Bisphenol A causes reproductive toxicity, decreases dnmt1 transcription, and reduces global DNA methylation in breeding zebrafish (Danio rerio).

Bisphenol A (BPA) is a commercially important high production chemical widely used in epoxy resins and polycarbonate plastics, and is ubiquitous in the environment. Previous studies demonstrated that BPA activates estrogenic signaling pathways associated with adverse effects on reproduction in vertebrates and that exposure can induce epigenetic changes. We aimed to investigate the reproductive effects of BPA in a fish model and to document its mechanisms of toxicity. We exposed breeding groups of zebrafish (Danio rerio) to 0.01, 0.1, and 1 mg/L BPA for 15 d. We observed a significant increase in egg production, together with a reduced rate of fertilization in fish exposed to 1 mg/L BPA, associated with significant alterations in the transcription of genes involved in reproductive function and epigenetic processes in both liver and gonad tissue at concentrations representing hotspots of environmental contamination (0.1 mg/L) and above. Of note, we observed reduced expression of DNA methyltransferase 1 (dnmt1) at environmentally relevant concentrations of BPA, along with a significant reduction in global DNA methylation, in testes and ovaries following exposure to 1 mg/L BPA. Our findings demonstrate that BPA disrupts reproductive processes in zebrafish, likely via estrogenic mechanisms, and that environmentally relevant concentrations of BPA are associated with altered transcription of key enzymes involved in DNA methylation maintenance. These findings provide evidence of the mechanisms of action of BPA in a model vertebrate and advocate for its reduction in the environment.

Effect of Molecular Weight on Spectroscopic and Spectroelectrochemical Properties of Regioregular Poly(3-hexylthiophene).

Using experimentally established sequence of extractions, we were able to fractionate regioregular poly(3-hexylthiophene) (R-P3HT) into four fractions differing significantly in their molecular weight (Mn) and exhibiting low polydispersity coefficients. 1H NMR analysis of low molecular fractions enabled us to propose the dominant chain termination mechanisms and identify the sources of regioregularity defects. In particular, it turned out that the presence of small amounts of undesired isomer of 2-bromo-3-hexylthiophene, namely, 2-bromo-4-hexylthiophene, strongly influences the molecular weight and to a much lesser extent the regioregularity of the polymer obtained via Grignard type polycondensation. In the reaction with the growing chain, 2-bromo-4-hexylthiophene either causes its termination, lowering in this manner the molecular weight of the resulting polymer, or introduces regioregularity defects of TT-HH (TT = tail to tail; HH = head to head) type. The average conjugation length in R-P3HT increases with the increase of Mn as manifested by a bathochromic shift of the lambdamax and the appearance of the vibrational structure in the UV-vis-near-IR spectra of the fractions of higher molecular weight. This conclusion is supported by FTIR data. The onset of the oxidative doping of R-P3HT shifts to lower potentials with the increase of the molecular weight as evidenced by cyclic voltammetry and UV-vis-near-IR spectroelectrochemistry.