Dissecting the structural and functional consequences of the evolutionary proline-glycine deletion in the wing 1 region of the forkhead domain of human FoxP1.

The human FoxP transcription factors dimerize via three-dimensional domain swapping, a unique feature among the human Fox family, as result of evolutionary sequence adaptations in the forkhead domain. This is the case for the conserved glycine and proline residues in the wing 1 region, which are absent in FoxP proteins but present in most of the Fox family. In this work, we engineered both glycine (G) and proline-glycine (PG) insertion mutants to evaluate the deletion events in FoxP proteins in their dimerization, stability, flexibility, and DNA-binding ability. We show that the PG insertion only increases protein stability, whereas the single glycine insertion decreases the association rate and protein stability and promotes affinity to the DNA ligand.

Exploring the Use of a Lipopeptide in Dipalmitoylphosphatidylcholine Monolayers for Enhanced Detection of Glyphosate in Aqueous Environments.

The growing reliance on pesticides for pest management in agriculture highlights the need for new analytical methods to detect these substances in food and water. Our research introduces a SPRWG-(C18H37) lipopeptide (LP) as a functional analog of acetylcholinesterase (AChE) for glyphosate detection in environmental samples using phosphatidylcholine (PC) monolayers. This LP, containing hydrophilic amino acids linked to an 18-carbon aliphatic chain, alters lipid assembly properties, leading to a more flexible system. Changes included reduced molecular area and peak pressure in Langmuir adsorption isotherms. Small angle X-ray scattering (SAXS) and atomic force microscopy (AFM) analyses provided insights into the LP's structural organization within the membrane and its interaction with glyphosate (PNG). Structural and geometric parameters, as derived from in silico molecular dynamics simulations (MD), substantiated the impact of LP on the monolayer structure and the interaction with PNG. Notably, the presence of the LP and glyphosate increased charge transfer resistance, indicating strong adherence of the monolayer to the indium tin oxide (ITO) surface and effective pesticide interaction. A calibration curve for glyphosate concentration adjustment revealed a detection limit (LOD) of 24 nmol L-1, showcasing the high sensitivity of this electrochemical biosensor. This LOD is significantly lower than that of a similar colorimetric biosensor in aqueous media with a detection limit of approximately 0.3 µmol L-1. Such an improvement in sensitivity likely stems from adding a polar residue to the amino acid chain of the LP.

Stereoselective synthesis of S-norvaline and related amino acids through a common intermediate.

A divergent, enantioselective synthetic strategy is reported to produce the non-proteinogenic, biologically active natural amino acids norvaline, 5-hydroxy-4-oxo-L-norvaline, and ɣ-oxonorvaline. These were synthesized in good yields (45-75%) from the common starting material (S)-allylglycine obtained by asymmetric transfer allylation of glycine Schiff base using the Corey catalyst derived from cinchonidine in more than 97% enantiomeric excess.

Interaction of glyphosate in matrices of cellulose and diethylaminoethyl cellulose biopolymers: theoretical viewpoint of the adsorption process.

Glyphosate is an herbicide widely used in agricultural activities causing contamination of soils and bodies of water and damage to the biodiversity of ecosystems. In this context, the present study aimed to theoretically study the adsorption potential of the biopolymer cellulose (CE) and its diethylaminoethyl cellulose derivative (DEAEC) with the herbicide glyphosate (GLY). Theoretical calculations were performed using the density functional theory. Molecular electrostatic potential and frontier molecular orbital analyses were performed, which allowed identifying the possible sites of interaction of biopolymers that were in the functional groups -OH and O- of cellulose and in the groups -O- and -NH+(CH2CH3)2 of the DEAEC. Reactivity indices chemical softness and hardness showed that both adsorbents could interact with adsorbate. Simulated IR indicated that the interactions could be evinced in experimental measurements by changes in the bands of glyphosate (ν(P = O), δ(P-O-H), δ(C-N-H)) or in the bands of CE and DEAEC (ν(C-O), ν(C-H), ν(N-H)). The binding energies showed that the GLY interacts more effectively with CE than DEAEC. The ΔH prove that all processes are exothermic and the CE-GLY1 interaction showed value of ΔG < 0. The topological results showed a greater number of interactions with electrostatic nature. The results found in the study show that the theoretical data provides useful information to support the use of biopolymers as matrices for glyphosate adsorption or other contaminants.

Enzyme-support interactions and inactivation conditions determine Thermomyces lanuginosus lipase inactivation pathways: Functional and florescence studies.

Lipase from Thermomyces lanuginosus (TLL) has been covalently immobilized on heterofunctional octyl-vinyl agarose. That way, the covalently immobilized enzymes will have identical orientation. Then, it has blocked using hexyl amine (HEX), ethylenediamine (EDA), Gly and Asp. The initial activity/stability of the different biocatalysts was very different, being the most stable the biocatalyst blocked with Gly. These biocatalysts had been utilized to analyze if the enzyme activity could decrease differently along thermal inactivation courses depending on the utilized substrate (that is, if the enzyme specificity was altered during its inactivation using 4 different substrates to determine the activity), and if this can be altered by the nature of the blocking agent and the inactivation conditions (we use pH 5, 7 and 9). Results show great changes in the enzyme specificity during inactivation (e.g., activity versus triacetin was much more quickly lost than versus the other substrates), and how this was modulated by the immobilization protocol and inactivation conditions. The difference in the changes induced by immobilization and inactivation were confirmed by fluorescence studies. That is, the functional and structural analysis of partially inactivated immobilized enzyme showed that their inactivation pathway is strongly depended on the support features and inactivation conditions.

The Effect of Goethites on the Polymerization of Glycine and Alanine Under Prebiotic Chemistry Conditions.

After pre concentration of monomers, polymerization is the second most important step for molecular evolution. The formation of peptides is an important issue for prebiotic chemistry and consequently for the origin of life. In this work, goethite was synthesized by two different routes, named goethite-I and goethite-II. Although both samples are goethite, Far-FT-IR spectroscopy and EPR spectroscopy showed differences between them, and these differences had an effect on the polymerization of glycine and alanine. For the amino acid polymerization, three protocols were used, that resembled prebiotic Earth conditions: a) amino acid plus goethite were mixed and heated at 90 °C for 10 days in solid state, b) a wet impregnation of the amino acid in the goethite, with subsequent heating at 90 °C for 10 days in solid state, and c) 10 wet/dry cycles each one for 24 h at 90 °C. Experiments with glycine plus goethite-II, using protocols B and C, produced only Gly-Gly. In addition, for the C protocol the amount of Gly-Gly synthesized was 3 times higher than the amount of Ala-Ala. Goethite-I presented a decrease in the EPR signal, when it was submitted to the protocols with and without amino acids. It is probable the decrease in the intensity of the EPR signal was due to a decrease in the imperfections of the mineral. For all protocols the mixture of alanine plus goethite-I or goethite-II produced c(Ala-Ala). However, for wet/dry cycles, protocol C presented higher yields (p < 0.05). In addition, Ala-Ala was produced using protocols A and C. The c(Ala-Ala) formation fitted a zero-order kinetic equation model. The surface areas of goethite-I and goethite-II were 35 m2 g-1 and 37 m2 g-1, respectively. Thermal analysis indicated that the mineral changes the thermal behavior of the amino acids. The main reactions for the thermal decomposition of glycine were deamination and dehydration and for alanine was deamination.

Technologies Employed in the Treatment of Water Contaminated with Glyphosate: A Review.

Glyphosate [N-(phosphonomethyl)-glycine] is a herbicide with several commercial formulations that are used generally in agriculture for the control of various weeds. It is the most used pesticide in the world and comprises multiple constituents (coadjutants, salts, and others) that help to effectively reach the action's mechanism in plants. Due to its extensive and inadequate use, this herbicide has been frequently detected in water, principally in surface and groundwater nearest to agricultural areas. Its presence in the aquatic environment poses chronic and remote hazards to human health and the environment. Therefore, it becomes necessary to develop treatment processes to remediate aquatic environments polluted with glyphosate, its metabolites, and/or coadjutants. This review is focused on conventional and non-conventional water treatment processes developed for water polluted with glyphosate herbicide; it describes the fundamental mechanism of water treatment processes and their applications are summarized. It addressed biological processes (bacterial and fungi degradation), physicochemical processes (adsorption, membrane filtration), advanced oxidation processes-AOPs (photocatalysis, electrochemical oxidation, photo-electrocatalysis, among others) and combined water treatment processes. Finally, the main operating parameters and the effectiveness of treatment processes are analyzed, ending with an analysis of the challenges in this field of research.

Adsorption mechanisms of atrazine isolated and mixed with glyphosate formulations in soil.

In Brazil, the atrazine has been applied frequently to join with glyphosate to control resistant biotypes and weed tolerant species to glyphosate. However, there are no studies about atrazine's behavior in soil when applied in admixture with glyphosate. Knowledge of atrazine's sorption and desorption mixed with glyphosate is necessary because the lower sorption and higher desorption may increase the leaching and runoff of pesticides, reaching groundwaters and rivers. Thereby, the objective of this study was to evaluate the adsorption mechanisms of atrazine when isolated and mixed with glyphosate formulations in a Red-Yellow Latosol. The maximum adsorbed amount of atrazine in equilibrium (qe) was not altered due to glyphosate formulations. The time to reach equilibrium was shortest when atrazine was mixed with the Roundup Ready® (te = 4.3 hours) due to the higher adsorption velocity (k2 = 2.3 mg min-1) in the soil. The highest sorption of atrazine occurred when mixed with the Roundup WG®, with the Freundlich sorption coefficient (Kf) equal to 2.51 and 2.43 for both formulation concentrations. However, other glyphosate formulations did not affect the sorption of atrazine. The desorption of atrazine was high for all treatments, with values close to 80% of the initial adsorbed amount, without differences among isolated and mixed treatments. The change in the velocity and capacity of sorption for the atrazine mixed with some glyphosate formulations indicates that further studies should be conducted to identify the mechanisms involved in this process.

Experimental and Theoretical Studies of Glyphosate Detection in Water by an Europium Luminescent Complex and Effective Adsorption by HKUST-1 and IRMOF-3.

Designing an effective and simple detection method to quantify glyphosate (GLY) herbicide is desirable. Current chromatography-mass spectrometry and electrochemical methods can be used for this purpose, but these methods are difficult to be made portable and need high-cost equipment. Here, we evaluate a luminescent ß-diketonate-Eu-ethylenediaminetetraacetic acid complex for GLY quantification in aqueous media on the basis of the luminescent quenching process. This complex successfully measured GLY at concentrations ranging from 5 × 10-7 to 10-5 mol L-1. Theoretical methods (LUMPAC) are also performed to identify the complex most probable structure in solution. We also demonstrate that the metal-organic frameworks HKUST-1 and IRMOF-3, easily synthesized, effectively adsorb GLY in water in about 30 min of contact.

Are glyphosate and glyphosate-based herbicides endocrine disruptors that alter female fertility?

Numerous evidences have alerted on the toxic effects of the exposure to glyphosate on living organisms. Glyphosate is the herbicide most used in crops such as maize and soybean worldwide, which implies that several non-target species are at a high risk of exposure. Although the Environmental Protection Agency (EPA-USA) has reaffirmed that glyphosate is safe for users, there are controversial studies that question this statement. Some of the reported effects are due to exposure to high doses; however, recent evidences have shown that exposure to low doses could also alter the development of the female reproductive tract, with consequences on fertility. Different animal models of exposure to glyphosate or glyphosate-based herbicides (GBHs) have shown that the effects on the female reproductive tract may be related to the potential and/or mechanisms of actions of an endocrine-disrupting compound. Studies have also demonstrated that the exposure to GBHs alters the development and differentiation of ovarian follicles and uterus, affecting fertility when animals are exposed before puberty. In addition, exposure to GBHs during gestation could alter the development of the offspring (F1 and F2). The main mechanism described associated with the endocrine-disrupting effect of GBHs is the modulation of estrogen receptors and molecules involved in the estrogenic pathways. This review summarizes the endocrine-disrupting effects of exposure to glyphosate and GBHs at low or "environmentally relevant" doses in the female reproductive tissues. Data suggesting that, at low doses, GBHs may have adverse effects on the female reproductive tract fertility are discussed.

Comparative acute toxicity of glyphosate-based herbicide (GBH) to Daphnia magna, Tisbe longicornis, and Emerita analoga.

The aim of this work was to know the differential composition of the dissolved fraction of a glyphosate-based herbicide (GBH), commercialized as GLIFOPAC, when reaches different aquatic environments and its ecotoxicological effects on crustaceans species living in them. Daphnia magna, Tisbe longicornis, and Emerita analoga were exposed to glyphosate herbicide called GLIFOPAC (480 g L-1 of active ingredient or a.i.) at concentrations between 0.5 and 4.8 g a.i. L-1. Acute toxicity in D. magna (48 h-LC50), E. analoga (48 h-LC50), and T. longicornis (96 h-LC50) was studied. Chromatographic analysis of the GBH composition used and water (freshwater/sea water) polluted with GLIFOPAC were evaluated. Results reported acute toxicity (48-96 h-LC50) values for D. magna, E. analoga and T. longicornis of 27.4 mg L-1, 806.4 mg L-1, and 19.4 mg L-1, respectively. Chromatographic evaluation described around 45 substances of the GLIFOPAC composition, such as from the surfactant structures (aliphatic chain with esther/ether group), metabolites (AMPA), and other substances (glucofuranose, glucopyranoside, galactopyranose). This study evidenced differences in the GLIFOPAC composition in freshwater and marine water, which may differentiate the toxic response at the crustacean-level in each aquatic environment.

Theoretical study of glycine amino acid adsorption on graphene oxide.

The non-dissociative and dissociative adsorptions of zwitterionic Gly on graphene oxide (GO) was studied in the framework of DFT using a cluster model approach. In this work, the interaction with an epoxy group of GO basal plane was mainly considered. As a comparison, the non-dissociative and dissociative adsorptions of neutral Gly were also taken into account. The non-dissociative adsorption modes for zwitterionic and neutral Gly conformers show binding energies of 12.2 and 14.4 kcal mol-1, respectively. These molecules are thought to remain over the GO surface due to attractive noncovalent interactions. Two dissociative adsorption modes, for Z-Gly and N-Gly, show smaller binding energies of 7.2 and 8.4 kcal mol-1, where the deprotonated species links strongly through a C-O or C-N covalent bond to the GO surface. The results obtained in the present theoretical approach to the glycine/graphene oxide system support the fact that glycine can be attached to epoxy groups of graphene oxide basal planes in addition to the anchoring on edge oxidation groups. In summary, we conclude that glycine can be used as a reducing agent as well as a functionalizer of GO sheets.

Identification and distribution of mycosporine-like amino acids in Brazilian cyanobacteria using ultrahigh-performance liquid chromatography with diode array detection coupled to quadrupole time-of-flight mass spectrometry.

RATIONALE: Mycosporine-like amino acids (MAAs) are UV-absorbing compounds produced by fungi, algae, lichens, and cyanobacteria when exposed to UV radiation. These compounds have photoprotective and antioxidant functions and have been widely studied for possible use in sunscreens and anti-aging products. This study aims to identify MAA-producing cyanobacteria with potential application in cosmetics. METHODS: A method for the identification of MAAs was developed using ultrahigh-performance liquid chromatography with diode array detection coupled to quadrupole time-of-flight mass spectrometry (UHPLC-DAD/QTOFMS). Chromatographic separation was carried out using a Synergi 4 µ Hydro-RP 80A column (150 × 2,0 mm) at 30°C with 0.1% formic acid aqueous solution + 2 mM ammonium formate and acetonitrile/water (8:2) + 0.1% formic acid as a mobile phase. RESULTS: Out of the 69 cyanobacteria studied, 26 strains (37%) synthesized MAAs. Nine different MAAs were identified using UHPLC-DAD/QTOFMS. Iminomycosporines were the major group detected (7 in 9 MAAs). In terms of abundance, the most representative genera for MAA production were heterocyte-forming groups. Oscilatoria sp. CMMA 1600, of homocyte type, produced the greatest diversity of MAAs. CONCLUSIONS: The UHPLC-DAD/QTOFMS method is a powerful tool for identification and screening of MAAs in cyanobacterial strains as well as in other organisms such as dinoflagellates, macroalgae, and microalgae. The different cyanobacterial genera isolated from diverse Brazilian biomes and environments are prolific sources of MAAs.

X-ray Spectroscopy Fostering the Understanding of Foliar Uptake and Transport of Mn by Soybean (Glycine max L. Merril): Kinetics, Chemical Speciation, and Effects of Glyphosate.

Increasing the yield of soybean is a challenge to humankind dependent on several management practices, such as fertilizing and weed control. While glyphosate contributes to controlling weeds, it can interfere with spray mixture stability and, supposedly, complex with micronutrients within the plant tissue. This study investigated the effects of glyphosate on soybean foliar uptake and transport of Mn supplied as MnSO4, MnHPO3, Mn-ethylenediamine tetraacetic acid (EDTA), and MnCO3. These fertilizers induced ultrastructural changes in the leaf cuticle, regardless of the glyphosate mixture. Except for MnCO3, all tested sources increased the Mn content in the petiole. The mixture of glyphosate impaired Mn transport from MnSO4 and MnHPO3, but no evidence of Mn-glyphosate complexation within the plant was found. Manganese is rather transported in a similar chemical environment regardless of the source, except for Mn-EDTA, which was absorbed and transported in its pristine form. Interferences of glyphosate seem to be related to complexations in the tank mixture rather than affecting nutrients' metabolism.

Supercell calculations of the geometry and lattice energy of α-glycine crystal.

Evidence about the presence of glycine in the interstellar medium (ISM) has been motivating studies aiming the understanding of the chemical behavior of this amino acid in such environment. Since glycine is expected to be predominantly found in the ISM in solid phase, this work focuses on the search for a theoretical methodology for obtaining a molecular cluster for α-glycine that provides a good description of the geometry of the unit cell and lattice energy. Calculations have been performed using the B3LYP-D3, PBE0-D3, and WB97X-D3 functionals, with def2-SVP, def2-TZVP, def2-TZVPP, and def2-QZVPP basis sets for two models: (a) the unit cell, containing 4 glycine units, and (b) the 2 × 1 × 2 expanded cell, with 16 glycine units. Corrections for the basis set superposition error have also been applied. No significant changes in geometries and lattice energy predictions from the different functionals and basis sets have been observed for each model. Nevertheless, results obtained for the larger molecular cluster are in better agreement with the experimental data. The best lattice energy prediction, obtained for the 2 × 1 × 2 supercell at the B3LYP-gCP-D3/def2-TZVPP level, is - 15.35 kcal mol-1, with a root mean square deviation of the predicted Cartesian coordinates of the inner molecules (with respect to the experimental α-glycine unit cell geometry) of 0.966 Å. This methodology is finally recommended for future studies of similar molecular cluster, and the predicted geometry is proposed for further studies aiming to describe glycine surface reactions in the ISM.

Adsorption of glyphosate on Brazilian subtropical soils rich in iron and aluminum oxides.

We investigated the adsorption of glyphosate onto five subtropical soils of Paraná and São Paulo states, Brazil, a region of intense agricultural activities, aiming at the determination of kinetic and isotherm adsorption parameters which enable the evaluation of the potential leaching of the herbicide. The adsorption was fast, being described by the pseudo-second order and intraparticle diffusion models, thus suggesting that mixed mechanisms are involved. The Oxisol containing the highest concentrations of metal oxides (209.5 g kg-1 Fe2O3 and 160.2 g kg-1 Al2O3) was the sample with the highest rate constant, indicating the adsorption sites are readily available. All the soils are rich in aluminum and iron oxides, explaining the Freundlich coefficients (KF) between 642 and 1360 mg1-1/n kg-1 L1/n, which are higher than most of the coefficients described for other soils around the world. The maximum desorption (15% of the adsorbed amount) was observed for the Oxisol. For the other soils, desorption ranged from 2 to 7%. These results suggest that the leaching of free glyphosate to nearby surface and groundwaters is unlikely unless excessive doses are used. The adsorption parameters are useful for managing the right doses applied to the crops, thus avoiding contamination of adjacent areas.

Compaction and Destruction Cross-Sections for α-Glycine from Radiolysis Process via 1.0 keV Electron Beam as a Function of Temperature.

Glycine is an amino acid that has already been detected in space. It is relevant to estimate its resistance under cosmic radiation. In this way, a sublimate of glycine in α-form on KBr substrate was exposed in the laboratory to a 1.0 keV electron beam. The radiolysis study was performed at 40 K, 80 K, and 300 K sample temperatures. These temperatures were chosen to cover characteristics of the outer space environment. The evolution of glycine compaction and degradation was monitored in real time by infrared spectroscopy (Fourier-transform infrared) by investigation in the spectral ranges of 3500-2100, 1650-1200, and 950-750 cm-1. The compaction cross-section increases as the glycine temperature decreases. The glycine film thickness layer of ∼160 nm was depleted completely after ∼15 min at 300 K under irradiation with ∼1.4 µA beam current on the target, whereas the glycine depletion at 40 K and 80 K occurred after about 4 h under similar conditions. The destruction cross-section at room temperature is found to be (13.8 ± 0.2) × 10-17 cm2, that is, about 20 times higher than the values for glycine depletion at lower temperatures (<80 K). Emerging and vanishing peak absorbance related to OCN- and CO bands was observed in 2230-2100 cm-1 during the radiolysis at 40 K and 80 K. The same new IR bands appear in the range of 1600-1500, 1480-1370, and 1350-1200 cm-1 after total glycine depletion for all temperature configurations. A strong N-H deformation band growing at 1510 cm-1 was observed only at 300 K. Finally, the destruction cross-section associated to tholin decay at room temperature is estimated to be (1.30 ± 0.05) × 10-17 cm2. In addition, a correlation between the formation cross-sections for daughter and granddaughter molecules at 300 K is also obtained from the experimental data.

Polyphosphate recovery by a native Bacillus cereus strain as a direct effect of glyphosate uptake.

Seven bacterial strains isolated from a glyphosate-exposed orange plantation site were exposed to 1 mM N-(phosphonomethyl)glycine supplied as a phosphorus source. While some exhibited good biodegradation profiles, the strain 6 P, identified as Bacillus cereus, was the only strain capable of releasing inorganic phosphate to the culture supernatant, while accumulating polyphosphate intracellularly along the experimentation time. The composition and purity of the intracellular polyphosphate accumulated by the strain 6 P were confirmed by FTIR analysis. To date, the biological conversion of glyphosate into polyphosphate has not been reported. However, given the importance of this biopolymer in the survival of microorganisms, it can be expected that this process could represent an important ecological advantage for the adaptation of this strain to an ecological niche exposed to this herbicide. The polyphosphate production yield was calculated as 4 mg l-1, while the glyphosate biodegradation kinetic constant was calculated on 0.003 h-1 using the modified Hockey-Stick first-order kinetic model, with a half-life of 279 h. Our results suggest that B. cereus 6 P is a potential candidate for the generation of an innovative biotechnological process to produce polyphosphate through the biodegradation of the herbicide glyphosate.

Genotoxicity of water samples from an area of the Pampean region (Argentina) impacted by agricultural and livestock activities.

The aim of this study was to assess the genotoxic potential of surface waters located in a rural area in the north east of Buenos Aires province (Argentina) using the Allium cepa test. Water samples were collected at four sites located in a drainage channel and two sites on the Burgos stream that receives water from the channel, taking into account the sowing and harvesting months and rainfall periods. Analytical determinations revealed high total concentrations of Cd, Cu, Pb, and Zn (maximum values: 0.030, 0.252, 0.176, and 0.960 mg L-1, respectively), and concentrations of glyphosate and its metabolite aminomethylphosphonic acid (AMPA), with maximum values of 13.6 and 9.75 µg L-1, respectively. Statistically positive correlations were observed between the total metal concentrations and precipitation. No cytotoxicity (mitotic index MI) was observed in A. cepa. However, several water samples showed significant increases in micronucleus (MN) frequencies with respect to the controls. No correlations were observed between MN and the abiotic variables or precipitation. These results showed a state of deterioration in the water quality at the rural area studied in Buenos Aires province, and heavy metal contamination may contribute to the genotoxic activity. A. cepa was shown to be a useful tool for the detection of genotoxicity in water samples from areas with agricultural and livestock activities.

Histological evaluation of vital organs of the livebearer Jenynsia multidentata (Jenyns, 1842) exposed to glyphosate: A comparative analysis of Roundup® formulations.

Roundup formulations are herbicides whose active principle is glyphosate. However, these formulations are potentially more toxic to non-target organisms than pure glyphosate. This study aimed to evaluate and compare the toxic potential of the Roundup formulations through histological alterations in fish. Thus, males and females of the neotropical fish species Jenynsia multidentata (Jenyns, 1842) were exposed for 24 or 96 h to the Roundup Original® (RO), Roundup Transorb® (RT) or Roundup WG® (RWG) formulations, at a fixed concentration of 0.5 mg/L of glyphosate. This concentration is close to the maximum glyphosate limits found in the environment and is non-lethal to J. multidentata. The three formulations caused histological damage to the liver, gills and brain of J. multidentata, which increased over the exposure time. Differences in the histological alterations between females and males were observed in the liver and brain. Females were more tolerant to RO and RT than RWG. Males did not exhibit these differences in sensitiveness with formulations. The RWG caused more damage in the liver and gills and RT in the brain. Overall, there were differences in the toxicity of RO, RT and RWG and the toxic effect was presented through histological damage, reinforcing the usefulness of histological biomarkers for Roundup® toxicity. The comparison of the toxic potential of glyphosate-based herbicides is important because it could give support to the governmental organizations to set protective rules for the water ecosystems and human health, as well as to reduce the use of highly toxic formulations in agriculture.