A water-soluble pyrazinium-based chemosensor for TNP detection: applications in MCF-7 cancer cell imaging and fingerprint visualization.
- 1Department of Chemistry, Birla Institute of Technology and Science, Pilani Pilani Campus, Vidya Vihar Pilani Rajasthan 333031 India [email protected].
- 2Department of Pharmacy, Birla Institute of Technology and Science, Pilani Pilani Campus, Vidya Vihar Pilani Rajasthan 333031 India.
Abstract
A pyrazinium-based Schiff base ligand, 3-((E)-(((Z)-2-amino-1,2-dicyanovinyl)imino)methyl)-1-benzylpyrazin-1-ium (BzPyz), was synthesized for the sensitive detection of TNP in aqueous media. The molecular structure of BzPyz was characterized using Fourier Transform Infrared Spectroscopy (FTIR), Powder X-ray Diffraction (PXRD), Nuclear Magnetic Resonance Spectroscopy (¹H and ¹³C NMR), and mass spectrometry. BzPyz exhibited blue emission in solution and yellowish-green fluorescence in the solid state, with pronounced solvatochromic behavior. Detailed photophysical studies indicated the involvement of both static and dynamic quenching pathways, with ground-state complex formation between BzPyz and TNP supporting a static contribution and (time-resolved photoluminescence) TRPL measurements providing evidence for an additional dynamic contribution arising from excited-state interactions. BzPyz exhibited a selective fluorescence turn-off response to TNP with a low detection limit of 4.43 nM. Spectroscopic analyses indicated a 1 : 1 binding stoichiometry for the [BzPyz-TNP] complex, with a strong binding affinity of K a = 8.82 × 10⁴ M⁻¹. Density functional theory (DFT) calculations were performed to support the experimental findings by elucidating the ground-state electronic structure and transitions, with particular emphasis on interactions between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO). The practical applicability of BzPyz was demonstrated through successful quantification of TNP in real water and soil samples, validated by HPLC and spike recovery studies. This was extended to advanced in vitro cellular imaging in human breast adenocarcinoma (MCF-7) cells, latent fingerprint visualization, smartphone-assisted detection, molecular logic gate operation, and portable sensing platforms.
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BibTeX
@article{nitika2026watersoluble,
title = {{A water-soluble pyrazinium-based chemosensor for TNP detection: applications in MCF-7 cancer cell imaging and fingerprint visualization.}},
author = {Nitika and Anshul Sharma and Murali Monohar Pandey and Bharti Khungar},
journal = {RSC advances},
year = {2026},
month = oct,
doi = {10.1039/d6ra06469h},
url = {https://europepmc.org/article/MED/42841105},
note = {CC BY-NC},
}
RIS
TY - JOUR
TI - A water-soluble pyrazinium-based chemosensor for TNP detection: applications in MCF-7 cancer cell imaging and fingerprint visualization.
AU - Nitika
AU - Anshul Sharma
AU - Murali Monohar Pandey
AU - Bharti Khungar
PY - 2026
DA - 2026/10/06
JO - RSC advances
DO - 10.1039/d6ra06469h
UR - https://europepmc.org/article/MED/42841105
AB - A pyrazinium-based Schiff base ligand, 3-((E)-(((Z)-2-amino-1,2-dicyanovinyl)imino)methyl)-1-benzylpyrazin-1-ium (BzPyz), was synthesized for the sensitive detection of TNP in aqueous media. The molecular structure of BzPyz was characterized using Fourier Transform Infrared Spectroscopy (FTIR), Powder X-ray Diffraction (PXRD), Nuclear Magnetic Resonance Spectroscopy (¹H and ¹³C NMR), and mass spectrometry. BzPyz exhibited blue emission in solution and yellowish-green fluorescence in the solid state, with pronounced solvatochromic behavior. Detailed photophysical studies indicated the involvement of both static and dynamic quenching pathways, with ground-state complex formation between BzPyz and TNP supporting a static contribution and (time-resolved photoluminescence) TRPL measurements providing evidence for an additional dynamic contribution arising from excited-state interactions. BzPyz exhibited a selective fluorescence turn-off response to TNP with a low detection limit of 4.43 nM. Spectroscopic analyses indicated a 1 : 1 binding stoichiometry for the [BzPyz-TNP] complex, with a strong binding affinity of K a = 8.82 × 10⁴ M⁻¹. Density functional theory (DFT) calculations were performed to support the experimental findings by elucidating the ground-state electronic structure and transitions, with particular emphasis on interactions between the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO). The practical applicability of BzPyz was demonstrated through successful quantification of TNP in real water and soil samples, validated by HPLC and spike recovery studies. This was extended to advanced in vitro cellular imaging in human breast adenocarcinoma (MCF-7) cells, latent fingerprint visualization, smartphone-assisted detection, molecular logic gate operation, and portable sensing platforms.
SN - 2046-2069
ER -