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Coordination of Distal Carboxylate Anion Alters Metal Ion Specific Binding in Imidazo[1,2-a]pyridine Congeners

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Abstract

Imidazo[1,2-a]pyridine derivatives have excellent potential for chelation with transition metal ions. Two new imidazo[1,2-a]pyridine-8-carboxylates were synthesized and characterized by 1H NMR, 13C NMR, HRMS, and single crystal-XRD techniques. Methyl carboxylate (probe 1) turns on fluorescence upon coordination with Zn2+, while sodium carboxylate (probe 2) turns off its fluorescence upon coordination with Co2+ or Cu2+ ions present in aqueous acetonitrile medium. 13C NMR study revealed that the change in metal ion specific binding was due to the involvement of carboxylate anion in complex formation with Co2+ or Cu2+ ions. The carboxylate anion at 8-position also enhanced the sensitivity of detection of probe 2 by an order of magnitude (detection limits: 3.804 × 10–7 M, probe 1/Zn2+; 0.420 × 10–7 M, probe 2/Co2+ and 0.304 × 10–7 M, probe 2/Cu2+). The detection limits of probes 1 and 2 comply well with the World Health Organization (WHO) and US Environmental Protection Agency (US-EPA) guidelines for detection of heavy metal ions present in drinking water and ground water. Both the probes form a 1:1 complex with Zn2+, Co2+ or Cu2+, and the stoichiometry was verified by Job plot and ESI-mass analysis. The sensing mechanism is explained using 13C NMR experiments, ESI-mass analytical data and theoretical DFT calculations. The suitability of probes 1 and 2 for on-site detection and quantitative determination of Zn2+, Co2+ and Cu2+ ions present in biological, environmental and industrial samples is demonstrated. In addition, both 1 and 2 are used for detection of intracellular contamination of Zn2+, Co2+ or Cu2+ ions in onion epidermal cells.

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Data Availability

Samples of probe molecules and spectroscopic data are available with the corresponding author.

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Acknowledgements

One of the authors, DD is thankful to DST, New Delhi for INSPIRE Fellowship. MR, thanks the UGC, New Delhi, India, for Senior Research Fellowship. Financial support from CSIR-CLRI MLP12 project is acknowledged. We thank the Department of Chemistry, Pondicherry University, for Q-TOF analysis.

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The authors declare that no funds, grants, or other support were received during the preparation of this manuscript.

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Authors and Affiliations

  1. Organic and Bioorganic Chemistry Laboratory, CSIR – Central Leather Research Institute, Adyar, Chennai, 600020, India

    Dhakshinamurthy Divya, Ramanjaneyulu Mala & Sathiah Thennarasu

  2. Academy of Scientific and Innovative Research (AcSIR), CSIR – Central Leather Research Institute, Adyar, Chennai, 600020, India

    Ramanjaneyulu Mala & Sathiah Thennarasu

  3. Biocontrol and Microbial Metabolites Lab, Centre for Advanced Studies in Botany, University of Madras, Guindy Campus, Chennai, 600025, India

    Manivannan Nandhagopal & Mathivanan Narayanasamy

  4. Department of Microbiology, Saveetha Medical College and Hospital, Thandalam, Chennai-602105, India

    Manivannan Nandhagopal

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  1. Dhakshinamurthy Divya
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Contributions

Dhakshinamurthy Divya: Conceptualization, Data collection, Investigation, Methodology, Writing – original draft, Writing – review & editing. Ramanjaneyulu Mala: Data collection, data processing and interpretation. Manivannan Nandhagopal: Cell imaging experiments. Mathivanan Narayanasamy: Cell imaging experiments. Sathiah Thennarasu: Conceptualization, Formal Analysis, Supervision, Validation, Visualization, Writing – review & editing.

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Correspondence to Sathiah Thennarasu.

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Highlights

• Two new imidazo[1,2-a]pyridine congeners bearing methyl carboxylate (1) and sodium carboxylate (2) moieties were synthesized using Ugi type reaction and characterized using 1H, 13C-NMR, HRMS, and single crystal-XRD techniques.

• Lack of involvement of methyl carboxylate at 8-position in complex formation leads to selective interaction of 1 with only Zn2+ and offers a fluorescence turn-on response with a detection limit value 3.804 × 10−7 M.

• Involvement of carboxylate anion at 8-position in complex formation favors selective quenching of fluorescence from 2 by only Co2+ and Cu2+ and enhances the detection limit by an order of magnitude (0.420 × 10−7 M for Co2+ and 0.304 × 10−7 M for Cu2+).

• Suitability of both 1 and 2 for naked-eye detection, cell imaging and quantitative determination of contaminated metal ions present in industrial, environmental and biological samples is demonstrated.

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Divya, D., Mala, R., Nandhagopal, M. et al. Coordination of Distal Carboxylate Anion Alters Metal Ion Specific Binding in Imidazo[1,2-a]pyridine Congeners. J Fluoresc 33, 1397–1412 (2023). https://doi.org/10.1007/s10895-022-03122-x

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