Synthesis of D-π-A′-π-A Chromophores with Quinoxaline Core as Auxiliary Acceptor and Effect of Various Silicon-Substituted Donor Moieties on Thermal and Nonlinear Optical Properties at Molecular and Material Level

Novel D-π-A′-π-A chromophores with quinoxaline cores as auxiliary acceptors and various donor moieties (aniline, carbazole, phenothiazine, tetrahydroquinoline) containing bulky tert-butyldimethylsilyloxy (TBDMSO) groups and tricyanofuranyl (TCF) acceptors with bulky cyclohexylphenyl substituents were synthesized via eight- to nine-step procedures, and their photo-physical and thermal properties were investigated. The values of the chromophores’ first hyperpolarizabilities were calculated in the framework of DFT at the M06-2X/aug-cc-pVDZ computational level; the effect of the introduction of the TBDMSO group into the donor fragment is shown to be inessential, as this group is not coupled to the π-conjugated system of the chromophore. The chromophore with the tetrahydroquinoline donor has a first hyperpolarizability value of 937 × 10−30 esu, which is the highest for the studied chromophores. Atomistic modeling of composite materials with the studied chromophores as guests demonstrated that the presence of bulky substituent in the donor fragment prevents notable aggregation of chromophores, even at high chromophore content (40 wt.%). The nonlinear optical performance of guest–host materials with 25 and 40 wt.% of suggested chromophore content was studied using a second harmonic generation technique to give the NLO coefficient, d33 up to 52 pm/V

<i>N</i>-(((1<i>S</i>,5<i>R</i>)-6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)methyl)-3-dodecan/tetradecanamido-<i>N</i>,<i>N</i>-dimethylpropan-1-aminium Bromide

The syntheses of the title compounds were performed using lauric and myristic acids. The compounds obtained were characterized using 1H-, 13C-NMR and 2D 1H-1H COSY, 1H-13C HSQC NMR, IR, and high-resolution mass spectrometry. Both compounds exhibited bactericidal activity on S. aureus comparable to that of a reference drug (miramistin). Compound 10, with lauric acid fragment, had a 16-fold higher activity on P. aeruginosa compared to compound 11, which in turn contains myristic acid fragment (with minimum inhibitory concentrations of 32 and 512 μg/mL, respectively). Compound 11 exhibited a pronounced activity against all types of fungi (higher than the activity of miramistin), while the activity of compound 10 was considerably lower. Thus, compound 11 can serve as a promising antimicrobial agent for the treatment of various fungal and staphylococcal infections, while compound 10 is of interest to treat P. aeruginosa-associated infections

Calix[4]Resorcinarene Carboxybetaines and Carboxybetaine Esters: Synthesis, Investigation of In Vitro Toxicity, Anti-Platelet Effects, Anticoagulant Activity, and BSA Binding Affinities

As a result of bright complexation properties, easy functionalization and the ability to self-organize in an aqueous solution, amphiphilic supramolecular macrocycles are being actively studied for their application in nanomedicine (drug delivery systems, therapeutic and theranostic agents, and others). In this regard, it is important to study their potential toxic effects. Here, the synthesis of amphiphilic calix[4]resorcinarene carboxybetaines and their esters and the study of a number of their microbiological properties are presented: cytotoxic effect on normal and tumor cells and effect on cellular and non-cellular components of blood (hemotoxicity, anti-platelet effect, and anticoagulant activity). Additionally, the interaction of macrocycles with bovine serum albumin as a model plasma protein is estimated by various methods (fluorescence spectroscopy, synchronous fluorescence spectroscopy, circular dichroic spectroscopy, and dynamic light scattering). The results demonstrate the low toxicity of the macrocycles, their anti-platelet effects at the level of acetylsalicylic acid, and weak anticoagulant activity. The study of BSA–macrocycle interactions demonstrates the dependence on macrocycle hydrophilic/hydrophobic group structure; in the case of carboxybetaines, the formation of complexes prevents self-aggregation of BSA molecules in solution. The present study demonstrates new data on potential drug delivery nanosystems based on amphiphilic calix[4]resorcinarenes for their cytotoxicity and effects on blood components