Organotin Dyes Bearing Anionic Boron Clusters as Cell‐Staining Fluorescent Probes

Abstract

Within the cell nucleus, in the nucleoli, ribosomal RNAs are synthesized and participate in several biological processes. To better understand nucleoli-related processes, their visualization is often required, for which specific markers are needed. Herein, we report the design of novel fluorescent organotin compounds derived from 4-hydroxy-N'-((2-hydroxynaphthalen-1-yl)methylene)benzohydrazide and their cytoplasm and nucleoli staining of B16F10 cells in vitro. Tin compounds bearing an aliphatic carbon chain (-C H ) and an electron-donating group (-OH) were prepared, and the latter could be derivatized to bear the boron cluster anions [B H ] and [3,3'-Co(1,2-C B H ) ] (COSAN). All of the conjugates have been fully characterized and their luminescence properties have been assessed. In general, they show good quantum yields in solution (24-49 %), those for the COSAN derivatives being lower. Remarkably, the linking of [B H ] and COSAN to the complexes made them more soluble, without being detrimental to their luminescence properties. Living B16F10 cells were treated with all of the compounds to determine their fluorescence staining properties; the compounds bearing the aliphatic chain showed a reduced staining capacity due to the formation of aggregates. Notably, the complexes bearing different boron clusters showed different staining effects; those bearing [B H ] showed extraordinary staining of the nucleoli and cytoplasm, whereas those bearing COSAN were only detected in the cytoplasm. The remarkable fluorescence staining properties shown by these organotin compounds make them excellent candidates for fluorescence bioimaging in vitro.

Two‐Photon Detection of Organotin Schiff Base Complexes in Cancer Cells

“…The structural diversity of the organotin compounds derived from Schiff bases, and their applications, have been a major impetus for the investigation of these molecules . Recently, we reported fluorescent organotin derivatives and their application in bioimaging studies . Here we show that a family of organotin compounds have attractive fluorescent properties, via one‐photon (1P) and two‐photon (2P) excitation, and that they can selectively penetrate and stain cancer cells and be differentiated from normal cells.…”

Photoluminescence in m-carborane–anthracene triads: a combined experimental and computational study

“…[19][20][21] . Owing to the intrinsic properties of carboranes, they have been used as exceptional building blocks for developing functional organic materials with enhanced thermal and chemical properties 22-25 . In the last decade, the development of boron cluster-based organic -conjugated systems have attracted huge interest as active materials in (opto)electronic devices, such as organic lightemitting diodes (OLEDs), organic field effect transistors (OFETs), solar cells, biological sensors and imaging, [26][27][28] among others. 29,30 It has been demonstrated the remarkable influence of the o-carborane cluster on the photophysical properties of luminescent materials in solution and solid state.…”

Composites of Nucleic Acids and Boron Clusters (C2B10H12) as Functional Nanoparticles for Downregulation of EGFR Oncogene in Cancer Cells

“…However, it cannot be ruled out that some amount of nanostructured fluorescent B-ASO is transported into the nuclei, as was already shown by some studies of antisense oligonucleotides [ 47 ]. The Viñas team has also shown that organotin dyes bearing boron clusters are localized mostly in the cytoplasm, but traces are also found in the cell nucleus [ 64 ].…”