Effect of boramidic acid modified carbon nanotubes on neurological, morphological and physiological responses of zebrafish (Danio rerio) embryos and larvae.

This study aimed to determine the potential toxicological effects of carbon nanotubes (CNTs), their modifications with ethylenediamine (ED) and boric acid (BA) on aquatic organisms. Specifically, the research focused on the morphological, physiological, and histopathological-immuno-histochemical responses in zebrafish (Danio rerio) embryos and larvae, via applying different concentrations of CNTs, CNT-ED, and CNT-ED-BA (Control, 5, 10, and 20 mg/L). The results indicated that 20 mg/L CNT nanoparticles were toxic to zebrafish larvae, with mortality rates increasing with CNT and CNT-ED concentrations, reaching 36.7 % at the highest CNT concentration. The highest dose caused considerable degeneration, necrosis, DNA damage, and apoptosis, as evidenced by histopathological and immunohistochemical tests. In contrast, despite their high concentration, CNT-ED-BA nanoparticles exhibited low toxicity. Behavioral studies revealed that CNT and CNT-ED nanoparticles had a more significant impact on sensory-motor functions compared to CNT-ED-BA nanoparticles. These findings suggest that modifying the nanosurface with boric acid, resulting in boramidic acid, can reduce the toxicity induced by CNT and CNT-ED.

Decolorization of methylene blue by silver/reduced graphene oxide-ethylene diamine nanomaterial: synthesis, characterization, and optimization.

In this study, ethylene diamine-coated reduced graphene oxide-supported silver composite (Ag/rGO-ED) was synthesized and used as an efficient catalyst for the decolorization of methylene blue (MB) in the presence of NaBH4. The morphology of the obtained material was elucidated using field emission scanning electron microscopy (FE-SEM), Fourier-transform infrared spectroscopy (FTIR), energy-dispersive X-ray analysis (EDX), transmission electron microscopy (TEM), and X-ray diffraction (XRD) techniques. The influences of four parameters (MB concentration (mg/L), NaBH4 amount (mM), catalyst amount (g/L), and contact time (s)) on the decolorization process were appraised and optimized via response surface methodology (RSM). For the decolorization of MB, the optimum solutions were obtained as Co of 32.49 mg/L, NaBH4 amount of 152.89 mM, catalyst amount of 0.83 g/L, and 101.39 s contact time with MB decolorization efficiency of 97.73%. MB, a pollutant in wastewater, was decolorized rapidly by Ag/rGO-ED with an efficiency of approximately 97%. The exploration of kinetics and thermodynamics was another major emphasis of the work. The activation energy (Ea) and rate constant (k) for the decolorization of MB were obtained as 37.9 kJ/mol and 0.0135 s-1, respectively. The obtained results show that the catalyst, a new composite material in the literature, is promising for decolorization of wastewater.

Design and Synthesis of ESIPT-Based Imidazole Derivatives for Cell Imaging.

Excited-state intramolecular proton transfer (ESIPT)-based fluorescent molecules offer several exciting applications and are utilized most frequently as a cell imaging agent. Because of this, four distinct imidazole derivatives with ESIPT emission have been synthesized, and their fluorescence characteristics have been assessed in a variety of settings. Measurements using fluorescence spectroscopy have shown a promising candidate for cell staining, and potential candidate was specifically investigated for cell imaging uses in HT-29, MDA-MB-231, and HaCaT. Cytotoxicity of candidate molecule (1d) was analyzed using HT-29 and HaCaT cell lines, and at a dosage of 160 µM, HT-29 and HaCaT cell lines showed no signs of important cell toxicity. When spectroscopically measured, compound 1d showed no fluorescence ability in phosphate-buffered saline (PBS) solution. However, after 8 h of incubation in several cell lines, excellent fluorescence characteristics were seen in the green and red filters.

Heterocyclic molecules with ESIPT emission: synthetic approaches, molecular diversities, and application strategies.

Excited-state intramolecular proton transfer (ESIPT) is one of the most essential emission processes in most circumstances because of its dual emission band in most cases and its high Stokes shifts. These distinguishing properties make ESIPT-based probes more suitable for a variety of applications, including analyte sensors, solid-state sensing mechanisms, optical technologies, and biomarkers for endogenous or exogenous compounds in various settings. As a result, researchers around the world are working on ESIPT emissions and developing different scaffolds for various applications or industry demands. This field of study is rapidly expanding and there is a need for an up-to-date review of synthesis methodologies and applications. This paper provides the highlights of ESIPT-based heterocyclic scaffolds, synthesis strategies, and application scenarios in the literature from 2017 to 2023.

Synthesis of spiroindolenine-cyclopentenedione skeletons and their chemical behaviours: the first example of a lactone-type spiroindolenine structure.

A manageable, one-pot, and high-yield protocol for synthesising highly reactive spiroindolenine derivatives is reported. Spiroindolenines are furnished by a reaction between DCC (dicyclohexylcarbodiimide) and indole-3-butenoic acid derivatives. The protocol proposed here involves the construction of a carbon-carbon bond through intramolecular domino cyclisation. The reaction mechanism for spirocyclisation is discussed; both NMR and X-ray analysis were used to verify the structure of spiroindolenine. The applied strategy allowed the formation of spiroindolenine with a dione substructure, which is an unknown compound with a spirocyclic nucleus. Further reactions of spiroindolenines with di-amines, a primary amine, and alcohol have been reported, and new types of indole derivatives, such as indoloquinoxalines, where the spirocentre atom undergoes a nucleophilic attack, are yielded.

A new synthetic approach for pyrazolo[1,5-a]pyrazine-4(5H)-one derivatives and their antiproliferative effects on lung adenocarcinoma cell line.

Starting from the 3,5-dimethyl pyrazole ring and acetophenone derivatives, five different N-propargylated C-3 substituted pyrazoles were obtained. These derivatives were reacted with different amine derivatives using Cs2CO3 in methanol and 11 different pyrazolo [1,5-a] pyrazine-4(5H)-one derivatives were obtained, which are not found in the literature. The cytotoxic effects of these derivatives in the A549 cell line were investigated. The 160 µM concentration of two derivatives was found to increase cell death rate to 50%, and two derivatives increased cell death rate by up to 40%. The structure-activity relationship (SAR) study revealed an amide group with a long alkyl chain and benzene ring with a p-CF3 group could be important for efficiency. With theoretical ADMET studies of pyrazolopyrazine derivatives, pharmacokinetic phases were predicted to be suitable.

A novel class for carbonic anhydrases inhibitors and evaluation of their non-zinc binding.

In this study, 23 different imidazole derivatives were synthesized, and the inhibitory properties of these derivatives against carbonic anhydrase I and II isoenzymes were investigated for the first time. The inhibition concentrations of the imidazole derivatives were found to be in the range of 2.89-115.5 nM. Docking studies examined the binding properties of the imidazole derivatives, and the structure-activity relationship is discussed. Theoretical calculations showed that the binding mode of the imidazole ring was non-zinc binding.

Excited State Intramolecular Proton Transfer (ESIPT)-Based Sensor for Ion Detection.

C-2 and C-5 substituted imidazole skeleton was synthesized through a one-pot two-step strategy. Synthesized molecule emits the light on ESIPT (excited-state intramolecular proton transfer). This molecule was utilized for its proton donor ability, and we have observed that fluoride and cyanide ions can be detected selectively. Different cations and anions were selected to observe the response of the synthesized molecule. However, there were not any fluorometric and colorimetric response except for fluoride and cyanide ions. Detection limits of fluoride and cyanide ions were found to be 9.22 µM and 11.48 µM, respectively. 1H-NMR spectra for the solution of the sensor and TBAF (tetrabuthylammoniumfluoride) were used for the identification of [L]-[HF2]- species. 3 equiv. TBAF saturated the solution of the sensor in d6-DMSO, and some of the proton resonances shifted to upfield due to the through-bond effect. The disappearance of NH proton with 0.5 equiv. TBAF or TBACN (tetrabuthylammoniumcyanide) showed that there was a proton abstraction by fluoride and cyanide ions, instead of the hydrogen bond. Solid-state application was utilized, and paper test strips were applied. Emission differences emerged when the sensor loaded strips were reacted with TBAF. Time resolved experiments revealed that solution of the sensor and TBAF in DMSO have multiexponential decay, and one of the lifetime was measured as 13.4 ns.

Mono- or di-substituted imidazole derivatives for inhibition of acetylcholine and butyrylcholine esterases.

Mono- or di-substituted imidazole derivatives were synthesized using a one-pot, two-step strategy. All imidazole derivatives were tested for AChE and BChE inhibition and showed nanomolar activity similar to that of the test compound donepezil and higher than that of tacrine. Structure activity relationship studies, docking studies to on X-ray crystal structure of AChE with PDB code 1B41, and adsorption, distribution, metabolism, and excretion (ADME) predictions were performed. The synthesized core skeleton was bound to important regions of the active site of AChE such as the peripheral anionic site (PAS), oxyanion hole (OH), and anionic subsite (AS). Selectivity of the reported test compounds was calculated and enzyme kinetic studies revealed that they behave as competitive inhibitors, while two of the test compounds showed noncompetitive inhibitory behavior. ADME predictions revealed that the synthesized molecules might pass through the blood brain barrier and intestinal epithelial barrier and circulate freely in the blood stream without binding to human serum albumin. While the toxicity of one compound on the WS1 (skin fibroblast) cell line was 1790 µM, its toxicity on the SH-SY5Y (neuroblastoma) cell line was 950 µM.

Synthesis of novel imidazopyridines and their biological evaluation as potent anticancer agents: A promising candidate for glioblastoma.

Novel imidazopyridine derivatives were synthesized according to a very simple protocol and then subjected to cytotoxicity testing against LN-405 cells. Two of the compounds exhibited antiproliferative effects on LN-405 cells at 10 and 75 µM and were selected as lead compounds for further study. Safety experiment for lead compounds on WS1 was carried out and IC50 values were calculated as 480 and 844 µM. LN-405 cell line were incubated with the lead compounds and then tested for DNA damage by comet assay and effects on cell cycle using flow cytometry. The results of these two tests showed that both lead compounds affected the G0/G1 phase and did not allow the cells to reach the synthesis phase. The log BB (blood-brain barrier) and Caco-2 permeability of the synthesized molecules were calculated and it was shown that imidazopyridine derivatives taken orally are likely to pass through gastrointestinal membrane and the blood-brain barrier.

Indole-containing new types of dyes and their UV-vis and NMR spectra and electronic structures: Experimental and theoretical study.

Indole containing dyes were synthesized via a simple method with high yield. These molecules have different colors and UV-vis spectra of them were recorded. Impact of solvents on absorbances was investigated and it was observed that basic solvent such as DMF and pyridine have blue shift. TD-DFT calculations were done and results were compared with experimental data. NMR data of molecules were analyzed and tautomeric forms of colorants and their ratio were determined. It was find out that two tautomers might be formed in solution, called indole and indolenine form. HOMO-LUMO and energy gaps were calculated and plotted. Furthermore, molecular electrostatic potentials were simulated to find out electrophilic and nucleophilic regions.

Synthesis of Pyrrole-Fused C,N-Cyclic Azomethine Imines and Pyrazolopyrrolopyrazines: Analysis of Their Aromaticity Using Nucleus-Independent Chemical Shifts Values.

The AgOTf-catalyzed reaction of C-2 substituted pyrrole hydrazones having an N-propargyl group was studied. The selective 6-endo-dig mode of cyclization was observed, giving rise to the formation of pyrrole-fused C,N-cyclic azomethine imine derivatives. The reaction of one azomethine imine derivative with various dipolarophiles resulted in the formation of cycloadducts having a pyrazolopyrrolopyrazine skeleton. The aromaticity of C,N-cyclic azomethine imines as well as that of pyrazolopyrrolopyrazines was determined by calculating of nucleus-independent chemical shifts values.

Gold-catalyzed formation of pyrrolo- and indolo-oxazin-1-one derivatives: The key structure of some marine natural products.

Various N-propargylpyrrole and indolecarboxylic acids were efficiently converted into 3,4-dihydropyrrolo- and indolo-oxazin-1-one derivatives by a gold(III)-catalyzed cyclization reaction. Some of the products underwent TFA-catalyzed double bond isomerization and some did not. Cyclization reactions in the presence of alcohol catalyzed by Au(I) resulted in the formation of hemiacetals after cascade reactions.

Gold-catalyzed oxime-oxime rearrangement.

The gold-catalyzed reaction of pyrrole and indole oximes having a propargyl group attached to the nitrogen atom was studied. The selective 6-endo-dig mode of cyclization was observed for the terminal alkynes giving rise to the formation of pyrazine N-oxides in the presence of a gold catalyst. However, the reaction with substituted alkyne transferred the oxime functionality intramolecularly from one carbon atom to another via the 7-endo-dig cyclization process. This transformation is unprecedented in the literature and is named an oxime-oxime rearrangement.

Design and synthesis of pyrrolotriazepine derivatives: an experimental and computational study.

The pyrrole derivatives having carbonyl groups at the C-2 position were converted to N-propargyl pyrroles. The reaction of those compounds with hydrazine monohydrate resulted in the formation of 5H-pyrrolo[2,1-d][1,2,5]triazepine derivatives. The synthesis of these compounds was accomplished in three steps starting from pyrrole. On the other hand, attempted cyclization of a pyrrole ester substituted with a propargyl group at the nitrogen atom gave, unexpectedly, the six-membered cyclization product, 2-amino-3-methylpyrrolo[1,2-a]pyrazin-1(2H)-one as the major product. The expected cyclization product with a seven-membered ring, 4-methyl-2,3-dihydro-1H-pyrrolo[2,1-d][1,2,5]triazepin-1-one was formed as the minor product and was converted quantitatively to the major product. The formation mechanism of the products was investigated, and the results obtained were also supported by theoretical calculations.