Abstract
In the presented paper we investigated a 2-pyridylthiazole derivative, 4-phenyl-2-(2-pyridyl)thiazole (2-PTP), as the molecular fluorescent switches. It was firstly found that 2-PTP could perform a “turn-on” fluorescent sensing for Fe(III) with selectivity and reversibility. A 2:1 stoichiometry between 2-PTP and Fe(III) was determined according to the molar ratio method. The binding constant was evaluated as (1.90 ± 0.05) × 105 (L/mol)2. The detection limit was found as 2.2 × 10−7 M (S/N = 3). Secondly, 2-PTP also exhibited a pH-dependent dual-emission. The pK a(2-PTP-H+/2-PTP) value was then estimated as 2.0. To explain the identical emission at 479 nm of both the Fe(III) coordinated form and the protonated form of the ligand, we proposed a “locked” conformation. Finally, combining the two external stimuli as inputs, an OR logic gate was constructed using the fluorescent emission at 479 nm as the output channel.
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de Silva AP, Gunaratne HQN, Gunnaugsson T, Huxley AJM, McCoy CP, Radmacher JT, Rice TE (1997) Signaling recognition events with fluorescent sensors and switches. Chem Rev 97:1515–1566
Valuer B (2002) Molecular fluorescence: principles and applications. Wiley-VCH, Weinheim
Feringa BL (2001) Molecular switches. Wiley-VCH, Weinheim
Szacilowski K (2008) Digital information processing in molecular systems. Chem Rev 108:3481–3548
Gonçalves MST (2009) Fluorescent labeling of biomolecules with organic probes. Chem Rev 109:190–212
Terai T, Nagano T (2013) Small-molecule fluorophores and fluorescent probes for bioimaging. Pflugers Arch - Eur J Physiol 465:347–359
Dai S, Schwendtmayer C, Schürmann P, Ramaswamy S, Eklund H (2000) Redox signaling in chloroplasts: cleavage of disulfides by an iron-sulfur cluster. Science 287:655–658
Beulter E (2004) “pumping” iron: the proteins. Science 306:2051–2053
Kaplan CD, Kaplan J (2009) Iron acquisition and transcriptional regulation. Chem Rev 109:4536–4552
Theil EC, Goss DJ (2009) Living with iron (and oxygen): questions and answers about iron homeostasis. Chem Rev 109:4568–4579
Atkinson A, Winge DR (2009) Metal acquisition and availability in the mitochondria. Chem Rev 109:4708–4721
Levi S, Rovida E (2009) The role of iron in mitochondrial function. Biochim Biophys Acta 1790:629–636
Cabantchik ZI (2014) Labile iron in cells and body fluids. Physiology, pathology and pharmacology. Front Pharmacol 5: 45
Sahoo SK, Sharma D, Bera RK, Crisponi G, Callan JF (2012) Iron(III) selective molecular and supramolecular fluorescent probes. Chem Soc Rev 41:7195–7227
Wang B, Hai J, Liu Z, Wang Q, Yang Z, Sun S (2010) Selective detection of iron(III) by rhodamine-modified Fe3O4 nanoparticles. Angew Chem Int Ed 49:4576–4579
Lee MH, Giap TV, Kim SH, Lee YH, Kang C, Kim JS (2010) A novel strategy to selectively detect Fe(III) in aqueous media driven by hydrolysis of a rhodamine 6G Schiff base. Chem Commun 46:1407–1409
Yang Z, She M, Yin B, Cui J, Zhang Y, Sun W, Li J, Shi Z (2011) Three rhodamine-based “off-on” chemosensors with high selectivity and sensitivity for Fe3+ imaging in living cells. J Organomet Chem 77:1143–1147
Chen W-D, Gong W-T, Ye Z-Q, Lin Y, Ning G-L (2013) FRET-based ratiometric fluorescent probes for selective Fe3+ sensing and their applications in mitochondria. Dalton Trans 42:10093–10096
Sui B, Tang S, Liu T, Kim B, Belfield KD (2014) Novel BODIPY-based fluorescence turn-on sensor for Fe3+ and its bioimaging application in living cells. ACS Appl Mater Interfaces 6:18408–18412
Li G, Tang J, Ding P, Ye Y (2015) A rohdamine-benzimidazole based chemosensor for Fe3+ and its application in living cells. J Fluoresc. doi:10.1007/s10895-0151696-9
Zheng M-H, Jin J-Y, Sun W, Yan C-H (2006) A new series of fluorescent 5-methoxy-2-pyridylthiazoles with a pH-sensitive dual-emission. New J Chem 30:1196–1196
Zheng M-H, Zhang M-M, Li H-H, Jin J-Y (2012) Digital pH fluorescent sensing shown by small organic molecules. J Fluoresc 22:1421–1424
Zheng M-H, Sun W, Jin J-Y, Yan C-H (2014) Molecular keypad locks based on gated photochromism and enhanced fluorescence by protonation effects. J Fluoresc 14:1169–1176
Zheng M-H, Hu X, Yang M-Y, Jin J-Y (2015) Ratiometrically fluorescent sensing of Zn(II) based on dual-emission of 2-pyridylthiazole derivatives. J Fluoresc 25:1831–1834
Khoroshilov GE, Yarotskii YV, Brovarets VS, Chernega AN (2010) Synthesis and structure of N-(aroylmethyl)-2-(4-aryl-2-thiazolyl)pyridinium bromides. Zh Org Farm Khim 8:57–60
Knott RF, Breckenridge JG (1954) Analogues of 2,2′-bipyridyl with isoquinoline and thiazole rings. Part I. Can J Chem 32:512–522
Yang R, Li K, Wang K, Zhao F, Li N, Liu F (2003) Porphyrin assembly on β-cyclodextrin for selective sensing and detection of a zinc ion based on the dual emission fluorescence ratio. Anal Chem 75:612–621
Du J, Fan J, Peng X, Li H, Sun S (2010) The quinoline derivative of ratiometric and sensitive fluorescent zinc probe based on deprotonation. Sensors Actuators B 144:337–341
Shortreed M, Kopelman R, Kuhn M, Hoyland B (1997) Fluorescent fiber-optic calcium sensor for physiological measurements. Anal Chem 68:1414–1418
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We thanks the financial supports from the National Natural Science Foundation of China (NSFC 21062023).
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Yang, MY., Zhao, XL., Zheng, MH. et al. Fluorescent Sensing of both Fe(III) and pH Based on 4-Phenyl-2-(2-Pyridyl)Thiazole and Construction of OR Logic Function. J Fluoresc 26, 1653–1657 (2016). https://doi.org/10.1007/s10895-016-1855-7
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DOI: https://doi.org/10.1007/s10895-016-1855-7