Acridine Yellow Research Articles

Acridine yellow G as a photo-induced electron transfer catalyzed radical [4 + 2] aza-Diels-Alder annulation of imines

For the preparation of polyfunctionalized piperidine scaffolds, a radical tandem five-condensation domino Knoevenagel-intramolecular [4 + 2] aza-Diels-Alder imin-based reaction was used. Based on acridine yellow G (AYG) as a photo-induced electron transfer (PET) photocatalyst, employing visible light as a renewable source of energy. AYG that is photochemically catalyzed has good yields, as well as outstanding atom economy, and ease of operation. As a result, a diverse set of chemical and environmental parameters can be measured across time. The turnover number (TON) and turnover frequency (TOF) of polyfunctionalized piperidine scaffolds have been computed. Also, gram-scale cyclization can occur, suggesting that the process might find application in industry.

Multiple dyes applications for fluorescent convertible polymer capsules as macrophages tracking labels

Tracing individual cell pathways among the whole population is crucial for understanding their behavior, cell communication, migration dynamics, and fate. Optical labeling is one approach for tracing individual cells, but it typically requires genetic modification to induce the generation of photoconvertible proteins. Nevertheless, this approach has limitations and is not applicable to certain cell types. For instance, genetic modification often leads to the death of macrophages. This study aims to develop an alternative method for labeling macrophages by utilizing photoconvertible micron-sized capsules capable of easy internalization and prolonged retention within cells. Thermal treatment in a polyvinyl alcohol gel medium is employed for the scalable synthesis of capsules with a wide range of fluorescent dyes, including rhodamine 6G, pyronin B, fluorescein, acridine yellow, acridine orange, thiazine red, and previously reported rhodamine B. The fluorescence brightness, photostability, and photoconversion ability of the capsules are evaluated using confocal laser scanning microscopy. Viability, uptake, mobility, and photoconversion studies are conducted on RAW 264.7 and bone marrow-derived macrophages, serving as model cell lines. The production yield of the capsules is increased due to the use of polyvinyl alcohol gel, eliminating the need for conventional filtration steps. Capsules entrapping rhodamine B and rhodamine 6G meet all requirements for intracellular use in individual cell tracking. Mass spectrometry analysis reveals a sequence of deethylation steps that result in blue shifts in the dye spectra upon irradiation. Cellular studies on macrophages demonstrate robust uptake of the capsules. The capsules exhibit minimal cytotoxicity and have a negligible impact on cell motility. The successful photoconversion of RhB-containing capsules within cells highlights their potential as alternatives to photoconvertible proteins for individual cell labeling, with promising applications in personalized medicine.

High-fidelity detection of picric acid following proton prompted fluorescence quenching by a novel acridine yellow G-based binuclear ZnII-metallacycle

Highly selective quenching-based fluorescence detection of picric acid in solid and liquid phases by a novel acridine yellow G based binuclear ZnII-metallacycle (1) with a calculated KSV and LOD of 3.44 × 104 M and 7.62 × 10−8 M, respectively.

A multifunctional organogel for constructing artificial light harvesting systems with excellent energy transfer efficiency

Fluorescent gels with excellent physical properties were synthesised using polyvinyl alcohol/telmisartan. An artificial light-harvesting system with high energy-transfer efficiency and antenna effect was constructed by adding acridine yellow G and rhodamine B.

A Facile Access to Metal-Free Synthesis of 3,4-Dihydropyrimidin-2-(1H)-Ones/Thiones using Acridine Yellow G as a Photo-Induced Electron Transfer Photocatalyst

A green approach for the metal-free synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones was developed using a radical tandem three-condensation domino Biginelli reaction of β-ketoesters, arylaldehydes, and urea/thiourea. Using acridine yellow G (AYG) as a photo-induced electron transfer (PET) photocatalyst using visible light as a sustainable energy source. The goal of this study is to increase the use of a nonmetal dye that is inexpensive and readily available. High yields, energy efficiency, and environmental friendliness are all advantages of photochemically catalyzed AYG, as are significant atom economy, time-saving features, and ease of usage. As a result, a variety of chemical and environmental variables can be monitored throughout time. The turnover number (TON) and turnover frequency (TOF) of 3,4-dihydropyrimidin-2-(1H)-ones/thiones have been computed. Surprisingly, gram-scale cyclization is conceivable, implying that the technique could be applied in industry.

Construction of Light‐Harvesting Systems Based on a Fluorescent Probe that Self‐Assembles in the Presence of Zn2+

AbstractA light‐harvesting system based on the coordination of benzimidazole derivatives (G) and Zn2+ was successfully prepared. Compared with G, the G−Zn2+ assembly exhibited a noticeably enhanced fluorescence emission band. As such, it was employed as the donor in fabricating the artificial concentrating light‐harvesting systems, with acridine yellow and acridine orange employed as acceptors. In these two systems (G−Zn2+/acridine yellow and G−Zn2+/acridine orange), the occurrence of an energy‐transfer process was confirmed from the G−Zn2+ assembly to acridine yellow and acridine orange, separately. The findings of this study will facilitate the development of artificial light‐harvesting systems.

Radical synthesis of dihydropyrano[2,3‐c]pyrazoles using acridine yellow G as a photo‐induced electron transfer photocatalyst

AbstractWe developed a green method for the synthesis of dihydropyrano[2,3‐c]pyrazole scaffolds using Knoevenagel‐Michael tandem cyclocondensation of ethyl acetoacetate, hydrazine hydrate, aldehydes, and malononitrile. Acridine yellow G (AYG) was used as a photo‐induced electron transfer (photo‐induced electron transfer) photocatalyst via visible light as a sustainable energy source in an aqueous solution. This study is aimed at the development of an inexpensive and readily available non‐metal dye. With photochemically catalyzed AYG, yields are high, energy efficiency and environmental friendliness are present, as are significant atom economies, speed‐saving features, and ease of use. The result is that a wide range of chemical and environmental variables can be monitored over time. In this study, we calculated the turnover number (TON) and turnover frequency (TOF) of dihydropyrano[2,3‐c]pyrazole scaffolds.

Assembly of Artificial Light‐Harvesting Systems Based on Supramolecular Self‐Assembly Metallogels

AbstractWe have designed and constructed two artificial light‐harvesting systems (ALHSs), which are based on the supramolecular self‐assembly of acylhydrazone functionalized quinoline (L), Al3+ and fluorescent dyes. The L‐Al3+ supramolecular assembly distinctly improved aggregation‐induced emission enhancement and served as a donor for ALHSs. Acridine yellow and acridine orange were found to be good acceptors to realize the energy transfer process with good efficiency.

A systematic computational study of acridine derivatives through conceptual density functional theory.

A detailed computational analysis of acridine derivatives viz. acridone, 9-amino acridine hydrochloride hydrate, proflavin, acridine orange and acridine yellow is done in terms of conceptual density functional theory (CDFT). CDFT-based global descriptors-ionization potential, electron affinity, HOMO-LUMO gap, hardness, softness, electronegativity and electrophilicity index of acridine derivatives for ground state as well as excited state are estimated with the help of different hybrid functionals B3LYP/6-31G (d, p), B3LYP/6-311G (d, p), B3LYP/DGDZVP and B3LYP/LANL2DZ. Acridine derivatives show higher values of ionization potential and electron affinity in excited state as compared to ground state, indicating that these compounds are willing to accept electrons in excited state rather than donating electron. Acridone shows the maximum HOMO-LUMO energy gap in ground and excited state which implies that one-way electron transfer is most feasible with this compound. Our computed results emphasize the pronounced electron acceptor behaviour of the acridine derivatives in the excited state which has already been experimentally verified. It is observed that the trend in the computed values of the descriptors is not much improved on refinement of the basis set.

Variation in electrophilicity on electronic excitation

AbstractThe rationality of the minimum electrophilicity principle (MElP) as a companion of minimum polarizability principle and maximum hardness principle is studied for simple diatomic, triatomic, and tetratomic molecules. The applicability is further justified considering organic molecules (e.g., pyrene and acridine yellow) are known for their photophysical properties and accordingly their excited state properties. Single excitation CI (CIS) and time‐dependent density functional theory (TDDFT) are employed to study the excited state reactivity. Two types of excitations, namely vertical and adiabatic, are considered. Processes involving conservation and change in spin multiplicity are included during excitation. The general trend is that the molecules are less electrophilic in the ground state than those in the corresponding excited states. It is found that adiabatic excitation validates the principle even for the triplet ground state molecules undergoing an excitation where spin multiplicity gets altered. The TDDFT method explains the validity of the MElP augmenting the CIS method. This study echoed the MElP during molecular electronic excitation.

Toward a Selective Analysis of Heavy Metal Salts in Aqueous Media with a Fluorescent Probe Array.

Detection of heavy meals in aqueous media challenges worldwide research in developing particularly fast and affordable methods. Fluorescent sensors look to be an appropriate instrument for such a task, as recently they have been found to have made large progress in the detection of chemical analytes, primarily in the environment, along with biological fluids, which still suffer from not enough selectivity. In this work, we propose a new fluorescent method to selectively recognize heavy metals in an aqueous solution via employing an array of several fluorescent probes: acridine yellow, eosin, and methylene blue, which were taken as examples, being sensitive to a microsurrounding of the probe molecules. The exemplary sensor array generated six channels of spectral information through the use of various combinations of excitation and detection wavelengths. Following the known multisensor approach, we applied a linear discriminant analysis to selectively distinguish the vector signals from the sensor array from salts of heavy metals—Cu, Pb, Zn, Cd, and Cz—at the concentration ranges of 2.41 × 10−6–1.07 × 10−5 M, 2.8 × 10−5–5.87 × 10−4 M, 1.46 × 10−6–6.46 × 10−6 M, 1.17 × 10−8–5.2 × 10−8 M, and 2.11 × 10−6–9.33 × 10−6 M, respectively. The suggested approach was found to be promising due to it employing only one cuvette containing the test solution, simplifying a sample preparation when compared to preparing a variety of solutions in tests with single fluorescence probes.

A novel fluorescent self-assembling material with gel properties: ion recognition and energy transfer

A novel fabrication strategy for preparing fluorescent materials has been proposed based on energy transfer system, which is composed of a supramolecular self-assembly complexes (DAF–Al3+, Donor) and a dye (Acridine yellow, Acceptor).

Electrochemical DNA Sensor Based on Acridine Yellow Adsorbed on Glassy Carbon Electrode.

Electrochemical DNA sensors offer unique opportunities for the sensitive detection of specific DNA interactions. In this work, a voltametric DNA sensor is proposed on the base of glassy carbon electrode modified with carbon black, adsorbed acridine yellow and DNA for highly sensitive determination of doxorubicin antitumor drug. The signal recorded by cyclic voltammetry was attributed to irreversible oxidation of the dye. Its value was altered by aggregation of the hydrophobic dye molecules on the carbon black particles. DNA molecules promote disaggregation of the dye and increased the signal. This effect was partially suppressed by doxorubicin compensate for the charge of DNA in the intercalation. Sensitivity of the signal toward DNA and doxorubicin was additionally increased by treatment of the layer with dimethylformamide. In optimal conditions, the linear range of doxorubicin concentrations determined was 0.1 pM–1.0 nM, and the detection limit was 0.07 pM. No influence of sulfonamide medicines and plasma electrolytes on the doxorubicin determination was shown. The DNA sensor was tested on two medications (doxorubicin-TEVA and doxorubicin-LANS) and showed recoveries of 102–105%. The DNA sensor developed can find applications in the determination of drug residues in blood and for the pharmacokinetics studies.

Revisiting magnetic field effects in homogeneous medium and bio-mimicking environments with emphasis on acridine derivatives

A weak external magnetic field, very close to the hyperfine interactions of the system, can acts as a tool to monitor spin dynamics and assess distance between the components of the spin-correlated transient radical pair or radical ion pair (RIP). The present review focuses on the magnetic field effect (MFE) on the photo-induced electron-transfer (PET) reactions among acridine derivatives and classical as well as biological electron acceptor or donor moieties, which produce spin-correlated RIPs, in homogeneous solvents, heterogeneous micellar media and in biological nanocavities of proteins. Although a confined medium is preferred to observe prominent MFE, yet unanticipated MFE on PET between acridine derivatives [Acridone (AD) and Acridine Yellow (AY)] and classical electron donors is obtained even in homogeneous medium when it consists of impurities like water molecules. In a comparative study of interaction of another acridine derivative, Proflavin (PF+) with two electron donors which are amines of aromatic nature, MFE on PET reveal that the bulk and the structure of the electron donor govern the mechanism as well as the spin dynamics of PET. While studying interaction of PF+ with a different amine which is aliphatic in nature, MFE on PET implies that it is the nature of the solvent matrix which determines the spin dynamics of PET. The cause of discrepancy in the experimental and calculated values of B1/2 for 9-amino acridine – methyl viologen system has been delineated. Apart from micellar medium, prominent MFE on PET is also observed while studying the interaction of PF+, AY and AD with tryptophan residues present in the nanocavities of serum albumins since the inter-radical distance within primary geminate RIP is enough to make exchange interaction negligible.

Microextraction–Colorimetric (Fluorimetric) Determination of Cationic and Anionic Surfactants in Food Products

A method is proposed for the determination of cationic and anionic surfactants in food products based on the use of dispersive liquid–liquid microextraction of surfactant ion pairs with organic reagents (eosin and acridine yellow) and measurements of the colorimetric parameters of the fluorescence of extracts using a smartphone. Upon the irradiation of the extracts of ion pairs anionic surfactant–acridine yellow and cationic surfactant–eosin with ultraviolet light (365 nm), green and yellow fluorescence were observed, respectively. The analytical signal (Ar) was the value of the colorimetric parameters in the RGB system: Ar = $$\sqrt {{{{{\text{(}}{{R}_{{\text{0}}}} - {{R}_{x}}{\text{)}}}}^{2}}{\text{ + (}}{{G}_{{\text{0}}}} - {{G}_{x}}{{{\text{)}}}^{2}}{\text{ + (}}{{B}_{{\text{0}}}} - {{B}_{x}}{{{\text{)}}}^{2}}} .$$ Procedures for determining the total amount of surfactants in food products (milk, vegetables and fruits, meat, and drinking water) are developed using an example of cetylpyridinium, myristalconium, benzalkonium, didecyldimethylammonium, alkyldimethyl(ethylbenzyl)ammonium, dodecyl sulfate and sodium alkylbenzenesulfonate chlorides. The limits of detection and quantification are in the ranges 0.005–0.05 and 0.01–0.1 mg/L, respectively. Calibration graphs are linear in the concentration range 0.01–1 mg/L with approximation confidence coefficients ≥0.99. The duration of analysis is 20–30 min; the relative standard deviation of the results of analysis does not exceed 0.24.

The vibronic absorption spectra and electronic states of acridine yellow in aqueous solution

The time-dependent density functional theory (TD-DFT) was used to obtain vibronic absorption spectra of acridine yellow (AY) dye in an aqueous solution that were in good agreement with the experiment. The protonated and neutral forms of the dye have been investigated. The results of calculations using various functionals and basis sets have been analyzed. The best agreement with experiment was given by the X3LYP/6-31G(d,p) theory level. AY molecular orbitals involved in electronic transitions due light absorption in the visible region of the spectrum have been obtained. The dipole moments and atomic charges of the ground and excited states of the AY molecule have been calculated. Maps of the electrostatic potential and electron densities have been drawn. An insignificant photoinduced electron transfer was found in the central ring of the chromophore of the dye molecule. According to our calculations, the vibronic coupling and the Boltzmann distribution play a significant role in the AY absorption spectra.

Microextraction-colorimetric determination of anionic surfactants in natural and waste waters

An eco-friendly, simple, rapid and cheap method for determining anionic surfactants in natural and waste waters by microextraction-colorimetric method has been developed. The essence of the proposed approach consisted in extraction and concentration of analytes in an acidic medium in the form of associates with organic reagents (methylene blue and acridine yellow) by dispersion liquid-liquid microextraction using a mixture of chloroform-acetonitrile as an extracting and dispersing solvent, followed by aggregation of extractant microparticles by centrifugation and subsequent measurements of color characteristics using a smartphone. The values of the basic components of the RGB colorimetric system were used as an analytical signal to calculate the final color: The selection of optimal conditions for microextraction concentration of anionic surfactants from natural waters (the nature of the extracting and dispergating solvents, the volume of the dispergating solvent) was performed for the sodium dodecyl sulfate — methylene blue system. To study the colorimetric characteristics of the prepared extracts, a smartphone «iPhone X» was used as a color-registering device equipped with a specialized software product «RGBer». To minimize the measurement error by fixing the distance to the object under study and lighting conditions, we propose an installation that increases the accuracy and sensitivity of the determination and makes the method more mobile. The total content of the most common components of detergents was determined: sodium dodecyl sulfate, sulfonol, laureth sulfate and disodium laureth-3-sulfosuccinate. The detection limits ranged within 0.01 – 0.02 and 0.05 mg/liter. The range of detectable contents for all analytes was 0.05 – 1.0 mg/liter. For the determined surfactants, the equations of the relationship between the analytical signal and the concentration were obtained. The calibration graphs are linear with coefficients of the approximation reliability ≤0.98. The correctness of the method was tested on samples of natural water using the spike test procedure. The relative standard deviation of the analysis results does not exceed 0.13. The analysis duration is 20 – 30 min.

Adsorption of acridine yellow G from aqueous solutions using functionalized graphene nanoplatelets/modified polybutadiene hybrid composite

AbstractThis paper presents an analysis of adsorption of acridine yellow G (AYG) from aqueous solutions through the use of functionalized grapheme nanoplatelets/modified polybutadiene hybrid composite (FGNPs/MPB). The adsorption of AYG onto FGNPs/MPB was investigated based on the AYG concentration, pH, contact time, temperature, and adsorbent dose. A maximum adsorption capacity was obtained at a pH of 7 (23.7 mg/g), an adsorbent dose of 1.0 g/L (20.8 mg/g), and an initial AYG concentration of 28.5 mg/L (16.9 mg/g). The value of qe of FGNPs/MPB increases with an increase in temperature from 293 to 323 K. Equilibrium isotherm data were analyzed using the Langmuir and Freundlich isotherm models. The Langmuir model best describes the adsorption processes of AYG, which showed that the monolayer adsorption capacity of FGNPs/MBP is 22.9 mg/g. The pseudofirst‐order, pseudosecond‐order, and intraparticle diffusion models were used to study the kinetics of the AYG adsorption onto FGNPs/MPB. The pseudosecond‐order model better described kinetic data for the adsorption of AYG onto FGNPs/MPB. Thermodynamic parameters, such as the Gibbs free energy, enthalpy, and entropy, indicated that the AYG adsorption onto FGNPs/MPB was spontaneous feasible, and endothermic.

In Situ Absorption and Fluorescence Microspectroscopy Investigation of the Molecular Incorporation Process into Single Nanoporous Protein Crystals.

Protein crystals exhibit distinct three-dimensional structures, which contain well-ordered nanoporous solvent channels, providing a chemically heterogeneous environment. In this paper, the incorporation of various molecules into the solvent channels of native hen egg-white lysozyme crystals was demonstrated using fluorescent dyes, including acridine yellow G, rhodamine 6G, and eosin Y. The process was evaluated on the basis of absorption and fluorescence microspectroscopy at a single-crystal level. The molecular loading process was clearly visualized as a function of time, and it was determined that the protein crystals could act as nanoporous materials. It was found that the incorporation process is strongly dependent on the molecular charge, leading to heterogeneous molecular aggregation, which suggests host–guest interaction of protein crystals from the viewpoint of nanoporous materials.

Functionalization ratio of isocyanate groups on plasma-processed multiwalled carbon nanotubes

This article reports the functionalization ratio of isocyanate (NCO) groups on multiwalled carbon nanotubes after exposure of plasma, which was generated with the gas mixture of nitrogen and carbon dioxide. The ratio was derived from measurements with an organic fluorescence, so-called acridine yellow G (AYG), which identifies the modified groups on carbon nanotubes (CNTs). First, the authors made several microscopic observations with the fluorescence. The observation showed that the fluorescence was especially intense from the area where small-sized CNTs exist, indicating that plasma-treated CNTs have more NCO density in small size than in large size. Second, the authors made a size selection on the CNTs with centrifugal forces and investigated the ratio of the groups over the total number of carbons in the CNTs to confirm the first observation and indication. This second investigation showed that the ratio increases as the degree of centrifugal force increases, i.e., the size of the nanotubes gets smaller, supporting the authors’ first microscopic observation. The authors also took the diameter distributions of the CNTs with an observation of an electron microscope, which proved that the centrifugation decreases the size distribution of the CNTs. As a result of overall experiments, the small diameter of plasma-processed CNTs has more NCO number density than the large diameter of the nanotubes in functionalizing isocyanate groups with the plasma.