A boron-dipyrromethene-based fluorescent probe for colorimetric and ratiometric detection of sulfite

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 22, 2011, Pages 11935-11939

  Gu, Xianfeng ^a,b   Liu, Chunhua ^c   Zhu, Yi Chun ^a   Zhu, Yi Zhun ^a  

^a FUDAN UNIVERSITY   (China)

^b PEKING UNIVERSITY   (China)

^c NANKAI UNIVERSITY   (China)

Author keywords

Boron dipyrromethene; ratiometric fluorescent probe; sulfite

Indexed keywords

ABSORPTION AND EMISSION SPECTRA; BORON-DIPYRROMETHENE; FLUORESCENT PROBES; FLUOROGENICS; PROTECTIVE GROUP; RATIOMETRIC; RATIOMETRIC DETECTION; RED SHIFT; SELECTIVE DETECTION; SULFITE;

BORON COMPOUNDS; COLOR; COLORIMETRY; EMISSION SPECTROSCOPY; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; PROBES;

BORON;

4,4 DIFLUORO 4 BORA 3A,4A DIAZA S INDACENE; 4,4-DIFLUORO-4-BORA-3A,4A-DIAZA-S-INDACENE; BORON; BORON DERIVATIVE; DIPYRROMETHENE; DRUG DERIVATIVE; FLUORESCENT DYE; PORPHOBILINOGEN; SULFITE;

ARTICLE; CHEMISTRY; COLORIMETRY; EVALUATION; METHODOLOGY; SPECTROFLUOROMETRY;

BORON; BORON COMPOUNDS; COLORIMETRY; FLUORESCENT DYES; PORPHOBILINOGEN; SPECTROMETRY, FLUORESCENCE; SULFITES;

EID: 81255195794     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf2032928     Document Type: Article

References (29)

1. Pizzoferrato, L.; Di Lullo, G.; Quattrucci, E. Determination of free, bound and total sulphites in foods by indirect photometry-HPLC Food Chem. 1998, 63, 275
2. Araujo, A. N.; Couto, C. M. C. M.; Lima, J. L. F. C.; Montenegro, M. C. B. S. M. Determination of SO2 in wines using a flow injection analysis system with potentiometric detection J. Agric. Food Chem. 1998, 46, 168
3. Lowinsohn, D.; Bertotti, M. Determination of sulphite in wine by coulometric titration Food Addit. Contam. 2001, 18, 773
4. Silva, K. R. B.; Raimundo, I. M.; Gimenez, I. F.; Alves, O. L. Optical sensor for sulfur dioxide determination in wines J. Agric. Food Chem. 2006, 54, 8697
5. Koch, M.; Köppen, R.; Siegel, D.; Witt, A.; Nehls, I. Determination of Total Sulfite in Wine by Ion Chromatography after In-Sample Oxidation J. Agric. Food Chem. 2010, 58, 9463
6. Choi, M. G.; Hwang, J.; Eor, S.; Chang, S. K. Chromogenic and fluorogenic signaling of sulfite by selective deprotection of resorufin levulinate Org. Lett. 2010, 12, 5624
7. Mohr, G. J. A chromoreactand for the selective detection of HSO3- based on the reversible bisulfite addition reaction in polymer membranes Chem. Commun. (Cambridge) 2002, 2646
8. Sun, Y. M.; Zhong, C.; Gong, R.; Mu, H. L.; Fu, E. Q. A Ratiometric Fluorescent Chemodosimeter with Selective Recognition for Sulfite in Aqueous Solution J. Org. Chem. 2009, 74, 7943
9. Carballo, R.; Dall'Orto, V. C.; Lo Balbo, A.; Rezzano, I. Determination of sulfite by flow injection analysis using a poly [Ni-(protoporphyrin IX)] chemically modified electrode Sens. Actuators, B 2003, 88, 155
10. Kalimuthu, P.; Tkac, J.; Kappler, U.; Davis, J. J.; Bernhardt, P. V. Highly Sensitive and Stable Electrochemical Sulfite Biosensor Incorporating a Bacterial Sulfite Dehydrogenase Anal. Chem. 2010, 82, 7374
11. Kumar, S. S.; Narayanan, S. S. Electrocatalytic oxidation of sulfite on a nickel aquapentacyanoferrate modified electrode: Application for simple and selective determination Electroanalysis 2008, 20, 1427
12. Gale, P. A. Structural and molecular recognition studies with acyclic anion receptors Acc. Chem. Res. 2006, 39, 465
13. Huang, X. M.; Guo, Z. Q.; Zhu, W. H.; Xie, Y. S.; Tian, H. A colorimetric and fluorescent turn-on sensor for pyrophosphate anion based on a dicyanomethylene-4H-chromene framework Chem. Commun. 2008, 5143
14. Kim, S. K.; Lee, D. H.; Hong, J. I.; Yoon, J. Chemosensors for Pyrophosphate Acc. Chem. Res. 2009, 42, 23
15. Lee, C. H.; Miyaji, H.; Yoon, D. W.; Sessler, J. L. Strapped and other topographically nonplanar calixpyrrole analogues. Improved anion receptors Chem. Commun. 2008, 24
16. Martinez-Manez, R.; Sancenon, F. Fluorogenic and chromogenic chemosensors and reagents for anions Chem. Rev. 2003, 103, 4419
17. Xu, Z.; Singh, N. J.; Lim, J.; Pan, J.; Kim, H. N.; Park, S.; Kim, K. S.; Yoon, J. Unique Sandwich Stacking of Pyrene-Adenine-Pyrene for Selective and Ratiometric Fluorescent Sensing of ATP at Physiological pH J. Am. Chem. Soc. 2009, 131, 15528
18. Zhao, J. Z.; Fyles, T. M.; James, T. D. Chiral binol-bisboronic acid as fluorescence sensor for sugar acids Angew. Chem. In.t Edit. 2004, 43, 3461
19. Gunnlaugsson, T.; Glynn, M.; Tocci, M. G.; Kruger, E. P.; Pfeffer, M. F. Anion recognition and sensing in organic and aqueous media using luminescent and colorimetric sensors Coord. Chem. Rev. 2006, 250, 3094
20. Komatsu, K.; Urano, Y.; Kojima, H.; Nagano, T. Development of an iminocoumarin-based zinc sensor suitable for ratiometric fluorescence imaging of neuronal zinc J. Am. Chem. Soc. 2007, 129, 13447
21. Lin, W. Y.; Long, L. L.; Chen, B. B.; Tan, W. A Ratiometric Fluorescent Probe for Hypochlorite Based on a Deoximation Reaction Chem.-Eur. J. 2009, 15, 2305
22. Qian, F.; Zhang, C. L.; Zhang, Y. M.; He, W. J.; Gao, X.; Hu, P.; Guo, Z. J. Visible Light Excitable Zn2+ Fluorescent Sensor Derived from an Intramolecular Charge Transfer Fluorophore and Its in Vitro and in Vivo Application J. Am. Chem. Soc. 2009, 131, 1460
23. Srikun, D.; Miller, E. W.; Dornaille, D. W.; Chang, C. J. An ICT-Based approach to ratiometric fluorescence imaging of hydrogen peroxide produced in living cells J. Am. Chem. Soc. 2008, 130, 4596
24. Cho, D. G.; Sessler, J. L. Modern reaction-based indicator systems Chem. Soc. Rev. 2009, 38, 1647
25. Nolan, E. M.; Lippard, S. J. Tools and tactics for the optical detection of mercuric ion Chem. Rev. 2008, 108, 3443
26. Damha, M. J.; Lackey, J. G.; Mitra, D.; Somoza, M. M.; Cerrina, F. Acetal Levulinyl Ester (ALE) Groups for 2 ′-Hydroxyl Protection of Ribonucleosides in the Synthesis of Oligoribonucleotides on Glass and Microarrays J. Am. Chem. Soc. 2009, 131, 8496
27. Ono, M.; Itoh, I. A New Deprotection Method for Levulinyl Protecting Groups under Neutral Conditions Chem. Lett. 1988, 585
28. Zhao, C.; Zhou, Y.; Lin, Q.; Zhu, L.; Feng, P.; Zhang, Y.; Cao, J. Development of an indole-based boron-dipyrromethene fluorescent probe for benzenethiols J. Phys. Chem. B 2011, 115, 642
29. Zhao, C.; Feng, P.; Cao, J.; Zhang, Y.; Wang, X.; Yang, Y.; Zhang, Y.; Zhang, J. 6-Hydroxyindole-Based Borondipyrromethene: Synthesis and Spectroscopic Studies. Org. Biomol. Chem. 2011, DOI: 10.1039/C1OB06200J.