A. I. Vovk et al. / Bioorg. Med. Chem. Lett. 19 (2009) 1314–1317
1317
7. Consoli, G. M. L.; Galante, E.; Daquino, C.; Granata, G.; Cunsolo, F.; Geraci, C.
Tetrahedron Lett. 2006, 47, 6611.
were prepared in methanol. The volume concentration of the organic solvent in
reaction mixture (2 mL) was 2%. The reaction was started by adding 0.008 U of
xanthine oxidase to the mixture incubated at 25 °C.
8. (a) Araki, K.; Nakamura, R.; Otsuka, H.; Shinkai, S. J. Chem. Soc., Chem. Commun.
1995, 2121; (b) Rajca, A.; Pink, M.; Rojsajjakul, T.; Lu, K.; Wang, H.; Rajca, S. J.
Am. Chem. Soc. 2003, 125, 8534; (c) Wang, Q.; Li, Y.; Wu, G. Chem. Commun.
2002, 1268; (d) Hu, X.; Li, Y.; Yang, H.; Luo, Y. Tetrahedron Lett. 2006, 47, 7463.
9. Kröck, L.; Shivanyuk, A.; Goodin, D. B.; Rebek, J., Jr. Chem. Commun. 2004, 273.
10. (a) MacGillivray, L. R.; Atwood, J. L. Chem. Commun. 1999, 181; (b) MacGillivray,
L. R.; Spinney, H. A.; Reid, J. L.; Ripmeester, J. A. Chem. Commun. 2000, 517; (c)
Murayama, K.; Aoki, K. Chem. Commun. 1998, 607; (d) Shivanyuk, A.; Friese, J.
C.; Döring, S.; Rebek, J., Jr. J. Org. Chem. 2003, 68, 6489.
20. Krishna, M. C.; Grahame, D. A.; Samuni, A.; Mitchel, J. B.; Russo, A. Proc. Natl.
Acad. Sci. USA 1992, 89, 5537.
21. (a) Goldstein, S.; Merenyi, G.; Russo, A.; Samuni, A. J. Am. Chem. Soc. 2003, 125,
789; (b) Israeli, A.; Patt, M.; Oron, M.; Samuni, A.; Kohen, R.; Goldstein, S. Free
Radic. Biol. Med. 2005, 38, 317.
22. The samples contained 0.1–0.2 mM NADH, 2.5 mM hypoxantine, 0.05 mM
EDTA, 250 U catalase and 0.01 mM paramagnetic resorcinarenes 2a,b or
0.04 mM 4-hydroxy-TEMPO in 50 mM phosphate buffer (pH 7.4). The
reactions were initiated by adding of xanthine oxidase (0.04 U/mL). EPR
signal intensity of nitroxide was compared to signal intensity measured after
the same time in control sample without NADH. The EPR spectra were
registered at 293 K using 2.5 mW microwave power, 100 kHz field modulation
of 2.0 G and Mn2+/MgO as an internal standard. Samples were accommodated
in 0.8 mm diameter glass capillaries which were placed in a standard EPR tube.
23. (a) Nilsson, U. A.; Olsson, L.-I.; Carlin, G.; Bylund-Fellenius, A.-C. J. Biol. Chem.
1989, 264, 11131; (b) Cimato, A. N.; Piehl, L. L.; Facorro, G. B.; Torti, H. B.;
Hager, A. A. Free Radic. Biol. Med. 2004, 37, 2042.
11. de Heer, M. I.; Mulder, P.; Korth, H. G.; Inhold, K. U.; Lusztyk, J. J. Am. Chem. Soc.
2000, 122, 2355.
12. Tunstad, L. M.; Tucker, J. A.; Dalcanale, E.; Weiser, J.; Bryant, J. A.; Sherman, J.
C.; Helgeson, R. C.; Knobler, C. B.; Cram, D. J. J. Org. Chem. 1989, 54, 1305.
13. (a) Matsushita, Y.-i.; Matsui, T. Tetrahedron Lett. 1993, 34, 7433; (b) Arnecke, R.;
Böhmer, V.; Paulus, E. F.; Vogt, W. J. Am. Chem. Soc. 1995, 117, 3286; (c) Airola,
K.; Böhmer, V.; Paulus, E. F.; Rissanen, K.; Schmidt, C.; Thondorf, I.; Vogt, W.
Tetrahedron 1997, 53, 10709; (d) Luostarinen, M.; Laitinen, T.; Schalley, C. A.;
Rissanen, K. Synthesis 2004, 255.
14. The detailed synthesis procedure and analytical data for compounds 2a and 2b
are given in Supplementary data.
15. The reaction of 1a, 2a–c and model compounds with DPPH was studied at 25 °C
in solution containing of 1.5 mL EtOH and 0.5 mL 0.2 M acetate buffer (pH 5.5).
Various initial concentration of compounds 1a, 2a–c ranging from 0.5 to
24. (a) Pryor, W. A.; Cornicelli, J. A.; Devall, L. J.; Tait, B.; Trivedi, B. K.; Witiak, D. T.;
Wu, M. J. Org. Chem. 1993, 58, 3521; (b) Foti, M.; Piattelli, M.; Baratta, M. T.;
Ruberto, G. J. Agric. Food Chem. 1996, 44, 497.
25. Kinetic measurements were performed as reported in Ref. 24. In our
experiments, reaction mixture contained 0.05 M phosphate buffer (pH 7.4),
0.02% Lubrol, 0.63 mM linoleic acid and 1 mM ABAP. The sample was incubated
under air atmosphere at 37 °C and the change in absorbance was monitored
25
lM, 4-hydroxy-TEMPO (0.01–7.5 mM), resorcinol (0.05–5 mM) and DPPH
(50–100
lM) were used. The ECR50 were calculate from the plots of the
percentage DPPH transformation after 5 min of reaction against the ratio
[Scavenger]/[DPPH]. Values obtained are the average of 3–5 experiments.
16. Bailly, F.; Maurin, C.; Teissier, E.; Vezin, H.; Cotelle, P. Bioorg. Med. Chem. 2004,
12, 5611.
17. (a) Mishra, B.; Priyadarsini, K. I.; Kumar, S. M.; Unnikrishnan, M. K.; Mohan, H.
Bioorg. Med. Chem 2003, 11, 2677; (b) Bielski, B. H. J.; Shiue, G. G.; Bajuk, S. J.
Phys. Chem. 1980, 84, 830.
over time at 234 nm. Inhibition was started by adding of 5 lL of inhibitor
solution to the reaction mixture with the constant rate of autooxidation. The
results are expressed in terms of relative antioxidant efficiency defined as the
ratio of the antioxidant efficiency of the inhibitor to that of Trolox C. The
stoichiometric factors n were determined from the ratio of the lag times for the
various concentrations of test antioxidant and Trolox C, the stoichiometric
factor of which was taken to be 2. The values of RAE represent mean of three
separate determinations and stoichiometric factors n are the average of 3–7
experiments.
18. Krishna, M. C.; Russo, A.; Mitchell, J. B.; Goldstein, S.; Dafni, H.; Samuni, A. J.
Biol. Chem. 1996, 271, 26026.
19. The reaction mixture (50 mM phosphate buffer, pH 7.4) contained 50
xanthine, 75 nitroblue tetrazolium, EDTA (0.1 mM) and 0.5–2
l
l
M
M
26. (a) Barton, D. H. R.; Le Gloahec, V. N.; Smith, J. Tetrahedron Lett. 1998, 39, 7483;
(b) Offer, T.; Samuni, A. Free Radic. Biol. Med. 2002, 32, 872; (c) Goldstein, S.;
Samuni, A. J. Phys. Chem. A 2007, 111, 1066.
l
M
resorcinarenes 2a,b or 4-hydroxy-TEMPO. Stock solution of compounds 2a,b