-70 μmol·L

-1

was obtained

from which the detection limit was deduced to be 2.9 μmol·L

-1

. Meanwhile

the addition of Cys could lead to an obvious colour transition from yellow to colourless

permitting a rapid identification of Cys by the naked eye. Moreover

the probe can simulate the detection of Cys in water samples

and the recoveries of Cys in tap water and river samples ranged from 98%-109%.

关键词

半胱氨酸姜黄素衍生物荧光探针选择性识别

Keywords

cysteinecurcumin derivativesfluorescent probeselective recognition

references

YUE Y K, HUO F J, NING P, et al. Dual-site fluorescent probe for visualizing the metabolism of Cys in living cells[J]. J. Am. Chem. Soc., 2017, 139(8): 3181-3185.

YANG Y, FENG Y, LI H, et al. Hydro-soluble NIR fluorescent probe with multiple sites and multiple excitations for distinguishing visualization of endogenous Cys/Hcy, and GSH[J]. Sens. Actuators B Chem., 2021, 333: 129189.

LI X R, MA H, QIAN J, et al. Ratiometric fluorescent probe based on ESIPT for the highly selective detection of cysteine in living cells[J]. Talanta, 2019, 194: 717-722.

MAURAIS A J, WEERAPANA E. Reactive-cysteine profiling for drug discovery[J]. Curr. Opin. Chem. Biol., 2019, 50: 29-36.

DOS SANTOS A P A, DA SILVA J K, NERI J M, et al. Nucleophilicity of cysteine and related biothiols and the development of fluorogenic probes and other applications[J]. Org. Biomol. Chem., 2020, 18(46): 9398-9427.

FENG B, LIU Y, HUANG S, et al. Highly selective discrimination of cysteine from glutathione and homo-cysteine with a novel AIE-ESIPT fluorescent probe[J]. Sens. Actuators B Chem., 2020, 325: 128786.

APELAND T, HOLDAAS H, MANSOOR M A. Kidney donors and kidney transplants have abnormal aminothiol redox status, and are at increased risk of oxidative stress and reduced redox buffer capacity[J]. Clin. Biochem., 2014, 47(6): 378-382.

YU Y T, WANG J B, XIANG H, et al. A new near-infrared ratiometric fluorescent probe based on quinoline-fused rhodamine dye for sensitive detection of cysteine and homocysteine in mitochondria[J]. Dyes Pigm., 2020, 183: 108710.

BLACHIER F, BEAUMONT M, KIM E. Cysteine-derived hydrogen sulfide and gut health:a matter of endogenous or bacterial origin[J]. Curr. Opin. Clin. Nutr. Metab. Care, 2019, 22(1): 68-75.

CALZETTA L, MATERA M G, ROGLIANI P, et al. Multifaceted activity of N-acetyl-l-cysteine in chronic obstructive pulmonary disease[J]. Expert Rev. Respir. Med., 2018, 12(8): 693-708.

ZHU M Q, FAN F G, ZHAO Z Y, et al. An ICT-based ratiometric fluorescent probe for cysteine and its application in biological issues[J]. J. Mol. Liq., 2019, 296: 111832.

CHEN X N, XU H, MA S N, et al. A simple two-photon turn-on fluorescent probe for the selective detection of cysteine based on a dual PeT/ICT mechanism[J]. RSC Adv., 2018, 8(24): 13388-13392.

JIAO S, HE X, XU L B, et al. A red-emitting fluorescence turn-on probe for the discrimination of cysteine from biothiols and its bioimaging applications in living cells[J]. Sens. Actuators B Chem., 2019, 290: 47-52.

ZHAO L H, HE X, HUANG Y B, et al. A novel near-infrared fluorescent probe for intracellular detection of cysteine[J]. Anal. Bioanal. Chem., 2020, 412(26): 7211-7217.

LI Y L, HE X, HUANG Y B, et al. Development of a water-soluble near-infrared fluorescent probe for endogenous cysteine imaging[J]. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2020, 226: 117544.

HE R K, ZHANG Y C, MADHU S, et al. BODIPY based realtime, reversible and targeted fluorescent probes for biothiol imaging in living cells[J]. Chem. Commun., 2020, 56(93): 14717-14720.

LIU Y N, YU Y N, ZHAO Q Y, et al. Fluorescent probes based on nucleophilic aromatic substitution reactions for reactive sulfur and selenium species:recent progress, applications, and design strategies[J]. Coord. Chem. Rev., 2021, 427: 213601.

YIN G X, YU T, GAN Y B, et al. A novel fluorescent probe with dual-sites for simultaneously monitoring metabolisms of cysteine in living cells and zebrafishes[J]. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2020, 241: 118602.

WANG S, ZHANG Q, CHEN S J, et al. A diazabenzoperylene derivative as ratiometric fluorescent probe for cysteine with super large Stokes shift[J]. Anal. Bioanal. Chem., 2020, 412(11): 2687-2696.

KAILASA S K, KATESHIYA M R, MALEK N I. Introduction of cellulose-cysteine Schiff base as a new ligand for the fabrication of blue fluorescent gold nanoclusters for the detection of indapamide drug[J]. J. Mol. Liq., 2020, 319: 114305.

陈莉, 黎俊波, 陈杜刚. 生物硫醇荧光探针的研究进展[J]. 有机化学, 2021, 41(2): 611-623.

CHEN L, LI J B, CHEN D G. Recent advances in fluorescent probes for biothiols[J]. Chin. J. Org. Chem., 2020, 41(2): 611-623. (in Chinese)

盛铭浩. 小分子生物硫醇荧光探针研究进展[J]. 山东工业技术, 2015(16): 281.

SHENG M H. Research progress of fluorescent probes for small molecule biological thiols[J]. Shandong Ind. Technol., 2015(16): 281. (in Chinese)

DAS S, GHOSH A, KUNDU S, et al. Development of a new fluorescent probe for cysteine detection in processed food samples[J]. Anal. Bioanal. Chem., 2019, 411(23): 6203-6212.

XIA S, ZHANG Y B, FANG M X, et al. A FRET-based near-infrared fluorescent probe for ratiometric detection of cysteine in mitochondria[J]. ChemBioChem, 2019, 20(15): 1986-1994.

ANUSUYADEVI K, WU S P, VELMATHI S. ESIPT triggered swift determination of cysteine in HeLa cell line during redox imbalance[J]. J. Photochem. Photobiol. A Chem., 2020, 403: 112875.

HOJI A, MUHAMMAD T, WUBULIKASIMU M, et al. Syntheses of BODIPY-incorporated polymer nanoparticles with strong fluorescence and water compatibility[J]. Eur. Polym. J., 2020, 141: 110058.

BARATTUCCI A, SALERNO T M G, KOHNKE F H, et al. Curcumin-based sulfenic acid as a light switch for the binding of biothiols[J]. New J. Chem., 2020, 44(45): 19508-19514.

魏雨菲, 于海川, 刘雪玲, 等. 姜黄主要化学成分及药理作用研究进展[J]. 新乡医学院学报, 2020, 37(10): 990-995.

WEI Y F, YU H C, LIU X L, et al. Research progress on main chemical constituents and pharmacological effects of Curcuma longa[J]. J. Xinxiang Med. Univ., 2020, 37(10): 990-995. (in Chinese)

ZHANG X, TAN X Y, HU Y P. Blue/yellow emissive carbon dots coupled with curcumin:a hybrid sensor toward fluorescence turn-on detection of fluoride ion[J]. J. Hazard. Mater., 2021, 411: 125184.

FANG Y Y, WANG M, SHEN Y R, et al. Highly sensitive and selective recognition behaviour for fluoride based on a homoditopic curcumin-difluoroboron receptor[J]. Inorganica Chim. Acta, 2020, 503: 119413.

Views

126

下载量

CSCD

Alert me when the article has been cited

提交

Tools

Publicity Resources

Fluorescent Probe Derived from 2-（2'-Hydroxyphenyl）-Benzothiazole for Hydrogen Peroxide Sensing: Synthesis, Characterization and Application

Construction and Bioimaging of PPi Fluorescent Probes Based on Iron Complexes

Construction and Properties of Colorimetric Zn²⁺ Fluorescent Probe Based on Naphthofuran

Research Progress in Upconversion Nanomaterials for Food Safety Detection

Related Author

Fan LUO

Dong-bin ZHENG

Zhi-qiang YANG

Yun DENG

SHI Lei

HUANG Ling

HUANG Zejian

LI Donghua

Related Institution

State Key Laboratory of Southwestern Chinese Medicine Resources， School of Pharmacy， Chengdu University of Traditional Chinese Medicine

College of Light Chemical Engineering， Guangdong Polytechnic Normal University

Anan Cosmetics and Healthcare Products Co.， Ltd.

College of Chemical Engineering， University of Science and Technology Liaoning

State Key Laboratory of Integrated Optoelectronics， Jilin Key Laboratory on Advanced Gas Sensor， College of Electronic Science and Engineering， Jilin University

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