Carcinogenic Non-Aminoazo Dye 1-Phenylazo-2-hydroxynaphthalene (Sudan I) Is Oxidized by Rat Liver Microsomal Cytochrome P-450 to Metabolites Binding to Macromolecules (Nucleic Acids and Proteins)

1992 ◽  
Vol 57 (7) ◽  
pp. 1537-1546 ◽  
Author(s):  
Marie Stiborová ◽  
Pavel Anzenbacher

Carcinogenic non-aminoazo dye 1-phenylazo-2-hydroxynaphthalene (Sudan I) is oxidized by microsomal cytochromes P-450 to reactive metabolite(s) binding to macromolecules (nucleic acids, proteins) in vitro. The extent of binding to macromolecules proceeded in the order: protein > rRNA > tRNA > DNA. The patern of products formed from Sudan I and binding of the reactive metabolites of this compound to macromolecules are dependent on the concentration of Sudan I, NADPH and on the duration of the incubation. The participation of the adducts formed with macromolecules in the initiation of chemical carcinogenesis is discussed.

1990 ◽  
Vol 55 (9) ◽  
pp. 2321-2327 ◽  
Author(s):  
Marie Stiborová ◽  
Pavel Anzenbacher

The peroxidase catalyzed oxidation of 1-phenylazo-2-hydroxynaphthalene (Sudan I) in the presence of NADH results in oxidation to oxidized NAD+. This oxidation is supposed to be caused by the reduction of reactive Sudan I metabolite(s). Under certain conditions NADH acts as the agent protecting the cellular nucleophilic compounds such as nucleic acids (DNA, tRNA) against modification caused by reactive metabolite(s) formed from carcinogenic Sudan I by the peroxidase/H2O2 system. The results are discussed from the point of view of the physiological significance of NADH in the initiation of chemical carcinogenesis.


1994 ◽  
Vol 59 (12) ◽  
pp. 2727-2733 ◽  
Author(s):  
Marie Stiborová ◽  
Befekadu Asfaw ◽  
Eva Frei ◽  
Heinz H. Schmeiser ◽  
Manfred Wiessler

The carcinogenic azo dye 1-phenylazo-2-hydroxynaphthalene (Sudan I, Solvent Yellow 14) is oxidized by rat liver microsomes to a number of azo-containing metabolites. One of the products of hitherto unknown structure has been shown to be identical with 1-(3,4-dihydroxyphenylazo)-2-hydroxynaphthalene. The identification of this product completed the pattern of major products of Sudan I oxidation by microsomal cytochrome P-450.


1985 ◽  
pp. 157-169
Author(s):  
Yoshiaki Fujii-Kuriyama ◽  
Kazuhiro Sogawa ◽  
Yuzuru Mizukami ◽  
Yorimasa Suwa ◽  
Masami Muramatsu ◽  
...  

1986 ◽  
Vol 35 (8) ◽  
pp. 1391-1394 ◽  
Author(s):  
Peng Renxiu ◽  
Zhu Xiu-Yuan ◽  
Chung S. Yang

1998 ◽  
Vol 116 (3) ◽  
pp. 181-198 ◽  
Author(s):  
Nobumitsu Hanioka ◽  
Hideto Jinno ◽  
Ken Kitazawa ◽  
Toshiko Tanaka-Kagawa ◽  
Tetsuji Nishimura ◽  
...  

1976 ◽  
Vol 25 (7) ◽  
pp. 779-784 ◽  
Author(s):  
Kathryn M. Ivanetich ◽  
Jean J. Bradshaw ◽  
Julia A. marsh ◽  
Laurence S. Kaminsky

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