Development of new agents for cell staining and bioimaging

This line began by addressing the design and synthesis of new chromophores that could be selective DNA intercalants. This type of molecules that exhibit the ability to insert themselves between the base pairs of this biomolecule show, in some cases, great interest as antiproliferative agents and potential application as antitumor agents. Another possible application lies in using them to generate DNA probes and/or agents for cell staining. This requires high fluorescence, permeability through the cell membrane, low or no toxicity, stability against long periods of illumination and absorption at wavelengths higher than UV. In this line we have developed DNA probes based on polycyclic heteroaromatic cations, analogues of the chromophore of the green fluorescent protein (GFP) and, more recently, dyes based on upconversion processes exploring systems for multiphoton absorption (2PA) based on push-pull chromophores with non-linear optical properties (NLO).

a) General structure of DNA probes (above) and staining of HeLa cells with a representative compound, b) Image of HEK cells stained with the compound V-MOP2 and confocal microscopy images of V-IDQc (green) and DAPI (blue) in U2OS cells, c) Analogue with restricted conformation of GFP.

Recent publications:

Highly efficient unbridged D-A+(D) chromophores based on the quinolizinium cation for nonlinear optical (NLO) applications.
Dyes Pigm. 2022, 205, 110323.
Two-photon activated precision molecular photosensitizer targeting mitochondria.
2021; 4(1):142.
A new family of fluorescent pyridazinobenzimidazolium cations with DNA binding properties.
Dyes and Pigments. 2021 Aug 1; :109443.
Synthesis and Photophysical Behavior of a Highly Fluorescent Family of Unsymmetrical Organoboron Complexes Containing 5-(Pyridin-2-ylmethylene)imidazolidine-2,4-dione Moieties.
J Org Chem. 2020, 85, 441
Dibenzopyridoimidazocinnolinium cations: a new family of light-up fluorescent DNA probes.
Org. Chem. Front. 2018, 5, 1916
Azonia aromatic heterocycles as a new acceptor unit in D-π-A%@2B vs D-A%@2B nonlinear optical chromophores.
Dyes Pigm. 2017, 144, 17
Imidazopyridinium cations: A new family of azonia aromatic heterocycles with applications as DNA intercalators.
Dyes Pigm. 2017, 138, 135
Quinolizinium as a new fluorescent lysosomotropic probe.
Biorg. Med. Chem. Lett. 2017, 27, 203
Highly Fluorescent Green Fluorescent Protein Chromophore Analogues Made by Decorating the Imidazolone Ring.
Chem. Eur. J. 2015, 21, 18758
Nonlinear Emission of Quinolizinium Based Dyes With Application in Fluorescence Lifetime Imaging.
J. Phys. Chem. A 2015, 119, 11, 2351
Targeting DNA with small molecules: a comparative study of a library of azonia aromatic chromophores.
Org Biomol Chem. 2015, 13, 527