Chromogenic sensors for anionic species based on indicator displacement approach

Mini-Reviews in Organic Chemistry

Volumn 9, Issue 1, 2012, Pages 118-124

  Liu, Kai ^a   Su, Xiumei ^a   Huo, Jianzhong ^a  

^a TIANJIN NORMAL UNIVERSITY   (China)

Author keywords

Indicator displacement assays; Molecular recognition; Optical sensors; Supramolecular chemistry

Indexed keywords

EID: 83455244905     PISSN: 1570193X     EISSN: None     Source Type: Journal    
DOI: 10.2174/157019312799079901     Document Type: Article

References (50)

1. Gale, P.A. Anion coordination and anion-directed assembly: highlights from 1997 and 1998. Coord. Chem. Rev., 2000, 199 (1), 181-233.
2. Schug, K.A.; Linder, W. Noncovalent binding between guanidinium and anionic groups: focus on biological- and synthetic-based arginine/guanidinium interactions with phosph[on]ate and sulf[on]ate residues. Chem. Rev., 2005, 105 (1), 67-114.
3. Kruppa, M.; König, B. Reversible coordinative bonds in molecular recognition. Chem. Rev., 2006, 106 (9), 3520-3560.
4. Mao, S.; Liu, K.; Lu, F.; Du, L. Colorimetric sensors based on hydrogenbond- induced 􀀁-delocalization and/or anion-triggered deprotonation. Mini- Rev. Org. Chem., 2010, 7 (3), 221-229.
5. Huh, S.; Wiench, J.W.; Yoo, J.-C.; Pruski, M.; Lin, V.S.-Y. Organic Functionalization and morphology control of mesoporous silicas via a cocondensation synthesis method. Chem. Mater., 2003, 15 (22), 4247-4256.
6. Martínez-Máñez, R.; Sancenón, F. Fluorogenic and chromogenic chemosensors and reagents for anions. Chem. Rev., 2003, 103 (11), 4419-4476.
7. Nguyen, B.T.; Anslyn, E.V. Indicator-displacement assays. Coord. Chem. Rev., 2006, 250 (23-24), 3118-3127.
8. Gale, P.A.; Twyman, L.J.; Handlin, C.I.; Sessler, J.L. A colourimetric calix[4]pyrrole-4-nitrophenolate based anion sensor. Chem. Commun., 1999, 1851-1852.
9. Costero, A.M.; Banuls, M.J.; Aurell, M.J.; De Arellano, M.C.R. Biphenyl macrolactams as colorimetric sensors for anions through displacement reactions. J. Incl. Phenom. Macro., 2006, 54 (1), 61-66.
10. Gale, P.A. Anion and ion-pair receptor chemistry: highlights from 2000 and 2001. Coord. Chem. Rev., 2003, 240 (1-2), 191-221.
11. Nicolini, J.; Testoni, F.M.; Schuhmacher, S.M.; Machado, V.G. Use of the interaction of a boronic acid with a merocyanine to develop an anionic colorimetric assay. Tetrahedron Lett., 2007, 48 (19), 3467-3470.
12. Linn, M.M.; Poncio, D.C.; Machado, V.G. An anionic chromogenic sensor based on the competition between the anion and a merocyanine solvatochromic dye for calix[4]pyrrole as a receptor site. Tetrahedron Lett., 2007, 48 (26), 4547-4551.
13. Ahn, Y.-H.; Lee, J.-S.; Chang, Y.-T. Selective human serum albumin sensor from the screening of a fluorescent rosamine library. J. Combin. Chem., 2008, 10 (3), 376-380.
14. Cane, D.E. Enzymic formation of sesquiterpenes. Chem. Rev., 1990, 90 (7), 1089-1103.
15. Chen, K.-H.; Liao, J.-H.; Chan, H.-Y.; Fang, J.-M. A fluorescence sensor for detection of geranyl pyrophosphate by the chemo-ensemble method. J. Org. Chem., 2008, 74 (2), 895-898.
16. Basurto, S.; Torroba, T.; Comes, M.; Martínez-Máñez, R.; Sancenón, F.; Villaescusa, L.A.; Amorós, P. New chromogenic probes into nanoscopic pockets in enhanced sensing protocols for amines in aqueous environments. Org. Lett., 2005, 7 (7), 5469-5472.
17. Comes, M.; Aznar, E.; Moragues, M.; Marcos, M.D.; Martínez-Máñez, R.; Sancenón, F.; Soto, J. L.; Villaescusa, A.; Gil, L.; Amorós, P. Mesoporous hybrid materials containing nanoscopic "binding pockets" for colorimetric anion signaling in water by using displacement assays. Chem. Eur. J., 2009,15 (36), 9024-9033.
18. Sheryl, L.; Ait-Haddou, W.H.; Lavigne, J.J.; Anslyn, E.V. Teaching old indicators new tricks. Acc. Chem. Res., 2001, 34 (12), 963-972.
19. Anslyn, E.V. Supramolecular analytical chemistry. J. Org. Chem., 2007, 72 (3), 687-699.
20. Anslyn, E.V. Differential receptor arrays and assays for solution-based molecular recognition. Chem. Soc. Rev., 2006, 35 (1), 14-28.
21. Zhu, L.; Zhong, Z.; Anslyn, E.V. Guidelines in implementing enantioselective indicator-displacement assays for alphahydroxycarboxylates and diols. J. Am. Chem. Soc., 2005, 127 (12), 4260-4269.
22. Zhu, L.; Anslyn, E.V. Facile quantification of enantiomeric excess and concentration with indicator-displacement assays: an example in the analyses of alpha-hydroxyacids. J. Am. Chem. Soc., 2004, 126 (12), 3676-3677.
23. Zhu, L.; Shabbir, S.H.; Anslyn, E.V. Two methods for the determination of enantiomeric excess and concentration of a chiral sample with a single spectroscopic measurement. Chem. Eur. J., 2007, 13 (1), 99-104.
24. Shabbir, S.H.; Joyce, L.A.; da Cruz, G.M.; Lynch, V.M.; Sorey, S.; Anslyn, E.V. Pattern-based recognition for the rapid determination of identity, concentration, and enantiomeric excess of subtly different threo diols. J. Am. Chem. Soc., 2009, 131 (36), 13125-13131.
25. Adams, M.M.; Anslyn, E.V. Differential sensing using proteins: exploiting the cross-reactivity of serum albumin to pattern individual terpenes and terpenes in perfume. J. Am. Chem. Soc., 2009, 131 (47), 17068-17069.
26. Lee, D.H.; Kim, S.Y.; Hong, J.I. A fluorescent pyrophosphate sensor with high selectivity over ATP in water. Angew. Chem. Int. Ed., 2004, 43 (36), 4777-4780.
27. Kim, S.K.; Lee, D.H.; Hong, J.I.; Yoon, J. Chemosensors for pyrophosphate. Acc. Chem. Res., 2009, 42 (1), 23-31.
28. Ojida, A.; Takashima, I.; Kohira, T.; Nonaka, H.; Hamachi, I. Turn-on fluorescence sensing of nucleoside polyphosphates using a xanthene-based Zn(II) complex chemosensor. J. Am. Chem. Soc., 2008, 130 (36), 12095.
29. Leevy, W.M.; Gammon, S.T.; Jiang, H.; Johnson, J.R.; Maxwell, D.J.; Jackson, E.N.; Marquez, M.; Piwnica-Worms, D.; Smith, B.D. Optical imaging of bacterial infection in living mice using a fluorescent near-infrared molecular probe. J. Am. Chem. Soc., 2006, 128 (51), 16476.
30. Young, M.J.; Chin, J. Dinuclear copper(II) complex that hydrolyzes RNA. J. Am. Chem. Soc., 1995, 117 (42), 10577-10578.
31. Tang, L.; Park, J.; Kim, H.-J.; Kim, Y.; Kim, S.J.; Chin, J.; Kim, K.M. Tight binding and fluorescent sensing of oxalate in water. J. Am. Chem. Soc., 2008, 130 (38), 12606-12607.
32. Su, J.; Sun, Y.Q.; Huo, F.J.; Yang, Y.T.; Yin, C.X. Naked-eye determination of oxalate anion in aqueous solution with copper ion and pyrocatechol violet. Analyst, 2010, 135 (11), 2918-2923.
33. Watchasit, S.; Kaowliew, A.; Suksai, C.; Tuntulani, T.; Ngeontae, W.; Pakawatchai, C. Selective detection of pyrophosphate by new tripodal amine calix[4]arene-based Cu(II) complexes using indicator displacement strategy. Tetrahedron Lett., 2010, 51 (26), 3398-3402.
34. Plante, J.P.; Glass, T.E. Shape-selective fluorescent sensing ensemble using a tweezer-type metalloreceptor. Org. Lett., 2006, 8 (10), 2163-2166.
35. Zhang, S.; Glass, T.E. An indicator displacement assay with independent dual wavelength emission, Tetrahedron Lett., 2010, 51 (1), 112-114.
36. Lee, D.H.; Kim, S.Y.; Hong, J.-I. Quencher-fluorophore ensemble for detection of pyrophosphate in water. Tetrahedron Lett, 2007, 48 (26), 4477-4480.
37. Hanshaw, R.G.; Hilkert, S.M.; Jiang, H.; Smith, B.D. An indicator displacement system for fluorescent detection of phosphate oxyanions under physiological conditions. Tetrahedron Lett., 2004, 45 (47), 8721-8725.
38. Morgan, B.P.; He, S.; Smith, R.C. Dizinc enzyme model/complexometric indicator pairs in indicator displacement assays for inorganic phosphates under physiological conditions. Inorg. Chem., 2007, 46 (22), 9262-9266.
39. Gruber, B.; Stadlbauer, S.; Woinaroschy, K.; Konig, B. Luminescent vesicular receptors for the recognition of biologically important phosphate species. Org. Biomol. Chem., 2010, 8 (16), 3704-3714.
40. Chen, Z.H.; Lu, Y.; He, Y.B.; Huang, X.H. Recognition of pyrophosphate anion in aqueous solution using the competition displacement method. Sens. Actuaturs B. Chem., 2010, 149 (2), 407-412.
41. Hirose, K.; Kadowaki, S.; Tanabe, M.; Takeshima, H.; Iino, M. Spatiotemporal dynamics of inositol 1,4,5-trisphosphate that underlies complex Ca2+ mobilization patterns. Science, 1999, 284 (5419), 1527-1530.
42. Aoki, S.; Zulkefeli, M.; Shiro, M.; Kohsako, M.; Takeda, K.; Kimura, E. A luminescence sensor of inositol 1,4,5-triphosphate and its model compound by ruthenium-templated assembly of a bis(Zn2+-cyclen) complex having a 2,2 '-bipyridyl linker (cyclen=1,4,7,10-tetraazacyclododecane). J. Am. Chem. Soc., 2005, 127 (25), 9129-9139.
43. Oh, D.J.; Ahn, K.H. Fluorescent sensing of IP3 with a trifurcate Zn(II)- containing chemosensing ensemble system. Org. Lett., 2008, 10 (16), 3539-3542.
44. Khatua, S.; Choi, S.H.; Lee, J.; Kim, K.; Do, Y.; Churchill, D.G. Aqueous fluorometric and colorimetric sensing of phosphate ions by a fluorescent dinuclear zinc complex. Inorg. Chem., 2009, 48 (7), 2993-2999.
45. Folmer-Andersen, J.F.; Lynch, V.M.; Anslyn, E.V. Colorimetric enantiodiscrimination of alpha-amino acids in protic media. J. Am. Chem. Soc., 2005, 127 (18), 7986-7987.
46. Folmer-Andersen, J.F.; Kitamura, M.; Anslyn, E.V. Pattern-based discrimination of enantiomeric and structurally similar amino acids: an optical mimic of the mammalian taste response. J. Am. Chem. Soc., 2006, 128 (17), 5652-5653.
47. Leung, D.; Folmer-Andersen, J.F.; Lynch, V.M.; Anslyn, E.V. Using enantioselective indicator displacement assays to determine the enantiomeric excess of alpha-amino acids. J. Am. Chem. Soc., 2008, 130 (37), 12318-12327.
48. Leung, D.; Anslyn, E.V. Transitioning enantioselective indicator displacement assays for alpha-amino acids to protocols amenable to highthroughput screening. J. Am. Chem. Soc., 2008, 130 (37), 12328-12333.
49. Buryak, A.; Severin, K. An organometallic chemosensor for the sequenceselective detection of histidine- and methionine-containing peptides in water at neutral pH. Angew. Chem. Int. Ed., 2004, 43 (36), 4771-4774.
50. Riis-Johannessen, T.; Severin, K. A Micelle-based chemosensing ensemble for the fluorimetric detection of chloride in water. Chem. Eur. J., 2010, 16 (28), 8291-8295.