Publication details

Chemical synthesis of benzo[a]pyrene derivatives and their use in development of ELISA method



Year of publication 2007
Type Article in Proceedings
Conference XI. Pracovní setkání biochemiků a molekulárních biologů, Brno, 31. – 1. února 2007.
MU Faculty or unit

Faculty of Science

Field Biochemistry
Keywords Bioconjugate Benzopyrene MALDI-TOF ELISA Immunization
Description Benzo[a]pyrene (BaP) belongs to the group of polycyclic aromatic hydrocarbons (PAHs) that have mutagenic and pro-carcinogenic properties. The PAHs compounds are ubiquitous environmental pollutants requiring metabolic activation tohave the carcinogenic properties. The activation steps are mainly presented by hydroxylation and epoxidation of thearomatic system by the group of cytochrome P450 isoenzymes (mainly the P450 1A1 isoenzyme). The epoxy-derivatives of the PAHs molecules are highly reactive electrophiles, able to bind to any primary aminogroup. When sucha molecule is bound to the nucleotide, the structure, as well as natural function, of the nucleic acid is corrupted; thecarcinogenic properties of the BaP molecule take effect in this way. The small molecules, such as benzo[a]pyrene, cannot induce the immunogenic response in animals; therefore it needs to be conjugated to the protein carrier molecule. Forthis reason, the BaP molecules was modified in the Friedel-Craft reaction to contain a carboxy-terminated spacer, whichwas further use to couple the polycyclic molecule to a protein molecule - bovine serum albumine, peroxidase, etc. Theappropriate procedures offering the BaP-carboxyderivative, and also the conjugation reactions will be discussed duringthe presentation, as a supplement for the experimental results. Various approaches for preparation of the nucleotide/DNA conjugates with benzo[a]pyrene, suitable for the immunization as well as for the subsequent immunochemicalassay performance, will be discussed at the end of the presentation.
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