Triphenylmethane and Related Dyes

Thetford, D.; Staff, Updated by

doi:10.1002/0471238961.2018091620080520.a01.pub2

Cited by 7 publications

(2 citation statements)

References 45 publications

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“…28 Importantly, triphenylmethane dyes have a long safety record for use in humans as topical antibiotics, and newborns with purple, triple-dye stained umbilical cords have experienced their use in a medical setting. 29−31 While the antibacterial, antiphagocytic properties of triphenylmethane dyes were assessed more than 80 years ago, 32 only recently has BG been proposed as an antibacterial additive for gloves and in mouthwash for immune-compromised individuals.…”

Section: Discussionmentioning

confidence: 99%

Triphenylmethane Dye Activation of Beta-Arrestin

et al. 2013

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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.

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Section: Discussionmentioning

confidence: 99%

Triphenylmethane Dye Activation of Beta-Arrestin

et al. 2013

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“…Additionally to their numerous technological applications, triphenylmethane (TPM) dyes have been widely used in spectroscopy to investigate the influence of symmetry and structural relaxation on properties as diverse as nonlinear optical response, − and ultrafast nonradiative transitions. − Among these dyes, crystal violet, CV, has attracted considerable attention because of the peculiar shape of its lowest-energy absorption band, characterized by a prominent shoulder on its blue side. As thoroughly reviewed by Lovell et al, the origin of this shoulder has been highly debated since the work of Lewis and co-workers in 1942, who proposed the existence of an equilibrium between two CV conformers, a symmetric propeller-shaped one and another with one of the branches twisted in the opposite direction.…”

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confidence: 99%

Torsional Disorder, Symmetry Breaking, and the Crystal Violet Shoulder Controversy

Sissaoui

Budkina

Vauthey

2023

J. Phys. Chem. Lett.

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The nature of the lowest-energy electronic absorption band of crystal violet (CV) and particularly the origin of its high-energy shoulder have been debated since the middle of the past century. The most recent studies invoke a splitting of the S1 state upon symmetry breaking induced by interactions with the solvent and/or the counterion. Using a combination of stationary and time-resolved polarized spectroscopy together with quantum-chemical calculations, we show that torsional disorder in the ground-state results in an inhomogeneous broadening of the absorption band of CV. The center of the band is mostly due to symmetric molecules with a degenerate S1 state, whereas the edges originate from transitions to the S1 and S2 states of distorted symmetry-broken molecules. Transient-absorption measurements with different excitation wavelengths reveal that these two groups of molecules interconvert rapidly in liquid but not in a rigid environment.

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Ultrafast Excited State Relaxation Dynamics of New Fuchsine‐ a Triphenylmethane Derivative Dye

Biswas

Soma

Chetti³

et al. 2021

ChemPhysChem

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An all-inclusive investigation of the ultrafast excited state relaxation dynamics of a triphenylmethane derivative molecule, New Fuchsine (NF), using a combined approach of density functional theory (DFT), femtosecond transient absorption spectroscopy (fs-TAS), and photoluminescence spectroscopy is presented in this work. The DFT calculations confirmed the formation of twisted molecular structure in the excited state of NF in ethanol solution with bond rotation of � 86°. TAS measurements of NF solution exhibited ultrafast ground staterecovery pathway via a conical intersection confirming an ultrafast structural reorientation. On the contrary, TAS measurements of NF thin-film exhibited a longer excited-state lifetime suggesting a hindered molecular twisted state formed as an intermediate step. Photophysical kinetic models are proposed to globally fit the fs-TAS data establishing the twisted intramolecular charge transfer (TICT) state mediated ground state recovery for NF in solution and thin film, respectively. Temperature-dependent photoluminescence study of NF film provided a clear insight into the effect of rotational motion of phenyl rings in NF molecules over the TICT mediated emission.

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Triphenylmethane and Related Dyes

Cited by 7 publications

References 45 publications

Triphenylmethane Dye Activation of Beta-Arrestin

Triphenylmethane Dye Activation of Beta-Arrestin

Torsional Disorder, Symmetry Breaking, and the Crystal Violet Shoulder Controversy

Ultrafast Excited State Relaxation Dynamics of New Fuchsine‐ a Triphenylmethane Derivative Dye

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