Search results for "Pyrene"
showing 10 items of 260 documents
Synthesis and Characterization of Adducts Derived from the syn-Diastereomer of Benzo[a]pyrene 7,8-Dihydrodiol 9,10-Epoxide and the 5‘-d(CCTATAGATATCC…
1996
5'-d(CCTATAGATATCC) was reacted with each syn-enantiomer of trans-7,8-dihydroxy 9,10-epoxy 7,8,9,10-tetrahydrobenzo[a]pyrene (syn-BPDE). The (-)-enantiomer yielded one dominating adduct, whereas the (+)-enantiomer resulted in two major adducts. As indicated by optical spectroscopic methods, the major adduct derived from both (-)- and (+)-syn-BPDE involves cis addition of the C-10 position of the diol epoxide to the exocyclic amino group of deoxyguanosine [(-)-syn-BPDEc-N2-dG and (+)-syn-BPDEc-N2-dG, respectively], whereas the minor (+)-syn-BPDE adduct is identical to a trans adduct [(+)-syn-BPDEt-N2-dG]. The cis adducts as well as the (+)-syn-BPDEt-N2-dG adduct are chemically stable for sev…
Critical parameters for adduct formation of the carcinogen (+)-anti-benzo[a]pyrene-7,8-dihydrodiol 9,10-epoxide with oligonucleotides.
1997
Various parameters relevant for the formation of dG adducts produced in the reaction of individual benzo[a]pyrene diol epoxide (BPDE) stereoisomers with oligonucleotides have been studied. Reaction time, temperature, pH, molar ratio of diol epoxide and oligonucleotide, base sequence, and buffer system were shown to affect the amount of (+)-anti-BPDE dG adducts formed. Optimum experimental conditions for dG adduct formation were different depending on the base sequence context of the oligonucleotide employed [5'-d(CCTATAGATATCC) or 5'-d(CCTATTGCTATCC)]. In general, low temperature to allow a longer reaction time, slightly alkaline Tris-HCl (pH 7.5-8.0) or alkaline phosphate buffer (pH 11), l…
Epoxide Hydratase: Purification to Apparent Homogeneity as a Specific Probe for the Relative Importance of Epoxides among Other Reactive Metabolites
1977
Aromatic and olefinic compounds can be metabolized by microsomal monooxygenases to epoxides which chemically represent electrophilic species (for reviews, see refs. 1–5). Spontaneous binding of such epoxides to DNA, RNA, and protein has been observed (6–10). Accordingly, such metabolites have been suggested and, in some instances, shown to disturb the normal functions of cells, leading to such effects as mutagenesis (11–14), malignant transformation (15–19), or cell necrosis (20). However, aromatic and olefinic compounds are biotransformed to a vast array of metabolites (cf. refs. 21–27), possibly including a considerable number of reactive metabolites other than epoxides. The relative impo…
Metabolic activation of dibenzo[a,l]pyrene by human cytochrome P450 1A1 and P450 1B1 expressed in V79 Chinese hamster cells.
1999
Metabolic activation of the strongly carcinogenic polycyclic aromatic hydrocarbon (PAH) dibenzo[a,l]pyrene (DB[a,l]P) and its trans-8,9-dihydrodiol (trans-8,9-diol) catalyzed by human cytochromes P450 (P450) 1A1 and 1B1 was investigated. DNA binding of DB[a,l]P in mammalian cell lines has previously been shown to be preferentially mediated by fjord region DB[a,l]P-11,12-dihydrodiol 13,14-epoxides (DB[a,l]PDE). In order to elucidate different capabilities of both P450 enzymes for metabolic activation of DB[a, l]P V79 Chinese hamster cells, stably expressing human P450s 1A1 or 1B1 have been exposed to the parent PAH or its racemic trans-8, 9-diol. For this purpose, synthesis and spectroscopic…
Structure elucidation of the adducts formed by fjord region Dibenzo[a,l]pyrene-11,12-dihydrodiol 13,14-epoxides with deoxyguanosine.
1999
Model adducts to be used in the identification of biologically formed adducts were synthesized by reaction of fjord-region dibenzo[a,l]pyrene 11,12-dihydrodiol 13,14-epoxides (DB[a,l]PDE) and deoxyadenosine (dA). The (+/-)-anti-DB[a,l]PDE was reacted with dA in dimethylformamide at 100 degrees C for 30 min to give four DB[a, l]PDE-14-N(6)dA adducts: (-)-anti-trans (26%), (+)-anti-trans (26%), (-)-anti-cis (17%), and (+)-anti-cis (17%). The (+/-)-syn-DB[a,l]PDE was reacted with dA under the same conditions to yield four DB[a, l]PDE-14-N(6)dA adducts and one N7Ade adduct: (+)-syn-cis (19%), (+)-syn-trans (13%), (-)-syn-cis (19%), (-)-syn-trans (13%), and (+/-)-syn-DB[a,l]PDE-14-N7Ade (22%). T…
Sulfotransferase-mediated mutagenicity of 1-hydroxymethylpyrene and 4H-cyclopenta[def]chrysen-4-ol and its enhancement by chloride anions.
1993
1-Hydroxymethylpyrene (HMP), a primary benzylic alcohol, and 4H-cyclopenta[def]chrysen-4-ol (OH-CPC), a secondary benzylic alcohol, were investigated for mutagenicity in Salmonella typhimurium (reversion of the his- strain TA98) in the presence of various xenobiotic-metabolizing systems. In the direct test, HMP was inactive and OH-CPC was very weakly active. In the presence of NADPH-fortified postmitochondrial fraction from rat liver (S9/NADPH), no activation of OH-CPC was observed, whereas strong mutagenic effects were elicited by HMP. In the presence of cytosol and 3'-phosphoadenosine-5'-phosphosulfate (PAPS), both alcohols were activated to potent mutagens. For equal mutagenic effects, a…
DFT/TD-DFT Framework of Mixed-Metal Complexes with Symmetrical and Unsymmetrical Bridging Ligands—Step-By-Step Investigations: Mononuclear, Dinuclear…
2021
Recently, mono- and dinuclear complexes have been in the interest of scientists due to their potential application in optoelectronics. Herein, progressive theoretical investigations starting from mononuclear followed by homo- and heterometallic dinuclear osmium and/or ruthenium complexes with NCN-cyclometalating bridging ligands substituted by one or two kinds of heteroaryl groups (pyrazol-1-yl and 4-(2,2-dimethylpropyloxy)pyrid-2-yl) providing the short/long axial symmetry or asymmetry are presented. Step-by-step information about the particular part that built the mixed-metal complexes is crucial to understanding their behavior and checking the necessity of their eventual studies. Evaluat…
Synthesis of Nonplanar Graphene Nanoribbon with Fjord Edges
2021
As a new family of semiconductors, graphene nanoribbons (GNRs), nanometer-wide strips of graphene, have appeared as promising candidates for next-generation nanoelectronics. Out-of-plane deformation of π-frames in GNRs brings further opportunities for optical and electronic property tuning. Here we demonstrate a novel fjord-edged GNR (FGNR) with a nonplanar geometry obtained by regioselective cyclodehydrogenation. Triphenanthro-fused teropyrene 1 and pentaphenanthro-fused quateropyrene 2 were synthesized as model compounds, and single-crystal X-ray analysis revealed their helically twisted conformations arising from the [5]helicene substructures. The structures and photophysical properties …
Ecocompatible Halloysite/Cucurbit[8]uril Hybrid as Efficient Nanosponge for Pollutants Removal
2016
Hybrid materials based on halloysite nanotubes (HNT) and cucurbit[8]uril (CB[8]) were prepared with the aim to obtain efficient nanosponges towards hydrocarbons both in liquid and vapor phases. The loading on both HNT surfaces and the hybrid morphology were evidenced by FTIR spectroscopy, thermogravimetric analysis and scanning electron microscopy. In order to highlight the interactions in the hybrid 13C {1H} CP-MAS NMR experiments were performed. The aqueous colloidal stability of HNT/CB[8] was highlighted through ζ potential and dynamic light scattering measurements. The HNT/CB[8] composite was employed as nanosponge to capture aromatic oils in aqueous phase as evidenced by fluorescence e…
Retene, pyrene and phenanthrene cause distinct molecular-level changes in the cardiac tissue of rainbow trout (Oncorhynchus mykiss) larvae, part 1 – …
2020
Polycyclic aromatic hydrocarbons (PAHs) are contaminants of concern that impact every sphere of the environment. Despite several decades of research, their mechanisms of toxicity are still poorly understood. This study explores the mechanisms of cardiotoxicity of the three widespread model PAHs retene, pyrene and phenanthrene in the rainbow trout (Oncorhynchus mykiss) early life stages. Newly hatched larvae were exposed to each individual compound at sublethal doses causing no significant increase in the prevalence of deformities. Changes in the cardiac transcriptome were assessed after 1, 3, 7 and 14 days of exposure using custom Salmo salar microarrays. The highest number of differentiall…