4
502
L. Fernandes et al. / Bioorg. Med. Chem. Lett. 18 (2008) 4499–4502
lowships, respectively. F.N., M.M.S., and H.T. thank CNPq for re-
search fellowships. Financial support by MCT/CNPq (Brazilian Re-
search Council), FAPESC (Santa Catarina State Research Council,
Brazil), FINEP (Financiadora de Estudos e Projetos), and PRONEX-
12, 1; (d) Thomas, C. J.; McCormick, M. M.; Vialas, C.; Tao, Z.-F.; Leitheiser, C. J.;
Rishel, M. J.; Wu, X.; Hecht, S. M. J. Am. Chem. Soc. 2002, 124, 3875.
(a) Yang, Q.; Xu, J.; Sun, Y.; Li, Z.; Li, Y.; Qian, X. Bioorg. Med. Chem.
Lett. 2006, 16, 803; (b) Wan, S.-H.; Liang, F.; Xiong, X.-Q.; Yang, L.; Wu,
X.-J.; Wang, P.; Zhou, X.; Wu, C.-T. Bioorg. Med. Chem. Lett. 2006, 16,
9
.
2804.
2
003 (CNPq/FAPESC) is also gratefully acknowledged.
1
0. (a) Hwu, J. R.; Yang, J.-R.; Tsay, S.-C.; Hsu, M.-H.; Chen, Y.-C.; Chou, S.-S. P.
Tetrahedron Lett. 2008, 49, 3312; (b) Hwu, J. R.; Tsay, S.-C.; Hong, S. C.; Leu, Y.-J.;
Liu, C.-F.; Chou, S.-S. P. Tetrahedron Lett. 2003, 44, 2957; (c) Hwu, J. R.; Lin, C. C.;
Chuang, S. H.; King, K. Y.; Su, T.-R.; Tsay, S.-C. Bioorg. Med. Chem. 2004, 12,
Supplementary data
2
2
509; (d) Qian, X.; Li, Y.; Xu, Y.; Liu, Y.; Qu, B. Bioorg. Med. Chem. Lett. 2004, 14,
665.
General information, experimental procedures, compound char-
acterization data (including 1H and/or 13C NMR spectra for com-
pounds 5–9), and full kinetic data for the DNA cleavage
11. (a) Musilek, K.; Holas, O.; Jun, D.; Dohnal, V.; Gunn-Moore, F.; Opletalova, V.;
Dolezal, M.; Kuca, K. Bioorg. Med. Chem. 2007, 15, 6733; (b) Yang, G. Y.;
Oh, K.-A.; Park, N.-J.; Jung, Y.-S. Bioorg. Med. Chem. 2007, 15, 7704.
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Lett. 2007, 17, 4861.
(
including inhibition experiments with distamycin, DMSO, and
glycerol).
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References and notes
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1
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Thesis, University of Alberta, 1991.
19. Preparation of plasmid DNA and screenings: Plasmid DNA pBSK-II (Stratagene) was
produced in Escherichia coli DH5-a and extracted following protocols described
in the literature.2 Plasmid DNA (pBSK-II BlueScript, Stratagene) was obtained
and purified according to standard techniques (Qiagen Plasmid Maxi Kit).21
Spectrophotometric DNA quantification was carried out assuming an
absorptivity at 260 nm. DNA-cleavage screenings were carried out by
0
1
1517; (e) Vijayalakshmi, R.; Kanthimathi, M.; Subramanian, V.; Nair, B. U.
Biochem. Biophys. Res. Commun. 2000, 271, 731.
(a) Otero, L.; Smircich, P.; Vieites, M.; Ciganda, M.; Severino, P. C.;
Terenzi, H.; Cerecetto, H.; Gambino, D.; Garat, B. J. Inorg. Biochem. 2007, 101,
incubating in
corresponding to a final concentration of 25.0
the presence of different concentrations of compounds (50.0 and 100.0
a
20.0
l
L
final volume: pBSK-II plasmid DNA 330 ng/
M bp (nucleotide base pairs), in
M) in
ll,
4
.
l
l
7
4; (b) Horn, A., Jr.; Vencato, I.; Bortoluzzi, A. J.; Hörner, R.; Silva, R. A. N.;
different buffersand temperatures (PIPES, pH 7.0, 37and 50 °C; HEPES, pH 8.0, 37
and 50 °C and CHES, pH 9.0, 37 and 50 °C) for 16 h (other conditions are depicted
in the figure legends). Reactions were stopped by chilling tubes on ice and adding
Szpoganicz, B.; Drago, V.; Terenzi, H.; Oliveira, M. C. B.; Werner, R.; Haase, W.;
Neves, A. Inorg. Chim. Acta 2005, 358, 339; (c) Rossi, L. M.; Neves, A.; Hörner, R.;
Terenzi, H.; Szpoganicz, B.; Sugai, J. Inorg. Chim. Acta 2002, 337, 366; (d) Neves,
A.; Terenzi, H.; Hörner, R.; Horn, A., Jr.; Szpoganicz, B.; Sugai, J. Inorg. Chem.
Commun. 2001, 4, 388.
Longhinotti, E.; Domingos, J. B.; Szpoganicz, B.; Neves, A.; Nome, F. Inorg. Chim.
Acta 2005, 358, 2089.
(a) Franklin, S. J. Curr. Opin. Chem. Biol. 2001, 5, 201; (b) Branum, M. E.; Tipton,
A. K.; Zhu, S.; Que, L., Jr. J. Am. Chem. Soc. 2001, 123, 1898; (c) Branum, M. E.;
Que, L., Jr. J. Biol. Inorg. Chem. 1999, 4, 593; (d) Moss, R. A.; Bracken, K.; Zhang, J. .
Chem. Commun. 1997, 563.
(a) Chin, J. Curr. Opin. Chem. Biol. 1997, 1, 514; (b) Komiyama, M.;
Sumaoka, J. Curr. Opin. Chem. Biol. 1998, 2, 751.
(a) Dai, W.-M.; Lai, K. W.; Wu, A.; Hamaguchi, W.; Lee, M. Y. H.; Zhou, L.; Ishii,
A.; Nishimoto, S.-I. J. Med. Chem. 2002, 45, 758; (b) Wipf, P.; Hopkins, C. R.;
Phillips, E. O.; Lazo, J. S. Tetrahedron 2002, 58, 6367; (c) Warner, P. M.; Qi, J.;
Meng, B.; Li, G.; Xie, L.; El-Shafey, A.; Jones, G. B. Bioorg. Med. Chem. Lett. 2002,
5.0
lL of ice-cold loading-buffer (50% glycerol, 0.25% bromophenol blue,
25.0 mM EDTA pH 8.0). All tests were performed in duplicate. Reaction
products were observed by agarose gel (0.8%) electrophoresis and stained with
ethidium bromide. The resulting gels were scanned with a photodocumentation
5
.
.
TM
system (UVP, Inc.) and analyzed with the software LabWorks Software v4.0
6
(
UVP, Inc.). The kinetic parameters were calculated from the non-linear fit of the
pseudo Michaelis-Menten equation kobs = (kcat  [compound])/([compound] +
).
K
M
2
0. Ausubel, F. M.; Brent, R.; Kingston, R. E.; Moore, D. D.; Seidman, J. G.;
Smith, J. A.; Struhl, K. In Short Protocols in Molecular Biology: A Compendium of
Methods from Current Protocols in Molecular Biology; Wiley: New York, 1999.
7
.
.
8
TM
21. QIAGEN. HiSpeed Plasmid Purification Handbook 2001, 46.
22. Camargo, M. A.; Neves, A.; Bortoluzzi, A. J.; Szpoganicz, B.; Martendal, A.;
Murgu, M.; Fischer, F. L.; Terenzi, H.; Severino, P. C. Inorg. Chem. 2008, 47, 2919.