Fluorescent sensing platform for low-cost detection of Cu2+ by coumarin derivative: DFT calculation and practical application in herbal and black tea samples

Fluorescent sensing platform for low-cost detection of Cu2+ by coumarin derivative: DFT calculation and practical application in herbal and black tea samples

A fluorogenic probe based on a coumarin-derivative for $Cu^{2+}$ sensing in $CH_3 CN/H_2 O$ media (v/v, 95/5, 5.0 µM) was developed and applied in real samples. 3-(4-chlorophenyl)-6,7-dihydroxy-coumarin (MCPC) probe was obtained by synthetic methodologies and identified by spectral techniques. The probe MCPC showed remarkable changes with a “turn-off” fluorogenic sensing approach for the monitoring of $Cu^{2+}$ at 456 nm under an excitation wavelength of 366 nm. The response time of the probe MCPC was founded as only 1 min. The detection limit of the probe MCPC was recorded to be 1.47 nM. The binding constant and possible stoichiometric ratio (1:1) values were determined by Benesi-Hildebrand and Job’s plot systems, respectively. The mechanism of the probe MCPC with $Cu^{2+}$ was further confirmed by ESI-MS and FT-IR analyses, as well as supported by theoretical calculations. Furthermore, the probe MCPC was successfully employed for the practical applications to sense $Cu^{2+}$ in different herbal and black tea samples. The proposed sensing method was also verified by ICP-OES method.

___

  • 1. Wang S, Ding H, Wang Y, Fan C, Liu G et al. A colorimetric and ratiometric fluorescent sensor for sequentially detecting $Cu ^{2+}$ and arginine based on a coumarin-rhodamine B derivative and its application for bioimaging. RSC Advances 2019; 9 (12): 6643-6649. doi: 10.1039/c8ra09943j
  • 2. Roy N, Nath S, Dutta A, Mondal P, Paul PC et al. A highly efficient and selective coumarin based fluorescent probe for colorimetric detection of $Fe ^{3+}$ and fluorescence dual sensing of $Zn ^{2+} and Cu ^{2+}$ . RSC Advances 2016;6 (68): 63837-63847. doi: 10.1039/c6ra12217e
  • 3. Bekhradnia A, Domehri E, Khosravi M. Novel coumarin-based fluorescent probe for selective detection of Cu (II). Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2016; 152 (1): 18-22. doi: 10.1016/j.saa.2015.07.029
  • 4. Jung HS, Kwon PS, Lee JW, Kim JII, Hong CS et al. Coumarin-derived $Cu ^{2+}$ -selective fluorescence sensor: synthesis, mechanisms, and applications in living cells. Journal of the American Chemical Society 2009; 131 (5): 2008-2012. doi: 10.1021/ja808611d
  • 5. Kim MH, Jang HH, Yi S, Chang SK, Han MS. Coumarin-derivative-based off-on catalytic chemodosimeter for $Cu ^{2+}$ ions. Chemical Communications 2009; 32 (1): 4838-4840. doi: 10.1039/b908638b
  • 6. Shi Y, Wang R, Yuan W, Liu Q, Shi M et al. Easy-to-use colorimetric cyanine probe for the detection of $Cu ^{2+}$ in Wilson’s disease. ACS Applied Materials & Interfaces, 2018; 10 (24): 20377-20386. doi: 10.1021/acsami.8b07081
  • 7. Yeh JT, Chen WC, Liu SR, Wu SP. A coumarin-based sensitive and selective fluorescent sensor for copper(II) ions. New Journal of Chemistry 2014; 38 (9): 4434-4439. doi: 10.1039/c4nj00695j
  • 8. Qian B, Váradi L, Trinchi A, Reichman SM, Bao L et al. The Design and synthesis of fluorescent coumarin derivatives and their study for $Cu ^{2+}$ sensing with an application for aqueous soil extracts. Molecules, 2019; 24 (19): 3569. doi: 10.3390/molecules24193569
  • 9. Arslan FN, Geyik GA, Koran K, Ozen F, Aydin D et al. Fluorescence “turn on-off” sensing of copper (II) ions utilizing coumarin-based chemosensor: experimental study, theoretical calculation, mineral and drinking water analysis. Journal of Fluorescence 2020; 30 (1): 317-327. doi: 10.1007/s10895-020-02503-4
  • 10. Wu X, Wang H, Yang S, Tian H, Liu Y et al. A novel coumarin-based fluorescent probe for sensitive detection of copper(II) in wine. Food Chemistry 2019; 284 (1): 23-27. doi: 10.1016/j.foodchem.2019.01.090
  • 11. Yan F, Bai Z, Chen Y, Zu F, Li X et al. Ratiometric fluorescent detection of copper ıons using coumarinfunctionalized carbon dots based on FRET. Sensors and Actuators B: Chemical 2018; 275 (1): 86-94. doi: 10.1016/j.snb.2018.08.034
  • 12. Karuk Elmas SN, Gunay IB, Koran K, Ozen F, Aydin D et al. An ultrasensitive and selective “turn off” fluorescent sensor with simple operation for the determination of trace copper (II) ions in water and various beverage samples. Supramolecular Chemistry 2019; 31 (12): 756-766. doi: 10.1080/10610278.2019.1702195
  • 13. Aksuner N, Henden E, Yilmaz I, Cukurovali A. A highly sensitive and selective fluorescent sensor for the determination of copper (II) based on a schiff base. Dyes and Pigments 2009; 83 (2): 211-217. doi: 10.1016/j.dyepig.2009.04.012
  • 14. Aksuner N, Henden E, Yilmaz I, Cukurovali A. Selective optical sensing of copper(II) ions based on a novel cyclobutane-substituted schiff base ligand embedded in polymer films. Sensors and Actuators B: Chemical 2008; 134 (2): 510-515. doi: 10.1016/j.snb.2008.05.041
  • 15. Wang Y, Meng Q, Han Q, He G, Hu Y et al. Selective and sensitive detection of cysteine in water and live cells using a coumarin-$Cu ^{2+}$ fluorescent ensemble. New Journal of Chemistry 2018; 42 (19): 15839-15846. doi: 10.1039/c8nj03809k
  • 16. Kumar A, Mondal S, Kayshap KS, Hira SK, Manna PP et al. Water switched aggregation/disaggregation strategies of a coumarin-naphthalene conjugated sensor and its selectivity towards $Cu ^{2+} and Ag^{+}$ ions along with cell ımaging studies on human osteosarcoma cells (U-2 OS). New Journal of Chemistry 2018; 42 (13): 10983-10988. doi: 10.1039/c8nj01631c
  • 17. Zhang J, Zhao B, Li C, Zhu X, Qiao R. A BODIPY-based “turn-on” fluorescent and colorimetric sensor for selective detection of $Cu ^{2+}$ in aqueous media and its application in cell imaging. Sensors and Actuators B: Chemical 2014; 196 (1): 117-122. doi: 10.1016/j.snb.2014.01.116
  • 18. Hormozi-Nezhad MR, Taghipour M. An ultrasensitive and selective turn-off fluorescent nanoprobe for the detection of copper ions. Analytical Methods 2015; 7 (12): 5067-5073. doi: 10.1039/c5ay00766f
  • 19. Joo DH, Mok JS, Bae GH, Oh SE, Kang JH et al. Colorimetric detection of $Cu ^{2+}$ and fluorescent detection of $PO^{3−}_{4} and S 2−$ by a multifunctional chemosensor. Industrial & Engineering Chemistry Research 2017; 56 (30): 8399-8407. doi: 10.1021/acs.iecr.7b01115
  • 20. Guo Z, Hu T, Wang X, Sun T, Li T et al. Highly sensitive and selective fluorescent sensor for visual detection of $Cu ^{2+}$ in water and food samples based on oligothiophene derivative. Journal of Photochemistry and Photobiology A: Chemistry 2019; 371 (1): 50-58. doi: 10.1016/j.jag.2018.07.004
  • 21. Chang Y, Li B, Mei H, Yang L, Xu K et al. Indole-based colori/fluorimetric probe for selective detection of Cu 2+ and application in living cell imaging. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2020; 226 (1): 117631. doi: 10.1016/j.saa.2019.117631
  • 22. Wu SP, Huang ZM, Liu SR, Chung PK. A pyrene-based highly selective turn-on fluorescent sensor for copper(II) ion and its application in live cell imaging. Journal of Fluorescence 2012; 22 (1): 253-259. doi: 10.1007/s10895-011- 0955-7
  • 23. Jiao X, Xiao Z, Hui P, Liu C, Wang Q et al. A highly selective and pH-tolerance fluorescent probe for $Cu ^{2+}$ based on a novel carbazole-rhodamine hybrid dye. Dyes and Pigments 2019; 160 (1): 633-640. doi: 10.1016/j.dyepig.2018.08.060
  • 24. Li J, Ge J, Zhang Z, Qiang J, Wei T et al. A cyanine dye-based fluorescent probe as ındicator of copper clock reaction for tracing Cu 2+ -catalyzed oxidation of cysteine. Sensors and Actuators B: Chemical 2019; 296 (1): 126578. doi: 10.1016/j.snb.2019.05.055
  • 25. Özen F, Tekin S, Koran K, Sandal S, Görgülü AO. Synthesis, structural characterization, and in vitro anticancer activities of new phenylacrylonitrile derivatives. Applied Biological Chemistry 2016; 59 (1): 239-248. doi: 10.1007/s13765-016-0163-x
  • 26. Buu-Hoi NP, Saint-Ruf G, Lobert B. Oxygen heterocycles. part XIV. hydroxylated 3-awl- and 3-pyridyl-coumarins. Journal of the Chemical Society C: Organic 1968; 16 (1): 2069-2070. doi: 10.1039/J39690002069
  • 27. Elgazzar E, Dere A, Özen F, Koran K, Al-Sehemi AG et al. Design and fabrication of dioxyphenylcoumarin substituted cyclotriphosphazene compounds photodiodes. Physica B: Condensed Matter 2017; 515 (1): 8-17. doi: 10.1016/j.physb.2017.03.025
  • 28. Aydin D. A novel turn on fluorescent probe for the determination of Al 3+ and Zn 2+ ions and its cells applications. Talanta 2020; 210 (1): 120615. doi: 10.1016/j.talanta.2019.120615
  • 29. Qiu S, Cui S, Shi F, Pu S. Novel diarylethene-based fluorescent switching for the detection of Al 3+ and construction of logic circuit. ACS Omega 2019; 4 (1): 14841-14848. doi: 10.1021/acsomega.9b01432
  • 30. Karuk Elmas ŞN, Yilmaz I. A turn off-on fluorescent chemosensor for sequential determination of mercury and biothiols. Journal of Fluorescence 2018; 28 (1): 1451-1458. doi: 10.1007/s10895-018-2320-6
  • 31. Karuk Elmas ŞN, Ozen F, Koran K, Görgülü AO, Sadi G et al. Selective and sensitive fluorescent and colorimetric chemosensor for detection of CO2−3 anions in aqueous solution and living cells. Talanta 2018; 188 (1): 614-622. doi: 10.1016/j.talanta.2018.06.036
  • 32. Huang CY. Determination of binding stoichiometry by the continuous variation method: the Job plot. Methods in Enzymol 1982; 87 (1): 509-525. doi: 10.1016/S0076-6879(82)87029-8
  • 33. Frisch AMJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA et al. Gaussian 09 Revision D.01. 2014.
  • 34. Dennington R, Keith TA, Millam JM. GaussView Version 5. 2009.
  • 35. Becke AD. Becke’s three parameter hybrid method using the LYP correlation functional. The Journal of Chemical Physics 1993; 98 (1): 5648-5652. doi: 10.1063/1.464913
  • 36. Lee C, Hill C, Carolina N. Development of the colic-salvetti correlation-energy formula into a functional of the electron density. Physical Review B 1988; 37 (2): 785-789. doi: 10.1103/PhysRevB.37.785
  • 37. Hay PJ, Wadt WR. Ab initio effective core potentials for molecular calculations. potentials for the transition metal atoms Sc to Hg. The Journal of Chemical Physics 1985; 82 (1): 270-283. doi: 10.1063/1.448799
  • 38. Yang S, Yin B, Xu L, Gao B, Sun H et al. A natural quercetin-based fluorescent sensor for highly sensitive and selective detection of copper ions. Analytical Methods 2015; 7 (1): 4546-4551. doi: 10.1039/C5AY00375J
  • 39. Duarte LGTA, Coelho FL, Germino JC, Costa GG, Berbigier JF et al. A selective proton transfer optical sensor for copper II based on chelation enhancement quenching effect (CHEQ). Dyes and Pigments 2020; 108566. doi: 10.1016/j.dyepig.2020.108566 40. Hildebrand JH, Benesi HA. A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. Journal of the American Chemical Society 1949; 71 (8): 2703-2707. doi: 10.1038/164963b0
  • 40. Duan YW, Tang HY, Guo Y, Song ZK, Peng MJ et al. The synthesis and study of the fluorescent probe for sensing $Cu ^{2+}$ 4 based on a novel coumarin Schiff-base. Chinese Chemistry Letters 2014; 25 (7): 1082-1086. doi: 10.1016/j.cclet.2014.05.001
  • 41. Zhou Z, Li N, Tong A. A new coumarin-based fluorescence turn-on chemodosimeter for Cu $Cu ^{2+}$ in water. Analytica Chimica Acta 2011; 702: 81-86. doi: 10.1016/j.aca.2011.06.041
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: 6
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

The use of water-soluble phthalocyanines as textile dyes in nylon/elastane fabric: fastness and antibacterial effectiveness

Armağan GÜNSEL, Ayşe USLUOĞLU, Ahmet Turgut BİLGİÇLİ, Büşra TOSUN, Gülnur ARABACI, Meryem Nilüfer YARAŞIR

Synthesis, biological evaluation of antioxidant-antibacterial activities and computational studies of novel anthracene- and pyrene-based Schiff base derivatives

Ayşegül GÜMÜŞ, Selçuk GÜMÜŞ, Veysi OKUMUŞ

Characterization, mechanical, and antibacterial properties of nanofibers derived from olive leaf, fumitory, and terebinth extracts

Nilşen SÜNTER EROĞLU, Suat CANOĞLU, Metin YÜKSEK

Meltem GOR BOLEN, Tevhit KARACALİ

Bis benzothiophene Schiff bases: synthesis and in silico-guided biological activity studies

Yasemin ÜNVER, Dilek ÜNLÜER, Serdar DURDAĞI, Şahin DİREKEL

Synthesis and bioactivities of 1-(4-hydroxyphenyl)-2-((heteroaryl)thio)ethanones as carbonic anhydrase I, II and acetylcholinesterase inhibitors

Yeliz DEMİR, İlhami GÜLÇİN, Cavit KAZAZ, Cem YAMALI, Halise İnci GÜL

Voltammetric determination of itopride using carbon paste electrode modified with Gd doped $TiO_2$ nanotubes

Abdulaziz Nabil AMRO, Khadijah EMRAN, Hessah ALANAZI

Preparation, structure elucidation, and antioxidant activity of new bis(thiosemicarbazone) derivatives

Hasan YAKAN

Bestenur YALCİN, Dogan AKCAN, Ibrahim Ertugrul YALCİN, Mehmet Can ALPHAN, Kenan SENTURK, Ibrahim Ilker OZYİGİT, Lutfi ARDA

Atike INCE YARDİMCİ, Metin TANOGLU, Selahattin YİLMAZ, Yusuf SELAMET