Nanoconfined Chlorine-Substituted Monomethine Cyanine Dye with a Propionamide Function Based on the Thiazole Orange Scaffold-Use of a Fluorogenic Probe for Cell Staining and Nucleic Acid Visualization.

The development of fluorescence-based methods for bioassays and medical diagnostics requires the design and synthesis of specific markers to target biological microobjects. However, biomolecular recognition in real cellular systems is not always as selective as desired. A new concept for creating fluorescent biomolecular probes, utilizing a fluorogenic dye and biodegradable, biocompatible nanomaterials, is demonstrated.

Aggregation induced nucleic acids recognition by homodimeric asymmetric monomethyne cyanine fluorochromes in mesenchymal stem cells.

In the light of recent retrovirus pandemics, the issue of discovering new and diverse RNA-specific fluorochromes for research and diagnostics became of acute importance. The great majority of nucleic acid-specific probes either do not stain RNA or cannot distinguish between DNA and RNA. The versatility of polymethine dyes makes them suitable as stains for visualization, analysis, and detection of nucleic acids, proteins, and other biomolecules.

Novel Tetrahydroisoquinoline-Based Heterocyclic Compounds Efficiently Inhibit SARS-CoV-2 Infection .

The ongoing COVID-19 pandemic has caused over six million deaths and huge economic burdens worldwide. Antivirals against its causative agent, SARS-CoV-2, are in urgent demand. Previously, we reported that heterocylic compounds, i.

Synthesis of Novel 1-Oxo-2,3,4-trisubstituted Tetrahydroisoquinoline Derivatives, Bearing Other Heterocyclic Moieties and Comparative Preliminary Study of Anti-Coronavirus Activity of Selected Compounds.

A series of novel 1-oxo-2,3,4-trisubstituted tetrahydroisoquinoline (THIQ) derivatives bearing other heterocyclic moieties in their structure were synthesized based on the reaction between homophthalic anhydride and imines. Initial studies were carried out to establish the anti-coronavirus activity of some of the newly obtained THIQ-derivatives against two strains of human coronavirus-229E and OC-43. Their antiviral activity was compared with that of their close analogues, piperidinones and thiomorpholinones, previously synthesized in our group, with aim to expand the range of the tested representative sample and to obtain valuable preliminary information about biological properties of a wider variety of compounds.

Styryl dyes with N-Methylpiperazine and N-Phenylpiperazine Functionality: AT-DNA and G-quadruplex binding ligands and theranostic agents.

New monomethine, unsymmetrical styryl dyes consisting of benzothiazole and N-methylpiperazine or N-phenylpiperazine scaffolds were synthesized, and their binding affinities for different ds-polynucleotides and G-quadruplex were studied. Substitution of piperazine unit with methyl or phenyl group strongly influenced their binding modes, binding affinities, spectroscopic responses and antiproliferative activities. Compounds with N-methylpiperazine substituents showed a significant preference for AT-DNA polynucleotides and demonstrated AT-minor groove binding, which manifested in strong fluorescence increase, significant double helix stabilization, and positive induced circular dichroism spectra.

Tetrathienothiophene Porphyrin as a Metal-Free Sensitizer for Room-Temperature Triplet-Triplet Annihilation Upconversion.

Optically excited triplet states of organic molecules serve as an energy pool for the subsequent processes, either photon energy downhill, such as room temperature phosphorescence, or photon energy uphill process-the triplet-triplet annihilation upconversion (TTA-UC). Manifestation of a high intersystem crossing coefficient is an unavoidable requirement for triplet state formation, following the absorption of a single photon. This requirement is even more inevitable if the excitation light is non-coherent, with moderate intensity and extremely low spectral power density, when compared with the light parameters of 1 Sun (1.

Polycationic Monomeric and Homodimeric Asymmetric Monomethine Cyanine Dyes with Hydroxypropyl Functionality-Strong Affinity Nucleic Acids Binders.

New analogs of the commercial asymmetric monomethine cyanine dyes thiazole orange (TO) and thiazole orange homodimer (TOTO) with hydroxypropyl functionality were synthesized and their properties in the presence of different nucleic acids were studied. The novel compounds showed strong, micromolar and submicromolar affinities to all examined DNA ds-polynucleotides and poly rA-poly rU. The compounds studied showed selectivity towards GC-DNA base pairs over AT-DNA, which included both binding affinity and a strong fluorescence response.

Precious metal-free molecular machines for solar thermal energy storage.

Four benzothiazolium crown ether-containing styryl dyes were prepared through an optimized synthetic procedure. Two of the dyes ( and ) having substituents in the 5-position of the benzothiazole ring are newly synthesized compounds. They demonstrated a higher degree of photoisomerization and a longer life time of the higher energy forms in comparison with the known analogs.

Halogen-containing thiazole orange analogues - new fluorogenic DNA stains.

Novel asymmetric monomeric monomethine cyanine dyes , which are analogues of the commercial dsDNA fluorescence binder thiazole orange (), have been synthesized. The synthesis was achieved by using a simple, efficient and environmetally benign synthetic procedure to obtain these cationic dyes in good to excellent yields. Interactions of the new derivatives of with dsDNA have been investigated by absorption and fluorescence spectroscopy.

Methyl trans-(±)-1-oxo-2-phenethyl-3-(thio-phen-2-yl)-1,2,3,4-tetra-hydro-isoquinoline-4-carboxyl-ate.

In the title compound, C(23)H(21)NO(3)S, the piperidine ring of the tetra-hydro-isoquinolinone unit adopts a screw-boat conformation. The thio-phene ring is disordered in a 0.700 (3):0.

(S)-Methyl 2-[(3R,4R)-2-benzyl-3-(2-fur-yl)-1-oxo-1,2,3,4-tetra-hydro-isoquinoline-4-carboxamido]-3-(1H-indol-3-yl)propanoate.

The title compound, C(33)H(29)N(3)O(5), was synthesized by the reaction of racemic trans-2-benzyl-3-(2-fur-yl)-1-oxo-1,2,3,4-tetra-hydro-isoquinoline-4-carboxylic acid, l-tryptophan methyl ester and diisopropylcarbodiimide in dry dichloro-methane. The furan ring is disordered over two positions in a 0.859 (14):0.

trans-rac-[1-Oxo-2-phenethyl-3-(2-thien-yl)-1,2,3,4-tetra-hydro-isoquinolin-4-yl]methyl 4-methyl-benzene-sulfonate.

The title compound, C(29)H(27)NO(4)S(2), was synthesized by reaction of trans-rac-4-(hydroxy-meth-yl)-2-phenethyl-3-(thio-phen-2-yl)-3,4-dihydro-isoquinolin-1(2H)-one and 4-methyl-benzene-1-sulfonyl chloride in the presence of Et(3)N in CH(2)Cl(2). The relative orientations of the benzene ring (A) of the 3,4-dihydro-isoquinolinone ring system, the thio-phene ring (B), the benzene ring (C) of the methyl-benzene group and the phenyl ring (D) result in the following dihedral angles: A/B = 80.91 (16), A/C = 22.

Methyl trans-rac-2-hexyl-1-oxo-3-(2-pyrid-yl)-1,2,3,4-tetra-hydroisoquinoline-4-carboxyl-ate.

The title compound, C(22)H(26)N(2)O(3), was synthesized by esterification of trans-rac-2-hexyl-1-oxo-3-(2-pyrid-yl)-1,2,3,4-tetra-hydro-isoquinoline-4-carboxylic acid in the presence of H(2)SO(4) in methanol. The dihedral angle between the benzene and pyridine rings is 84.46 (17)°.

Synthesis of new trans-2-benzyl-3-(furan-2-yl)-4-substituted-1,2,3,4-tetrahydroisoquinolinones.

The reaction of homophthalic anhydride and N-(furan-2-yl-methylidene)- benzylamine in different solvents and varying temperatures was studied in detail. Mixtures of the expected trans- and cis-1,2,3,4-tetrahydroisoquinoline-4-carboxylic acids trans-5 and cis-5, along with by-products 6 and 7 were obtained in dichloroethane or benzene. In pyridine, used for the first time, the reaction became completely diastereoselective, giving only the trans isomer.

Preliminary evaluation of antimicrobial activity of diastereomeric cis/trans-3-aryl(heteroaryl)-3,4-dihydroisocoumarin-4-carboxylic acids.

Preliminary differentiating screening of the antibacterial and antifungal activity of a series of diastereomeric cis/trans-3-aryl(heteroaryl)-3,4-dihydroisocoumarin-4-carboxylic acids (3a-i) was performed by the agar diffusion method against twelve microorganism strains of different taxonomic groups. S. aureus and A.