1918
T. Miron et al. / European Journal of Medicinal Chemistry 45 (2010) 1912–1918
Scheme 8. The S-allyl mixed disulfide exchange reactions (a 2 step general scheme).
quantitatively by HPLC separation at different time periods and
their molecular weight was determined by (ESI-MS).
Acknowledgement
This work was supported by grants from La Foundation Raphael
et Regina Levy and the Atran Foundation.
References
[1] A. Stoll, E. Seebeck, Adv. Enzymol. 11 (1951) 377–400.
[2] T. Miron, A. Rabinkov, D. Mirelman, M. Wilchek, L. Weiner, Biochim. Biophys.
Acta 1463 (2000) 20–30.
[3] H.J. Bremer, M. Duran, J.P. Kamerling, H. Przyrembel, S.K. Wadman, in:
H.J. Bremer, M. Duran, J.P. Kamerling, H. Przyrembel, S.K. Wadman (Eds.),
Disturbance of Amino Acid Metabolism: Clinical Chemistry and Diagnosis,
Urban & Schwarzenberg, Baltimore-Munich, 1981, pp. 80–82.
[4] A. Meister, M.E. Anderson, Annu. Rev. Biochem. 52 (1983) 711–760.
[5] F.Q. Schafer, G.R. Buettner, Free Radic. Biol. Med. 30 (2001) 1191–1212.
[6] D.F. Dourado, P.A. Fernandes, M.J. Ramos, Curr. Protein Pept. Sci. 9 (2008) 325–337.
[7] M.M. Gallogly, J.J. Mieyal, Curr. Opin. Pharmacol. 7 (2007) 381–391.
[8] D.M. Townsend, Mol. Interv. 7 (2007) 313–324.
[9] I. Dalle–Donne, A. Milzani, N. Gagliano, R. Colombo, D. Giustarini, R. Rossi,
Antioxid. Redox Signal. 10 (2008) 445–473.
[10] J.J. Mieyal, M.M. Gallogly, S. Qanungo, E.A. Sabens, M.D. Shelton, Antioxid.
Redox Signal. 10 (2008) 1941–1988.
[11] J. Milner, J. Nutr. 136 (2006) 827S–831S.
[12] J.T. Pinto, C. Qiao, J. Xing, R.S. Rivlin, M.L. Protomastro, M.L. Weissler, et al., Am.
J. Clin. Nutr. 66 (1997) 398–405.
[13] S. Biswas, A.S. Chida, I. Rahman, Biochem. Pharmacol. 71 (2006) 551–564.
[14] S.K.Jensen, R.E.Hansen, J.R. Winther, Antioxid.RedoxSignal.11 (2009)1047–1058.
[15] A. Rabinkov, T. Miron, D. Mirelman, M. Wilchek, S. Glozman, E. Yavin, et al.,
Biochim. Biophys. Acta 1499 (2000) 144–153.
Scheme 9. A general scheme depicting the fate of allicin and S-allylmercapto deriv-
atives in cells.
5.2.6. S-allylthio-2-nitro-5-thiobenzoate(SA-NTB) [20](compound 6)
[16] M. Azarkan, A. El Moussaoui, D. van Wuytswinkel, G. Dehon, Y. Looze,
J. Chromatogr. B 790 (2003) 229–238.
[17] I.A. Cotgreave, R. Gerdes, I. Schuppe-Koistinen, C. Lind, Meth. Enzymol. 348
(2002) 175–182.
[18] T. Miron, A. Rabinkov, E. Peleg, T. Rosenthal, D. Mirelman, M. Wilchek, Am. J.
Hypertens. 17 (2004) 71–73.
[19] T. Miron, F. Arditti, L. Konstantinovski, A. Rabinkov, D. Mirelman, A. Berrebi, et
al., Eur. J. Med. Chem. 44 (2009) 541–550.
1H NMR (400 MHz, DMSO)
d in ppm: 8.0 (d,1H), 7.86 (d,1H), 7.84
(dd, 1H), 5.77 (m, 1H), 5.1 (m, 2H), 3.49 (d, 2H). [M þ Na] at m/z 294.
5.3. Modification of proteins with S-allyl derivatives
Protein modification was carried out at a ratio of protein: S-allyl
derivative (1:10) at pH 6.2–7.4 in buffer (acetate or phosphate) for
18–24 h. After purification proteins were subjected to ESI-MS
analysis.
[20] T. Miron, A. Rabinkov, D. Mirelman, L. Weiner, M. Wilchek, Anal. Biochem. 265
(1998) 317–325.
[21] M. Patya, M.A. Zahalka, A. Vanichkin, A. Rabinkov, T. Miron, D. Mirelman, et al.,
Int. Immunol. 16 (2004) 275–281.
[22] Y. Meyer, B.B. Buchanan, F. Vignols, J.P. Reichheld [Epub ahead of print]. Annu.
Rev. Genet. (2009).
[23] H. Nian, B. Delage, J.T. Pinto, R.H. Dashwood, Carcinogenesis 29 (2008) 1816–1824.
[24] L.D. Lawson, Z.J. Wang, Planta Med. 59 (Suppl.) (1993) A688–A689.
[25] F. Freeman, Y. Kodera, J. Agric. Food Chem. 43 (1995) 2332–2338.
[26] Y.L. Zhang, Z.Y. Zhang, Anal. Biochem. 261 (1998) 139–148.
[27] T. Miron, H. SivaRaman, A. Rabinkov, D. Mirelman, M. Wilchek, Anal. Biochem.
351 (2006) 152–154.
5.4. The reaction of glutathione with various S-allylthio-derivatives
GSH was added at 1:1 or 10:1 M ratios to S-allyl mixed disulfide
(AS-SX), X representing; captopril, 6-mercaptopurine (6-MP) or 6-
mercaptopurine riboside (6-MPR), in phosphate buffer pH 5.5–7.2
at room temperature. The reaction products were analyzed
[28] G.L. Ellman, Arch. Biochem. Biophys. 82 (1959) 70–77.
[29] P.W. Riddles, R.L. Blakeley, B. Zerner, Anal. Biochem. 94 (1979) 75–81.