Cationic Triphenylmethane Dye Research Articles

Suppression of NF-κB activation by gentian violet promotes osteoblastogenesis and suppresses osteoclastogenesis.

Skeletal mass is regulated by the coordinated action of bone forming osteoblasts and bone resorbing osteoclasts. Accelerated rates of bone resorption relative to bone formation lead to net bone loss and the development of osteoporosis, a devastating disease that predisposes the skeleton to fractures. Bone fractures are associated with significant morbidity and in the case of hip fractures, high mortality. Gentian violet (GV), a cationic triphenylmethane dye, has long been used as an antifungal and antibacterial agent and is presently under investigation as a potential chemotherapeutic and antiangiogenic agent. However, effects on bone cells have not been previously reported and the mechanisms of action of GV, are poorly understood. In this study we show that GV suppresses receptor activator of NF-κB ligand (RANKL)-induced differentiation of RAW264.7 osteoclast precursors into mature osteoclasts, but paradoxically stimulates the differentiation of MC3T3 cells into mineralizing osteoblasts. These actions stem from the capacity of GV to suppress activation of the nuclear factor kappa B (NF-κB) signal transduction pathway that is required for osteoclastogenesis, but inhibitory to osteoblast differentiation and activity. Our data reveal that GV is an inhibitor of NF-κB activation and may hold promise for modulation of bone turnover to promote a balance between bone formation and bone resorption, favorable to gain of bone mass.

Application of conventional and statistical experimental methodology to optimize malachite green dye removal from aqueous solutions

In the present study, the removal of a cationic triphenylmethane dye, malachite green (MG) solution was being investigated by adsorption and photodegradation methods. The adsorbent and photocatalyst used was banana pith (BP) and titanium dioxide (TiO2), respectively. Plackett–Burman design was applied to identify the most significant factors in the removal of MG. The effect of various operating parameters on removal of MG was studied and a mathematical model showing the influence of each variable was obtained. Response surface methodology was applied to determine the interaction between the factors and their optimum levels for maximum percentage removal of MG. The percentage removal predicted by the model was in good agreement with the experimental values. The optimum conditions for maximum MG removal were identified as pH 8.00 and contact time of 120 min. Under these optimum conditions, the model predicted that the maximum percentage removal of dye by adsorption on BP could be more than 50%, whereas a combination system of photodegradation and adsorption processes could further enhance the percentage removal of MG to above 70%. The results showed that the combination system of adsorption using BP and photocatalytic degradation using TiO2 was a promising method for the removal of MG from aqueous solution.

Triphenylmethane Dye Activation of Beta-Arrestin

β-Arrestins regulate G protein-coupled receptor signaling as competitive inhibitors and protein adaptors. Low molecular weight biased ligands that bind receptors and discriminate between the G protein dependent arm and β-arrestin, clathrin-associated arm of receptor signaling are considered therapeutically valuable as a result of this distinctive pharmacological behavior. Other than receptor agonists, compounds that activate β-arrestins are not available. We show that within minutes of exposure to the cationic triphenylmethane dyes malachite green and brilliant green, tissue culture cells recruit β-arrestins to clathrin scaffolds in a receptor-activation independent manner. In the presence of these compounds, G protein signaling is inhibited, ERK and GSK3β signaling are preserved, and the recruitment of the beta2-adaptin, AP2 adaptor complex to clathrin as well as transferrin internalization is reduced. Moreover, malachite green binds β-arrestin2-GFP coated immunotrap beads relative to GFP only coated beads. Triphenylmethane dyes are FDA approved for topical use on newborns as components of triple-dye preparations and are not approved but used effectively as aqueous antibiotics in fish husbandry. As possible carcinogens, their chronic ingestion in food preparations, particularly through farmed fish, is discouraged in the U.S. and Europe. Our results indicate triphenylmethane dyes as a result of novel pharmacology may have additional roles as β-arrestin/clathrin pathway signaling modulators in both pharmacology research and clinical therapy.

Sonochemical degradation of malachite green in water

In this study, removal of malachite green (MG), a cationic triphenylmethane dye, by 300kHz ultrasound was investigated. The effects of operating parameters such as initial dye concentration, ultrasound power and initial pH on the sonochemical degradation were studied. The initial rate of MG degradation and hydrogen peroxide formation as a function of initial concentration were determined. The obtained results show that the degradation rate increases with increasing initial dye concentration up to a plateau. The rate of hydrogen peroxide formation decreases with increasing substrate concentration and reaches a minimum, followed by almost constant production rate for higher MG concentrations. The dominant degradation mechanism is the reaction of substrate with OH radicals both at the gas bubble–liquid interface and in the bulk solution. Sonochemical degradation of MG occurs via two competitive processes: N-demethylation and destruction of the conjugated structure. The degradation rate increased proportionally with increasing ultrasonic power, but decreased with the increase of initial pH value from 2 to 7. In the presence of 10mg/L Fe(II), the initial degradation rate of MG became 2 times larger for initial dye concentration of 5mg/L and 1.5 times larger for initial substrate concentration of 10mg/L, respectively.

Elucidation of Electrostatic Interaction between Cationic Dyes and Ag Nanoparticles Generating Enormous SERS Enhancement in Aqueous Solution

Addition of a trace quantity of cationic triphenylmethane (TPM+) dyes to isolated Ag nanoparticles in an aqueous solution yielded Ag flocculates composed of a few closely adjacent suspended nanoparticles. This change was evidenced by coupled LSP peaks emerged at 600−800 nm. However, neutral para-rosaniline (p-RA) molecules as well as neutral rhodamine 123 did not cause the Ag flocculation in contrast to their cations, indicating a crucial role of electrostatic interaction between cationic dyes and negatively charged Ag surfaces for the flocculation. Accordingly, cationic dye molecules are located in the nanogap between closely adjacent Ag nanoparticles which evoked enormous SERS intensity. The formation of the Ag flocculates was insensitive to steric hindrance by different amino groups −NH2, −N(CH3)2, and −N(C2H5)2 in TPM dyes. This observation is consistent with dominant role of the electrostatic interaction. Nevertheless, distinct red shifts of fluorescence peaks were observed depending on the molecular...

Premicellar and micelle formation behavior of aqueous anionic surfactants in the presence of triphenylmethane dyes: protonation of dye in ion pair micelles

AbstractThe premicellar and micelle formation behaviors of four cationic triphenylmethane dyes, viz, Pararosaniline (RN), Crystal violet (CV), Ethyl violet (EV), and Malachite green (MG), in aqueous anionic surfactant solutions of sodium dodecyl sulfate (SDS), sodium dodecyl benzene sulfonate (SDBS), and sodium dodecyl sulfonate (SDSN) have been studied by spectral and surface tension measurements. The study was carried out within a pH range where the dyes are stable in their quinoid forms. The dyes have been found to form dye–surfactant ion pairs (DSIPs) with the surfactants, at the surfactant concentrations well below their critical micelle concentration, CMC*. The DSIPs behave like nonionic surfactants and form an air–water interfacial monolayer. The DSIPs have a lower critical micelle concentration (CMCIP), greater efficiency, and lower effectiveness than the corresponding pure surfactants. As the surfactant concentration is increased below the CMC*, the DSIPs start forming micelles of their own where the dye gets protonated and exists as a protonated dye–surfactant ion pair (PDSIP) in the ion pair micelles. As the concentration of the surfactant exceeds the CMC* of the pure surfactant, the protonation reverses gradually with the dye remaining in the micelles in solubilized form and the DSIPs in the air–water interfacial monolayer are replaced by pure surfactants. The distorted helical isomeric form (isomer B) of the dyes is favored in the PDSIPs. Copyright © 2009 John Wiley & Sons, Ltd.

Studies on the photochemical interaction of Fuchsin Basic dye with Triton X-100

A new solarchemical cell consisting of Fuchsin Basic, a cationic triphenyl methane dye, and triethanol amine as reductant in solution of surfactant separated from a saturated aqueous solution of iodine by a pyrex sintered glass membrane, has been developed. The surfactants used was Triton X-100 (non-ionic). The results show that the photopotential and photocurrent of the cell is increased in Triton X-100 and decreased with the cell without surfactant. The photopotential and photocurrent of the cell were observed as 690 mV, 175 μA respectively and power of the cell was 63.4 μA/min. The possible mechanisms of the cell in the various surfactants are discussed.

C60 Fulleride Molecular Nanowire Crystals

ABSTRACTThe novel low-dimensional nanostructural self-alignment of molecular nanowire composed of a C60 anion radical moiety (fulleride) formed by electrocrystallization was revealed by single crystal structure analysis of C60 fulleride salts stabilized by triphenylmethane dye cations. The structure should be noted as molecular nanowire and anticipated to be an organic novel semiconductor from the preliminary four-probe conductance measurement. C60 fulleride has drawn much attention because of its interesting physical properties, such as superconducting of alkali-metal doped C60(A3C60) and unique ferromagnetic behavior of tetrakis(dimethylamino)ethane salts of C60 fulleride, (TDAE)C60.[20]. These intriguing solid-state properties of C60 fulleride should arise from electronic cooperative interactions, mainly due to electron-accepting ability of C60 and the ball-to-ball van der Waals interaction. However, there have been rather a limited number of well-characterized C60 anion radical salts, in particular, molecular discrete fulleride, predominantly because of their sensitivity to air.We have succeeded in obtaining highly ordered single crystals of C60 anion radical salts stabilized by cationic triphenylmethane dyes, some of which were found to give rise to an intriguing nanostructural columnar alignment like molecular nanowire of C60 fullerides. The single-crystal structure of [Crystal Violet]+C60−. C6H5Cl, reveals that the C60 fulleride aligns like molecular nanowire with the columnar structure along the a axis (crystal growth direction), as well as a zigzag structure along the b axis, with contacts of almost van der Waals magnitude (ca. 10 Å, distance of the C60–C60 center of mass), stabilized by mutual interactions of C60−. and dye, due to such as CH-π, π-π, and face-to-face mutual interactions.Magnetic susceptibility measurements for crystal violet salts demonstrate antiferromagnetic behavior, which can be fitted fairly by one-dimensional Heisenberg model (uniform chain), associated with the one-dimensional columnar crystal structure of the C60 fulleride molecular nanowire. These results also account for the semiconducting properties of the corresponding salts.

Photodegradation of malachite green under natural sunlight irradiation: Kinetic and toxicity of the transformation products

This article describes the photolytic degradation of malachite green (MG), a cationic triphenylmethane dye used worldwide as a fungicide and antiseptic in the aquaculture industry. Photolysis experiments were performed by direct exposure of a solution of MG in water to natural sunlight. The main transformation products (TPs) generated during the process were identified by liquid chromatography time-of-flight mass spectrometry (LC–TOF-MS) and gas chromatography mass spectrometry (GC–MS). The 28 TPs identified with this strategy indicate that MG undergoes three main reactions, N-demethylation, hydroxylation and cleavage of the conjugated structure forming benzophenone derivatives. These processes involve hydroxyl radical attack on the phenyl ring, the N, N-dimethylamine group and the central carbon atom. The Vibrio fischeri acute toxicity test showed that the solution remains toxic after MG has completely disappeared. This toxicity could be assigned, at least in part, to the formation of 4-(dimethylamine)benzophenone, which has an EC 50,30 min of 0.061 mg l −1, and is considered “very toxic to aquatic organisms” by current EU legislation.

UV light induced photodegradation of malachite green on TiO 2 nanoparticles

The photodegradation of malachite green (MG), a cationic triphenylmethane dye, is examined both under different pH values and amounts of TiO 2. After 15 W UV-365 nm irradiation for 4 h, ca. 99.9% of MG was degraded with addition of 0.5 g L −1 TiO 2 to solutions containing 50 mg L −1 of the MG dye. The HPLC–PDA–ESI-MS technique was used to obtain a better understanding on the mechanistic details of this TiO 2-assisted photodegradation of the MG dye with UV irradiation. Five intermediates of the process were separated, identified, and characterized for the first time. The results indicated that the N-de-methylation degradation of MG dye took place in a stepwise manner to yield mono-, di-, tri-, and tetra- N-de-methylated MG species generated during the processes. Under acidic conditions, the results indicated that the photodegradation mechanism is favorable to cleavage of the whole conjugated chromophore structure of the MG dye. Under basic conditions, the results showed that the photodegradation mechanism is favorable to a formation of a series of N-de-methylated intermediates of the MG dye.

Photocatalytic degradation of a mixture of Crystal Violet (Basic Violet 3) and Methyl Red dye in aqueous suspensions using Ag + doped TiO 2

The photocatalytic degradation of a mixture of two dyes: Crystal Violet (CV), also known as C.I. Basic Violet 3, which is a cationic triphenylmethane dye and Methyl Red (MR), which is an anionic azo dye was studied using untreated TiO 2 and silver ion doped TiO 2 under UV irradiation. To increase the photocatalytic efficiency of TiO 2 and to make its separation from the treated effluent after degradation easier, it was doped with silver ion using liquid impregnation method. The degradation of the dyes in the mixture was measured spectrophotometrically at their respective λ max values. The degradation kinetics fitted well to the Langmuir–Hinselwood pseudo first order rate law. The effects of pH and different interfering substances like Cl −, NO 3 −, SO 4 2−, HPO 4 2−, Ca 2+, Fe 2+, humic acid, O 2 and electron acceptors like H 2O 2, (NH 4) 2S 2O 8 and KBrO 3 on the degradation were also investigated. Several mixtures of these dyes prepared by mixing CV (5 × 10 −5 mol dm −3) and MR (7.5 × 10 −5 mol dm −3) in the V/V ratios of 1:1, 1:5 and 1:10 degraded by >99% on UV irradiation for 90 min in the presence of Ag + doped TiO 2 and about 70% under similar conditions in presence of TiO 2. COD removal was measured at regular intervals to quantify the mineralization of the dye. Above 86% mineralization was observed using 90 min irradiation.

Nanoliter segment formation in micro fluid devices for chemical and biological micro serial flow processes in dependence on flow rate and viscosity

Micro segmentation of liquids inside micro channels and micro tubes opens an easy way for highly parallelized chemical, biochemical and microbiological processes. The production of liquid segments can be done as a fast serial process and leads to a linear arrangement of samples, which are always individually characterized by their position. The segment formation is a function of injector geometry, interface forces, viscosity of the carrier liquid and flow rate. The formation of droplets inside channels of about 500 μm diameter was investigated. Therefore, a micro module made by polymethyl-methacrylate (PMMA) was used for segmentation and integrated in a modular micro fluid arrangement. Microscopic imaging controlled fluidic processes. The inert aliphatic liquid tetradecane and a mineral oil were used as embedding liquids. Segmentation occurred in aqueous solutions of the cationic triphenylmethane dye Malachite Green. The influence of the flow rate on the segment volumes was found to be strongly dependent on the viscosity of the embedding liquid. Operations with series of segments in serial processes as well as possible applications are discussed.

Pulsed Electric Linear Dichroism of Triphenylmethane Dyes Adsorbed on Montmorillonite K10 in Aqueous Media

Electric linear dichroism (ELD) spectra of two cationic triphenylmethane dyes, crystal violet (CV) and malachite green (MG), bound to sodium montmorillonite K10 (MK-10) were studied at 20°C in aqueous media at two mixing ratios, D/S, of 0.10 and 0.24 in the 700- to 400-nm wavelength region and in the applied electric field strength range between 0 and 3 kV/cm. The specific parallel and perpendicular dichroism (Δ A‖/A and Δ A⊥/A) spectra of dye-adsorbed MK-10 suspension were measured at a fixed field strength with an apparatus equipped with a 512-channel photodiode array detector. By changing the field strength over a wide range, a series of the reduced dichroism values of the bound dyes were measured at a fixed wavelength. By fitting these dichroism values to theoretical orientation functions, the intrinsic reduced dichroism (Δ A/A)int spectra at the limiting high fields (ELD spectrum) were determined for CV and MG bound to MK-10. No appreciable difference was observed at the two D/S values. The ELD spectra of these bound dyes are undulatory but never constant, throughout their absorption region; thus, the dye plane does not lie flatly either on the surface or between layers of MK-10 particle. The isotropic absorption spectra, A, of bound CV and MG were each deconvoluted to eight partial absorption bands, which were grouped into three differently polarized transitions, i.e., one out-of-plane and two mutually perpendicular in-plane. The optical transition dipole moment direction of each group was found to make a considerable angle with respect to the symmetry axis of the disklike MK-10 particle, whose plane (or surface) tends to orient toward the applied electric field at the limiting high fields. By simulating the observed ELD spectra of bound CV and MG with those deconvoluted bands, the roll, tilt, and inclination angles of both dyes were evaluated quantitatively with a new analytical method. The average angles (±θR, ± θT, |θN|) are −(34–47)°, 34°, and 51° for bound CV and −44°, 32°, and 53° for bound MG at two D/S values; thus, the triangular plane of each dye is rolled as well as tilted with a large inclination angle.

Influence of cationic triphenylmethane dyes upon DNA polymerization and product hydrolysis by Escherichia coli polymerase I

The cationic triphenylmethane dyes crystal violet, methyl green, and malachite green inhibited DNA synthesis catalyzed by Escherichia coli B polymerase I (polymerase I). Lower concentrations of the dyes inhibited DNA replication as a direct function of the proportion of AT to GC in the DNA of Clostridium perfringens, Escherichia coli, and Micrococcus lysodeikticus. When the intercalant proflavin was employed, the GC-rich micrococcal DNA was most severely inhibited. In addition, both the triphenylmethanes and proflavin inhibited product hydrolysis catalyzed by polymerase I.

Microvascular effects of a topically applied cationic triphenylmethane dye (crystal violet)

The effects of local application of crystal violet on the microcirculatory system are reported. The testing system consisted of vital microscopy of the cheek pouch of the hamster and microangiography of rabbit's ear. It appeared that the early microcirculatory disturbances caused by a dilute aqueous solution of crystal violet were transient, whereas considerable tissue toxicity was shown in the long-term experimental model. A direct cytotoxic effect is suggested.

Banding of human chromosomes with basic fuchsin.

In this paper a technique is described for the banding of human metaphase chromosomes with basic fuchsin. The main characteristics of the G-banding pattern obtained with this cationic triphenylmethane dye are: the secondary constriction regions of chromosomes Nos. 1 and 16 are strongly stained, especially in the latter one; the heterochromatic area of chromosome No. 9, usually negative with most other G-banding techniques, is clearly visible as an intensely stained band adjacent to the centromere; the chromosomal outline is often very distinct, facilitating the study of the telomeres; a number of chromosomal regions with bright Q fluorescence such as the polymorphic regions of the chromosomes Nos. 3, 4, and Y also stain strongly with basic fuchsin. The basic fuchsin technique combines therefore properties of G-, C-, and Q-banding methods and seems very suitable for use in e.g., family and linkage studies. Several triphenylmethanes closely related to basic fuchsin produce similar banding patterns. The band-producing ability is, however, diminished in those dyes which contain methylated amino groups. If the methyl groups are attached to the carbon atoms at the 3-positions in the phenyl rings, band formation seems unaffected. The way in which basic fuchsin and chromatin may interact as well as the possible mechanism(s) of band formation with this dye are discussed.

The effect of cationic triphenylmethane dye (crystal violet) on rabbit granulation tissue. Oxygen consumption and RNA and protein synthesis in tissue slices

Abstract is not availeble.

Effects of two cationic triphenylmethane dyes on the healing of skin incisions. A tensiometric and histologic study in the rat

Abstract i not available.

Influence of a cationic triphenylmethane dye on granulation tissue growth in vivo. An experimental study in rats

Abstract i not available.

Mikrospektralphotometrische Untersuchungen an lebenden Zellen der Schuppenblattepidermen von Allium cepa nach Färbung mit den Triphenylmethanfarbstoffen Methyl-, Gentiana- und Kristallviolett

Electrophoretic and spectrophotometric investigations have shown that in aqueous solution the cationic triphenyl methane dyes methyl violet 6B and crystal violet are present as molecules from p H 4.5—10.0 and are dissociated only at a p H below 3.0. Since maximum absorption of aqueous dye solutions with stable p H is dependent upon the concentration of the dye, it is supposed that the used dyes build associates. In shake out experiments with organic solvents methyl violet 6B and crystal violet show different absorption curves according to the polarity of the solvent. Rutin casues negative metachromasy. Except for high concentrations sodium nucleinat causes a positive metachromasy. The concentration of sodium nucleinate gives the actual site of the maximum. Comparing the given spectra results in the conclusion that an accumulation of electrical neutral dye particles of the cationic triphenyl methane dyes is possible in the protoplast as well as in the nucleus, principally in free polar lipids of the lecithine type and partly in free fatty acids. According to the conditions of dissociation for the dyes in question their intake is only made possible by “full” cell saps. The accumulation of “full” cell saps is due to a salt-like complex formation between dye particles and flavonoles genuine to the cell. A comparison between “in vivo” spectra of particles resulting from disintegration and the ”in vitro” results supposes a dyeflavonole complex; associates and free dye particles, respectively, are present in addition to this complex.