RESUMEN
Two-photon fluorescence microscopy has become an indispensable technique for cellular imaging. Whereas most two-photon fluorescent probes rely on well-known fluorophores, here we report a new fluorophore for bioimaging, namely azulene. A chemodosimeter, comprising a boronate ester receptor motif conjugated to an appropriately substituted azulene, is shown to be an effective two-photon fluorescent probe for reactive oxygen species, showing good cell penetration, high selectivity for peroxynitrite, no cytotoxicity, and excellent photostability.
Asunto(s)
Azulenos/química , Colorantes Fluorescentes/química , Microscopía de Fluorescencia por Excitación Multifotónica/métodos , Especies de Nitrógeno Reactivo/análisis , Especies Reactivas de Oxígeno/análisis , Azulenos/toxicidad , Supervivencia Celular/efectos de los fármacos , Colorantes Fluorescentes/toxicidad , Células HeLa , Humanos , Límite de DetecciónRESUMEN
Dye azulene and heavy metal chromium are two different types of persistent toxic compounds present in textile effluent. These compounds contaminate the soil and harm plant productivity during unchecked disposal of textile effluent to the farm soil. Environmental and safety concerns associated with crops, soil, and human health encourage the exploration of biological tools to control the issue. We hereby propose the application of biosurfactant (lipopeptide) to reduce the toxic effects of azulene and chromium in plants. Results of the study indicated that the augmentation of biosurfactant with azulene and chromium promoted seed germination, plant biomass, specific leaf weight (SLW), chlorophyll content, protein content, soluble sugar and ascorbic acid concentration in cultivars of wheat and chilli. Decreasing the level of proline under biosurfactant augmentation further confirms the reduction of oxidative stress caused by azulene and chromium amendment. The results indicated that lipopeptide biosurfactant could be an effective biological tool to reduce the toxic effect of persistent substances in soil, thus maintaining soil health and sustainable agriculture.
Asunto(s)
Azulenos/toxicidad , Capsicum/efectos de los fármacos , Cromo/toxicidad , Tensoactivos/farmacología , Triticum/efectos de los fármacos , Agricultura , Capsicum/crecimiento & desarrollo , Capsicum/metabolismo , Restauración y Remediación Ambiental , Lipopéptidos/farmacología , Estrés Oxidativo/efectos de los fármacos , Contaminantes del Suelo/toxicidad , Triticum/crecimiento & desarrollo , Triticum/metabolismoRESUMEN
The polycyclic aromatic hydrocarbon azulene and its naturally occurring derivative guaiazulene (1,4-dimethyl-7-isopropylazulene) are known to absorb light in the UV-vis region of the spectrum. Both compounds were reported to be mutagenic in the Salmonella typhimurium bacterial mutagenicity assay (Ames test) in strain TA102, and to cause DNA damage in the comet assay in vitro upon exposure to UVA light. In contrast, another study reported a photoprotective effect in vitro of guaiazulene. We present here a comprehensive assessment of the photo(cyto)toxicity (3T3 fibroblast Neutral Red uptake test), the photomutagenicity (Ames test) and photogenotoxicity (comet assay and micronucleus test in L5178Y cells in vitro) of azulene. In the Ames test, the mutagenicity of azulene was assessed in the presence and absence of UV light by use of the Salmonella strains TA102, TA104, TA2638 and E. coli WP2. Azulene was irradiated before being plated with bacteria (pre-irradiation), or concomitantly with the bacteria either after plating or while in suspension. Guaiazulene was included in some of the experiments. Neither in the photo-Ames test nor in the other photogenotoxicity tests, azulene or guaiazulene showed any photomutagenic or photogenotoxic activity. Weak photo(cyto)toxicity (estimate of PIF≥1.67) was observed with azulene in the 3T3 NRU test, the Alamar Blue test and the relative cell count, which may be due to the generation of reactive oxygen species, as reported recently.
Asunto(s)
Azulenos/toxicidad , Procesos Fotoquímicos , Rayos Ultravioleta/efectos adversos , Células 3T3 , Animales , Ensayo Cometa/métodos , Daño del ADN , Leucemia L5178 , Luz/efectos adversos , Ratones , Pruebas de Micronúcleos/métodos , Pruebas de Mutagenicidad/métodos , Salmonella typhimurium/efectos de los fármacos , Sesquiterpenos/toxicidad , Sesquiterpenos de GuayanoRESUMEN
Guaiazulene (GA) is widely used as a natural ingredient in many health care products and solutions. Although it has been reported to have interesting biological effects, GA and azulene derivatives have been proven to be cytotoxic against normal human cells and human tumor cells; moreover, guaiazulene has shown photomutagenic properties on bacterial strains. Therefore, we evaluated and compared the cytotoxicity of GA at different concentrations on human gingival fibroblast (HGF) cell cultures under normal conditions and under UV irradiation (UV-A dose: 6.4 J/cm(2)). The compound tested was found to significantly reduce cell viability (dose-dependent trend, IC(50) 72.1 µM), decrease protein procollagen α1 type I synthesis, a marker for HGF protein, and COL1A1 mRNA expression. The cytotoxic effects were accompanied by activation of an intrinsic apoptotic pathway, studied using transmission electron microscopy (TEM) and caspase-3 activation. The light exposure of the cell culture treated decreased GA-induced cell death (IC(50) 128.9 µM), suggesting a photoprotective effect due to the photodegradation of the toxic agent, guaiazulene. Furthermore, the products of the photodegradation reaction of GA proved not to be toxic against HGFs.
Asunto(s)
Apoptosis/efectos de los fármacos , Azulenos/efectos de la radiación , Azulenos/toxicidad , Encía/efectos de los fármacos , Oxidantes Fotoquímicos/efectos de la radiación , Oxidantes Fotoquímicos/toxicidad , Sesquiterpenos/efectos de la radiación , Sesquiterpenos/toxicidad , Rayos Ultravioleta , Biomarcadores/metabolismo , Caspasa 3/metabolismo , Supervivencia Celular/efectos de los fármacos , Células Cultivadas , Colágeno Tipo I/genética , Colágeno Tipo I/metabolismo , Cadena alfa 1 del Colágeno Tipo I , Fibroblastos/citología , Fibroblastos/efectos de los fármacos , Fibroblastos/metabolismo , Fibroblastos/ultraestructura , Regulación de la Expresión Génica/efectos de los fármacos , Encía/citología , Encía/metabolismo , Encía/ultraestructura , Humanos , Concentración 50 Inhibidora , Fotólisis , ARN Mensajero/metabolismo , Sesquiterpenos de GuayanoRESUMEN
The relationship between the structure and cytotoxic activity of azulenequinones and trihaloacetylazulenes was investigated based on theoretical calculations. Four different dipole moments (mu(G), mu(ESP-G), mu(W) and mu(ESP-W)) and heats of formation (DeltaH(f)) of the azulenequinones [1-27] and trihaloacetylazulenes [28a,b-40a,b] were separately calculated in gas phase and aqueous solution using the conductor-like screening model/parametric method 3 (COSMO/PM3) method. The cytotoxic activity of azulenequinones was well correlated to DeltaDeltaH(f) HOMO energy and mu(ESP-w). The cytotoxic activity of trihaloacetylazulenes was correlated to DeltaDeltaH(f) LUMO energy and mu(ESP-W). QSAR may be applicable to predict the cytotoxicity of azulenequinones and trihaloacetylazulenes.
Asunto(s)
Azulenos/química , Azulenos/toxicidad , Electrones , Quinonas/química , Quinonas/toxicidad , Acetilación , Línea Celular Tumoral , Supervivencia Celular/efectos de los fármacos , Simulación por Computador , Halogenación , Humanos , Relación Estructura-Actividad CuantitativaRESUMEN
The structure-activity relationship of the cytotoxic activity of azulene and azulene derivatives was discussed, using theoretically calculated results. In order to clearly divide the azulenes into three groups according to their functional groups, the CC50, four different dipole moments (muG, muESP-G, muwand muESP-W) and heats of formation (deltaHf) of the azulenes [1-24] were separately calculated in two states, gas-phase and water, by the conductor-like screening model/parametric method 3 (COSMO/PM3). For the halogenated azulenes and isopropyl azulenes, the cytotoxic activity might follow the three quantitative structure-activity relationship (QSAR) parameters: deltadeltaHf, HOMO energy and muw Whereas, for the other ten compounds [3-5, 7-8, 10, 15-18], the cytotoxic activity might be related to the three QSAR parameters, deltadeltaHf, LUMO energy and muG