Structure-dependent mitochondria or lysosome-targeting styryl fluorophores bearing remarkable Stokes shift

Čipor, Ivona; Kurutos, Atanas; Dobrikov, Georgi M.; Kamounah, Fadhil S.; Majhen, Dragomira; Nestić, Davor; Piantanida, Ivo

doi:10.1016/j.dyepig.2022.110626

Cited by 6 publications

(4 citation statements)

References 62 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Section: Introductionmentioning

confidence: 99%

“…Some dyes showed promising antiproliferative activity combined with selective fluorimetric intracellular staining (thus acting as theranostic agents), while others were biologically inactive but still selectively staining various cellular organelles [ 28 , 29 ]. Further, we very recently designed and studied monocationic styryl dyes [ 30 ] with fluorescence quantum yields strongly dependent on the selection of the N -quaternary heterocycle. New dyes interacted non-covalently with DNA/RNA by micromolar affinity, yielding a strong fluorescence increase strongly dependent on a heterocycle of a dye.…”

Section: Introductionmentioning

confidence: 99%

“…Intrigued by the obtained results for mono- and bis-styryl dyes [ 28 , 30 ], the question arose whether the multiplicity of the styryl motif in one molecule could improve some aforementioned properties. Thus, we designed a novel generation of styryl dyes ( Scheme 1 ) based on a variation of three distinct structural features: multiplicity of styryl motif through attaching three or four styryl moieties to one central aromatic core; type of positive charge by comparing heterocyclic cationic species with exocyclic per-alkylated amines; steric shielding of positive charge by the introduction of smaller or larger alkylating groups.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Trimeric and Tetrameric Cationic Styryl Dyes as Novel Fluorescence and CD Probes for ds-DNA and ds-RNA

Pavlović Saftić,

Krošl Knežević,

de Lera Garrido

et al. 2024

IJMS

Self Cite

View full text Add to dashboard Cite

The wide use of mono- or bis-styryl fluorophores in biomedical applications prompted the presented design and study of a series of trimeric and tetrameric homo-analogues, styryl moieties arranged around a central aromatic core. The interactions with the most common biorelevant targets, ds-DNA and ds-RNA, were studied by a set of spectrophotometric methods (UV-VIS, fluorescence, circular dichroism, thermal denaturation). All studied dyes showed strong light absorption in the 350–420 nm range and strongly Stokes-shifted (+100–160 nm) emission with quantum yields (Φf) up to 0.57, whereby the mentioned properties were finely tuned by the type of the terminal cationic substituent and number of styryl components (tetramers being red-shifted in respect to trimers). All studied dyes strongly interacted with ds-DNA and ds-RNA with 1–10 nM−1 affinity, with dye emission being strongly quenched. The tetrameric analogues did not show any particular selectivity between ds-DNA or ds-RNA due to large size and consequent partial, non-selective insertion into DNA/RNA grooves. However, smaller trimeric styryl series showed size-dependent selective stabilization of ds-DNA vs. ds-RNA against thermal denaturation and highly selective or even specific recognition of several particular ds-DNA or ds-RNA structures by induced circular dichroism (ICD) bands. The chiral (ICD) selectivity was controlled by the size of a terminal cationic substituent. All dyes entered efficiently live human cells with negligible cytotoxic activity. Further prospects in the transfer of ICD-based selectivity into fluorescence-chiral methods (FDCD and CPL) is proposed, along with the development of new analogues with red-shifted absorbance properties.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Trimeric and Tetrameric Cationic Styryl Dyes as Novel Fluorescence and CD Probes for ds-DNA and ds-RNA

Pavlović Saftić,

Krošl Knežević,

de Lera Garrido

et al. 2024

IJMS

Self Cite

View full text Add to dashboard Cite

show abstract

“…In the literature, there are more and more works on the study of styryl dyes as fluorescent probes for biomolecules and organelles (e.g., mitochondria and lysosomes) [7][8][9][10][11]. Their structural tunability and excellent photophysical properties have made them highly suitable for fluorescence-based studies.…”

Section: Introductionmentioning

confidence: 99%

Specific Fluorescent Probes for Imaging DNA in Cell-Free Solution and in Mitochondria in Living Cells

et al. 2023

View full text Add to dashboard Cite

New styryl dyes consisting of N-methylpyridine or N-methylquinoline scaffolds were synthesized, and their binding affinities for DNA in cell-free solution were studied. The replacement of heterocyclic residue from the pyridine to quinoline group as well as variation in the phenyl part strongly influenced their binding modes, binding affinities, and spectroscopic responses. Biological experiments showed the low toxicity of the obtained dyes and their applicability as selective dyes for mitochondria in living cells.

show abstract

Nitrobenzene and Aniline‐Mediated Direct Olefination of Methyl Substituted N‐Heteroarenes With Benzylic Alcohols

Dong,

Mei,

et al. 2024

ChemistrySelect

View full text Add to dashboard Cite

Metal‐free, strong‐base‐free, and solvent‐free synthesis of alkenyl heteroarenes through PhNO2/PhNH2 mediated direct olefination of methyl substituted N‐heteroarenes with benzylic alcohols was described. Detailed mechanistic studies indicated that in situ formed imine was the active intermediate for the olefination. PhNO2 protected benzylic alcohols from overoxidation, and PhNH2 not only acted as the coupling partner for the formation of intermediate imine, but also provides an alkaline condition for the generation of enamine salt. Gram scale reaction and the synthesis of three pharmaceutically relevant conjugated olefins were also successful using this methodology.

show abstract

Structure-dependent mitochondria or lysosome-targeting styryl fluorophores bearing remarkable Stokes shift

Cited by 6 publications

References 62 publications

Trimeric and Tetrameric Cationic Styryl Dyes as Novel Fluorescence and CD Probes for ds-DNA and ds-RNA

Trimeric and Tetrameric Cationic Styryl Dyes as Novel Fluorescence and CD Probes for ds-DNA and ds-RNA

Specific Fluorescent Probes for Imaging DNA in Cell-Free Solution and in Mitochondria in Living Cells

Nitrobenzene and Aniline‐Mediated Direct Olefination of Methyl Substituted N‐Heteroarenes With Benzylic Alcohols

Contact Info

Product

Resources

About