A fluorescein-based fluorogenic probe for fluoride ion based on the fluoride-induced cleavage of tert-butyldimethylsilyl ether

Journal of Fluorescence

Volumn 17, Issue 1, 2007, Pages 81-87

  Yang, Xiao Feng ^a   Ye, Si Jie ^a   Bai, Quan ^a   Wang, Xiao Qing ^a  

^a NORTHWEST UNIVERSITY   (China)

Author keywords

Fluorescein; Fluorescent probe; Fluoride ion; Tert butyldimethylsilyl ether

Indexed keywords

FLUORESCEIN; FLUORESCENCE INTENSITY; FLUORIDE IONS; FLUOROGENIC PROBES;

CONCENTRATION (PROCESS); ETHERS; FLUORESCENCE; FLUORINE COMPOUNDS; IONS; SILICON; SYNTHESIS (CHEMICAL);

PROBES;

FLUORESCEIN; FLUORESCENT DYE; FLUORIDE; ORGANOSILICON DERIVATIVE; T BUTYLDIMETHYLSILYL COMPOUNDS; T-BUTYLDIMETHYLSILYL COMPOUNDS; TOOTHPASTE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SENSITIVITY AND SPECIFICITY; SPECTROFLUOROMETRY; SYNTHESIS;

FLUORESCEIN; FLUORESCENT DYES; FLUORIDES; MOLECULAR STRUCTURE; ORGANOSILICON COMPOUNDS; SENSITIVITY AND SPECIFICITY; SPECTROMETRY, FLUORESCENCE; TOOTHPASTE; WATER;

EID: 33845926388     PISSN: 10530509     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10895-006-0140-6     Document Type: Article

References (34)

1. Ekstrand J (1996) In Fejerskov O, Ekstrand J, Burt BA (ed.), Fluoride in Dentistry, 2nd ed. Munksgaard, Copenhagen, pp. 55
2. Kazuyoshi I, Humio T (2001) Highly sensitive and rapid method for determination of fluoride ion concentrations in serum and urine using flow injection analysis with a fluoride ion-selective electrode. Clin Chim Acta 308:163-171
3. Marian KM, Kjell B, Kåre J (2001) Determination of fluoride in food by the use of alkali fusion and fluoride ion-selective electrode. Food Chem 73:373-379
4. Hirokazu H, Keiko Y, Mayumi H, Masahiro O (1998) Determination of free and total fluoride in rain water using a continuous-flow system equipped with a fluoride ion-selective electrode detector. Anal Chim Acta 364:117-123
5. Arancibia JA, Rullo A, Olivieri AC, Nezio SD, Pistonesi M, Lista A, Band BSF (2004) Fast spectrophotometric determination of fluoride in ground waters by flow injection using partial least-squares calibration. Anal Chim Acta 512:157-163
6. Khalifa ME, Hafez MAH (1998) Spectrophotometric and complexometric methods for the determination of thorium and fluoride using bromocresol orange reagent. Talanta 47(3):547-559
7. Themelis DG, Tzanavaras PD (2001) Simultaneous spectrophotometric determination of fluoride and monofluorophosphate ions in toothpastes using a reversed flow injection manifold. Anal Chim Acta 429(1):111-116
8. Themelis DO, Tzanavaras PD, Tzanavaras HD (2001) Simple, rapid reagent-injection spectrophotometric determination of fluorides in pharmaceutical formulations. J Pharm Biomed Anal 25:971-976
9. Vasconcelos MTSD, Gomes CAR, Machado AASC (1994) Ion chromatographic determination of fluoride in welding fumes with elimination of high contents of iron by solid-phase extraction. J Chroamtogr A 685:53-60
10. Kalyakina OP, Dolgonosov AM (2003) Ion-chromatographic determination of fluoride ions in atmospheric precipitates and natural waters. J Anal Chem 58(10):951-953.
11. 3 by in situ analyte distillation - ion chromatography. J Chroamtogr A 1074(1-2):229-233
12. -8 level by ion chromatography. J Chromatogr B 800(1-2):321-323
13. 3+ - alizarin complexone ternary complex. Chromatographia 59(11-12):745-747
14. Garrido M, Lista AG, Palomeque M, Band BSF (2002) Fluorimetric determination of fluoride in a flow assembly integrated on-line to an open/closed FIA system to remove interference by solid phase extraction. Talanta 58(5):849-853
15. Nishimoto J, Yamada T, Tabata M (2001) Solvent extraction and fluorometric determination of fluoride ion at ppb level in the presence of large excess of aluminum(III) and iron(III) by using an expanded porphyrin, sapphyrin. Anal Chim Acta 428:201-208
16. Cho EJ, Moon JW, Ko SW, Lee JY, Kim SK, Yoon J, Nam KC (2003) A new fluoride selective fluorescent as well as chromogenic chemosensor containing a naphthalene urea derivative. J Am Chem Soc 125(41): 12376-12377
17. Badugu R, Lakowicz JR, Geddes CD (2005) A wavelength-ratiometric fluoride-sensitive probe based on the quinolinium nucleus and boronic acid moiety. Sens Actuators, B 104:103-110
18. Zhou G, Cheng Y, Wang L, Jing X, Wang F (2005) Novel polyphenylenes containing phenol-substituted oxadiazole moieties as fluorescent chemosensors for fluoride ion. Macromolecules 38:2148-2153
19. Corey EJ, Venkateswarlu A (1972) Protection of hydroxyl groups as tert-butyldemethylsilyl derivatives. J Am Chem Soc 94:6190-6191
20. Kendall PM, Johnson JV, Cook CE (1979) Synthetic route to an aromatic analogue of strigol. J Org Chem 44(9): 1421-1424
21. Ronald RC, Lansinger JM, Lillie TS, Wheeler CJ (1982) Total synthesis of frustulosin and aurocitrin. J Org Chem 47:2541-2549
22. Liu AJ, Dillon K, Campbell RM, Cox DC, Huryn DM (1996) Synthesis of E-selectin Inhibitors: Use of an aryl-cyclohexyl ether as a disaccharide scaffold. Tetrahedron Lett 37:3785-3788
23. Corey EJ, Snider BB (1972) A total synthesis of ( ±)-fumagillin. J Am Chem Soc 94:2549-2550
24. Ranu BC, Jana U, Majee A (1999) A simple and efficient method for selective deprotection of t-butyldimethylsilyl ethers by zinc tetrafluoroborate in water. Tetrahedron Lett 40:1985-1988
25. Farras J, Serra C, Vilarrasa J (1998) Cleavage of tert-butyldimethylsilyl ethers by chloride ion. Tetrahedron Lett 39:327-330
26. Sartori G, Ballini R, Bigi F, Bosica G, Maggi R, Righi P (2004) Protection (and deprotection) of functional groups in organic synthesis by heterogeneous catalysis. Chem Rev 104:199-250
27. 2+ sensor of the zinpyr family. J Am Chem Soc 125:1778-1787
28. Urano Y, Kamiya M, Kanda K, Ueno T, Hirose K, Nagano T (2005) Evolution of fluorescein as a platform for finely tunable fluorescence probes. J Am Chem Soc 127(13):4888-4894
29. Descalzo AB, Jiménez D, Haskouri JE, Beltrán D, Amorós P, Marcos MD, Martínez-Máñez R, Soto J (2002) A new method for fluoride determination by using fluorophores and dyes anchored onto MCM-41. Chem Commun 562-563
30. Zhu C-Q, Chen J-L, Zheng H, Wu Y-Q, Xu J-G (2005) A colorimetric method for fluoride determination in aqueous samples based on the hydroxyl deprotection reaction of a cyanine dye. Anal Chim Acta 539:311-316
31. Chen XQ, Sun M, Ma HM (2006) Progress in spectroscopic probes with cleavable active bonds. Current Org Chem 10:477-489
32. Chang MCY, Pralle A, Isacoff EY, Chang CJ (2004) A selective cell-permeable optical probe for hydrogen peroxide in living cells. J Am Chem Soc 126:15392-15393
33. Maeda H, Yamamoto K, Nomura Y, Kohno I, Hafsi L, Ueda N, Yoshida S, Fukuda M, Fukuyasu Y, Yamauchi Y, Itoh N (2005) A design of fluorescent probe for Superoxide based on a nonredox mechanism. J Am Chem Soc 127:68-69
34. Mchedlov-Petrossyan NO, Kukhtik VI, Bezugliyz VD (2003) Dissociation, tautomerism and electroreduction of xanthene and sulfonephthalein dyes in N,N-dimethylformamide and other solvents. J Phys Org Chem 16:380-397