Conversion of a hemoglobin alpha chain aspartate(47) ester to N-(2,3-dihydroxypropyl)asparagine as a method for identification of the principal binding site for benzo[a]pyrene anti-diol epoxide.

@article{Day1991ConversionOA,
  title={Conversion of a hemoglobin alpha chain aspartate(47) ester to N-(2,3-dihydroxypropyl)asparagine as a method for identification of the principal binding site for benzo[a]pyrene anti-diol epoxide.},
  author={Billy W. Day and Paul L. Skipper and Robert H. Rich and Stephen Naylor and Steven R Tannenbaum},
  journal={Chemical research in toxicology},
  year={1991},
  volume={4 3},
  pages={
          359-63
        }
}
Human hemoglobin was alkylated with (+/-)-7 beta,8 alpha-dihydroxy-9 alpha,10 alpha-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene (BPDE) and then treated with aqueous (+/-)-3-amino-1,2-propanediol to convert alkylated carboxyl side chains to N-(2,3-dihydroxypropyl) amides. Tryptic peptides produced from the modified protein were subjected to affinity chromatography on phenylboronic acid. The bound fraction was further purified by HPLC on C-4 reverse-phase medium to yield one modified peptide, which… Expand
Benzo[a]pyrene diol epoxide and related polynuclear aromatic hydrocarbon adducts of hemoglobin.
TLDR
Benzo[ a ]pyrene is metabolized by several isozymes of the cytochrome P -450 superfamily of enzymes to an array of oxygenated products, and it appears that alkylation of hemoglobin carboxyl groups by diol epoxides is a general reaction. Expand
Chromatographic Characterization of Hemoglobin Benzo[a]pyrene-7,8-diol-9,10-epoxide Adducts
Abstract The formation of hemoglobin–carcinogen adducts has been detected in carcinogen-treated animals and in human populations. Although polynuclear aromatic hydrocarbons are ubiquitous in theExpand
KINETICS OF FORMATION OF (±)-ANTI-7, 8-DIHYDROXY-9α,10α -EPOXY-7, 8, 9, 10-TETRAHYDROBENZO[A]PYRENE ADDUCTS WITH MOUSE AND HUMAN HEMOGLOBIN
Previous studies on the metabolic activation of polycyclic aromatic hydrocarbons have shown conclusively that activation to reactive electrophilic intermediates occurs via metabolism of theExpand
Characterization of various classes of protein adducts.
TLDR
It was shown that human subjects experiencing exposure to ambient levels of environmental PAH do take up and metabolize chrysene and benzo[a]pyrene, and four compounds were detected that exhibited spectra characteristic of a polynuclear chromophore. Expand
Binding of 3‐hydroxybenzo[a]pyrene to bovine hemoglobin and albumin
TLDR
Results indicate that an oxidative process is involved in formation of the heme adduct and that 3‐OHBaP or BaP‐3G might be a precursor of the bound metabolite. Expand
Evidence That a Hemoglobin Adduct
metabolic activation of NNK in people exposed to tobacco products. In this study, labeling experiments were carried out with [l80]NaOH that provide strong evidence that the globin adduct thatExpand
A gas chromatography-isotope dilution high-resolution mass spectrometry method for quantification of isomeric benzo[a]pyrene diol epoxide hemoglobin adducts in humans.
TLDR
A gas chromatography-isotope dilution high-resolution mass spectrometry method for quantifying isomeric BaP tetrol metabolites resulting from hydrolysis of benzo[a]pyrene-diol-epoxide hemoglobin (BaPDE-Hb) adducts has found detectable concentrations in the low fmol range for BPTII-1 and BPTI-1 in all donors tested. Expand
Characteristics of high energy collision-induced dissociation tandem Mass Spectra of Polycyclic aromatic Hydrocarbon diolepoxide adducted peptides
  • J. Zaia, K. Biemann
  • Chemistry, Medicine
  • Journal of the American Society for Mass Spectrometry
  • 1994
Polycyclic aromatic hydrocarbon (PAH) diolepoxides are known to covalently modify serum albumin and hemoglobin. Mass spectrometric techniques have proven quite useful in the characterization of theExpand
Hemoglobin Adducts of Benzo[a]Pyrene in Tobacco Smokers : Characterization of Benzo[a]Pyrene Adducts in Maternal and Fetal Blood Samples
Abstract The formation of hemoglobin - carcinogen adducts has been detected in carcinogen treated animals and in human populations. Although polynuclear aromatic hydrocarbons are ubiquitous in theExpand
Conditions for sample preparation and quantitative HPLC/MS-MS analysis of bulky adducts to serum albumin with diolepoxides of polycyclic aromatic hydrocarbons as models
TLDR
Stable adducts to serum albumin (SA) from electrophilic and genotoxic compounds/metabolites can be used as biomarkers for quantification of the corresponding in vivo dose through a sensitive and reproducible quantitative method. Expand
...
1
2
3
...