Sensitive Colorimetric and Fluorescent Detection of Mercury Using Fluorescein Derivations

Zhihui Xie, Fangjun Huo, Jing Su, Yutao Yang, Caixia Yin, Xuxiu Yan, Shuo Jin

Key Laboratory of Chemical Biology and Molecular, Engineering of Ministry of Education, Institute of Molecular Science (IMS), Shanxi University, Taiyuan, China.
Key Laboratory of Chemical Biology and Molecular, Engineering of Ministry of Education, Institute of Molecular Science (IMS), Shanxi University, Taiyuan, China; Research Institute of Applied Chemistry (RIAC), Shanxi University, Taiyuan, China.
Research Institute of Applied Chemistry (RIAC), Shanxi University, Taiyuan, China.

DOI: 10.4236/ojab.2012.13006                

Abstract

A colorimetric and fluorometric dual-model probe for mercury (II) ion was developed employing fluorescein hydrazide (FH) in ethanol-HEPES solution (1:1, v/v, pH 8.0). The probe exhibited high selectivity and sensitivity for Hg²⁺ detection using UV/Vis and fluorescence spectroscopy. Addition of Hg²⁺ caused a visual color change from colorless to coloured and a fluorescence change from colorless to bright green. Other metal ions did not interfere with the detection of Hg²⁺.

Keywords

Fluorescein Hydrazide; Hg²⁺; Fluorescent; UV-Visible; Sensor

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	A. P. De Silva, H. Q. N. Gunaratne, T. Gunnlaugsson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher and T. E. Rice, “ChemInform Abstract: Signaling Recognition Events with Fluorescent Sensors and Switches,” Chemical Reviews, Vol. 97, No. 5, 1997, pp. 1515-1566. doi:10.1002/chin.199744337
[2]	X. Peng, J. Du, J. Fan, J. Wang, Y. Wu, J. Zhao, S. Sun and T. Xu, “A Selective Fluorescent Sensor for Imaging Cd2+ in Living Cells,” Journal of the American Chemical Society, Vol. 129, No. 6, 2007, pp. 1500-1501. doi:10.1021/ja0643319
[3]	M. Royzen, Z. Dai and J. W. Cannry, “Ratiometric Displacement Approach to Cu (II) Sensing by Fluorescence,” Journal of the American Chemical Society, Vol. 127, No. 6, 2005, pp. 1612-1613. doi:10.1021/ja0431051
[4]	P. M. Bolger and B. A. Schwetz, “Mercury and Health,” The New England Journal of Medicine, Vol. 347, No. 22, 2002, pp. 1735-1736. doi:10.1056/NEJMp020139
[5]	H. H. Harris, I. J. Pickering and G. N. George, “The Chemical Form of Mercury in Fish,” Science, Vol. 301, No. 5637, 2003, p. 1203. doi:10.1126/science.1085941
[6]	T. W. Clarkson, L. Magos and G. J. Myers, “The Toxicology of Mercury-Current Exposures and Clinical Mani- festations,” The New England Journal of Medicine, Vol. 349, No. 18, 2003, pp. 1731-1737. doi:10.1056/NEJMra022471
[7]	A. Renzoni, F. Zino and E. Franchi, “Mercury Levels along the Food Chain and Risk for Exposed Populations, Environmental Research,” Vol. 77, No. ER983832, 1998, pp. 68-72. doi:10.1006/enrs.1998.3832
[8]	D. B. Gil, M. I. Rodriguez-Cáceres, M. del C. Hurtado- Sánchez and A. M. de la Pena, “Fluorescent Determination of Hg2+ in Water and Fish Samples Using a Chemodosimeter Based in a Rhodamine 6G Derivative and a Portable Fiber-Optic Spectrofluorimeter,” Applied Spectroscopy, Vol. 64, No. 5, 2010, pp. 520-527. doi:10.1366/000370210791211600
[9]	O. Malm, “Gold Mining as a Source of Mercury Exposure in the Brazilian Amazon,” Environmental Research, Vol. 77, 1998, pp. 73-78, Article ID: 983828. doi:10.1006/enrs.1998.3828
[10]	E. M. Nolan and S. J. Lippard, “Turn-On and Ratiometric Mercury Sensing in Water with a Red-Emitting Probe,” Journal of the American Chemical Society, Vol. 129, No. 18, 2007, pp. 5910-5918. doi:10.1021/ja068879r
[11]	S. Hardy and P. Jones, “Capillary Electrophoresis Determination of Methylmercury in Fish and Crab Meat after Extraction as the Dithizone Sulphonate Complex,” Journal of Chromatography A, Vol. 791, No. 1-2, 1997, pp. 333-338. doi:10.1016/S0021-9673(97)00829-7
[12]	Z. D. Wang, J. H. Lee and Y. Lu, “Highly Sensitive ‘Turn- On’ Fluorescent Sensor for Hg2+ in Aqueous Solution Based on Structure-Switching DNA,” Chemical Communication, No. 45, 2008, pp. 6005-6007. doi:10.1039/b812755g
[13]	M. Harada, “Minamata Disease: Methylmercury Poisoning in Japan Caused by Environmental Pollution,” Critical Reviews in Toxicology, Vol. 25, No. 1, 1995, pp. 1-24. doi:10.3109/10408449509089885
[14]	L. Prodi, C. Bargossi, M. Montalti, N. Zaccheroni, N. Su, J. S. Bradshaw, R. M. Izatt and P. B. Savage, “An Effective Fluorescent Chemosensor for Mercury Ions,” Journal of the American Chemical Society, Vol. 122, No. 28, 2000, pp. 6769-6770. doi:10.1021/ja0006292
[15]	X. Guo, X. Qian and L. Jia, “A Highly Selective and Sensitive Fluorescent Chemosensor for Hg2+ in Neutral Buffer Aqueous Solution,” Journal of the American Chemical Society, Vol. 126, No. 8, 2004, pp. 2272-2278. doi:10.1021/ja037604y
[16]	Y. K. Yang, K. J. Yook and J. Tae, “A Rhodamine-Based Fluorescent and Colorimetric Chemodosimeter for the Rapid Detection of Hg2+ Ions in Aqueous Media,” Journal of the American Chemical Society, Vol. 127, No. 48, 2005, pp. 16760-16761. doi:10.1021/ja054855t
[17]	M. H. Ha-Thi, M. Penhoat, V. Michelet and I. Leray, “Highly Selective and Sensitive Phosphane Sulfide Derivative for the Detection of Hg2+ in an Organoaqueous Medium,” Organic Letters, Vol. 9, No. 6, 2007, pp. 1133- 1136. doi:10.1021/ol070118l
[18]	E. M. Nolan and S. J. Lippard, “Turn-On and Ratiometric Mercury Sensing in Water with a Red-Emitting Probe,” Journal of the American Chemical Society, Vol. 129, No. 18, 2007, pp. 5910-5918. doi:10.1021/ja068879r
[19]	Z. X. Han, H. Y. Luo, X. B. Zhang, R. M. Kong, G. L. Shen and R. Q. Yua, “A Ratiometric Chemosensor for Fluorescent Determination of Hg(2+) Based on a New Porphyrin-Quinoline Dyad,” Spectrochimica Acta Part A, Vol. 72, No. 5, 2009, pp. 1084-1088. doi:10.1016/j.saa.2009.01.003
[20]	Y. M. Li, X. L. Zhang, B. C. Zhu, J. Xue and L. L. Yan, “A Disulfide-Linked Naphthalimide Dimer for Hg(II) Detection in Aqueous Solution,” The Journal of Fluorescence, Vol. 21, No. 4, 2011, pp. 1343-1348. doi:10.1007/s10895-010-0820-0
[21]	S. V. Wegner, A. Okesli, P. Chen and C. He, “Design of an Emission Ratiometric Biosensor from MerR Family Proteins: A Sensitive and Selective Sensor for Hg2+,” Journal of the American Chemical Society, Vol. 129, No. 12, 2007, pp. 3474-3475. doi:10.1021/ja068342d
[22]	K. C. Chiang, C. Huang, C. W. Liu and H. T. Chang, “Oligonucleotide-Based Fluorescence Probe for Sensitive and Selective Detection of Mercury(II) in Aqueous Solution,” Analytical Chemistry, Vol. 80, No. 10, 2008, pp. 3716-3721. doi:10.1021/ac800142k
[23]	C. X. Tang, Y. Zhao, X. W. He and X. B. Yin, “A ‘Turn- On’ Electrochemiluminescent Biosensor for Detecting Hg2+ at Femtomole Level Based on the Intercalation of Ru(phen)32+ into ds-DNA,” Chemical Communications, Vol. 46, No. 47, 2010, pp. 9022-9024. doi:10.1039/c0cc03495a
[24]	M. Virta, J. Lampinen and M. Karp, “A Luminescence- Based Mercury Biosensor,” Analytical Chemistry, Vol. 67, No. 3, 1995, pp. 667-669. doi:10.1021/ac00099a027
[25]	X. Liu, Y. Tang, L. Wang, J. Zhang, S. Song, C. Fan and S. Wang, “Optical Detection of Mercury (II) in Aqueous Solutions Using Conjugated Polymers and Label-Free Oligonucleotides,” Advanced Materials, Vol. 19, No. 11, 2007, pp. 1471-1474. doi:10.1002/adma.200602578
[26]	Y. Zhao and Z. Zhong, “Tuning the Sensitivity of a Fold- amer-Based Mercury Sensor by Its Folding Energy,” Journal of the American Chemical Society, Vol. 128, No. 31, 2006, pp. 9988-9989. doi:10.1021/ja062001i
[27]	W. H. Chan, R. H. Yang and K. M. Wang, “Development of a Mercury Ion-Selective Optical Sensor Based on Fluorescence Quenching of 5,10,15,20-Tetraphenylporphyrin,” Analytica Chimica Acta, Vol. 444, No. 2, 2011, pp. 261-269. doi:10.1016/S0003-2670(01)01106-0
[28]	V. Ostatna and E. Palecek, “Self-Assembled Monolayers of Thiol-End-Labeled DNA at Mercury Electrodes,” Langmuir, Vol. 22, No. 15, 2006, pp. 6481-6484. doi:10.1021/la061424v
[29]	G. K. Darbha, A. Ray and P. C. Ray, “Gold Nanoparticle- Based Miniaturized Nanomaterial Surface Energy Transfer Probe for Rapid and Ultrasensitive Detection of Mercury in Soil, Water, and Fish,” ACS Nano, Vol. 1, No. 3, 2007, pp. 208-214. doi:10.1021/nn7001954
[30]	D. Li, A. Wieckowska and I. Willner, “Optical Analysis of Hg2+ Ions by Oligonucleotide-Au Nanoparticles Hybrids and DNA-Based Machines,” Angewandte Chemie International Edition, Vol. 47, No. 21, 2008, pp. 3927- 3931. doi:10.1002/ange.200705991
[31]	X. Xue, F. Wang and X. Liu, “One-Step, Room Temperature, Colorimetric Detection of Mercury (Hg2+) Using DNA/Nanoparticle Conjugates,” Journal of the American Chemical Society, Vol. 130, No. 11, 2008, pp. 3244-3245. doi:10.1021/ja076716c
[32]	L. Wang, J. Zhang, X. Wang, Q. Huang, D. Pan, S. Song and C. Fan, “Gold Nanoparticle-Based Optical Probes for Target-Responsive DNA Structures,” Gold Bull, Vol. 41, No. 1, 2008, pp. 37-41. doi:10.1007/BF03215621
[33]	X. J. Zhu, S. T. Fu, W. K. Wong, J. P. Guo and W. Y. Wong, “A Near-Infrared Fluorescent Chemodosimeter for Mercuric Ion Based on an Expanded Porphyrin,” Angewandte Chemie International Edition, Vol. 118, No. 19, 2006, pp. 3222-3226. doi:10.1002/ange.200600248
[34]	J. Wang and X. Qian, “A Series of Polyamide Receptor Based PET Fluorescent Sensor Molecules: Positively Cooperative Hg2+ Ion Binding with High Sensitivity,” Organic Letters, Vol. 8, No. 17, 2006, pp. 3721-3724. doi:10.1021/ol061297u
[35]	L. Praveen, V. B. Ganga, R. hirumalai, T. T. Sreeja, M. L. P. Reddy and R. L. Varma, “A New Hg2+-Selective Fluorescent Sensor Based on a 1,3-Alternate Thiacalix[4]arene Anchored with Four 8-Quinolinoloxy Groups,” Inorganic Chemistry, Vol. 46, No. 16, 2007, pp. 6277-6282. doi:10.1021/ic070259j
[36]	E. M. Nolan and S. J. Lippard, “Tools and Tactics for the Optical Detection of Mercuric Ion,” Chemical Reviews, Vol. 108, No. 50, pp. 3443-3480. doi:10.1002/chin.200850280
[37]	M. H. Lee, S. Lee, S. H. Kim, C. Kang and J. S. Kim, “Nanomolar Hg(II) Detection Using Nile Blue Chemodosimeter in Biological Media,” Organic Letters, Vol. 11, No. 10, 2009, pp. 2101-2104, doi:10.1021/ol900542y
[38]	S. Yoon, E. W. Miller, Q. He, P. H. Do and C. J. Chang, “A Bright and Specific Fluorescent Sensor for Mercury in Water, Cells, and Tissue,” Angewandte Chemie International Edition, Vol. 46, No. 35, 2007, pp. 6658-6661. doi:10.1002/anie.200701785
[39]	M. Zhu, M. Yuan, X. Liu, J. Xu, J. Lv, C. Huang, H. Liu, Y. Li, S. Wang and D. Zhu, “Visible Near-Infrared Chemosensor for Mercury Ion,” Organic Letters, Vol. 10, No. 7, 2008, pp. 1481-1484. doi:10.1021/ol800197t
[40]	A. B. Othman, J. W. Lee, J. S. Wu, J. S. Kim, R. Abidi, P. Thuery, J. M. Strub, A. V. Dorsselaer and J. Vicens, “Calix[4]arene-based, Hg2+-Induced Intramolecular Fluorescence Resonance Energy Transfer Chemosensor,” Journal of Organic Chemistry, Vol. 72, No. 20, 2007, pp. 7634-7640. doi:10.1021/jo071226o
[41]	S. H. Kim, J. S. Kim, S. M. Park and S. K. Chang, “Hg2+- Selective OFF-ON and Cu2+-Selective ON-OFF Type Fluoroionophore Based upon Cyclam,” Organic Letters, Vol. 8, No. 3, 2006, pp. 371-374. doi:10.1021/ol052282j
[42]	J. V. Ros-Lis, R. Martinez-Manez, K. Rurack, F. Sancenon, J. Soto and M. Spieles, “Highly Selective Chromogenic Signaling of Hg2+ in Aqueous Media at Nanomolar Levels Employing a Squaraine-Based Reporter,” Inorganic Chemistry, Vol. 43, No. 17, 2004, pp. 5183- 5185. doi:10.1021/ic049422q
[43]	Y. Cheng, M. Zhang, H. Yang, F. Li, T. Yi, C. Huang, “Azo Dyes Based on 8-Hydroxyquinoline Benzoates: Synthesis and Application as Colorimetric Hg2+-Selective Chemosensors,” Dyes and Pigments, Vol. 76, No. 3, 2008, pp. 775-783. doi:10.1016/j.dyepig.2007.01.022
[44]	A. Caballero, R. Martinez, V. Lloveras, I. Ratera, J. Vidal-Gancedo, K. Wurst, A. Tárraga, P. Molina and J. Veciana, “Highly Selective Chromogenic and Redox or Fluorescent Sensors of Hg2+ in Aqueous Environment Based on 1,4-Disubstituted Azines,” Journal of the American Chemical Society, Vol. 127, No. 45, 2005, pp. 15666- 15667. doi:10.1021/ja0545766
[45]	G. Hennrich, W. Walther, U. Resch-Genger and H. Sonnenschein, “Cu(II)- and Hg(II)-Induced Modulation of the Fluorescence Behavior of a Redox-Active Sensor Molecule,” Inorganic Chemistry, Vol. 40, No. 4, 2001, pp. 641-644. doi:10.1021/ic000827u
[46]	G. Zhang, D. Zhang, S. Yin, X. Yang, Z. Shuaia and D. Zhu, “1,3-Dithiole-2-thione Derivatives Featuring an Anthracene Unit: New Selective Chemodosimeters for Hg(II) ion,” Chemical Communication, Vol. 16, 2005, pp. 2161- 2163. doi:10.1039/b417952h
[47]	E. M. Nolan, M. E. Racine and S. J. Lippard, “Selective Hg(II) Detection in Aqueous Solution with Thiol Derivatized Fluoresceins,” Inorganic Chemistry, Vol. 45, No. 6, 2006, pp. 2742-2749. doi:10.1021/ic052083w
[48]	X. Q. Chen and H. M. Ma, “A Selective Fluorescence- On Reaction of Spiro form Fluorescein Hydrazide with Cu(II),” Analytica Chimica Acta, Vol. 575, No. 2, 2006, pp. 217-222. doi:10.1016/j.aca.2006.05.097
[49]	T. Li, Z. Yang, Y. Li, Z. Liu, G. Qi and B. Wang, “A Novel Fluorescein Derivative as a Colorimetric Chemosensor for Detecting Copper(II) Ion,” Dyes and Pigments, Vol. 88, No. 1, 2011, pp. 103-108. doi:10.1016/j.dyepig.2010.05.008
[50]	G. M. Sheldrick, “SADABS,” University of Gottingen, Gottingen, 1997.
[51]	G. M. Sheldrick, “Program for the Refinement of Crystal Structure,” University of Goettingen, Gottingen, 1997
[52]	X. F. Yang, D. B. Wu and H. Li, “Sensitive Determination of Cobalt(II) Using a Spiro Fluorescein Hydrazide as a Chemiluminogenic Reagent,” Microchimica Acta, Vol. 149, No. 1-2, 2005, pp. 123-129. doi:10.1007/s00604-004-0285-4
[53]	V. Dujols, F. Ford and A. W. Czarnik, “A Long- Wavelength Fluorescent Chemodosimeter Selective for Cu(II) Ion in Water,” Journal of the American Chemical Society, Vol. 119, No. 31, 1997, pp. 7386-7387.