The Investigation of Fluorescence Biothiol Sensor Properties of 2-(N-hexyl-carbazole-3'-yl)-4- formylpyridine

Yıl 2021, Cilt: 11 Sayı: 3, 2184 - 2194, 01.09.2021

Nuray Altınölçek , Ahmet Battal

https://doi.org/10.21597/jist.941474

Cited By: 1

Öz

The biothiol sensor properties of 2-(N-hexyl-carbazole-3'-yl)-4-formylpyridine molecule were examined. This probe has carbazole moiety as a fluorophore and aldehyde group as a recognition site. Three different biothiol molecules as an analytes were chosen that they are cysteine (Cys), homocysteine (Hcy) and glutathione (GSH). We monitored the adduct formation between probe and analyte (biothiols) by 1H NMR, MS, UV-vis and PL Spectrometers.

Anahtar Kelimeler

Aldehyde group, Carbazole, Cysteine, Glutathione, Homocysteine, Biothiol sensor

Proje Numarası

1059B191800354

Kaynakça

• Altinolcek N, Battal A, Tavasli M, Peveler WJ, Yu HA, Skabara PJ, 2020. Synthesis of novel multifunctional carbazole-based molecules and their thermal, electrochemical and optical properties. Beilstein Journal of Organic Chemistry, 16, 1066-1074.
• Babür B, Seferoğlu N, Öcal M, Sonugur G, Akbulut H, Seferoğlu Z, 2016. A novel fluorescence turn-on coumarin-pyrazolone based monomethine probe for biothiol detection. Tetrahedron, 72(30), 4498-4502.
• Baert JJ, De Clippeleer J, De Cooman L, Aerts G, 2015. Exploring the Binding Behavior of Beer Staling Aldehydes in Model Systems. Journal of the American Society of Brewing Chemists, 73(1), 100-108.
• Chai G, Liu Q, Fei Q, Zhang J, Sun X, Shan H, Feng G, Huan Y, 2018. A selective and sensitive fluorescent sensor for cysteine detection based on bi-8-carboxamidoquinoline derivative and Cu2+ complex. Luminescence, 33(1), 153-160.
• Chen C, Zhou L, Huang X, Liu W, 2017. Rapid detection of intracellular Cys over Hcy and GSH using a novel two-photon coumarinocoumarin-based colorimetric and fluorescent probe. Journal of Materials Chemistry B, 5(29), 5892-5897.
• Ding S, Liu M, Hong Y, 2018. Biothiol-specific fluorescent probes with aggregation-induced emission characteristics. Science China Chemistry, 61(8), 882-891.
• Fu Z-H, Han X, Shao Y, Fang J, Zhang Z-H, Wang Y-W, Peng Y, 2017. Fluorescein-Based Chromogenic and Ratiometric Fluorescence Probe for Highly Selective Detection of Cysteine and Its Application in Bioimaging. Analytical Chemistry, 89(3), 1937-1944.
• Hopkinson RJ, Barlow PS, Schofield CJ, Claridge TDW, 2010. Studies on the reaction of glutathione and formaldehyde using NMR. Organic & Biomolecular Chemistry, 8(21), 4915-4920.
• Hu Y, Heo CH, Kim G, Jun EJ, Yin J, Kim HM, Yoon J, 2015. One-Photon and Two-Photon Sensing of Biothiols Using a Bis-Pyrene-Cu(II) Ensemble and Its Application To Image GSH in the Cells and Tissues. Analytical Chemistry, 87(6), 3308-3313.
• Jang G, Kim J, Kim D, Lee TS, 2015. Synthesis of triphenylamine-containing conjugated polyelectrolyte and fabrication of fluorescence color-changeable, paper-based sensor strips for biothiol detection. Polymer Chemistry, 6(5), 714-720.
• Kamps JJAG, Hopkinson RJ, Schofield CJ, Claridge TDW, 2019. How formaldehyde reacts with amino acids. Communications Chemistry, 2(1), 126.
• Kaur M, Yoon B, Kumar R, Cho Min J, Kim HJ, Kim JS, Choi DH, 2014. A Carbazole Based Bimodal "Turn-On" Fluorescent Probe for Biothiols (Cysteine/Homocysteine) and Fluoride: Sensing, Imaging and its Applications. Bulletin of the Korean Chemical Society, 35(12), 3437-3442.
• Li C, Shang X, Chen Y, Chen H, Wang T, 2019. Biothiol detection by “ON-OFF-ON” fluorescence probe based on anthracene derivative. Journal of Molecular Structure, 1179, 623-629.
• Liu T, Huo F, Yin C, Li J, Niu L, 2015. A highly selective fluorescence sensor for cysteine/homocysteine and its application in bioimaging. RSC Advances, 5(36), 28713-28716.
• Mahapatra AK, Roy J, Sahoo P, Mukhopadhyay SK, Banik A, Mandal D, 2013. Carbazole phenylthiosemicarbazone-based ensemble of Hg2+ as selective fluorescence turn-on sensor toward cysteine in water. Tetrahedron Letters, 54(23), 2946-2951.
• Mei J, Wang Y, Tong J, Wang J, Qin A, Sun JZ, Tang BZ, 2013. Discriminatory Detection of Cysteine and Homocysteine Based on Dialdehyde-Functionalized Aggregation-Induced Emission Fluorophores. Chemistry – A European Journal, 19(2), 613-620.
• Niu L-Y, Guan Y-S, Chen Y-Z, Wu L-Z, Tung C-H, Yang Q-Z, 2012. BODIPY-Based Ratiometric Fluorescent Sensor for Highly Selective Detection of Glutathione over Cysteine and Homocysteine. Journal of the American Chemical Society, 134(46), 18928-18931.
• Peng L, Zhou Z, Wei R, Li K, Song P, Tong A, 2014. A fluorescent probe for thiols based on aggregation-induced emission and its application in live-cell imaging. Dyes and Pigments, 108, 24-31.
• Sok N, Nikolantonaki M, Guyot S, Nguyen TD, Viaux A-S, Bagala F, Rousselin Y, Husson F, Gougeon R, Saurel R, 2017. Design of new sensitive α,β-unsaturated carbonyl 1,8-naphtalimide fluorescent probes for thiol bioimaging. Sensors and Actuators B: Chemical, 242: 865-871.
• Song H, Zhang J, Wang X, Zhou Y, Xu C, Pang X, Peng X, 2018. A novel “turn-on” fluorescent probe with a large stokes shift for homocysteine and cysteine: Performance in living cells and zebrafish. Sensors and Actuators B: Chemical, 259, 233-240.
• Tong H, Zhao J, Li X, Zhang Y, Ma S, Lou K, Wang W, 2017. Orchestration of dual cyclization processes and dual quenching mechanisms for enhanced selectivity and drastic fluorescence turn-on detection of cysteine. Chemical Communications, 53(25), 3583-3586.
• Wang F, Zhou L, Zhao C, Wang R, Fei Q, Luo S, Guo Z, Tian H, Zhu W-H, 2015. A dual-response BODIPY-based fluorescent probe for the discrimination of glutathione from cystein and homocystein. Chemical Science, 6(4), 2584-2589.
• Wang J, Zhang F, Yang L, Wang B, Song X, 2021. A red-emitting fluorescent probe for sensing and imaging biothiols in living cells. Journal of Luminescence, 234, 117994.
• Wang L, Zhuo S, Tang H, Cao D, 2018. An efficient fluorescent probe for rapid sensing of different concentration ranges of cysteine with two-stage ratiometric signals. Dyes and Pigments, 157, 284-289.
• Wang Y, Zhu M, Jiang E, Hua R, Na R, Li QX, 2017. A Simple and Rapid Turn On ESIPT Fluorescent Probe for Colorimetric and Ratiometric Detection of Biothiols in Living Cells. Scientific Reports, 7(1), 4377.
• Yue Y, Guo Y, Xu J, Shao S, 2011. A Bodipy-based derivative for selective fluorescence sensing of homocysteine and cysteine. New Journal of Chemistry, 35(1), 61-64.
• Zhai D, Lee S-C, Yun S-W, Chang Y-T, 2013. A ratiometric fluorescent dye for the detection of glutathione in live cells and liver cancer tissue. Chemical Communications, 49(65), 7207-7209.
• Zhang H, Liu R, Liu J, Li L, Wang P, Yao SQ, Xu Z, Sun H, 2016. A minimalist fluorescent probe for differentiating Cys, Hcy and GSH in live cells. Chemical Science, 7(1), 256-260.
• Zhang J, Wang N, Ji X, Tao Y, Wang J, Zhao W, 2020. BODIPY-Based Fluorescent Probes for Biothiols. Chemistry – A European Journal, 26(19), 4172-4192.