Lysine-enediyne conjugates as photochemically triggered DNA double-strand cleavage agents

Chemical Communications

Volumn , Issue 11, 2005, Pages 1444-1446

  Kovalenko, Serguei V ^a   Alabugin, Igor V ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYLDIALKYNE DERIVATIVE; ANTINEOPLASTIC ANTIBIOTIC; DOUBLE STRANDED DNA; LYSINE; SINGLE STRANDED DNA; UNCLASSIFIED DRUG;

ARTICLE; CONJUGATE; CYCLIZATION; DEPROTECTION REACTION; DNA BINDING; DNA CLEAVAGE; DNA STRAND BREAKAGE; GEL ELECTROPHORESIS; NITRATION; PHOTOACTIVATION; POISSON DISTRIBUTION; SONOGASHIRA REACTION; ULTRAVIOLET IRRADIATION;

EID: 16444382688     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b417012a     Document Type: Article

References (32)

1. B. Armitage, Chem. Rev., 1998, 98, 1171 and references therein.
2. DNA-cleavage studies: (a) J. Kagan, X. Wang, X. Chen, K. Y. Lau, I. V. Batac, R. W. Tuveson and J. B. Hudson, J. Photochem. Photobiol. 1993, 21, 1352;
3. (b) R. L. Funk, E. R. R. Young, R. M. Williams, M. F. Flanagan and T. L. Cecil, J. Am. Chem. Soc., 1996, 118, 3291;
4. (c) N. Choy, B. Blanko, J. Wen, A. Krishan and K. C. Russell, Org. Lett., 2000, 2, 3761;
5. (d) Intramolecular PET activation: M. Schmittel, G. Viola, F. Dall'Acqua and G. Morbach, Chem. Commun., 2003, 646;
6. (e) MLCT-promoted Bergman cyclization: P. J. Benites, R. C. Holmberg, D. S. Rawat, B. J. Kraft, L. J. Klein, D. G. Peters, H. H. Thorp and J. M. Zaleski, J. Am. Chem. Soc., 2003, 125, 6434.
7. Fundamental photochemistry; (f) A. Evenzahav and N. J. Turro, J. Am. Chem. Soc., 1998, 120, 1835;
8. (g) T. Kaneko, M. Takanashi and M. Hirama, Angew. Chem., Int. Ed. Engl., 1999, 38, 1267.
9. Peptide cleavage and optimization of delivery strategies:; (h) G. B. Jones, J. M. Wright, G. Plourde, II, A. D. Purohit, J. K. Wyatt, G. Hynd and F. Fouad, J. Am. Chem. Soc., 2000, 122, 9872; F. S. Fouad, C. F. Crasto, Y. Lin and G. B. Jones, Tetrahedron Lett., 2004, 45, 7753.
10. Peptide cleavage and optimization of delivery strategies:; (h) G. B. Jones, J. M. Wright, G. Plourde, II, A. D. Purohit, J. K. Wyatt, G. Hynd and F. Fouad, J. Am. Chem. Soc., 2000, 122, 9872; F. S. Fouad, C. F. Crasto, Y. Lin and G. B. Jones, Tetrahedron Lett., 2004, 45, 7753.
11. (a) L. F. Povirk, Mutat. Res., 1996, 355, 71;
12. (b) D. T. Weaver, Crit. Rev. Eukaryot. Gene Exp., 1996, 6, 345;
13. (c) A. Sancar, Annu. Rev. Biochem., 1996, 65, 43;
14. (d) C. Rajani, J. R. Kincaid and D. H. Petering, J. Am. Chem. Soc., 2004, 126, 3829.
15. Experiment: I. V. Alabugin and S. V. Kovalenko, J. Am. Chem. Soc., 2002, 124, 9052. Theoretical treatment: I. V. Alabugin and M. Manoharan, J. Am. Chem. Soc., 2003, 125, 4495 Thermodynamics of peptide binding to nucleic acids.
16. Experiment: I. V. Alabugin and S. V. Kovalenko, J. Am. Chem. Soc., 2002, 124, 9052. Theoretical treatment: I. V. Alabugin and M. Manoharan, J. Am. Chem. Soc., 2003, 125, 4495 Thermodynamics of peptide binding to nucleic acids.
17. Thermodynamics of peptide binding to nucleic acids: T. M. Lohman and D. P. Mascotti, Methods Enzymol., 1992, 212, 400.
18. L. F. Povirk, W. Wübker, W. Köhnlein and F. Hutchinson, Nucleic Acids Res., 1977, 4, 3573; L. F. Povirk and C. W. Houlgrave, Biochemistry, 1988, 27, 3850. For an alternative approach based on multicomponent kinetic fitting, see: J. Goodisman, C. Kirk and J. C. Dabrowiak, Biophys. Chem., 1997, 69, 249.
19. L. F. Povirk, W. Wübker, W. Köhnlein and F. Hutchinson, Nucleic Acids Res., 1977, 4, 3573; L. F. Povirk and C. W. Houlgrave, Biochemistry, 1988, 27, 3850. For an alternative approach based on multicomponent kinetic fitting, see: J. Goodisman, C. Kirk and J. C. Dabrowiak, Biophys. Chem., 1997, 69, 249.
20. L. F. Povirk, W. Wübker, W. Köhnlein and F. Hutchinson, Nucleic Acids Res., 1977, 4, 3573; L. F. Povirk and C. W. Houlgrave, Biochemistry, 1988, 27, 3850. For an alternative approach based on multicomponent kinetic fitting, see: J. Goodisman, C. Kirk and J. C. Dabrowiak, Biophys. Chem., 1997, 69, 249.
21. -1, 30 μM per bp) in 20 mM potassium phosphate buffer was incubated for 1 h at 25 °C. After incubation, 10 samples (10 μL of each) in a Pyrex tubes (OD 0.11 in.) were sealed tightly with Parafilm. The sample was placed at a distance of 20 cm from 200 W Hg-Xe lamp (Spectra-Physics, Laser & Photonics Oriel Instruments with long pass filter with 324 nm cut-on wavelength) and cooled with the stream of air. The relative quantities of the supercoiled, nicked, and linear DNA were calculated by the image analyzer software Total/Lab (Nonlinear Dynamics Ltd., UK). The amount of supercoiled DNA was multiplied by factor of 1.4 to account for reduced ethidium bromide intercalation into supercoiled DNA.
22. 2)].
23. 1 = 1.5).
24. D. Freifelder and B. Trubo, Biopolymers, 1969, 7, 681.
25. L. F. Povirk, W. Wübker and R. J. Steighner, Biochemistry, 1989, 28, 5808; M. J. Absalon, J. W. Kozarich and J. Stubbe, Biochemistry, 1995, 34, 2065; J. Stubbe, J. W. Kozarich, W. Wu and D. E. Vanderwall, Acc. Chem. Res., 1996, 29, 322; K. Charles and L. F. Povirk, Chem. Res. Toxicol., 1998, 11, 1580.
26. L. F. Povirk, W. Wübker and R. J. Steighner, Biochemistry, 1989, 28, 5808; M. J. Absalon, J. W. Kozarich and J. Stubbe, Biochemistry, 1995, 34, 2065; J. Stubbe, J. W. Kozarich, W. Wu and D. E. Vanderwall, Acc. Chem. Res., 1996, 29, 322; K. Charles and L. F. Povirk, Chem. Res. Toxicol., 1998, 11, 1580.
27. L. F. Povirk, W. Wübker and R. J. Steighner, Biochemistry, 1989, 28, 5808; M. J. Absalon, J. W. Kozarich and J. Stubbe, Biochemistry, 1995, 34, 2065; J. Stubbe, J. W. Kozarich, W. Wu and D. E. Vanderwall, Acc. Chem. Res., 1996, 29, 322; K. Charles and L. F. Povirk, Chem. Res. Toxicol., 1998, 11, 1580.
28. L. F. Povirk, W. Wübker and R. J. Steighner, Biochemistry, 1989, 28, 5808; M. J. Absalon, J. W. Kozarich and J. Stubbe, Biochemistry, 1995, 34, 2065; J. Stubbe, J. W. Kozarich, W. Wu and D. E. Vanderwall, Acc. Chem. Res., 1996, 29, 322; K. Charles and L. F. Povirk, Chem. Res. Toxicol., 1998, 11, 1580.
29. (a) K. D. Stewart and T. A. Gray, J. Phys. Org. Chem, 1992, 5, 461;
30. (b) B. F. Cain, B. C. Baguley and W. A. Denny, J. Med. Chem., 1978, 21, 658;
31. (c) H.-P. Hsieh, J. G. Muller and C. J. Burrows, J. Am. Chem. Soc., 1994, 116, 12077;
32. (d) D. L. Boger, B. E. Fink, S. R. Brunette, W. C. Tse and M. P. Hedrick, J. Am. Chem. Soc., 2001, 123, 12077.