2038-15-5Relevant articles and documents
Symmetric Meso-Chloro-Substituted Pentamethine Cyanine Dyes Containing Benzothiazolyl/Benzoselenazolyl Chromophores Novel Synthetic Approach and Studies on Photophysical Properties upon Interaction with bio-Objects
Kurutos, Atanas,Ryzhova, Olga,Trusova, Valeriya,Gorbenko, Galyna,Gadjev, Nikolay,Deligeorgiev, Todor
, p. 177 - 187 (2016)
A series of symmetric pentamethine cyanine dyes derived from various N-substituted benzothiazolium/benzoselenazolium salts, and a conjugated bis-aniline derivative containing a chlorine atom at meso-position with respect to the polymethine chain, were synthesized using a novel improved synthetic approach under mild conditions at room temperature. The reaction procedure was held by grinding the starting compounds for relative short times. The novel method is reliable and highly reproducible. Some photophysical characteristics were recorded in various solvents, including absorption, and fluorescence quantum yields using Cy-5 as a reference. Additional studies on interactions with several bio-objects such as liposomes, DNA, and proteins have been investigated in the present work.
RNA-targeting low-molecular-weight fluorophores for nucleoli staining: synthesis,in silicomodelling and cellular imaging
Kurutos, Atanas,Nikodinovic-Runic, Jasmina,Veselinovic, Aleksandar,Veselinovi?, Jovana B.,Kamounah, Fadhil S.,Ilic-Tomic, Tatjana
supporting information, p. 12818 - 12829 (2021/08/03)
Herein we present our work on the synthesis, investigation of the photophysical properties, interactions with nucleic acids, molecular docking, and imaging application of three carbocyanine dyes. The described low-molecular-weight compounds were found to exhibit high resistance against photobleaching and showed promising optical properties as fluorescent labeling agents for ribonucleic acids. They form strong biocomplexes (log?Ks= 6.11-7.84) and revealed remarkable sensitivity towards RNA, reaching up to a 379 times increase of the emission signal when bound to AU-rich sequences. According to the score values obtained from the molecular docking studies, the compounds show strong binding affinity towards RNA macromolecules. All fluorophores exhibit significant cell tolerance since they were found to be 16 to 60 times less toxic against MRC5 cells (healthy human fibroblasts) compared to the conventional Thiazole Orange - TO. The IC50 concentrations for the compounds were calculated up to 40 μM in human fibroblasts MRC5, A549 adenocarcinomic human alveolar basal epithelial cells, the HCT116 human colon cancer cell line, and MDA-MB-231 adenocarcinoma cells. Analyzing the dyes for preferential cytotoxicity towards cancer cell lines in comparison to the normal human fibroblasts, we found a candidate exhibiting promising anticancer potential. Based on the selectivity (Si) towards cancer cells and more specifically against difficult to treat colon HCT116 carcinoma, we can suggest these small molecules as an interesting platform for further development. We have also demonstrated the efficiency of the carbocyanines as staining agents forin vivolabeling of human cells as well as microbial and eukaryotic cells.
Reactivite du nitrite de sodium. II. Action sur les sels d'iminium heterocycliques. Etude par RMN multinucleaire
Gouesnard, Jean-Paul,Dorie, Jean
, p. 253 - 258 (2007/10/02)
The structure and the electronic delocalisation of various heterocyclic iminium salts - and their precursors - have been studied by 13C and 15N NMR.The 13C and 15N chemical shifts are correlated with the nucleophilicity of the second heteroatom.The observation of δ13C explains satisfactorily the reactivity of heterocyclic iminium salts towards nucleophilic reagents and their catalytic activity as model compounds for thiamine or cocarboxylase.Different products are obtained by the reaction of sodium nitrite - in aqueous or non-aqueous medium - : they have been identified by NMR.The products are those expected and allow the determination of the reaction mechanisms.
