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Selective Cadmium Fluorescence Probe Based on Bis-heterocyclic Molecule and its Imaging in Cells

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A Correction to this article was published on 22 February 2022

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Abstract

Fluorescence probes that selectively image cadmium are useful for detecting and tracking the amount of Cd2+ in cells and tissues. In this study, we designed and synthesized a novel Cd2+ fluorescence probe based on the pyridine-pyrimidine structure, 4-(methylsulfanyl)-6-(pyridin-2-yl)pyrimidin-2-amine (3), as a low-molecular-weight fluorescence probe for Cd2+. Compound 3 could successfully discriminate between Cd2+ and Zn2+ and exhibited a highly selective turn-on response toward Cd2+ over biologically related metal ions. The dissociation constant (Kd) and the limit of detection (LOD) of 5.4 × 10− 6 mol L− 1 and 4.4 × 10− 7 mol L− 1, respectively, were calculated using fluorescence titration experiments. Studies with closely related analogs showed that the bis-heterocyclic moiety of 3 acted as both a coordination site for Cd2+ and a fluorophore. Further, the methylsulfanyl group of compound 3 is essential for achieving selective and sensitive Cd2+ detection. Fluorescence microscopy studies using living cells revealed that the cell membrane permeability of compound 3 is sufficient to detect intracellular Cd2+. These results indicate that novel bis-heterocyclic molecule 3 has considerable potential as a fluorescence probe for Cd2+ in biological applications.

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Funding

This work was partly supported by the Konica Minolta Imaging Science Encouragement Award of Konica Minolta Science and Technology Foundation.

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Authors and Affiliations

  1. Faculty of Pharmaceutical Sciences, Mukogawa Women’s University, 11-68 Koshien Kyubancho, Nishinomiya, 663-8179, Japan

    Masayori Hagimori & Fumiko Hara

  2. Graduate School of Biomedical Sciences, Nagasaki University, 1-7-1 Sakamoto, Nagasaki, 852- 8501, Japan

    Masayori Hagimori & Yasushi Karimine

  3. Division of Medical Innovation, Translational Research Center for Medical Innovation, 1-5-4 Minatojima-minamimachi, Chuo-ku, Kobe, 650-0047, Japan

    Naoko Mizuyama

  4. Graduate School of Science and Engineering, Saitama University, 255 Shimo-Okubo, Sakura- ku, 338-8570, Saitama, Japan

    Takeshi Fujino

  5. Graduate School of Pharmaceutical Sciences, Kyoto University, 46–29 Yoshida-Shimoadachi- cho, Sakyo-ku, Kyoto, 606-8501, Japan

    Hideo Saji

  6. Department of Biophysical Chemistry, Kobe Pharmaceutical University, 4-19-1 Motoyamakita Machi, Higashinada-Ku, Kobe, 658-8558, Japan

    Takahiro Mukai

Authors
  1. Masayori Hagimori
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  2. Yasushi Karimine
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  3. Naoko Mizuyama
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  4. Fumiko Hara
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  5. Takeshi Fujino
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  6. Hideo Saji
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  7. Takahiro Mukai
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Contributions

All the authors (M. Hagimori, Y. Karimine, N. Mizuyama, F. Hara, T. Fujino, H. Saji, T. Mukai) made substantial contribution while preparing the manuscript.

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Correspondence to Masayori Hagimori.

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The original online version of this article was revised: The equation under “Experimental -- Spectroscopic Studies" section should be corrected.

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Hagimori, M., Karimine, Y., Mizuyama, N. et al. Selective Cadmium Fluorescence Probe Based on Bis-heterocyclic Molecule and its Imaging in Cells. J Fluoresc 31, 1161–1167 (2021). https://doi.org/10.1007/s10895-021-02748-7

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  • DOI: https://doi.org/10.1007/s10895-021-02748-7

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