浏览全部资源
扫码关注微信
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
[ "罗凡(1997-),女,四川南充人,硕士研究生,2019年于成都中医药大学获得学士学位,主要从事荧光探针的设计合成及其性能的研究。E-mail: 1737630090@qq.com" ]
[ "邓赟(1975-),男,四川三台人,博士,研究员,博士研究生导师,2003年于中国科学院成都有机化学研究所获得博士学位,主要从事中药化学和天然产物化学的研究。E-mail: dengyun@cdutcm.edu.cn" ]
纸质出版日期:2021-11-01,
收稿日期:2021-06-18,
修回日期:2021-06-28,
扫 描 看 全 文
罗凡, 郑东滨, 阳志强, 等. 新型姜黄素衍生物荧光探针的合成及对半胱氨酸的选择性识别[J]. 发光学报, 2021,42(11):1810-1817.
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.
罗凡, 郑东滨, 阳志强, 等. 新型姜黄素衍生物荧光探针的合成及对半胱氨酸的选择性识别[J]. 发光学报, 2021,42(11):1810-1817. DOI: 10.37188/CJL.20210211.
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.
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%。
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%.
半胱氨酸姜黄素衍生物荧光探针选择性识别
cysteinecurcumin derivativesfluorescent probeselective recognition
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.
0
浏览量
76
下载量
1
CSCD
关联资源
相关文章
相关作者
相关机构