A new synthetic analogue of the bracken ultimate carcinogen: Elevation of stability and alteration of DNA alkylation site selectivity

Tetrahedron Letters

Volumn 38, Issue 18, 1997, Pages 3235-3238

  Kigoshi, Hideo ^a   Kitamura, Yuusi ^a   Fujita, Tatsuya ^a   Ohashi, Hidekazu ^a   Atsumi, Toshiyuki ^a   Takagi, Junko ^a   Mutou, Tsuyoshi ^a   Yamada, Kiyoyuki ^a   Kusakabe, Tetsuya ^b   Sasaki, Daisuke ^b   Sugiura, Yukio ^b  

^a NAGOYA UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARCINOGEN; NAPHTHALENE DERIVATIVE; SPIRO COMPOUND;

ARTICLE; DNA ALKYLATION; DNA CLEAVAGE; DNA STRAND; DRUG SYNTHESIS; IN VITRO STUDY;

PTERIDIUM AQUILINUM;

EID: 0030976050     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00572-8     Document Type: Article

References (16)

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2. (a) Ojika, M.; Sugimoto, K.; Okazaki, T.; Yamada, K. J. Chem. Soc., Chem. Commun. 1989, 1775-1777.
3. (b) Kushida, T.; Uesugi, M.; Sugiura, Y.; Kigoshi, H.; Tanaka, H.; Hirokawa, J.; Ojika, M.; Yamada, K. J. Am. Chem. Soc. 1994, 116, 479-486.
4. Ojika, M.; Wakamatsu, K.; Niwa, H.; Yamada, K. Tetrahedron 1987, 43, 5261-5274.
5. Hurley, L. H.; Warpehoski, M. A.; Lee, C.-S.; McGovren, J. P.; Scahill, T. A.; Kelly, R. C.; Mitchell, M. A.; Wicnienski, N. A.; Gebhard, I.; Johnson, P. D.; Bradford, V. S. J. Am. Chem. Soc. 1990, 112, 4633-4649.
6. Sun, D.; Hurley, L. H. Biochemistry 1992, 31, 2822-2829.
7. 2COOMe) on the benzene ring in 4 was introduced as a linker part, to which a variety of DNA binding moieties can be attached for further studies.
8. Loewenthal, H. J. E.; Gottlieb, L. J. Org. Chem. 1992, 57, 2631-2641.
9. +.
10. 1H NMR, and mass spectra) and analytical (microanalyses or high-resolution mass spectra) data were obtained for all new compounds.
11. 1/2) was determined in 1:3 acetonitrile-Tris borate buffer (pH 7.5) at 26 °C.
12. Kigoshi, H.; Tanaka, H.; Hirokawa, J.; Mizuta, K.; Yamada, K. Tetrahedron Lett. 1992, 33, 6647-6650.
13. 2EDTA, pH 8.0). When required, the sample was subsequently treated with 1 M piperidine at 90 °C for 30 min. Each lyophilized sample was dissolved in 3 μl of 90% (v/v) deionized formamide containing 1 mM EDTA and 0.01% (w/v) bromphenol blue and loaded into a 15% (w/v) polyacrylamide sequencing gel. Electrophoresis was performed at 2000 V in TBE buffer (pH 8.0). DNA sequencing was carried out using the Maxam-Gilbert method.
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