Fluorescent probes for Al(III) and Cr(III) based on a photochromic diarylethene bearing a fluorescent rhodamine unit

Microchimica Acta

Volumn 174, Issue 3, 2011, Pages 329-336

  Liu, Weijun ^a   Pu, Shouzhi ^a   Jiang, Duohua ^a   Cui, Shiqiang ^a   Liu, Gang ^a   Fan, Congbin ^a  

^a JIANGXI SCIENCE AND TECHNOLOGY NORMAL UNIVERSITY   (China)

Author keywords

Al(Sh cyrillic ) Cr(Sh cyrillic ) probe; Diarylethene; Photochromism; Rhodamine

Indexed keywords

EID: 80051669347     PISSN: 00263672     EISSN: 14365073     Source Type: Journal    
DOI: 10.1007/s00604-011-0610-7     Document Type: Article

References (62)

1. Barceló J, Poschenrieder C (2002) Fast root growth responses, root exudates, and internal detoxification as clues to the mechanisms of aluminium toxicity and resistance: a review. Environ Exp Bot 48: 75-92.
2. Alstad NEW, Kjelsberg BM, Vøllestad LA, Lydersen E, Poléo ABS (2005) The significance of water ionic strength on aluminium toxicity in brown trout. Environ Pollut 133: 333-342.
3. Àlvarez E, Fernández-Marcos ML, Monterroso C, Fernández-Sanjurjo MJ (2005) Application of aluminium toxicity indices to soils under various forest species. For Ecol Manag 211: 227-239.
4. Perl DP, Brody AR (1980) Alzheimer's disease: X-ray spectrometric evidence of aluminum accumulation in neurofibrillary tangle-bearing neurons. Science 208: 297-299.
5. Flaten TP (2001) Aluminum as a risk factor in Alzheimer's disease with emphasis on drinking water. Brain Res Bull 55: 187-196.
6. Jeffery EH, Abreo K, Burgess E, Cannata J, Greger JL (1996) Systemic Al toxicity; effects on bone, hematopoietic tissue, and kidney. J Toxicol Environ Health 48: 649-666.
7. Becaria A, Campbell A, Bondy SC (2002) Aluminum as a toxicant. Toxicol Ind Health 18: 309-320.
8. Spinelli JJ, Demers PA, Le ND, Friesen MD, Lorenzi MF, Fang R, Gallagher RP (2006) Cancer risk in aluminum reduction plant workers. Cancer Cause Control 17: 939-948.
9. Armstrong B, Tremblay C, Baris D, Thériault G (1994) Lung cancer mortality and polynuclear aromatic hydrocarbons: a case-cohort study of aluminum production workers in Arvida, Quebec, Canada. Am J Epidemiol 139: 250-262.
10. 2+ selective wlectrode based on 3-(6-aminopyridin-2-ylimino)-1, 3-diphenylpropylidene)pyridine-2, 6-diamine. Anal Chim Acta 585: 171-178.
11. Zayed A, Terry N (2003) Chromium in the environment: factors affecting biological remediation. Plant Soil 249: 139-156.
12. De Silva PA, Gunaratne HQN, Gunnlaugsson T, Huxley AJM, McCoy CP, Rademacher JT, Rice TE (1997) Signaling recognition events with fluorescence sensors and switches. Chem Rev 97: 1515-1566.
13. Nolan EM, Lippard SJ (2008) Tools and tactics for the optical detection of mercuric ion. Chem Rev 108: 3443-3480.
14. 2+ based on a rhodamine derivative with a ferrocene unit. Org Lett 9: 4729-4732.
15. Li XH, Duerkop A, Wolfbeis OS (2009) A fluorescent probe for diacetyl detection. J Fluorese 19: 601-606.
16. 2+ in aqueous solution with a broad pH range and its application in live cell imaging. Org Biomol Chem 8: 4143-4147.
17. 2+ chemosensor based on a receptor composed of a thiol atom and an alkene moiety for living cell fluorescence imaging. Org Biomol Chem 8: 3618-3620.
18. Zheng AF, Chen JL, Wu GN, Wei HP, He CY, Kai XM, Wu GH, Chen YC (2009) Optimization of a sensitive method for the "switch-on" determination of mercury(II) in waters using Rhodamine B capped gold nanoparticles as a fluorescence sensor. Microchim Acta 164: 17-27.
19. 2-contained receptor. J Org Chem 74: 2167-2170.
20. Zeng X, Dong L, Wu C, Mu L, Xue SF, Tao Z (2009) Highly sensitive chemosensor for Cu(II) and Hg(II) based on the tripodal rhodamine receptor. Sens Actuators B 141: 506-510.
21. 2+ selective fluorescent and colorimetric sensor: its crystal structure and application to the bio-imaging. Org Lett 22: 5235-5238.
22. Lee SY, Kim HJ, Wu JS, No K, Kim JS (2008) Metal ion-induced FRET modulationin bifluorophore system. Tetrahedron Lett 49: 6141-6144.
23. Zhang X, Shiraishi Y, Hirai T (2007) Cu(II)-selective strong green fluorescence of a rhodamine-siacetic acid xonjugate. Org Lett 9: 5039-5042.
24. 2+ and its application in living cell imaging. Chem Eur J 14: 6892-6900.
25. 2+. Sens Actuators B 137: 597-602.
26. Xi PX, Dou JY, Huang L, Xu M, Chen FJ, Wu YJ, Bai DC, Li WG, Zeng ZZ (2010) A selective turn-on fluorescent sensor for Cu(II) and its application in imaging in living cells. Sens Actuators B 148: 337-341.
27. Xiang Y, Tong AJ, Jin PY, Ju Y (2006) New fluorescent rhodamine hydrazone chemosensor for Cu(II) with high selectivity and sensitivity. Org Lett 8: 2863-2866.
28. Mao J, Wang LN, Dou W, Tang XL, Yan Y, Liu WS (2007) Tuning the selectivity of two chemosensors to Fe(III) and Cr(III). Org Lett 9: 4567-4570.
29. 3+ in neutral ethanol aqueous solution. Sens Actuators B 145: 433-437.
30. Zhang M, Gao YH, Li MY, Yu MX, Li FY, Li L, Zhu MW, Zhang JP, Yi T, Huang CH (2007) A selective turn-on fluorescent sensor for Fe(III) and application to bioimaging. Tetrahedron Lett 48: 3709-3712.
31. Chen XL, Zou JL (2007) Application of rhodamine B hydrazide as a new fluorogenic indicator in the highly sensitive determination of hydrogen peroxide and glucose based on the catalytic effect of iron(III)-tetrasulfonato-phthalocyanine. Microchim Acta 157: 133-138.
32. Chatterjee A, Santra M, Won N, Kim S, Kim JK, Kim SB, Ahn KH (2009) Selective fluorogenic and chromogenic probe for detection of silver ions and silver nanoparticles in aqueous media. J Am Chem Soc 131: 2040-2041.
33. 3+ and its application in bioimaging Org. Org Lett 10: 2557-2560.
34. 3+. Tetrahedron Lett 50: 6407-6410.
35. 3+). Anal Chim Acta 665: 215-220.
36. Hu XY, Zhang XL, He GJ, He C, Duan CY (2011) A FRET approach for luminescence sensing Cr(III) in aqueous solution and living cells through functionalizing glutathione and glucose moieties. Tetrahedron 67: 1091-1095.
37. Zhou ZG, Yu MX, Yang H, Huang KW, Li FY, Yi T, Huang CH (2008) FRET-based sensor for imaging chromium(III) in living cells. Chem Commun 3387-3389.
38. Irie M (2000) Diarylethenes for memories and switches. Chem Rev 100: 1685-1716.
39. Higashiguchi K, Matsuda K, Tanifuji N, Irie M (2005) Full-color photochromism of a fused dithienylethene trimer. J Am Chem Soc 127: 8922-8923.
40. Pu SZ, Liu G, Shen L, Xu JK (2007) Efficient synthesis and properties of isomeric photochromic diarylethenes having a pyrrole unit. Org Lett 9: 2139-2142.
41. Pu SZ, Zheng CH, Le ZG, Liu G, Fan CB (2008) Substituent effects on the properties of photochromic diarylethenes. Tetrahedron 64: 2576-2585.
42. Fan CB, Pu SZ, Liu G, Yang TS (2008) Substituent position effect on the properties of new unsymmetrical isomeric diarylethenes having a chlorine atom. J Photoch Photobio A 197: 415-425.
43. Zhang JJ, Tan WJ, Meng XL, Tian H (2009) Soft mimic gear-shift with a multi-stimulus modified diarylethene. J Mater Chem 19: 5726-5729.
44. Zheng HY, Zhou WD, Yuan MJ, Yin XD, Zuo ZC, Ouyang CB, Liu HB, Li YL, Zhu DB (2009) Optic and proton dual-control of the fluorescence of Rhodamine based on photochromic diarylethene: mimicking the performance of an integrated logic gate. Tetrahedron Lett 50: 1588-1592.
45. Wolfbeis OS (2007) The click reaction in the luminescent probing of metal ions, and its implications on biolabeling techniques. Angew Chem Int Ed 46: 2980-2982.
46. Achatz DE, Mezo{double acute} G, Kele P, Wolfbeis OS (2009) Probing the activity of matrix metalloproteinase II with a sequentially click-labeled silica nanoparticle FRET probe. Chembiochem 10: 2316-2320.
47. Nagl S, Schaeferling M, Wolfbeis OS (2005) Fluorescence analysis in microarray technology. Microchim Acta 151: 1-21.
48. 2+ ions in living cells. Angew Chem Int Ed 47: 8025-8029.
49. Zheng CH, Pu SZ, Xu JK, Luo MB, Huang DC, Shen L (2007) Synthesis and the effect of alkyl chain length on optoelectronic properties of diarylethene derivatives. Tetrahedron 63: 5437-5449.
50. Kawai S, Nakashima T, Atsumi K, Sakai T, Harigai M, Imamoto Y, Kamikubo H, Kataoka M, Kawai T (2007) Novel photochromic molecules based on 4, 5-dithienyl thiazole with fast thermal bleaching rate. Chem Mater 19: 3479-3483.
51. Pu SZ, Yang TS, Xu JK, Shen L, Li GZ, Xiao Q, Chen B (2005) Syntheses and optoelectronic properties of four photochromic dithienylethenes. Tetrahedron 61: 6623-6629.
52. Pu SZ, Fan CB, Miao WJ, Liu G (2008) New photochromic diarylethenes with a six-membered aryl unit. Tetrahedron 64: 9464-9470.
53. Pu SZ, Fan CB, Miao WJ, Liu G (2009) The effect of substituent position upon unsymmetrical isomeric diarylethenes bearing a methoxy group. Dyes Pigm 84: 25-35.
54. Pu SZ, Liu WJ, Liu G (2010) The photochromism of unsymmetrical diarylethene isomers with an electron-withdrawing cyano substituent. Dyes Pigm 87: 1-9.
55. Fan CB, Pu SZ, Liu G, Yang TS (2008) Substituent position effect on the properties of isomeric photochromic diarylethenes bearing chlorine atoms. J Photoch Photobio A 194: 333-343.
56. Pu SZ, Liu WJ, Miao WJ (2009) Photochromism of new unsymmetrical isomeric diarylethenes bearing a methoxyl group. J Phys Org Chem 22: 954-963.
57. Tian H, Yang SJ (2004) Recent progresses on diarylethene based photochromic switches. Chem Soc Rev 33: 85-97.
58. Giordano L, Jovin TM, Irie M, Jares-Erijman EA (2002) Diheteroarylethenes as thermally stable photo-switchable acceptors in Photochromic Fluorescence Resonance Energy Transfer (pcFRET). J Am Chem Soc 124: 7481-7489.
59. Lu HC, Schöps O, Woggon U, Niemeyer CM (2008) Self-Assembled donor comprising quantum dots and fluorescent proteins for long-range fluorescence resonance energy transfer. J Am Chem Soc 130: 4815-4827.
60. Piao XJ, Zou Y, Wu JC, Li CY, Yi T (2009) Multiresponsive switchable diarylethene and its application in bioimaging. Org Lett 11: 3818-3821.
61. Zou Y, Yi T, Xiao SZ, Li FY, Li CY, Gao X, Wu JC, Yu MX, Huang CH (2008) Amphiphilic diarylethene as a photoswitchable probe for imaging living cells. J Am Chem Soc 130: 15750-15751.
62. Zhu MQ, Zhang GF, Chong L, Aldred MP, Chang E, Drezek RA, Li ADQ (2010) Reversible two-photon photoswitching and two-photon imaging of immunofunctionalized nanoparticles targeted to cancer cells. J Am Chem Soc 133: 365-372.