Interaction of mutagenic tryptophan pyrolysate with DNA

FEBS Letters

Doi, Mitsunobu¹  Inohara, Takeo¹  Tarui, Mariko¹  Inoue, Masatoshi¹  Ishida, Toshimasa¹ 

[1] Department of Physical Chemistry, Osaka University of Pharmaceutical Sciences, 2-10-65 Kawai, Matsubara, Osaka 580, Japan

关键词: Trp-P-1;    Tryptophan pyrolysate;    DNA;    Interaction;    CD;    poly(dA-dT);    alternating copolymer of poly(dA-dT)-poly(dA-dT);    poly(dG-dC);    alternating copolymer of poly(dG-dC)-poly(dG-dC);    poly(dG-m5dC);    alternating copolymer of poly(dG-m5dC)-poly(dG-m5dC);    CT DNA;    calf thymus deoxyribonucleic acid;    CD;    circular dichroism;    Trp-P;    3-amino-5H-pyrido[4;    3-b]indole derivative;    Trp-P-1;    3-amino-1;    4-dimethyl-5H-pyrido[4;    3-b]indole;    Trp-P-2;    3-amino-1-methyl-5H-pyrido[4;    3-b]indole;    Glu-P;    2-aminodipyrido[1;    2-a:3';    2'-d]imidazole derivative;    Glu-P-1;    2-amino-6-methyldipyrido[1;    2-a:3';    2'-d]imidazole;    Glu-P-2;    2-aminodipyrido[1;    2-a:3';    2'-d]imidazole;    N-O-acyl-Trp-P;    O-acetylated N-hydroxy-Trp-P;    N-O-acyl-Glu-P;    O-acetylated N-hydroxy-Glu-P;    Gua-Trp-P;    3-(8-guanyl)amino-Trp-P;    Gua-Glu-P;    2-(8-guanyl)amino-Glu-P;    HPLC;    high-pressure liquid chromatography;   

DOI  :  10.1016/0014-5793(93)80139-L

学科分类：生物化学/生物物理

来源: John Wiley & Sons Ltd.

【 摘 要 】

The interactions of DNA duplexes with 3-amino 1,4-dimethyl-5H-pyrido[4,3-b]indole(Trp-P-1), a potent mutacarcinogen isolated from tryptophan pyrolysate, have been studied using CD spectroscopy. The results are that (a) the spectral change of B-form DNA caused by the interaction with Trp-P-1 is biphasic, i.e. the enlargement of CD bands characteristic to the B-DNA conformation in the range of r ([Trp-P-1]/[DNA]) = 0–2.5, followed by the rapid transition to the non-B conformation at r > 2.5; (b) this transition degree of B to non-B conformation of DNA is not necessarily dependent on the G-C content; and (c) the salt-induced Z-DNA is transformed to B-DNA (0 < r < 0.1) and then to non-B-DNA (r > 5), depending on the concentration of Trp-P-1 added. These data indicate that the non-covalent interaction of Trp-P-1 with DNA is mainly dependent on the B-DNA conformation.

【 授权许可】

Unknown