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5137167 
Journal Article 
MUTAGENICITY OF NEWLY SYNTHESIZED 6-AZABENZO(A)PYRENE 
Fukuhara, K; Miyata, N; Kamiya, S 
1991 
1 
Mutation Research Letters
ISSN: 0165-7992 
ELSEVIER SCIENCE BV 
AMSTERDAM 
3 
245-245 
English 
WOS:A1991GT81200012 
MUTAGENICITY AND CARCINOGENICITY OF AZA-POLY-CYCLIC AROMATIC HYDROCARBONS ARE A MATTER OF CONCERN IN THESE YEARS. AS AZA-ANALOGS OF BENZO[A]PYRENE (AZABAP), 4-, 7-, 8-, 10- AND 12-AZABAPS HAVE BEEN SYNTHESIZED AND A FEW OF THEIR MUTAGENIC PROPERTIES HAVE REPORTED. NO COMPOUNDS ARE KNOWN WHICH HAVE A NITROGEN ATOM IN THE 1,3 OR 6 POSITION OF BAP. SINCE THESE POSITIONS ARE INVOLVED IN THE METABOLISM OF BAP, 1-, 3- AND 6-AZABAPS SHOULD BE OF PARTICULAR INTEREST. RECENTLY WE SYNTHESIZED 6-AZABAP AND ITS N-OXIDE USING PERINAPHTHENONE AND 1-IODO-2-NITROBENZENE AS STARTING MATERIALS (FUKUHARA ET AL., TETRAHEDRON LETT., 31 (1990) 3743). NOW WE REPORT THEIR MUTAGENIC PROPERTY. THE MUTAGENIC ACTIVITIES OF 6-AZABAP AND ITS N-OXIDE WERE TESTED ON SALMONELLA TYPHIMURIUM STRAINS TA98 AND TA100 WITH OR WITHOUT S9 MIX. 6-AZABAP, LIKE BAP, SHOWED STRONG MUTAGENICITY IN BOTH STRAINS IN THE PRESENCE OF S9 MIX, AND THE ACTIVITY IN TA100 WAS HIGHER THAN IN TA98. THE MUTAGENICITY OF 6-AZABAP-N-OXIDE WAS HIGHER THAN THAT OF 6-AZABAP. EVEN IN THE ABSENCE OF S9 MIX, 6-AZABAP-N-OXIDE SHOWED WEAK MUTAGENICITY IN TA98. OUR RESULTS SHOW THAT 6-AZABAP IS A POTENT MUTAGEN ACTIVATED BY METABOLIC OXIDATION AND THE ACTIVITY IS FURTHER INCREASED BY N-OXIDATION. THE METABOLIC STUDY OF 6-AZABAP IS NOW IN PROGRESS.