Beilstein J. Org. Chem. 2011, 7, 813–823.
10.Alabugin, I. V.; Yang, W.-Y.; Pal, R. Enediyne photochemistry. In CRC
Handbook of Organic Photochemistry and Photobiology, 3rd ed.;
Taylor & Francis: Boca Raton, FL, in press.
the p-, m-, and o-conjugates 1, 6, and 7 produced 34, 15, and
0% of ds DNA cleavage, respectively. The large DNA-
protecting effect on reactivity of the meta-conjugate 6, imposed
by hydroxyl radical/singlet oxygen scavengers, suggests triplet
photoreactivity which leads to efficient sensitization of singlet
oxygen. This observation is consistent with the efficient triplet
reactivity of its chromophore. The inhibition of human
melanoma cell growth by the three conjugates was also tested.
The para-substituted conjugate 1 has the lowest CC50 value of
1.49 × 10−7 M.
11.Celli, J. P.; Spring, B. Q.; Rizvi, I.; Evans, C. L.; Samkoe, K. S.;
Verma, S.; Pogue, B. W.; Hasan, T. Chem. Rev. 2010, 110,
12.Alabugin, I. V.; Timokhin, V. I.; Abrams, J. N.; Manoharan, M.;
Abrams, R.; Ghiviriga, I. J. Am. Chem. Soc. 2008, 130, 10984–10995.
13.Pal, R.; Clark, R. J.; Manoharan, M.; Alabugin, I. V. J. Org. Chem.
14.Zeidan, T. A.; Kovalenko, S. V.; Manoharan, M.; Alabugin, I. V.
15.Pickard, F. C., IV; Shepherd, R. L.; Gillis, A. E.; Dunn, M. E.;
Feldgus, F.; Kirschner, K. N.; Shields, G. C.; Manoharan, M.;
Alabugin, I. V. J. Phys. Chem. A 2006, 110, 2517–2526.
Supporting Information
Supporting information features details for experimental
procedures, emission titration spectra, fluorescence decay
traces, picture of plasmid relaxation assay, characterization
data, and NMR spectra (1H, 13C NMR, HSQC, and
HMBC).
16.Vasilevsky, S. F.; Mikhailovskaya, T. F.; Mamatyuk, V. I.;
Salnikov, G. E.; Bogdanchikov, G. A.; Manoharan, M.; Alabugin, I. V.
17.Alabugin, I. V.; Gilmore, K.; Patil, S.; Manoharan, M.; Kovalenko, S. V.;
Clark, R. J.; Ghiviriga, I. J. Am. Chem. Soc. 2008, 130, 11535–11545.
Supporting Information File 1
18.Vasilevsky, S. F.; Baranov, D. S.; Mamatyuk, V. I.; Gatilov, Y. V.;
Alabugin, I. V. J. Org. Chem. 2009, 74, 6143–6150.
Experimental details, characterization data, emission
titration spectra, fluorescence decay traces, plasmid
relaxation assays and NMR spectra (1H, 13C NMR, HSQC,
and HMBC).
19.Alabugin, I. V.; Manoharan, M. J. Am. Chem. Soc. 2005, 127,
20.Alabugin, I. V.; Manoharan, M. J. Am. Chem. Soc. 2005, 127,
21.Zeidan, T.; Manoharan, M.; Alabugin, I. V. J. Org. Chem. 2006, 71,
22.Baroudi, A.; Mauldin, J.; Alabugin, I. V. J. Am. Chem. Soc. 2010, 132,
Acknowledgements
Partial support from the National Science Foundation (CHE-
0848686) and James & Esther King Biomedical Research
Program (09KC-03) is gratefully appreciated.
23.Alabugin, I. V.; Manoharan, M. J. Comput. Chem. 2007, 28, 373–390.
24.Kovalenko, S. V.; Alabugin, I. V. Chem. Commun. 2005, 1444–1446.
25.Yang, W.-Y.; Breiner, B.; Kovalenko, S. V.; Ben, C.; Singh, M.;
LeGrand, S. N.; Sang, Q.-X.; Strouse, G. F.; Copland, J. A.;
Alabugin, I. V. J. Am. Chem. Soc. 2009, 131, 11458–11470.
References
2. Shiraki, T.; Sugiura, Y. Biochemistry 1990, 29, 9795–9798.
26.Breiner, B.; Schlatterer, J. C.; Alabugin, I. V.; Kovalenko, S. V.;
Greenbaum, N. L. Proc. Natl. Acad. Sci. U. S. A. 2007, 104,
3. Jones, G. B.; Wright, J. M.; Plourde, G., II; Purohit, A. D.; Wyatt, J. K.;
Hynd, G.; Fouad, F. J. Am. Chem. Soc. 2000, 122, 9872–9873.
27.Yang, W.-Y.; Cao, Q.; Callahan, C.; Galvis, C.; Sang, Q.-X.;
Alabugin, I. V. J. Nucleic Acids 2010, 931394.
4. Kar, M.; Basak, A. Chem. Rev. 2007, 107, 2861–2890.
28.Breiner, B.; Schlatterer, J. C.; Kovalenko, S. V.; Greenbaum, N. L.;
Alabugin, I. V. Angew. Chem., Int. Ed. 2006, 45, 3666–3670.
5. Kagan, J.; Wang, X.; Chen, X.; Lau, K. Y.; Batac, I. V.; Tuveson, R. W.;
Hudson, J. B. J. Photochem. Photobiol., B: Biol. 1993, 21, 135–142.
29.Nielsen, P. E.; Jeepesen, C.; Egholm, M.; Buchardt, O.
30.Chatterjee, M.; Rokita, S. E. J. Am. Chem. Soc. 1990, 112, 6397–6399.
6. Benites, P. J.; Holmberg, R. C.; Rawat, D. S.; Kraft, B. J.; Klein, L. J.;
Peters, D. G.; Thorp, H. H.; Zaleski, J. M. J. Am. Chem. Soc. 2003,
31.Henriksen, U.; Larsen, C.; Karup, G.; Jeepesen, C.; Nielsen, P. E.;
Buchardt, O. Photochem. Photobiol. 1991, 53, 299–305.
7. Schmittel, M.; Viola, G.; Dall’Acqua, F.; Morbach, G. Chem. Commun.
8. Poloukhtine, A.; Popik, V. V. J. Org. Chem. 2003, 68, 7833–7840.
32.Chatterjee, M.; Rokita, S. E. J. Am. Chem. Soc. 1994, 116, 1690–1697.
9. Polukhtine, A.; Karpov, G.; Popik, V. V. Curr. Top. Med. Chem. 2008,
822