Chemosensors for pyrophosphate

Accounts of Chemical Research

Volumn 42, Issue 1, 2009, Pages 23-31

  Kyung, K I M Sook ^a   Dong Hoon, L E E ^b   Hong, Jong I N ^b   Yoon, Juyoung ^a  

^a Ewha Womans University   (South Korea)

^b Seoul National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 61849141765     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar800003f     Document Type: Article

References (38)

1. For recent reviews for anion receptors, see: (a) Gale, P. A. Structural and Molecular Recognition Studies with Acylic Anion Receptors, Acc. Chem. Res. 2006, 39, 465- 475.
2. (b) Yoon, J.; Kim, S. K.; Singh, N. J.; Kim, K. S. Imidazolium Receptors for the Recognition of Anions. Chem. Soc. Rev. 2006, 35, 355-360.
3. Gunnlaugsson, T.; Glynn, M.; Tocci, G. M.; Kruger, P. E.; Pfeffer, F. M. Anion Recognition and Sensing in Organic and Aqueous Media Using Luminescent and Colorimetric Sensors. Coord. Chem. Rev. 2006, 250, 3094-3117.
4. Beer, P. D.; Gale, P. A. Anion Recognition and Sensing: The State of the Art and Future Perspectives. Angew. Chem., Int. Ed. 2001, 40, 486-516.
5. (e) Wisker, S. L; Ait-Haddou, H.; Lavigne, J. J.; Anslyn, E. V. Teaching Old Indicators New Tricks. Acc. Chem. Res. 2001, 34, 963-972.
6. (f) Schmidtchen, F. P.; Berger, M. Artificial Organic Host Molecules for Anions. Chem. Rev. 1997, 97, 1609-1646.
7. (g) Ojida, A.; Miyahara, Y.; Wongkongkatep, J.; Tamaru, S.-i.; Sada, K.; Hamachi, I. Design of Dual-Emission Chemosensors for Ratiometric Detection of ATP Derivatives. Chem.-Asian. J. 2006, 1, 555-563.
8. Martínez-Máñez, R.; Sancanón, F. Fluorogenic and Chromogenic Chemosensors and Reagents for Anions. Chem. Rev. 2003, 103, 4419-4476.
9. (a) Callan, J. F.; de Silva, A. P.; Magri, D. C. Luminescent Sensors and Switches in the Early 21st Century. Tetrahedron 2005, 61, 8551-8588.
10. (b) de Silva, A. P.; Gunaratne, H. Q. N.; Gunnlaugsson, T. A.; Huxley, T. M.; McCoy, C. P.; Rademacher, J. T.; Rice, T. E. Signaling Recognition Events with Fluorescent Sensors and Switches. Chem. Rev. 1997, 97, 1515-1566.
11. Czarnik, A. W. Chemical Communication in Water Using Fluorescent Chemosensors. Acc. Chem. Res. 1994, 27, 302-308.
12. Mathews, C. P.; van Hold, K. E. Biochemistry, The Benjamin/Cummings Publishing Company, Inc.: Redwood City, CA, 1990.
13. Ronaghi, M.; Karamohamed, S.; Pettersson, B.; Uhlén, M.; Nyrén, P. Real-Time DNA Sequencing Using Detection of Pyrophosphate Release. Anal. Biochem. 1996, 242, 84-89.
14. Xu, S.; He, M.; Yu, H.; Cai, X.; Tan, X.; Lu, B.; Shu, B. A Quantitative Method to Measure Telomerase Activity by Bioluminescence Connected with Telomeric Repeat Amplification Protocol. Anal. Biochem. 2001, 299, 188-193.
15. (a) Doherty, M.; Becher, C; Regan, M.; Jones, A.; Ledingham, J. Association between Synovial Fluid Levels of Inorganic Pyrophosphate and Short Term Radiographic Outcome of Knee Osteoarthritis. Ann. Rheum. Dis. 1996, 66, 432- 436.
16. (b) Timms, A. E.; Zhang, Y.; Russell, R. G.; Brown, M. A. Genetic Studies of Disorders of Calcium Crystal Deposition. Rheumatology 2002 41, 725-729.
17. Vance, D. H.; Czarnik, A. W. Real-Time Assay of Inorganic Pyrophosphatase Using a High-Affinity Chelation-Enhanced Fluorescence Chemosensor. J. Am. Chem. Soc. 1994, 116, 9397-9398.
18. Mizukami, S.; Nagano, T.; Urano, Y.; Odani, A.; Kikuchi, K. A Fluorescent Anion Sensor That Works in Neutral Aqueous Solution for Bioanalytical Application. J. Am. Chem. Soc. 2002, 124, 3920-3925.
19. Lee, D. H.; Im, J. H.; Son, S. U.; Chung, Y. K.; Hong, J.-I. An Azaphenoi-Based Chromogenic Pyrophosphate Sensor in Water. J. Am. Chem. Soc. 2003, 725, 7752-7753.
20. 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, 4777-4780.
21. Lee, J. H.; Park, J.; Lah, M. S.; Chin, J.; Hong, J.-l. High-Affinity Pyrophosphate Receptor by a Synergistic Effect between Metal Coordination and Hydrogen Bonding in Water. Org. Lett. 2007, 9, 3729-3731.
22. 4- in 100% Aqueous Solution. J. Org. Chem. 2005, 70, 9603-9606.
23. Lee, H. N.; Swamy, K. M. K.; Kim, S. K.; Kwon, J.-Y.; Kim, Y.; Kim, S.-J.; Yoon, Y. J.; Yoon, J. Simple, but an Effective Way to Sense Pyrophosphate and Inorganic Phosphate by Fluorescence Changes. Org. Lett. 2007, 9, 243-246.
24. Cho, H. K.; Lee, D. H.; Hong, J.-I. A Fluorescent Pyrophosphate Sensor via Eximer Formation in Water. Chem. Commun. 2005, 1690-1692.
25. Lee, H. N.; Xu, Z.; Kim, S. K.; Swamy, K. M. K.; Kim, Y.; Kim, S.-J.; Yoon, J. Pyrophosphate Selective Fluorescent Chemosensor at Physiological pH: A Unique Excimer Formation upon the Addition of Pyrophosphate. J. Am. Chem. Soc. 2007, 129, 3828-3829.
26. Fabbrizzi, L; Marcotte, N.; Stomeo, F.; Taglietti, A. Pyrophosphate Detection in Water by Fluorescence Competition Assay: Inducing Selectivity through the Choice of the Indicator. Angew. Chem., Int. Ed. 2002, 41, 3811-3814.
27. McDonough, M. J.; Reynolds, A. J.; Lee, W. Y. G.; Jolliffe, K. A. Selective Recognition of Pyrophiosphate in Water Using a Backbone Modified Cyclic Peptide Receptor. Chem. Commun. 2006, 2971-2973.
28. Lee, D. H.; Kim, S. Y.; Hong, J.-I. Quencher-Fluorophore Ensemble for Detection of Pyrophosphate in Water. Tetrahedron Lett. 2007, 48, 4477-4480.
29. Nishizawa, S.; Kato, Y.; Teramae, N. Fluorescence Sensing of Anions via Intramolecular Excimer Formation in a Pyrophosphate-lnduced Self-Assembly of a Pyrene-Functionalized Guanidinium Receptor. J. Am. Chem. Soc. 1999, 121, 9463-9464.
30. Anzenbacher, P., Jr.; Jursíková, K.; Sessler, J. L. Second Generation Calixpyrrole Anion Sensors. J. Am. Chem. Soc. 2000, 122, 9350-9351.
31. (a) Aldakov, D.; Palacios, M. A.; Anzenbacher, P., Jr. Benzothiadiszoles and Dipyrrolyl Quinoxalines with Extended Conjugated Chromophores-Fluorophores and Anion Sensors. Chem. Mater. 2005, 17, 5238-5241.
32. (b) Aldakov, D.; Anzenbacher, P., Jr. Sensing of Aqueous Phosphates by Polymers with Dual Modes of Signal Transduction. J. Am. Chem. Soc. 2004, 126, 4752-4753.
33. Aldakov, D.; Anzenbacher, P., Jr. Dipyrrolyl Quinoxalines with Extended Chromophores as Efficient Fluorimetric Sensors for Pyrophosphate. Chem. Commun. 2003, 1394-1395.
34. (a) Kwon, J. Y.; Singh, N. J.; Kim, H.; Kim, S. K.; Kim, K. S.; Yoon, J. Fluorescent GTP-Sensing in Aqueous Solution of Physiological pH. J. Am. Chem. Soc. 2004, 126, 8892-8893.
35. -. J. Org. Chem. 2004, 69, 581 -583.
36. 4". Org. Lett. 2003, 5, 2083-2086.
37. Kim, S. K.; Singh, N. J.; Kwon, J.; Hwang, l.-C; Park, S. J.; Kim, K. S.; Yoon, J. Fluorescent Imidazolium Receptors for the Recognition of Pyrophosphate. Tetrahedron 2006, 62, 6065-6072.
38. Lee, D. H.; Hong, J.-l. A Fluorescent Confirmation Method for DNA Amplification in PCR through a Fluorescent Pyrophosphate Sensor. Bull. Korean Chem. Soc. 2008, 29, 497-498.