New advances in fluorogenic anion chemosensors

Journal of Fluorescence

Volumn 15, Issue 3, 2005, Pages 267-285

  Martínez Máñez, Ramón ^a   Sancenón, Félix ^a  

^a UNIVERSITAT POLITÈCNICA DE VALÈNCIA   (Spain)

Author keywords

Anion; Fluorescence; Sensors

Indexed keywords

ADENOSINETRIPHOSPHATE; COORDINATION REACTIONS; DOSIMETERS; FLUORESCENCE; NEGATIVE IONS; QUENCHING; REACTION KINETICS; SIGNAL PROCESSING; SUPRAMOLECULAR CHEMISTRY;

BINDING SITE-SIGNALLING; CHEMODOSIMETERS; FLUORESCENCE EMISSIONS; FLUOROGENIC CHEMOSENSORS;

CHEMICAL SENSORS;

EID: 21844448582     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10895-005-2626-z     Document Type: Review

References (71)

1. J. Scheerder, J. F. J. Engbersen, and D. N. Reinhoudt (1996). Synthetic receptors for anion complexation. Recl. Trav. Chim. Pays-Bas 115, 307-320.
2. F. P. Schmidtchen and M. Berger (1997). Artificial organic host molecules for anions. Chem. Rev. 97, 1609-1646.
3. P. D. Beer and D. K. Smith (1997). Anion binding and recognition by inorganic based receptors. Prog. Inorg. Chem. 46, 1-96.
4. M. M. G. Antonisse and D. N. Reinhoudt (1998). Neutral anion receptors: Design and application. Chem. Commun. 443-448.
5. P. D. Beer and P. A. Gale (2001). Anion recognition and sensing: The state of the art and future perspectives. Angew. Chem. Int. Ed. 40, 486-516.
6. P. A. Gale (2000). Anion coordination and anion-diercted assembly: Highlights from 1997 and 1998. Coord. Chem. Rev. 199, 181-233.
7. P. A. Gale (2001). Anion receptor chemistry: Highlights from 1999. Coord. Chem. Rev. 213, 79-128.
8. P. A. Gale (2003). Anion and ion-pair receptor chemistry: Highlights from 2000 and 2001. Coord. Chem. Rev. 240, 191-221.
9. L. Fabbrizzi, M. Licchelli, G. Rabaioli, and A. Taglietti (2000). The design of luminescent sensors for anions and ionisable analytes. Coord. Chem. Rev. 205, 85-108.
10. P. D. Beer (1998). Transition-metal receptor systems for the selective recognition and sensing of anionic guest species. Acc. Chem. Res. 31, 71-80.
11. P. D. Beer and J. Cadman, (2000). Electrochemical and optical sensing of anions by transition metal based receptors. Coord. Chem. Rev. 205, 131-155.
12. R. Martínez-Máñez and F. Sancenón (2003). Fluorogenic and chromogenic chemosensors and reagents for anions. Chem. Rev. 103, 4419-4476.
13. P. de Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher, and T. E. Rice (1997). Signaling recognition events with fluorescent sensors and switches. Chem. Rev. 97, 1515-1566.
14. T. Gunnlaugsson, A. P. Davis, G. M. Hussey, J. Tierney, and M. Glynn (2004). Design, synthesis and photophysical studies of simple fluorescent anion PET sensors using charge neutral thiourea receptors. Org. Biomol. Chem. 2, 1856-1863.
15. Z.-Y. Zeng, Y.-B. He, J.-L. Wu, L.-H. Wei, X. Liu, L.-Z. Meng, and X. Yang (2004). Synthesis of two branched fluorescent receptors and their binding properties for dicarboxylate anions. Eur. J. Org. Chem. 2888-2893.
16. Q.-Y. Chen and C. F. Chen (2004). A new fluorescent as well as chromogenic chemosensor for anions based on an anthracene carbamate derivative. Tetrahedron Lett. 45, 6493-6496.
17. M. T. Albelda, J. Aguilar, S. Alves, R. Aucejo, P. Díaz, C. Lodeiro, J. C. Lima, E. García-España, F. Pina, and C. Soriano (2003). Potentiometric, NMR, and fluorescence-emission studies on the binding of adenosine 5′-triphosphate (ATP) by open-chain polyamine receptors containing naphthylmethyl and/or anthrylmethyl groups. Helv. Chim. Acta 86, 3118-3135.
18. K. J. Wallace, W. J. Belcher, D. R. Turner, K. F. Syed, and J. W. Steed (2003). Slow anion exchange, conformational equilibria, and fluorescent sensing in venus flytrap aminopyridinium-based anion hosts. J. Am. Chem. Soc. 125, 9699-9715.
19. -. Org. Lett. 5, 2083-2086.
20. -. J. Org. Chem. 69, 581-583.
21. J. Y. Kwon, N. J. Singh, H. N. Kim, S. K. Kim, K. S. Kim, and J. Yoon (2004). Fluorescent GTP-sensing in aqueous solution of physiological pH. J. Am. Chem. Soc. 126, 8892-8893.
22. A. Ojida, Y. Mito-oka, M. Inoue, and I. Hamachi (2002). First artificial receptors and chemosensors toward phosphorylated peptide in aqueous solution. J. Am. Chem. Soc. 124, 6256-6258.
23. A. Ojida, Y. Mito-oka, K. Sada, and I. Hamachi (2004). Molecular recognition and fluorescence sensing of monophosphorylated peptides in aqueous solution by bis(zinc(II)-dipicolylamine)-based artificial receptors. J. Am. Chem. Soc. 126, 2454-2463.
24. X. Qian and F. Liu (2003). Promoting effects of the hydroxymethyl group on the fluorescent signalling recognition of anions by thioureas. Tetrahedron Lett. 44, 795-799.
25. S.-Y. Liu, Y.-B. He, J.-L. Wu, L.-H. Wei, H.-J. Qin, L.-Z. Meng, and L. Hu (2004). Calix[4]arenes containing thiourea and amide moieties: Neutral receptors towards α,ω-dicarboxylate anions. Org. Biomol. Chem. 2, 1582-1586.
26. F. Otón, F. Tárraga, M. D. Velasco, A. Espinosa, and P. Molina (2004). A new fluoride selective electrochemical and fluorescent chemosensor based on a ferrocene-naphthalene dyad. Chem. Commun. 1658-1659.
27. G. Xu and M. A. Tarr (2004). A novel fluoride sensor based on fluorescence enhancement. Chem. Commun. 1050-1051.
28. E. J. Cho, J. W. Moon, S. W. Ko, J. Y. Lee, S. K. Kim, J. Yoon, and K. C. Nam (2003). A new fluoride selective fluorescent as well as chromogenic chemosensor containing a naphthalene urea derivative. J. Am. Chem. Soc. 125, 12376-12377.
29. J. Y. Lee, E. J. Cho, S. Mukamel, and K. C. Nam (2004). Efficient fluoride-selective fluorescent host: Experiment and theory. J. Org. Chem. 69, 943-950.
30. S.-I. Kondo, M. Nagamine, and Y. Yano (2003). Synthesis and anion recognition properties of 8,8′-dithioureido-2,2′-binaphthalene. Tetrahedron Lett. 44, 8801-8804.
31. Y. Kubo, M. Kato, Y. Misawa, and S. Tokita (2004). A fluorescenceactive 1,3-bis(isothiouronium)-derived naphthalene exhibiting versatile binding modes toward oxoanions in aqueous MeCN solution: New methodology for sensing oxoanions. Tetrahedron Lett. 45, 3769-3773.
32. X. Zhang, L. Guo, F.-Y. Wu, and Y.-B. Jiang (2003). Development of fluorescent sensing of anions under excited-state intermolecular proton transfer signaling mechanism. Org. Lett. 5, 2667-2670.
33. C.-F. Chen and Q.-Y. Chen (2004). A tetra-sulfonamide derivative bearing two dansyl groups designed as a new fluoride selective fluorescent chemosensor. Terahedron. Lett. 45, 3957-3960.
34. R. Miao, Q.-Y. Zheng, C.-F. Chen, and Z.-T. Huang (2004). A Clinked peptidocalix[4]arene bearing four dansyl groups: A highly selective fluorescence chemosensor for fluoride ions. Tetrahedron Lett. 45, 4959-4962.
35. T. Gunnlaugsson, P. E. Kruger, T. C. Lee, R. Parkesh, F. M. Pfeffer, and G. M. Hussey (2003). Dual responsive chemosensors for anions: The combination of fluorescent PET (photoinduced electron transfer) and colorimetric chemosensors in a single molecule. Tetrahedron Lett. 44, 6575-6578.
36. D. H. Lee, S. Y. Kim, and J.-L Hong (2004). A fluorescent pyrophosphatesensor with high selectivity over ATP in water. Angew. Chem. Int. Ed. 43, 4777-4780.
37. Y. Kaneyiko, R. Naganawa, and H. Tao (2004). Fluorescence detection of ATP based on the ATP-mediated aggregation of pyreneappended boronic acid on a polycation. Chem. Commun. 1006-1007.
38. H. Abe, Y. Mawatari, H. Teraoka, K. Fujimoto, and M. Inouye (2004). Synthesis and molecular recognition of pyrenophanes with polycationic or amphiphilic functionalities: Artificial plate-shaped cavitant incorporating arenes and nucleotides in water. J. Org. Chem. 69, 495-504.
39. L.-J. Kuo, J.-H. Liao, C.-T. Chen, C.-H. Huang, C.-S. Chen, and J.-M. Fang (2003). Two-arm ferrocene amide compounds: Synclinal conformations for selective sensing of dihydrogen phosphate ion. Org. Lett. 5, 1821-1824.
40. R. Pohl, D. Aldakov, P. Kubát, K. Jursíková, M. Marquez, and P. Anzenbacher Jr. (2004). Strategies toward improving the performance of fluorescence-based sensors for inorganic anions. Chem. Commun. 1282-1283.
41. J. Ren, Q. Wang, D. Qu, X. Zhao, and H. Tian (2004). New fluoride-selective red fluorescent chemosensors based on perylene derivatives. Chem. Lett. 33, 974-975.
42. J. Ren, X.-L. Zhao, Q.-C. Wang, C.-E Ku, D.-H. Qu, C. P. Chang, and H. Tian (2005). New fluoride fluorescent chemosensors based on perylene derivatives linked by urea. Dyes Pigments 64, 193-200.
43. S. Arimori, M. G. Davidson, T. M. Fyles, T. G. Hibbert, T. D. James, and G. I. Kociok-Köhn (2004). Synthesis and structural characterisation of the first bis(bora)calixarene: A selective, bidentate, fluorescent fluoride sensor. Chem. Commun. 1640-1641.
44. L.-L. Zhou, H. Sun, H.-P. Li, H. Wang, X.-H. Zhang, S.-K. Wu, and S.-T. Lee (2004). A novel colorimetric and fluorescent anion chemosensor based on the flavone quasi-crown ether-metal complex. Org. Lett. 6, 1071-1074.
45. V. Amendola, L. Fabbrizzi, and E. Monzani (2004). A concave fluorescent sensor for anions based on 6-methoxy-1-methylquinolinium. E. Chem. Eur. J. 10, 76-82.
46. A. Kovalchuk, J. L. Bricks, G. Reck, K. Rurack, B. Schulz, A. Szumna, and H. Weißhoff (2004). A charge transfer-type fluorescent molecular sensor that "lights up" in the visible upon hydrogen bond-assisted complexation of anions. Chem. Commun. 1946-1947.
47. H. Tong, L. Wang, X. Jing, and F. Wang (2003). "Turn-on" conjugated polymer fluorescent chemosensor for fluoride ion. Macromolecules 36, 2584-2586.
48. L. Basabe-Desmonts, J. Beld, R. S. Zimmerman, J. Hernando, P. Mela, M. F. García Parajó, N. F. van Hulst, A. van den Bergh, D. N. Reinhoudt, and M. Crego-Calama (2004). A simple approach to sensor discovery and fabrication on self-assembled monolayers on glass. J. Am. Chem. Soc. 126, 7293-7299.
49. J. L. Sessler, J. M. Davis, V. Král, T. Kimbrough, and V. Lynch (2003). Water soluble sapphyrins: Potential fluorescent phosphate anion sensors. Org. Biomol. Chem. 1, 4113-4123.
50. A. Ojida, M. Inoue, Y. Mito-oka, and I. Hamachi (2003). Cross-linking strategy for molecular recognition nad fluorescent sensing of a multi-phosphorylated peptide in aqueous solution. J. Am. Chem. Soc. 125, 10184-10185.
51. B. García-Acosta, X. Albiach-Martí, E. García, L. Gil, R. Martínez-Máñez, K. Rurack, F. Sancenón, and J. Soto (2004). Coordinative and electrostatic forces in action: From the design of differential chromogenic anion sensors to selective carboxylate recognition. Chem. Commun. 774-775.
52. S.-S. Sun, A. J. Lees, and P. Y. Zavalij (2003). Highly sensitive luminescent metal-complex receptors for anions through charge-assited amide hydrogen bonding. Inorg. Chem. 42, 3445-3453.
53. 2 and selected anions. Coord. Chem. Rev. 205, 109-130.
54. P. Atkinson, Y. Bretonniere, and D. Parker (2004). Chemoselective signalling of selected phospho-anions using lanthanide luminescence. Chem. Commun. 438-439.
55. Y. Bretonniere, M. J. Cann, D. Parker, and R. Slater (2004). Design, synthesis and evaluation of ratiometric probes for hydrogencarbonate based on europium emission. Org. Biomol. Chem. 2, 1624-1632.
56. 3+ complex with pendant aza-15-crown-5 showing recognition of lactate and salicylate in aqueous solution. Tetrahedron Lett. 45, 6055-6058.
57. Z. Lin, M. Wu, M. Schäferling, and O. S. Wolfbeis (2004). Fluorescent imaging of citrate and other intermediates in the citric acid cycle. Angew. Chem. Int. Ed. 43, 1735-1738.
58. - anion. Chem. Commun. 2238-2239.
59. M. J. Perry (1995). In J. R. Birch and E. S. Lennox (Eds.), Monoclonal Antibodies: Principles and Applications, Wiley-Liss, New York, pp. 107-120.
60. S. L. Wiskur, H. Aït-Haddou, J. J. Lavigne, and E. V. Anslyn (2001). Teaching old indicators new tricks. Acc. Chem. Res. 34, 963-972.
61. M. Boiocchi, M. Bonizzoni, L. Fabbrizzi, G. Piovani, and A. Taglietti (2004). A dimetallic cage with long ellipsoidal cavity for the fluorescent detection of dicarboxylate anions in water. Angew. Chem. Int. Ed. 43, 3847-3852.
62. K. Niikura and E. V. Anslyn (2003). Triton X-100 enhances ion-pair-driven molecular recognition in aqueous media. Further work on a chemosensor for inositol triphosphate. J. Org. Chem. 68, 10156-10157.
63. T.-H. Kim and T. M. Swager (2003). A fluorescent self-amplifying wavelenght-responsive sensory polymer for fluoride ion. Angew. Chem. Int. Ed. 42, 4803-4806.
64. F. Tanaka, N. Mase, and C. F. Barbas, III (2004). Determination of cysteine concentration by fluorescence increase: Reaction of cysteine with a fluorogenic aldehyde. Chem. Commun. 1762-1763.
65. A. Coskun and E. U. Akkaya (2004). Difluorobora-s-diazaindacene dyes as highly selective dosimetric reagents for fluoride anions. Tetrahedron Lett. 45, 4947-4949.
66. R. Badugu, J. R. Lakowicz, and C. D. Geddes (2005). Cyanide-sensitive fluorescent probes. Dyes Pigments 64, 49-55.
67. N. DiCesare and J. R. Lakowicz (2002). New sensitive and selective fluorescent probes for fluoride using boronic acids. Anal. Biochem. 301, 111-116.
68. R. Bagudu, J. R. Lakowicz, and C. D. Geddes (2004). Fluorescence intensity and lifetime-based cyanide sensitive probes for physiological safeguard. Anal. Chim. Acta 522, 9-17.
69. R. Badugu, J. R. Lakowicz, and C. D. Geddes (2004). Excitation and emission wavelenght ratiometric cyanide-sensitive probes for physiological sensing. Anal. Biochem. 327, 82-90.
70. J. V. Ros-Lis B. García, D. Jiménez, R. Martínez-Máñez, F. Sancenón, J. Soto, F. Gonzalvo, and M. C. Valldecabres (2004). Squaraines as fluoro-chromogenic probes for thiol-containing compounds and their application to the detection of biorelevant thiols. J. Am. Chem. Soc. 126, 4064-4065.
71. J. A. Cruz-Aguado, Y. Chen, Z. Zhang, N. H. Elowe, M. A. Brook, and J. D. Brennan (2004). Ultrasensitive ATP detection using firefly luciferase entrapped in sugar-modified sol-gel-derived silica. J. Am. Chem. Soc., 126, 6878-6879.