Dibenzoyldiazomethane-acridine conjugate: A novel DNA photofootprinting agent

Tetrahedron Letters

Volumn 38, Issue 34, 1997, Pages 6047-6050

  Nakatani, Kazuhiko ^a   Shirai, Junya ^a   Sando, Shinsuke ^a   Saito, Isao ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACRIDINE DERIVATIVE;

ARTICLE; DNA CLEAVAGE; DNA FOOTPRINTING; DRUG SYNTHESIS; IN VITRO STUDY; PHOTOCHEMISTRY; TECHNIQUE;

EID: 0030797392     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01357-9     Document Type: Article

References (14)

1. Dervan, P. B. Science 1986, 232, 464-471.
2. Sigman, D. S. Ace. Chem. Res. 1986, 19, 180-186.
3. Pyle, A. M.; Long, E. C.; Barton, J. K. J. Am. Chem. Soc. 1989, 111, 4520-4522.
4. Jeepesen, C.; Nielsen, P. E. Eur. J. Biochem. 1989, 182, 437-444.
5. Nielsen, P. E.; Hiort, C.; Sönnichsen, S. O.; Buchardt, O.; Dahl, O.; Norden, B. J. Am. Chem. Soc. 1992, 114, 4967-4975.
6. Breiner, K. M.; Daugherty, M. A.; Oas, T. G.; Thorp, H. H. J. Am. Chem. Soc. 1995, 117, 11673-11679.
7. Saito, I.; Nakatani, K. Bull. Chem. Soc. Jpn. 1996, 69, 3007-3019.
8. Nakatani, K.; Shirai, J.; Tamaki, R.; Saito, I. Tetrahedron Lett. 1995, 36, 5363-5366.
9. +], 514.2132; Found 514.2114.
10. UV-Vis titration of 4 (100μM) with calf thymus DNA (0-300 μM) was carried out in 5 mM sodium cacodylate buffer (pH 7.0). Absorbance change at 434 nm induced by the addition of DNA was analyzed by Scatchard plot.
11. (a) Houba-Herin, N.; Calberg-Bacq, C. M.; Piette, J.; Van de Vorst, A. Photochem. Photobiol. 1982, 36, 297-306.
12. (b) Iwamoto, Y.; Yoshioka, H.; Yanagihara, Y. Chem. Pharm. Bull. 1987, 35, 2478-2483.
13. For a recent reference of guanine oxidation by singlet oxygen, see: Raoul, S.; Cadet, J. J. Am. Chem. Soc. 1996, 118, 1892-1898.
14. Photoreaction of 4 in aqueous acetonitrile in the presence of 2-propanol actually produced dibenzoylmethane derivative 12 by hydrogen abstraction, but accompanied with the formation of unidentified complex mixtures, indicating that other processes besides triplet carbene formation are also involved in the photodecomposition of 4.