Tag: M.W=400-450

Mazur, Christopher S. published the artcileHuman and Rat ABC Transporter Efflux of Bisphenol A and Bisphenol A Glucuronide: Interspecies Comparison and Implications for Pharmacokinetic Assessment, Product Details of C21H24O8, the publication is Toxicological Sciences (2012), 128(2), 317-325, database is CAplus and MEDLINE.

Significant interspecies differences exist between human and rodent with respect to absorption, distribution, and excretion of bisphenol A (BPA) and its primary metabolite, BPA-glucuronide (BPA-G). ATP-Binding Cassette (ABC) transporter enzymes play important roles in these physiol. processes, and their enzyme localization (apical vs. basolateral) in the plasma membrane allows for different cellular efflux pathways. In this study, we utilized an ATPase assay to evaluate BPA and BPA-G as potential substrates for the human and rat ABC transporters: P-glycoprotein (MDR1), multidrug resistance-associated proteins (MRPs), and breast cancer-resistant protein (BCRP). Based on high ATPase activity, BPA is likely a substrate for rat mdr1b but not for human MDR1 or rat mdr1a. Results indicate that BPA is a potential substrate for rat mrp2 and human MRP2, BCRP, and MRP3. The metabolite BPA-G demonstrated the highest apparent substrate binding affinity for rat mrp2 and human MRP3 but appeared to be a nonsubstrate or potential inhibitor for human MRP2, MDR1, and BCRP and for rat mdr1a, mdr1b, and bcrp. Anal. of ABC transporter amino acid sequences revealed key differences in putative binding site composition that may explain substrate specificity. Collectively, these results suggest that in both rat and human, apical transporters efflux BPA into the bile and/or intestinal lumen. BPA-G would follow a similar pathway in rat; however, in human, due to the basolateral location of MRP3, BPA-G would likely enter systemic and portal blood supplies. These differences between human and rodent ABC transporters may have significant implications for interspecies extrapolation used in risk assessment.

Toxicological Sciences published new progress about 267244-08-6. 267244-08-6 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Chiral,Carboxylic acid,Benzene,Phenol,Alcohol,Ether,, name is (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, and the molecular formula is C21H24O8, Product Details of C21H24O8.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Li, Zhenming published the artcileFirst report on occurrence of bisphenol A isomers in human serum and whole blood, Synthetic Route of 267244-08-6, the publication is Journal of Hazardous Materials (2022), 424(Part_C), 127549, database is CAplus and MEDLINE.

Studies have demonstrated the worldwide presence of bisphenol A (BPA) and its toxic effects on human health. BPA may exist as several structural isomers, which are byproducts in industrial BPA production However, nearly nothing is known about the occurrence of BPA isomers in human blood and the partitioning of BPA metabolites between human serum and whole blood. In this study, BPA, BPA-sulfate (BPA-S), and BPA-glucuronide (BPA-G) were quantified in 144 pairs of serum and whole blood samples from Chinese participants. BPA was detected in 115 serum and 121 whole blood samples, with mean concentrations of 0.53 and 0.88 ng/mL, resp. A structural isomer of BPA, tentatively termed B1-BPA, was identified for the first time, and measurable in 53% and 57% of serum (<LOD-1.9 ng/mL) and whole blood (<LOD-1.4 ng/mL) samples, resp. BPA-S was the predominant BPA metabolite (mean 2.3 and 1.4 ng/mL, resp.), significantly higher (p < 0.01) than BPA-G (1.3 and 0.64 ng/mL) in both serum and whole blood. The calculated partitioning coefficients between serum and whole blood were the highest for B1-BPA (mean ± SD, 1.8 ± 0.25), followed by BPA-S (1.6 ± 0.36), BPA-G (1.4 ± 0.37), and BPA (1.3 ± 0.39), indicating their preferential enrichment in the serum fraction. Overall, this study first identifies a BPA isomer, which has not been previously reported in any environmental or human samples. Measuring BPA isomers in human serum and whole blood is critical for accurate human BPA exposure risk assessment.

Journal of Hazardous Materials published new progress about 267244-08-6. 267244-08-6 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Chiral,Carboxylic acid,Benzene,Phenol,Alcohol,Ether,, name is (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, and the molecular formula is C21H24O8, Synthetic Route of 267244-08-6.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Elsby, Robert published the artcileComparison of the modulatory effects of human and rat liver microsomal metabolism on the estrogenicity of bisphenol A: implications for extrapolation to humans, Category: tetrahydropyran, the publication is Journal of Pharmacology and Experimental Therapeutics (2001), 297(1), 103-113, database is CAplus and MEDLINE.

Bisphenol A [BPA, 2,2-bis(4-hydroxyphenyl)propane], a xenoestrogen, is a monomer for the synthesis of polycarbonate plastics, epoxy resins, and composites. Metabolism of BPA to the monoglucuronide will determine the extent of its estrogenicity in vivo. Investigation of the metabolism of BPA (500 μM) by isolated female rat hepatocytes confirmed the formation of BPA glucuronide as the major metabolite. There was a significant difference (p < 0.05) between the V_max (mean ± S.E.M., n = 4) of glucuronidation by pooled male or female human (four livers in each case) and immature female rat liver microsomes (5.9±0.4, 5.2±0.3, and 31.6±8.1 nmol/min/mg of protein, resp.). Estrogenic activity of BPA, assessed in a coupled microsomal metabolism-yeast estrogenicity assay, was decreased 3- and 7-fold following glucuronidation by human female and immature female rat liver microsomes, resp. Incubations of BPA with pooled human or rat liver microsomes, in the presence of NADPH, resulted in the formation of 5-hydroxybisphenol A [2-(4,5-dihydroxyphenyl)-2-(4-hydroxyphenyl)propane], which was 10-fold less potent than BPA in the yeast estrogenicity assay. However, there was insufficient turnover to achieve a significant effect on the estrogenic activity of BPA. Because human liver microsomes did not glucuronidate BPA as extensively as the rat liver microsomes, estrogen target tissues in humans may be subject to greater exposure to BPA than the tissues of the immature female rats used for assessing estrogenicity of xenobiotics.

Journal of Pharmacology and Experimental Therapeutics published new progress about 267244-08-6. 267244-08-6 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Chiral,Carboxylic acid,Benzene,Phenol,Alcohol,Ether,, name is (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, and the molecular formula is C21H24O8, Category: tetrahydropyran.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Huang, Qiansheng published the artcileNew insights into the metabolism and toxicity of bisphenol A on marine fish under long-term exposure, Quality Control of 267244-08-6, the publication is Environmental Pollution (Oxford, United Kingdom) (2018), 242(Part_A), 914-921, database is CAplus and MEDLINE.

Bisphenol A (BPA) exposure receives great ecotoxicol. concern. However, gaps in knowledge, such as metabolism of BPA and inconsistent reports on reproductive toxicity, still exist. In this study, a marine fish model (Oryzias melastigma) was exposed to serial concentrations of BPA throughout its whole life cycle. The level of BPA-glucuronide (BPAG) dramatically increased throughout the embryonic stage since 4 dpf. Accordingly, the mRNA level and enzymic activity of UDP-glucuronosyltransferases (UGTs) increased across the embryonic stage. The mRNA level of UGT2 subtype rather than UGT1 or UGT5 showed a concentration dependent response to BPA exposure. BPA exposure led to the morphol. disruption of the chorion and villi as shown by SEM; however, the hatchability was not significantly influenced after exposure. Newly hatching larvae were continuously exposed to BPA for 120 days. Lower mRNA levels of hormone metabolism-related genes, decreased ratio of E2/T, slower ovary development and decreased egg production confirmed the inhibitory effect of BPA on reproduction Overall, our results showed the conjugation of BPA into BPAG by UGT2 at the embryonic stage and convinced the reproductive toxicity from multiple levels after whole life exposure to BPA.

Environmental Pollution (Oxford, United Kingdom) published new progress about 267244-08-6. 267244-08-6 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Chiral,Carboxylic acid,Benzene,Phenol,Alcohol,Ether,, name is (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, and the molecular formula is C21H24O8, Quality Control of 267244-08-6.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Peng, Bo published the artcileCompetitive Biotransformation Among Phenolic Xenobiotic Mixtures: Underestimated Risks for Toxicity Assessment, Safety of (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, the publication is Environmental Science & Technology (2019), 53(20), 12081-12090, database is CAplus and MEDLINE.

Humans are inevitably exposed to a complex mixture of organic contaminants (i.e., xenobiotics) through diet, environment, and behavior. Biotransformation makes key contributions to the elimination of xenobiotics and greatly mediates the toxicity. However, most biotransformation studies were conducted using individual chem., and whether coexposure of multiple environmental chems. will affect each other’s fate in the human body is still in its infancy. In this study, bisphenol A (BPA) was selected as a model compound Its biotransformation was investigated under single exposure/coexposure to other phenolic xenobiotics (triclosan, tetrabromobisphenol A, and bisphenol S) in liver microsome and cell models. The result shows that binary exposures exhibit significant inhibitory effects on the BPA metabolism, especially the sulfate conjugation. In combination of anal. on inhibition models and enzyme activity, the inhibition effect was suggested to be primarily driven by competition for metabolizing enzymes. A mixture with 22 phenolic chems. was further examined to disrupt BPA at various human-relevant levels. Again, the result demonstrates significant inhibition on the BPA metabolism, indicating the possible natural existence of our finding. Overall, our results show that biotransformation of phenolic xenobiotics can be significantly altered by coexposure, which provides referential evidence on underestimated risks of simultaneous exposure to environmental toxicants.

Environmental Science & Technology published new progress about 267244-08-6. 267244-08-6 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Chiral,Carboxylic acid,Benzene,Phenol,Alcohol,Ether,, name is (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, and the molecular formula is C21H24O8, Safety of (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Liu, Jiaying published the artcileBisphenol A Metabolites and Bisphenol S in Paired Maternal and Cord Serum, Computed Properties of 267244-08-6, the publication is Environmental Science & Technology (2017), 51(4), 2456-2463, database is CAplus and MEDLINE.

Human studies show associations between maternal bisphenol A (BPA) exposure and developmental effects in children, yet biomonitoring of BPA metabolites in maternal and fetal serum remains limited, and less is known for BPA alternatives. BPA-glucuronide, BPA-sulfate and bisphenol S (BPS) were quantified in 61 pairs of maternal and cord sera from Chinese participants. Total BPS was only detectable in 4 maternal (<0.03-0.07 ng/mL) and 7 cord sera (<0.03-0.12 ng/mL), indicating low exposure but providing the first evidence that BPS crosses the human placenta. Total BPA metabolites in cord serum were significantly higher than in maternal serum, suggesting that these may be formed in the fetus or cleared more slowly from the fetoplacental compartment. Unlike the pharmacokinetic results from controlled oral exposure studies where BPA-glucuronide is the major BPA metabolite, here BPA-sulfate was the dominant metabolite (GM: 0.06 ng/mL, 0.08 ng/mL), significantly higher than BPA-glucuronide (GM: 0.02 ng/mL, 0.04 ng/mL) in both maternal and cord sera. Moreover, the proportion of BPA-sulfate increased with total BPA. These are the first human data for BPA metabolites in paired maternal and cord serum, and results suggest that the human fetus, and pregnant mother, have a unique exposure to BPA metabolites. Direct anal. of BPA metabolites in serum provides complementary information for evaluating early life-stage exposure and risks of BPA.

Environmental Science & Technology published new progress about 267244-08-6. 267244-08-6 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Chiral,Carboxylic acid,Benzene,Phenol,Alcohol,Ether,, name is (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, and the molecular formula is C21H24O8, Computed Properties of 267244-08-6.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

David, Arthur published the artcileDisruption of the Prostaglandin Metabolome and Characterization of the Pharmaceutical Exposome in Fish Exposed to Wastewater Treatment Works Effluent As Revealed by Nanoflow-Nanospray Mass Spectrometry-Based Metabolomics, Safety of (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, the publication is Environmental Science & Technology (2017), 51(1), 616-624, database is CAplus and MEDLINE.

Fish can be exposed to a complex mixture of chem. contaminants, including pharmaceuticals, present in discharges of wastewater treatment works (WwTWs) effluents. There is little information on the effects of effluent exposure on fish metabolism, especially the small mol. signaling compounds which are the biol. target of many pharmaceuticals. The authors applied a newly developed sensitive nanoflow-nanospray mass spectrometry nontargeted profiling technique to identify changes in the exposome and metabolome of roach (Rutilus rutilus) exposed to a final WwTWs effluent for 15 days. Effluent exposure resulted in widespread reduction (between 50% and 90%) in prostaglandin (PG) profiles in fish tissues and plasma with disruptions also in tryptophan/serotonin, bile acid and lipid metabolism Metabolite disruptions were not explained by altered expression of genes associated with the PG or tryptophan metabolism Of the 31 pharmaceutical metabolites that were detected in the effluent exposome of fish, 6 were nonsteroidal anti-inflammatory drugs but with plasma concentrations too low to disrupt PG biosynthesis. PGs, bile acids, and tryptophan metabolites are important mediators regulating a diverse array of physiol. systems in fish and the identity of wastewater contaminants disrupting their metabolism warrants further investigation on their exposure effects on fish health.

Environmental Science & Technology published new progress about 267244-08-6. 267244-08-6 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Chiral,Carboxylic acid,Benzene,Phenol,Alcohol,Ether,, name is (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, and the molecular formula is C21H24O8, Safety of (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Pritchett, J. J. published the artcileMetabolism of bisphenol A in primary cultured hepatocytes from mice, rats, and humans, Application of (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, the publication is Drug Metabolism and Disposition (2002), 30(11), 1180-1185, database is CAplus and MEDLINE.

Studies have shown that in the rat, bisphenol A (BPA) is metabolized and eliminated primarily as a monoglucuronide, a metabolite without estrogenic activity. The purpose of this study was to determine the extent of monoglucuronide formation in monolayers of hepatocytes from rats, mice, and humans. Noncytotoxic concentrations of BPA (10, 20, and 35 μM; 1.0 μCi), as assessed by lactate dehydrogenase leakage, were incubated with isolated hepatocytes for 0-6 h. Media were collected and analyzed for metabolites by radiochem. high performance liquid chromatog. and liquid chromatog.-tandem mass spectrometry. The metabolites identified include a monoglucuronide (major metabolite), a sulfate conjugate, and a glucuronide/sulfate diconjugate (minor metabolites). In hepatocytes of male Fischer-344 rats, the predominate metabolite was the diconjugate (glucuronide/sulfate). Under these conditions, the extent of metabolism by 3 h was similar in all species tested because all BPA was converted to conjugates by 3 h. Initial rates of metabolism in hepatocytes followed the order of mice > rats > humans. However, when extrapolated to the whole liver (i.e., cells per liver), the hepatic capacity for BPA glucuronidation is predicted to be humans > rats > mice.

Drug Metabolism and Disposition published new progress about 267244-08-6. 267244-08-6 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Chiral,Carboxylic acid,Benzene,Phenol,Alcohol,Ether,, name is (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, and the molecular formula is C21H24O8, Application of (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Kim, Yong-Hak published the artcileGender differences in the levels of bisphenol A metabolites in urine, Formula: C21H24O8, the publication is Biochemical and Biophysical Research Communications (2003), 312(2), 441-448, database is CAplus and MEDLINE.

The metabolism of bisphenol A (BPA), a suspected endocrine disruptor, should be considered for monitoring human exposure to BPA, because the conjugation with β-D-glucuronide and sulfate reduces the estrogenic activity. In this study, BPA levels in 30 healthy Koreans (men, N=15, 42.6±2.4 yr; women, N=15, 43.0±2.7 yr) were analyzed from urine treated with/without β-glucuronidase and/or sulfatase by an RP-HPLC with fluorescence detection. The total BPA concentrations including free BPA and the urinary conjugates were similar in men and women (2.82±0.73 and 2.76±0.54 ng ml^-1, resp.), but gender differences were found in the levels of urinary BPA conjugates. Men had significantly higher levels of BPA-glucuronide (2.34±0.85 ng ml^-1) than women (1.00±0.34 ng ml^-1), whereas women had higher levels of BPA-sulfate (1.20±0.32 ng ml^-1) than men (0.49±0.27 ng ml^-1).

Biochemical and Biophysical Research Communications published new progress about 267244-08-6. 267244-08-6 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Chiral,Carboxylic acid,Benzene,Phenol,Alcohol,Ether,, name is (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, and the molecular formula is C21H24O8, Formula: C21H24O8.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Veiga-Lopez, Almudena published the artcileGender-specific effects on gestational length and birth weight by early pregnancy BPA exposure, Synthetic Route of 267244-08-6, the publication is Journal of Clinical Endocrinology and Metabolism (2015), 100(11), E1394-E1403, database is CAplus and MEDLINE.

Context and Objective: Effects of prenatal exposure to bisphenol A (BPA) on gestational and birth outcomes are controversial. The aim of the study was to evaluate the relationship between prenatal exposure to BPA and birth and gestational outcomes. Design, Setting, Participants, and Outcome: Levels of unconjugated (uBPA) and BPA glucuronide in 80 matching samples of pregnant women during the first trimester of pregnancy and at delivery and matching term cord blood obtained from a prospective study conducted at the University of Michigan Hospitals were determined using a methodol. validated in the National Institutes of Environmental Health Sciences funded Round Robin study and related to pregnancy outcomes. Results: Highest levels of uBPA were found in maternal term samples followed by first trimester maternal (M1) samples and cord blood. A 2-fold increase in M1 uBPA was associated with 55-g less birth weight when male and female pregnancies were combined and 183-g less birth weight with only female pregnancies. A 2-fold increase in maternal term uBPA was associated with an increased gestational length of 0.7 days for all pregnancies and 1.1 days for only female pregnancies. Conclusion: Higher uBPA exposure levels during first trimester and term are associated with sex-specific reduction in birth weight and increase in gestational length, resp. Race, parity, and employment have an effect on BPA exposure. Because low birth weight is associated with adverse health outcomes, effect of early pregnancy BPA levels on reducing birth weight highlights the risk posed by developmental exposure to BPA.

Journal of Clinical Endocrinology and Metabolism published new progress about 267244-08-6. 267244-08-6 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Chiral,Carboxylic acid,Benzene,Phenol,Alcohol,Ether,, name is (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, and the molecular formula is C10H9IO4, Synthetic Route of 267244-08-6.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics