Establishment of Cysteine Detection Method in Food Based on Fluorescent Probe

HAN Rui; WU Qiong; ZHAO Xin; MAO Shuhong

doi:10.13386/j.issn1002-0306.2021060066

Volume 43 Issue 4

Feb. 2022

Turn off MathJax

Article Contents

Abstract

References

Science and Technology of Food Industry > 2022 > 43(4): 305-311. > DOI: 10.13386/j.issn1002-0306.2021060066

HAN Rui, WU Qiong, ZHAO Xin, et al. Establishment of Cysteine Detection Method in Food Based on Fluorescent Probe[J]. Science and Technology of Food Industry, 2022, 43(4): 305−311. (in Chinese with English abstract). doi: 10.13386/j.issn1002-0306.2021060066.

Citation:

PDF (3803 KB)

Establishment of Cysteine Detection Method in Food Based on Fluorescent Probe

School of Biotechnology, Tianjin Univercity of Science & Technology, Tianjin 300457, China

More Information

Received Date: June 07, 2021
Available Online: December 13, 2021

Graphical Abstract

Abstract

Abstract

A novel, simple and sensitive fluorescenct method for determination of cysteine in water, milk, milk powder, cabbage, apple, pear and radish was established based on rosamine fluorescent probe. The probe was constructed by rosamine as the signal reporter and phenylalkynyl as the reaction site. Through Michael addition and intramolecular reaction, the probe could detect cysteine with high selectivity and sensitivity. Results indicated that under the optimized conditions of phosphoric acid buffer concentration of 10 mmol/L, pH9.5, methanol/water volume ratio of 1:9 and room temperature reaction for 35 min, the probe selectively recognized cysteine, and its relative fluorescence intensity increased with the increasing of cysteine concentration. Furthermore, the fluorescence signal of the probe had a good linear relationship with cysteine in the concentration range from 18.0 to 70.0 μmol/L (R²=0.992) with detection limit of 0.18 μmol/L. Furthermore, the method was used to determinate cysteine in water, milk, milk powder, cabbage, apple, pear and radish with good recoveries (96.4%~102.97%) and RSD (0.1%～2%). This suggested that the approach would have high selectivity, sensitivity and the feasibility of cysteine detection in practical sample, as well as a good application prospect.
- rosamine,
- cysteine,
- phenylacetylene,
- fluorescent probe,
- Michael addition

FullText(HTML)

References (30)

References

[1]	ANTON R, BARLOW S, BOSKOU D, et al. Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) to review the toxicology of a number of dyes illegally present in food in the EU[J]. The EFSA Journal,2005,263:1−71.
[2]	CHEN X, ZHOU Y, PENG X, et al. Fluorescent and colorimetric probes for detection of thiols[J]. Chemical Society Reviews,2010,39(6):2120−2135. doi: 10.1039/b925092a
[3]	WU B, XUE T, HE Y. Design of activatable red-emissive assay for cysteine detection in aqueous medium with aggregation induced emission characteristics[J]. Chinese Chemical Letters,2021,32(2):932−937. doi: 10.1016/j.cclet.2020.03.047
[4]	CHANG Y, QIN H, WANG X, et al. Visible and reversible restrict of molecular configuration by copper ion and pyrophosphate[J]. ACS Sensors,2020,5(8):2438−2447. doi: 10.1021/acssensors.0c00619
[5]	YANG M, FAN J, DU J, et al. Small-molecule fluorescent probes for imaging gaseous signaling molecules: Current progress and future implications[J]. Chemical Science,2020,11(20):5127−5141. doi: 10.1039/D0SC01482F
[6]	REN H, HUO F, ZhANG Y, et al. An NIR ESIPT-based fluorescent probe with large stokes shift for specific detection of Cys and its bioimaging in cells and mice[J]. Sensors and Actuators B:Chemical,2020,319:128248. doi: 10.1016/j.snb.2020.128248
[7]	QIAN M, XIA J, ZHANG L, et al. Rationally modifying the dicyanoisophorone fluorophore for sensing cysteine in living cells and mice[J]. Sensors and Actuators B:Chemical,2020,321:128441. doi: 10.1016/j.snb.2020.128441
[8]	LI Y, HE X, HUANG Y, et al. Development of a water-soluble near-infrared fluorescent probe for endogenous cysteine imaging[J]. Spectrochimica Acta Part A:Molecular and Biomolecular Spectroscopy,2020,226:117544. doi: 10.1016/j.saa.2019.117544
[9]	JUNG H S, CHEN X, KIM J S, et al. Recent progress in luminescent and colorimetric chemosensors for detection of thiols[J]. Chemical Society Reviews,2013,42(14):6019−6031. doi: 10.1039/c3cs60024f
[10]	YIN C X, XIONG K M, HUO F J, et al. Fluorescent probes with multiple binding sites for the discrimination of Cys, Hcy, and GSH[J]. Angewandte Chemie International Edition,2017,56(43):13188−13198. doi: 10.1002/anie.201704084
[11]	GUO B, PAN X, LIU Y, et al. A reversible water-soluble naphthalimide-based chemosensor for imaging of cellular copper(II) ion and cysteine[J]. Sensors and Actuators B:Chemical,2018,256:632−638. doi: 10.1016/j.snb.2017.09.196
[12]	ZHANG Y, YAO W, LIANG D, et al. Selective detection and quantification of tryptophan and cysteine with pyrenedione as a turn-on fluorescent probe[J]. Sensors and Actuators B:Chemical,2018,259:768−774. doi: 10.1016/j.snb.2017.12.059
[13]	SHARMA P, KUMAR K, KAUR S, et al. Near-IR discriminative detection of H₂S and cysteine with 7-nitro-2, 1, 3-benzoxadiazole-perylenediimide conjugate in water, live cells and solid state: mimicking IMP, INH and NOR/OR complimentary logic[J]. Journal of Photochemistry and Photobiology A:Chemistry,2020,388:112151. doi: 10.1016/j.jphotochem.2019.112151
[14]	DAI C G, LIU X L, DU X J, et al. Two-input fluorescent probe for thiols and hydrogen sulfide chemosensing and live cell imaging[J]. ACS Sensors,2016,1(7):888−895. doi: 10.1021/acssensors.6b00291
[15]	XUE H, YU M, HE K, et al. A novel colorimetric and fluorometric probe for biothiols based on MnO₂ NFs-Rhodamine B system[J]. Analytica Chimica Acta,2020,1127:39−48. doi: 10.1016/j.aca.2020.06.039
[16]	ZHANG H, LI W, CHEN J, et al. Simultaneous detection of Cys/Hcy and H₂S through distinct fluorescence channels[J]. Analytica Chimica Acta,2020,1097:238−244. doi: 10.1016/j.aca.2019.11.029
[17]	WANG J, LI B, ZHAO W, et al. Two-photon near infrared fluorescent turn-on probe toward cysteine and its imaging applications[J]. ACS Sensors,2016,1(7):882−887. doi: 10.1021/acssensors.5b00271
[18]	ZHAO X, JI H, HASRAT K, et al. A mitochondria-targeted single fluorescence probe for separately and continuously visualizing H₂S and Cys with multi-response signals[J]. Analytica Chimica Acta,2020,1107:172−182. doi: 10.1016/j.aca.2020.02.017
[19]	DAI Y, ZHENG Y, XUE T, et al. A novel fluorescent probe for rapidly detection cysteine in cystinuria urine, living cancer/normal cells and BALB/c nude mice[J]. Spectrochimica Acta Part A:Molecular and Biomolecular Spectroscopy,2020,225:117490. doi: 10.1016/j.saa.2019.117490
[20]	CARDOSO I C S, AMORIM A L, QUEIRÓS C, et al. Microwave-assisted synthesis and spectroscopic properties of 4′-substituted rosamine fluorophores and naphthyl analogues[J]. European Journal of Organic Chemistry,2012,2012(29):5810−5817. doi: 10.1002/ejoc.201200783
[21]	CHENG J, SONG J, NIU H, et al. A new rosamine-based fluorescent chemodosimeter for hydrogen sulfide and its bioimaging in live cells[J]. New Journal Chemistry,2016,40(7):6384−6388. doi: 10.1039/C6NJ00177G
[22]	YANG L, NIU J Y, SUN R, et al. Rosamine with pyronine-pyridinium skeleton: unique mitochondrial targetable structure for fluorescent probes[J]. Analyst,2018,143(8):1813−1819. doi: 10.1039/C7AN02041D
[23]	LEEN V, YUAN P, WANG L, et al. Synthesis of meso-halogenated BODIPYs and access to meso-substituted analogues[J]. Organic Letters,2012,14(24):6150−6153. doi: 10.1021/ol3028225
[24]	LIU Y, LV X, HOU M, et al. Selective fluorescence detection of cysteine over homocysteine and glutathione based on a cysteine-triggered dual michael addition/retro-aza-aldol cascade reaction[J]. Analytical Chemistry,2015,87(22):11475−11483. doi: 10.1021/acs.analchem.5b03286
[25]	YANG L, NIU J Y, SUN R, et al. The pH-influenced PET processes between pyronine and different heterocycles[J]. Organic & Biomolecular Chemistry,2017,15(30):8402−8409.
[26]	CHEN T, PEI X, YUE Y, et al. An enhanced fluorescence sensor for specific detection Cys over Hcy/GSH and its bioimaging in living cells[J]. Spectrochimica Acta Part A:Molecular and Biomolecular Spectroscopy,2019,209:223−237. doi: 10.1016/j.saa.2018.10.049
[27]	LIU K, GU H, SUN Y, et al. A novel rosamine-based fluorescent probe for the rapid and selective detection of cysteine in BSA, water, milk, cabbage, radish, apple, and pea[J]. Food Chemistry,2021,356:129658. doi: 10.1016/j.foodchem.2021.129658
[28]	SONG H, ZHANG J, WANG X, et al. A novel “turn-on” fluorescent probe with a large stokes shift for homocysteine and cysteine: Performance in living cells and zebrafish[J]. Sensors and Actuators B:Chemical,2018,259:232−240.
[29]	HE L, YANG X, XU K, et al. Improved aromatic substitution–rearrangement-based ratiometric fluorescent cysteine-specific probe and its application of real-time imaging under oxidative stress in living zebrafish[J]. Analytical Chemistry,2017,89(17):9567−9573. doi: 10.1021/acs.analchem.7b02649
[30]	ARROYO I J, HU R, TANG B Z, et al. 8-Alkenylborondipyrromethene dyes. general synthesis, optical properties, and preliminary study of their reactivity[J]. Tetrahedron,2011,67(38):7244−7250. doi: 10.1016/j.tet.2011.07.067

Supplements (0)

Cited By

Cited by

Periodical cited type(4)

1.	季佳琪，李明初，李冬霞，谭雅宁，高爽，王颉，牟建楼. 高温蒸煮结合蜗牛酶法改性葡萄皮不溶性膳食纤维工艺优化及体外降血糖作用. 食品工业科技. 2024(16): 249-258 . 本站查看
2.	林良美，肖少香，张丽红. 响应面优化复合酶法提取红薯皮膳食纤维. 粮食科技与经济. 2024(04): 96-100+115 .
3.	竹娟，王译晗，陈立莉，曲文鑫，刘荣. 芍药花提取物中黄酮的测定及其体外抗氧化和降脂活性研究. 天然产物研究与开发. 2024(11): 1838-1844+1899 .
4.	赵习爱，傅婧，任娟蕊. 燕麦萌动对膳食纤维结构和功能的影响. 食品与发酵工业. 2024(24): 229-237 .