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Metabolism of and DNA Adduct Formation by Carcinogenic o-Anisidine and its Metabolite N-(2-Methoxyphenyl) hydroxylamine
Naiman, Karel ; Stiborová, Marie (advisor) ; Sofrová, Danuše (referee) ; Befekadu, Asfaw (referee)
CHARLES UNIVERSITY IN PRAGUE FACULTY OF SCIENCE DEPARTMENT OF BIOCHEMISTRY Metabolism of and DNA Adduct Formation by Carcinogenic o-Anisidine and its Metabolite N-(2-Methoxyphenyl)hydroxylamine Summary of Ph.D. Thesis RNDr. Karel Naiman Supervisor: Prof. RNDr. Marie Stiborová, DrSc. PRAGUE 2010 Introduction - 2 - INTRODUCTION Aromatic amines are potent toxic or carcinogenic compounds, presenting a considerable danger to the human population (NTP, 1978; IARC, 1982; Garner et al., 1984). They are widely distributed environmental pollutants found in workplaces (e.g. in chemical industry), in emissions from diesel and gasoline engines and on the surface of ambient air particulate matter (NTP, 1978; IARC, 1982), where they add to local and regional pollution (car exhausts, technological spills). Their toxicity and carcinogenicity has been widely examined, but the knowledge in metabolism of several aromatic amines and their physiological effects in humans are still incomplete. This is also the case of o-anisidine. 2-Methoxyaniline (o-anisidine, Fig. 1) is a potent carcinogen, causing tumours of the urinary bladder in both genders of F344 rats and B6C3F1 mice (NTP, 1978; IARC, 1982). The International Agency for Research on Cancer (IARC) has classified o-anisidine as a group 2B carcinogen (IARC, 1982), which is...
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Biochemical properties of quaternary benzo(c)phenanthrene alkaloids
Přenosilová, Lenka ; Naiman, Karel (referee) ; Stiborová, Marie (advisor)
Quaternary benzo(c)phenanthridine alkaloids are plant products found in many plants. The richest sources are mainly Chelidonieae plants and the family Papaveraceae. The basis of the structure of quaternary benzo(c)phenanthridine alkaloids (sanguinarine, chelerythrine, sanguiluthine, sanguirubine, chelirubine, cheliluthine, macarpine) is N- methylbenzo(c)phenanthridine cation. Chemical structure of quaternary benzo(c)phenanthridine alkaloids related to their cytotoxic properties, the ability to intercalation into DNA and the fluorescence capabilities. Quaternary benzo(c)phenanthridine alkaloids occur in two forms, one of which operates reversible equilibrium depending on pH. Very important are the biological effects of quaternary benzo(c)phenanthridine alkaloids. These alkaloids could be used as fluorescent DNA probes and as supravital dye of nucleic acids. Individual quaternary benzo(c)phenanthridine alkaloids have many uses. Sanguinarine is used for its antiplaque and anti-inflammatory effects of oral hygiene. For its effect against the coagulation of blood platelets may play an important role in preventing cardiovascular diseases. Sanguinarine may be used as a potential cytostatic drug for the treatment of cancer. Chelerythrine is similar to use in oral hygiene products and is known for its...
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