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Peer-reviewedCC BYChemical & biomedical imaging

A Structure-Programmable Palette of Compact Cationic Dyes Enables Predictable Organelle Addressing and Multicolor Mitochondrial Imaging.

  • Jean C Neto1
  • Xavier J Salom-Roig2
  • Eva Falomir1
  • Rosa de Llanos3
  • Juan F Miravet1
  • Francisco Galindo1
  1. 1Departamento de Química Inorgánica y Orgánica, Universitat Jaume I de Castellón, Avda Vicente Sos Baynat, s/n, 12071 Castellón de la Plana, Spain.
  2. 2Institut des Biomolécules Max Mousseron. Université de Montpellier, CNRS, ENSCM, 1019, route de Mende, 34293 Montpellier, France.
  3. 3Unidad Predepartamental de Medicina, Universitat Jaume I de Castellón, Avda Vicente Sos Baynat, s/n, 12071 Castellón de la Plana, Spain.
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Abstract

Cationic pyrylium/pyridinium (Katritzky-type) frameworks have a long history in dye chemistry and have been repeatedly adapted as compact, modular fluorophores for bioimaging. Building on this foundation, we assembled a 20-member library of diversifiable pyrylium/pyridinium salts accessible in one to two steps from readily available precursors, providing a multicolor palette that spans the visible-to-far-red region while maintaining high absorptivity, large Stokes shifts, and bright emission in organic media. In live A549 cancer cells at nanomolar loading, most derivatives rapidly accumulate in mitochondria and show strong colocalization with commercial mitochondrial markers. Importantly, by systematically relating the side-chain structure to calculated lipophilicity, we uncover a practical and predictive localization map: mitochondrial staining is maximized within a narrow cLogP window (ca. 4-6), whereas increased hydrophobicity promotes aqueous aggregation and progressively shifts uptake toward endo/lysosomal compartments. This lipophilicity-governed "address switch" enables organelle destination to be programmed without changing the fluorophore core, providing a practical design guideline for building next-generation chemical imaging tools and functional reporters on pyrylium/pyridinium scaffolds. In addition, the probes can be used for mitochondrial staining in the pathogenic yeast Candida albicans, extending their applicability beyond mammalian cells.

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Cite

BibTeXRIS
BibTeX
@article{neto2026structureprogrammable,
  title = {{A Structure-Programmable Palette of Compact Cationic Dyes Enables Predictable Organelle Addressing and Multicolor Mitochondrial Imaging.}},
  author = {Jean C Neto and Xavier J Salom-Roig and Eva Falomir and Rosa de Llanos and Juan F Miravet and Francisco Galindo},
  journal = {Chemical \& biomedical imaging},
  year = {2026},
  month = jun,
  doi = {10.1021/cbmi.6c00056},
  url = {https://europepmc.org/article/MED/42953690},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - A Structure-Programmable Palette of Compact Cationic Dyes Enables Predictable Organelle Addressing and Multicolor Mitochondrial Imaging.
AU  - Jean C Neto
AU  - Xavier J Salom-Roig
AU  - Eva Falomir
AU  - Rosa de Llanos
AU  - Juan F Miravet
AU  - Francisco Galindo
PY  - 2026
DA  - 2026/06/08
JO  - Chemical & biomedical imaging
DO  - 10.1021/cbmi.6c00056
UR  - https://europepmc.org/article/MED/42953690
AB  - Cationic pyrylium/pyridinium (Katritzky-type) frameworks have a long history in dye chemistry and have been repeatedly adapted as compact, modular fluorophores for bioimaging. Building on this foundation, we assembled a 20-member library of diversifiable pyrylium/pyridinium salts accessible in one to two steps from readily available precursors, providing a multicolor palette that spans the visible-to-far-red region while maintaining high absorptivity, large Stokes shifts, and bright emission in organic media. In live A549 cancer cells at nanomolar loading, most derivatives rapidly accumulate in mitochondria and show strong colocalization with commercial mitochondrial markers. Importantly, by systematically relating the side-chain structure to calculated lipophilicity, we uncover a practical and predictive localization map: mitochondrial staining is maximized within a narrow cLogP window (ca. 4-6), whereas increased hydrophobicity promotes aqueous aggregation and progressively shifts uptake toward endo/lysosomal compartments. This lipophilicity-governed "address switch" enables organelle destination to be programmed without changing the fluorophore core, providing a practical design guideline for building next-generation chemical imaging tools and functional reporters on pyrylium/pyridinium scaffolds. In addition, the probes can be used for mitochondrial staining in the pathogenic yeast Candida albicans, extending their applicability beyond mammalian cells.
SN  - 2832-3637
ER  -