A New Heptamethine Cyanine-Based Near-Infrared Fluorescent Probe for Divalent Copper Ions with High Selectivity

Abstract

A new near-infrared fluorophore 2-(2-Aminoethyl) pyridine-tricarbocyanine (1) was rationally designed and synthe-sized as a fluorescent probe for detection of Cu2+ with high selectivity. The response of Probe 1 is based on the fluorescence quenching upon binding to Cu2+. The sensing performance of the proposed Cu2+-sensitive Probe 1 was then investigated. The probe can be applied to the quantification detection of Cu2+ with a linear concentration range covering from 4.8 × 10-7 to 1.6 × 10-4 mol/L and a detection limit of 9.3 × 10-8 mol/L. The experimental results showed that the response of 1 to Cu2+ was independent of pH in medium condition (pH 6.0-8.0), and exhibited excellent selectivity towards Cu2+ over other common metal cations.

Share and Cite:

Z. Han, Q. Yang, L. Liang and X. Zhang, "A New Heptamethine Cyanine-Based Near-Infrared Fluorescent Probe for Divalent Copper Ions with High Selectivity," Advances in Materials Physics and Chemistry, Vol. 3 No. 8, 2013, pp. 314-319. doi: 10.4236/ampc.2013.38043.

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1] A. P. de Silva, H. Q. Gunaratne, T. Gunnlaugsson, A. J. Huxley, C. P. McCoy, J. T. Rademacher and T. E. Rice, “Signaling Recognition Events with Fluorescent Sensors and Switches,” Chemical Reviews, Vol. 97, No. 5, 1997, pp. 1515-1566. http://dx.doi.org/10.1021/cr960386p
[2] E. Vuori, A. Huunan-Seppala and J. O. Kilpio, “Biologically Active Metals in Human Tissues. I. The Effect of Age and Sex on the Concentration of Copper in Aorta, Heart, Kidney, Liver, Lung, Pancreas and Skeletal Muscle,” Scandinavian Journal of Work, Environment & Health, Vol. 4, No. 2, 1978, pp. 167-175.
http://dx.doi.org/10.5271/sjweh.2712
[3] D. Radisky and J. Kaplan, “Regulation of Transition Metal Transport across the Yeast Plasma Membrane,” The Journal of Biological Chemistry, Vol. 274, 1999, pp. 4481-4484.
http://dx.doi.org/10.1074/jbc.274.8.4481
[4] B. M. Rode and Y. Suwannachot, “The Possible Role of Cu(II) for the Origin of Life,” Coordination Chemistry Reviews, Vol. 190-192, 1999, pp. 1085-1099.
http://dx.doi.org/10.1016/S0010-8545(99)00159-9
[5] C. Barranguet, F. P. van den Ende, M. Rutgers, A. M. Breure, M. Greijdanus, J. J. Sinke and W. Admiraal, “Copper-Induced Modifications of the Trophic Relations in Riverine Algal-Bacterial Biofilms,” Environmental Toxicology and Chemistry, Vol. 22, No. 6, 2003, pp. 1340-1349.
http://dx.doi.org/10.1002/etc.5620220622
[6] N. Pourreza and R. Hoveizavi, “Simultaneous Preconcentration of Cu, Fe and Pb as Methylthymol Blue Complexes on Naphthalene Adsorbent and Flame Atomic Absorption Determination,” Analytica Chimica Acta, Vol. 549, No. 1-2, 2005, pp. 124-128.
http://dx.doi.org/10.1016/j.aca.2005.06.037
[7] J. S. Becker, M. V. Zoriy, C. Pickhardt, N. Palomero-Gallagher and K. Zilles, “Imaging of Copper, Zinc, and Other Elements in Thin Section of Human Brain Samples (Hippocampus) by Laser Ablation Inductively Coupled Plasma Mass Spectrometry,” Analytical Chemistry, Vol. 77, No. 10, 2005, pp. 3208-3216.
http://dx.doi.org/10.1021/ac040184q
[8] Z. H. Li, L. Zhang, Z. P. Zang, X. J. Chang and X. J. Zou, “Attapulgite Modified with 2-Hydroxy-1-Naphthaldehyde as Selective Solid-Phase Extractant for Determination of Copper(II) in Environmental Samples by ICP-OES,” Microchim Acta, Vol. 171, No. 1-2, 2010, pp. 161-168.
http://dx.doi.org/10.1007/s00604-010-0407-0
[9] J. J. Pinto, C. Moreno and M. Garciaa-Vargas, “A Very Sensitive Flow System for the Direct Determination of Copper in Natural Waters Based on Spectrophotometric Detection,” Talanta, Vol. 64, No. 2, 2004, pp. 562-565. http://dx.doi.org/10.1016/j.talanta.2004.03.009
[10] V. Beni, V. Ogurtsov, N. Bakunin, D. W. Arrigan and M. Hill, “Development of A Portable Electroanalytical System for the Stripping Voltammetry of Metals: Determination of Copper in Acetic Acid Soil Extracts,” Analytica Chimica Acta, Vol. 552, No. 1-2, 2005, pp. 190-200.
http://dx.doi.org/10.1016/j.aca.2005.07.058
[11] Y. Zheng, X. Cao, J. Orbulescu, V. Konka, F. M. Andreopoulos, A. M. Pham and R. M. Leblanc, “Peptidyl Fluorescent Chemosensors for the Detection of Divalent Copper,” Analytical Chemistry, Vol. 75, No.7, 2003, pp. 1706-1712. http://dx.doi.org/10.1021/ac026285a
[12] L. A. Saari and W. R. Seitz, “Immobilized Calcein for Metal Ion Preconcentration,” Analytical Chemistry, Vol. 56, No. 4, 1984, pp. 810-813.
http://dx.doi.org/10.1021/ac00268a051
[13] X. Q. Chen, T. Pradhan, F. Wang, J. S. Kim and J. Yoon, “Fluorescent Chemosensors Based on Spiroring-Opening of Xanthenes and Related Derivatives,” Chemical Reviews, Vol. 112, No. 3, 2012, pp. 1910-1956.
http://dx.doi.org/10.1021/cr200201z
[14] X. H. Qian, Y. Xiao, Y. F. Xu, X. F. Guo, J. H. Qian and W. P. Zhu, “ ‘Alive’ Dyes as Fluorescent Sensors: Fluorophore, Mechanism, Receptor and Imagesin Living Cells,” Chemical Communications, Vol. 46, 2010, pp. 6418-6436.
http://dx.doi.org/10.1039/c0cc00686f
[15] X. H. Zhao, Q. J. Ma, X. B. Zhang, B. Huang, Q. Jiang, J. Zhang, G. L. Shen and R. Q. Yu, “A Highly Selective Fluorescent Sensor for Cu2+ Based on a Covalently Immobilized Naphthalimide Derivative,” Analytical Science, Vol. 26, No. 5, 2010, pp. 585-590.
http://dx.doi.org/10.2116/analsci.26.585
[16] R. Martínez, F. Zapata, A. Caballero, A. Espinosa , A. Tarraga and P. Molina, “2-Aza-1,3-butadiene Derivatives Featuring an Anthracene or Pyrene Unit:Highly Selective Colorimetric and Fluorescent Signaling of Cu2+ Cation,” Organic Letters, Vol. 8, No. 15, 2006, pp. 3235-3238. http://dx.doi.org/10.1021/ol0610791
[17] H. J. Kim, J. Hong, A. Hong, S. Ham, J. H. Lee and J. S. Kim, “Cu2+-Induced Intermolecular Static Excimer Formation of Pyrenealkylamine,” Organic. Letters, Vol. 10, No. 10, 2008, pp. 1963-1966.
http://dx.doi.org/10.1021/ol800475d
[18] C. L. He, F. L. Ren, X. B. Zhang, Y. Y. Dong and Y. Zhao, “A Fluorescent Chemosensor for Copper(II) Based on a Carboxylic Acid-functionalized Tris(2,2’-bipyridine)-ruthenium(II) Complex,” Analytical Science, Vol. 22, No. 12, 2006, pp. 1547-1551.
http://dx.doi.org/10.2116/analsci.22.1547
[19] X. B. Zhang, J. Peng, C. L. He, G. L. Shen and R. Q. Yu, “A Highly Selective Fluorescent Sensor for Cu2+ Based on 2-(2’-Hydroxyphenyl)benzoxazole in a Poly(vinyl chloride) Matrix,” Analytica Chimica Acta, Vol. 567, No. 2, 2006, pp. 189-195.
http://dx.doi.org/10.1016/j.aca.2006.03.025
[20] H. Y. Luo, X. B. Zhang, J. H. Jiang, C. Y. Li, J. Peng, G. L. Shen and R. Q. Yu, “An Optode Sensor for Cu2+ with High Selectivity Based on Porphyrin Derivative Appended with Bipyridine,” Analytical Science, Vol. 23, No. 5, 2007, pp. 551-555.
http://dx.doi.org/10.2116/analsci.23.551
[21] Y. Q. Weng, F. Yue, Y. R. Zhong and B. H. Ye, “A Copper(II) Ion-Selective On-Off-Type Fluoroionophore Based on Zinc Porphyrin-Dipyridylamino,” Inorganic Chemistry, Vol. 46, No. 19, 2007, pp. 7749-7755.
http://dx.doi.org/10.1021/ic061709v
[22] N. Shao, Y. Zhang, S. M. Cheung, R. H. Yang, W. H. Chan, T. Mo, K. A. Li and F. Liu, “Copper Ion-Selective Fluorescent Sensor Based on the Inner Filter Effect Using a Spiropyran Derivative,” Analytical Chemistry, Vol. 77, No. 22, pp. 2005, pp. 7294-7303.
http://dx.doi.org/10.1021/ac051010r
[23] N. Shao, J. Y. Jin, H. Wang, Y. Zhang, R. H. Yang and W. H. Chan, “Tunable Photochromism of Spirobenzopyran via Selective Metal Ion Coordination: An Efficient Visual and Ratioing Fluorescent Probe for Divalent Copper Ion,” Analytical Chemistry, Vol. 80, No. 9, 2008, pp. 3466-3475. http://dx.doi.org/10.1021/ac800072y
[24] X. Qi, E. J. Jun, L. Xu, S. J. Kim, J. S. Hong and Y. J. Yoon and J. Yoon, “New BODIPY Derivatives as OFF-ON Fluorescent Chemosensor and Fluorescent Chemodosimeter for Cu2+: Cooperative Selectivity Enhancement toward Cu2+,” The Journal of Organic Chemistry, Vol. 71, No. 7, 2006, pp. 2881-2884.
http://dx.doi.org/10.1021/jo052542a
[25] N. Narayanan and G. Patonay, “A New Method for the Synthesis of Heptamethine Cyanine Dyes: Synthesis of New Near-Infrared Fluorescent Labels,” The Journal of Organic Chemistry, Vol. 60, No. 8, 1995, pp. 2391-2395. http://dx.doi.org/10.1021/jo00113a018
[26] L. Yuan, W. Y. Lin, K. B. Zheng, L. W. He and W. M. He, “Far-red to Near Infrared Analyte-Responsive Fluorescent Probes Based on Organic Fluorophore Platforms for Fluorescence Imaging,” Chemical Society Reviews, Vol. 42, 2013, pp. 622-661.
http://dx.doi.org/10.1039/c2cs35313j
[27] P. Li, X. Duan, Z. Z. Chen, Y. Liu, T. Xie, L. B. Fang, X. R. Li, M. Yin and B. Tang, “A Near-Infrared Fluorescent Probe for Detecting Copper(II) with High Selectivity and Sensitivity and Its Biological Imaging Applications,” Chemical Communications, Vol. 47, 2011, pp. 7755-7757.
http://dx.doi.org/10.1039/c1cc11885d
[28] B. Tang, H. Huang, K. H. Xu, L. H. Tong, G. W. Yang, X. Liu and L. G. An, “Highly Sensitive and Selective Near-Infrared Fluorescent Probe for Zinc and Its Application to Macrophage Cells,” Chemical Communications, Vol. 34, 2006, pp. 3609-3611.
http://dx.doi.org/10.1039/b606809j
[29] W. H. Liu, Y. Wang, J. H. Tang, G. L. Shen and R. Q. Yu, “An Optical Fiber Sensor for Berberine Based on Immobilized 1,4-Bis(Naphth[2,1-d]Oxazole-2-yl)Benzene in a New Copolymer,” Talanta, Vol. 46, No. 4, 1998, pp. 679-688. http://dx.doi.org/10.1016/S0039-9140(97)00330-5

Copyright © 2024 by authors and Scientific Research Publishing Inc.

Creative Commons License

This work and the related PDF file are licensed under a Creative Commons Attribution 4.0 International License.