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PubMed1986

Species differences in the formation of benzo(a)pyrene-DNA adducts in rodent and human endometrium.

The formation of adducts of benzo(a)pyrene metabolites on DNA was investigated in endometrial tissue from humans, hamsters, mice, and rats. anti-Benzo(a)pyrene-7,8-diol-9,10-epoxide was the predominant adduct identified in all the species studied. The amount of (+)-anti-benzo(a)pyrene-7,8-diol-9,10-epoxide bound to DNA from human endometrium was approximately 3 times higher than to DNA from hamster tissue. Among the three animal species examined, the level of this adduct was highest in hamsters and lowest in rats. The high pressure liquid chromatography profiles of adducts formed in endometrium from humans and hamsters were similar, but the specific activity (pmol/mg DNA) of each adduct formed was different. syn-7,8-Dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene adduct was present in humans, hamsters, and rats but was not detected in mouse endometrium. There was an unidentified adduct present only in rat tissue. Rats had the lowest level of total DNA-bound radioactivity and the largest percentage of this total eluted as an uncharacterized radioactive peak that eluted with water (53%). These results demonstrate that endometrial tissues from humans and three rodent species differ with regard to the quantities and proportions of benzo(a)pyrene-DNA adducts formed from benzo(a)pyrene.

7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide↗
PubMedDate not supplied

Simple luminescence method for estimation of benzo[a]pyrene in a complex mixture of polycyclic aromatic hydrocarbons without a pre-separation procedure.

Benzo[a]pyrene causes cancer at cellular level and is widely present in the environment. Conventional spectroscopic methods for analysis of this compound need a pre-separation procedure due to severe spectral overlap from other polycyclic aromatic hydrocarbons. We report a simple method that avoids spectral overlap of benzo[a]pyrene from other impurities or polycyclic aromatic hydrocarbons (PAHs), thus it can easily identify benzo[a]pyrene in a complex PAH mixture. The method could easily identify benzo[a]pyrene in an 18-component PAH mixture. Calibration plots in methanol solution and in micellar media show a good linearity (R > 0.9997) in the benzo[a]pyrene concentration range generally found in the environment. The method gives a detection limit of 1.52 x 10(-9) mol/L in CTAB micellar medium and 2.55 x 10(-9) mol/L in methanol solution. The proposed method is selective, sensitive and fast. The fluorescence response of benzo[a]pyrene is found to be a potential candidate to sense the critical micellar concentration (CMC) of CTAB micelles.

Algorithms↗
PubMed1999

UV-B-Induced acute toxicity of pyrene to the waterflea Daphnia magna in natural freshwaters.

The effects of various water characteristics in natural freshwaters on the acute toxicity of one polycyclic aromatic hydrocarbon (PAH), pyrene, to a pelagic invertebrate Daphnia magna was studied under ultraviolet B (UV-B) radiation and in the dark. Pyrene was photoactivated and was more toxic to D. magna in the presence of UV-B radiation. Dissolved organic material (DOM), measured as dissolved organic carbon (DOC), significantly reduced the photoenhanced toxicity of pyrene. Under UV-B radiation the EC(50) values were lower and in relation to the amount of DOM, ranging from 3.0 to 30.0 microg/L pyrene, whereas in the dark they were between 29.2 and 54.8 microg/L and not related to the amount of DOM in the waters. Although the condition and mortality of the daphnids in the control groups were not affected by UV-B irradiation, the increased toxicity was considered to be either an additive or a synergistic effect of both the photomodified pyrene and the stressing light conditions of UV-B. The measured binding of pyrene to DOM was low, although it was related to the amount of DOC. Despite the relatively high intensity of UV-B used, humic substances in the waters remained undegraded. It was thus concluded that with their brownish-yellowish color, waters rich in humic substances decreased the photomodification of the freely dissolved parent compound simply by diminishing the light penetration in these waters and, by implication, contact with the intact compound. These results suggest that DOM in surface waters plays an important role in protecting against the photoinduced toxicity of PAHs.

Animals↗
PubMed1983

Pyrene actin: documentation of the validity of a sensitive assay for actin polymerization.

The fluorescence of pyrene-labelled actin is much higher after polymerization. We have characterized in detail the polymerization properties of pyrene actin and report that native and pyrene actin are identical using the following criteria: (1) the time course of polymerization; (2) the elongation rate constants; (3) the intrinsic viscosity; and (4) the critical concentration. Native and pyrene actin copolymerize. Fluorescence of polymerized pyrene actin is 7-10 times higher than monomer. The fluorescent signal is proportional to polymer weight concentration and is insensitive to filament length distribution. Bleaching can be minimized by appropriate filters to allow continuous monitoring of signal. Measurements do not influence polymerization kinetics. This establishes that pyrene actin fluorescence is a valid assay for actin polymerization that is more sensitive than any other current assay.

Actins↗
PubMed1996

Degradation of pyrene by Mycobacterium flavescens.

A strain of Mycobacterium flavescens was isolated from polluted sediments. It was capable of utilizing pyrene as a sole source of carbon and energy. When pyrene was supplied as a suspension at 50 micrograms/ml, the generation time was 9.6 h and the rate of pyrene utilization was 0.56 microgram ml-1 day-1. In addition to pyrene, the strain could mineralize phenanthrene (17.7%) and fluoranthene (17.9%), but failed to mineralize naphthalene, chrysene, anthracene, fluorene, acenaphthene and benzo[a]pyrene, as determined by recovery of radiolabeled CO2 in incubations conducted for 2 weeks under growth conditions. Metabolites produced during growth on pyrene were detected and characterized by HPLC and GC-MS. The product of initial ring oxidation, 4,5-dihydroxy-4,5-dihydropyrene was identified, as well as ring-fission products including 4-phenanthroic acid, phthalic acid, and 4,5-phenanthrenedioic acid.

Biodegradation, Environmental↗
PubMed1999

Optimization of pyrene oxidation by Penicillium janthinellum using response-surface methodology.

At present, there is little information on the optimization of the degradation of polycyclic aromatic hydrocarbons (PAH) by deuteromycete filamentous fungi, a reaction catalyzed by cytochrome P450 monooxygenases. We utilized response-surface methodology to determine the optimal growth conditions for the oxidation of the PAH pyrene by Penicillium janthinellum SFU403, with respect to the variables glucose concentration, nitrate concentration and bioconversion time. Models were derived for the relationship between the variables tested and the level of the pyrene oxidation products. 1-pyrenol (1-PY) and pyrenequinones (PQ). Production of 1-PY and PQ were optimized by the same glucose and nitrate concentrations: 2.5% glucose and 1.5% sodium nitrate. The optimized 1-PY and PQ bioconversion times were 71 h and 73 h respectively. These conditions improved the yield of 1-PY by fivefold and PQ were more than 100-fold higher than the baseline levels obtained in this study. The optimized PQ yield represented 95% of the initial pyrene, thus the total optimised pyrene bioconversion to 1-PY and PQ was approximately 100%. Concentrations of glucose exceeding 4.0% repressed pyrene hydroxylation. Pyrene hydroxylation occurred almost exclusively during the deceleration phase of culture growth.

Biodegradation, Environmental↗
PubMed2001

DNA strand breaks, oxidative damage, and 1-OH pyrene in roofers with coal-tar pitch dust and/or asphalt fume exposure.

OBJECTIVE: To determine the potential for asphalt fume exposure to increase DNA damage, we conducted a cross-sectional study of roofers involved in the application of roofing asphalt. METHODS: DNA strand breaks and the ratio of 8-hydroxydeoxyguanosine (8-OHdG) to 2-deoxyguanosine (dG) were measured in peripheral blood leukocytes of roofers. In addition, urinary excretion of 8-OHdG and 8-epi-prostaglandin F2alpha (8-epi-PGF) was also measured. The study population consisted of 26 roofers exposed to roofing asphalt and 15 construction workers not exposed to asphalt during the past 5 years. A subset of asphalt roofers (n = 19) was exposed to coal-tar pitch dust (coal tar) during removal of existing roofs prior to applying hot asphalt. Personal air monitoring was performed for one work-week to measure exposure to total particulates, benzene-soluble fraction of total particulates, and polycyclic aromatic compounds (PACs). Urinary 1-OH-pyrene levels were measured as an internal biomarker of PAC exposure. RESULTS: Full-shift breathing zone measurements for total particulates, benzene-solubles and PACs were significantly higher for coal-tar exposed workers than for roofers not exposed to coal tar. Similarly, urinary 1-OH-pyrene levels were higher in coal-tar exposed roofers than roofers not exposed to coal tar. Total particulates or benzene-soluble fractions were not associated with urinary 1-OH-pyrene, but PAC exposure was highly correlated with urinary 1-OH-pyrene. When stratified by 1-OH-pyrene excretion, DNA strand breaks increased in a dose-dependent manner, and leukocyte 8-OHdG/dG decreased in a dose-dependent manner. Significant changes in DNA damage appeared to be linked to PACs from coal-tar exposure, although asphalt fume alone was associated with a small but significant increase in urinary 1-OH-pyrene and DNA strand breaks. CONCLUSIONS: Results are consistent with previous reports that asphalt or coal-tar exposure can cause DNA damage. Urinary 8-epi-PGF remained relatively constant during the week for virtually all subjects, regardless of exposure indicating that neither asphalt nor coal-tar exposure induces an overt oxidative stress. A small, but statistically significant increase in 8OHdG was evident in end-of-week urine samples compared with start-of-week urine samples in roofers exposed to coal-tar. The increase in urinary 8OHdG coupled with the decrease in leukocyte 8-OHdG/dG, suggests that coal-tar exposure induces protective or repair mechanisms that result in reduced levels of steady-state oxidative-DNA damage.

8-Hydroxy-2'-Deoxyguanosine↗
PubMed1989

A sensitive and continuous fluorometric assay for phospholipase A2 using pyrene-labeled phospholipids in the presence of serum albumin.

Phospholipase A2 activity can be determined fluorometrically in the presence of serum albumin using phospholipids labeled at the sn-2-acyl position with 10-pyrenyldecanoic acid. In the water reaction medium 10-pyrene phospholipids form vesicles and the monomer fluorescence of the pyrene is negligible due to pyrene-pyrene interaction. Upon phospholipid hydrolysis 10-pyrenyldecanoic acids are produced and tightly bind to albumin so that a monomer pyrene fluorescence is observed. We obtained an excellent parallelism between hydrolysis determined by a classical extraction method and that followed by direct and continuous spectrofluorometric recording of the monomer emission of pyrene. This assay can measure picomole amounts of phospholipids hydrolyzed per minute so that picogram quantities of phospholipases A2 from pancreas or from venoms can be measured. Phospholipase activity remains proportional to enzyme concentration over three orders of magnitude. The method can be used to quantify the phospholipase A2 activity of crude extracts of low specific activity.

Hydrolysis↗
PubMed1979

A method for measuring membrane microviscosity using pyrene excimer formation. Application to human erythrocyte ghosts.

In order to determine the microviscosity of human erythrocyte membrane suspensions, a method has been developed which is based on pyrene excimer formation. First, measurements of partitioning of pyrene into membranes, in conjunction with known values for the volume of the lipid compartment of erythrocyte ghosts are used to determine the concentration of pyrene in the membrane lipid. Secondly, reported measurements of the diffusion constants of aromatic hydrocarbons similar in structure to pyrene, are used to derive an empirical equation relating solvent viscosity and the diffusion constant of pyrene. Then, measurements of pyrene excimer formation in a series of solvents ranging up to several poise in viscosity are used to determine that the interaction diameter of the excimer formation reaction is 3 +/- 1 A. Finally all these data are brought together in order to conclude that the viscosity of the lipid in the human erythrocyte ghost is 8.0, 4.0 and 1.6 P at 10, 25 and 40 degrees C, respectively.

Erythrocyte Membrane↗
PubMed1994

Transfer of pyrene-labelled diacyl-, alkylacyl-, and alkenylacyl-glycerophospholipids from vesicles to human blood platelets.

The present study was aimed at investigating the spontaneous transfer of fluorescently labelled serine- and choline-glycerophospholipids from unilamellar vesicles to resting human blood platelets. The most effectively transferred phospholipids were pyrene-phosphatidylserine (PS) and the ether analogues of choline-glycerophospholipids, e.g., pyrene-alkylacyl- and pyrene-1'-alkenylacyl-glycerophosphocholines (plasmalogens). Transfer of pyrene-diacyl-glycerophosphocholine and pyrene-phosphatidic acid was almost not detectable under the same experimental conditions. The fast intermembrane PS-transfer could be explained by the very high degree of adsorption of PS donor vesicles to the platelet plasma membrane. The short halftime of transfer rate (12-14 min) and the high incorporation (1.08-2.16% of total platelet glycerophosphocholines) observed for ether choline-phospholipids in contrast to pyrene-PS (20 min, 0.8% of total platelet PS), could be interpreted in terms of their bulk membrane properties.

Blood Platelets↗
PubMed1985

Purification and spectroscopic properties of pyrene fatty acids.

Pyrene fatty acids are routinely purified by silica based column chromatography and analyzed on thin-layer silica plates (H.-J. Galla et al., Chem. Phys. Lipids, 23 (1979) 239-251). Although pyrene decanoic acid runs as a single spot on thin-layer chromatography (TLC), gas-liquid chromatography (GC) of the methyl ester derivatives of a representative sample revealed four separate peaks with the major component only 92% of the total. High performance reverse phase liquid chromatography (HPLC) was used to purify pyrene decanoic acid and separate the contaminants. After two passes on a C18 reverse phase HPLC column, pyrene decanoic acid is 99.98% pure by GC analysis. Absorption, fluorescence, and NMR spectra were recorded for pyrene decanoic acid and the major impurities. The results indicate that one impurity is a C10 fatty acid with an altered aromatic moiety. Two other impurities are pyrene derivatives but their acyl chains probably are not decanoic acid.

Chromatography, Gas↗
PubMed1984

The uptake and distribution of [3H]benzo[a]pyrene in the Northern pike (Esox lucius). Examination by whole-body autoradiography and scintillation counting.

The uptake and distribution of the polyaromatic hydrocarbon benzo[a]pyrene in Northern pike (Esox lucius) were investigated by whole body autoradiography and scintillation counting. [3H]Benzo[a]pyrene was administered either in the diet or in the water. The levels of this xenobiotic employed corresponded to levels found in moderately polluted water. The uptake and distribution of this compound and its metabolites were followed from 10 hr to 21 days after the initial exposure. The autoradiography patterns observed here with both routes of administration suggest, as expected, that benzo[a]pyrene is taken up through the gastrointestinal system and the gills, metabolized in the liver, and excreted in the urine and bile. Other findings indicate that the gills may not be a major route of excretion for benzo[a]pyrene and its metabolites in the Northern pike; that benzo[a]pyrene may be taken up from the water directly into the skin of this fish; that benzo[a]pyrene and its metabolites are heterogeneously distributed in the kidney of the Northern pike; and that very little radioactivity accumulates in the adipose tissue. With scintillation counting, uptake of radioactivity from the water was found to occur rapidly in all organs, reaching a plateau in most cases after about 0.8 days. The concentrations of radioactivity in different organs ranged between 50 (many organs) and 80,000 (gallbladder + bile) times that found in the surrounding water. Since most of the radioactivity recovered in different organs of the pike after 8.5 days of exposure was in the form of metabolites, we feel that metabolism may play an important role in the bioconcentration of xenobiotics in fish.

Animals↗
PubMed1992

Pyrene butanol--an efficient, selective and non-metabolized photosensitizing agent for human myeloid leukemia cells.

Methods for ex vivo purging of neoplastic cells from harvested marrow are being developed to increase the efficacy of autologous transplantation. One approach is selective photosensitization, using sensitizing compounds and light radiation. Pyrene-containing fatty acids and lipids are potent photosensitizers, e.g. 12-(1-pyrene)dodecanoic acid (P12), is taken up preferentially by leukemic cells and undergo photoexcitation when exposed to long wave ultra-violet light, resulting in selective killing of leukemic cells. These compounds are incorporated into the neutral- and phospho-lipids of the cells. The presence of intracellular pyrene-linked lipids might present a potential hazard in applying these agents for clinical use. We have, therefore, studied a series of other pyrene-linked compounds with the objective of finding a non-metabolizable photosensitizing agent that can be easily removed from the cells. In the present paper we report the results with pyrene butanol (P4-OH), a pyrene linked short-chain alcohol. When compared to P12, P4-OH was found to be taken up by cells most rapidly and reached saturation within minutes. It did not undergo any metabolism and washing the cells with serum-containing salt solutions removed practically all the P4-OH. This compound was found to be an efficient photosensitizer (in terms of concentrations and time of incubation with the cells) and selective to leukemic cells--it caused a 99% reduction in leukemic clonogenic cells under conditions that normal hemopoietic progenitors remained almost intact. These properties make P4-OH a potential photosensitizer for clinical application.

Acute Disease↗
PubMed1980

Fluorescence decay kinetics of pyrene in membrane vesicles.

The fluorescence decay kinetics of pyrene incorporated into artificial and natural membrane vesicles has been studied by pulse fluorimetry. The emission of monomeric pyrene and its excimer embedded in sonicated liposomes prepared from dipalmitoylphosphatidylcholine and a mixture of this phospholipid and dipalmitoylphosphatidylserine follows a multiple exponential decay law at temperatures both below and above their thermal transitions (10--48 degrees C). When pyrene is incorporated into fragmented skeletal sarcoplasmic reticulum vesicles, the emission decay exhibits similar multiple exponential character. The decay of the monomer in the phospholipid vesicles can be adequately described by three exponential terms. The experimental decays observed with both types of vesicles deviate significantly from a previously proposed model in which departure of the decay of pyrene monomer from monoexponentiality is qualitatively related to a time dependence in the diffuslipid vesicles can be adequately described by three exponential terms. The experimental decays observed with both types of vesicles deviate significantly from a previously proposed model in which departure of the decay of pyrene monomer from monoexponentiality is qualitatively related to a time dependence in the diffuslipid vesicles can be adequately described by three exponential terms. The experimental decays observed with both types of vesicles deviate significantly from a previously proposed model in which departure of the decay of pyrene monomer from monoexponentiality is qualitatively related to a time dependence in the diffusion-controlled formation of excimers from ground state and excited monomers. It is suggested that the observed decays are compatible with a reaction scheme involving excited state interaction.

Animals↗
PubMed2005

Transcriptome responses to carbon tetrachloride and pyrene in the kidney and liver of juvenile rainbow trout (Oncorhynchus mykiss).

We report the effects of the hepatotoxic compound carbon tetrachloride (CCl(4)) and pyrene, a model polycyclic aromatic hydrocarbon, on the transcriptomes of juvenile rainbow trout kidneys and livers. Fish were exposed to sublethal doses for 4 days and expression of 1273 genes was measured using a cDNA microarray. Efforts were focused on differentiating between unspecific responses and those that can be regarded as molecular signatures of CCl(4) and pyrene toxicities. Expression profiles were analyzed in terms of Gene Ontology categories. Universal reactions to chemical toxicity were observed in metallothionein, HSP90 and mitochondrial proteins of oxidative phosphorylation, which were induced in both tissues. Several genes showed similar responses to both compounds in either kidney or liver; most of the effects are implicated in hematopoiesis and immune response. Stimulation of mitochondrial and heat shock proteins was greater in the liver than in the kidney, whereas genes involved in transcription, humoral immune response and apoptosis were suppressed. Pyrene and CCl(4) caused opposite effects on expression of several genes, including HSP-27, macrophage receptor Marco, metalloproteinases (MMP9 and MMP13), and delta-6 fatty acid desaturase. Pyrene affected mainly genes implicated in the maintenance of the genetic apparatus, immune response, glycolysis, and iron homeostasis. CCl(4) affected the structural proteins and genes involved in cellular stress, protein folding, and steroid metabolism. Overall, pyrene suppressed a range of protective or acclimative reactions, many of which were stimulated with CCl(4). Additionally, gene profiling analyses indicated adaptive and potentially maladaptive reactions to toxicity. For instance, stimulation of mitochondrial proteins coincided with suppression of catalase, whereas CCl(4) down-regulated fatty acid metabolism and peroxisomal proteins. A number of candidate biomarkers for ecotoxicological risk assessment were identified as our understanding of mechanisms of pyrene and CCl(4) toxicities in rainbow trout increased.

Animals↗
PubMed2004

Polyethylene glycol-polyamidoamine dendritic micelle as solubility enhancer and the effect of the length of polyethylene glycol arms on the solubility of pyrene in water.

Unimolecular dendritic micelles designed as solubility enhancers were obtained by coupling polyethylene glycol (PEG) to Starburst polyamidoamine (PAMAM) dendrimers. Micelles-750, -2000, and -5000 have a generation 3.0 dendrimer core (32 primary amine end groups) and PEG arms with molecular weights of 750, 2000, and 5000, respectively. The conjugate of dendrimer core and PEG was characterized by MALDI-TOF MS and 1H NMR. 1H NMR was also used to estimate the average number of PEG arms on each dendrimer molecule. A typical hydrophobic compound, pyrene, was sonicated in an excess amount together with micelles at 50 degrees C for 6 h to produce its saturated water solution. The change of the solubility of pyrene was monitored at 334 nm, its maximum adsorption wavelength, by UV-VIS spectra. Concentrated micelles tended to dissolve more pyrene. However, there is no obvious linear relationship between micelle type and the amount of pyrene entrapped within micelles. Micelle-2000 could solubilize more pyrene than micelle-750. It is hypothesized that micelle-5000 did not solubilize more pyrene than micelle-2000 because of the PEG shell disruption by adjacent interpenetration of individual micelles when PEG arm length increased.

Dendrites↗
PubMed2006

Microbial bioavailability of pyrene in three laboratory-contaminated soils under aerobic and anaerobic conditions.

Changes in bioavailability of pyrene in three uncontaminated soils were examined under aerobic and anaerobic conditions. Three soils were aerobically aged with pyrene and [(14)C]pyrene for 63 days, then incubated with water, nitrate, or sulfate under aerobic or anaerobic conditions for one year. Under aerobic conditions, microorganisms in two soils mineralized 58-82% of the added [(14)C]pyrene. The two soils amended with nitrate were seen to have enhanced aerobic mineralization rates. In one of these soils, non-extractable pyrene was seen to decrease over the course of the study due to desorption and mineralization, nitrate amendment enhanced this effect. Under anaerobic conditions, generated with a N(2):CO(2)(g) headspace, two soils with nitrate or sulfate amendment showed an increase in extractable [(14)C]pyrene at 365 days relative to inhibited controls, presumably due to microbially mediated oxidation-reduction potential and pH alteration of the soil environment. These observations in different soils incubated under aerobic and anaerobic conditions have important implications relative to the impact of microbial electron acceptors on bioavailability and transport of non-polar organic compounds in the environment suggesting that, given enough time, under the appropriate environmental conditions, non-extractable material becomes bioavailable. This information should be considered when assessing site specific exposure risks at PAH contaminated locations.

Aerobiosis↗
PubMed2004

Differential gene expression in mummichogs (Fundulus heteroclitus) following treatment with pyrene: comparison to a creosote contaminated site.

Mummichogs, Fundulus heteroclitus, an estuarine fish with a relatively small home range found along the eastern coast of the United States are well-suited to monitoring contaminant effects, including those of polycyclic aromatic hydrocarbons (PAHs). One of the common PAHs in estuaries is pyrene. We report here on efforts to develop multiple biomarkers of pyrene exposure in this species. Adult male mummichogs were exposed in the laboratory to the weak aryl hydrocarbon receptor (AhR) agonist pyrene at 0, 30, or 50 microg/L in 7-day static renewal exposures. The RNA was extracted from livers and alterations in mRNA expression were assessed by subtractive hybridization and differential display in order to produce multiple biomarkers of pyrene exposure. Genes demonstrating differential expression were confirmed by quantitative-PCR (Q-PCR) and include cytochrome P-450 1A (CYP1A), a putative hepatocyte growth factor activator, a X-ray inducible retrotransposon, and several expressed sequenced tags (ESTs). Some of these genes represent new biomarkers of pyrene exposure and potential biomarkers of PAH exposure. Therefore, similar changes were investigated at a Superfund site in Charleston, SC. Mummichogs from a creosote contaminated site and from a reference site (North Inlet National Estuarine Research Reserve near Georgetown, SC) were trapped, RNA extracted from the livers, and Q-PCR performed. Many of the genes differentially expressed following pyrene exposure were not altered at the creosote contaminated site in comparison to the reference site. However, CYP1A and an EST were induced. CYP1A induction at Diesel Creek indicates that this population of fish does not demonstrate refractory CYP1A phenotypes observed at several sites with high levels of AhR agonists. Ultimately, we anticipate that the use of multiple biomarkers of PAH exposure will provide useful information on the potential effects of toxicants.

Amino Acid Sequence↗