Long-chain aminoalcohol and diamine derivatives induce apoptosis through a caspase-3 dependent pathway

Bioorganic and Medicinal Chemistry Letters

Volumn 12, Issue 18, 2002, Pages 2621-2626

  Del Olmo, Esther ^a   Macho, Antonio ^b   Alves, Mario ^a   López, José L ^a   Banoua, Fadwa ^b   Muoz, Eduardo ^b   San Feliciano, Arturo ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

^b Universidad de Cordoba   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; AMINE; AMINOALCOHOL; CASPASE 3; DIAMINE; DNA FRAGMENT; HYDROGEN;

APOPTOSIS; ARTICLE; ATOM; CELL CYCLE G1 PHASE; CELL CYCLE S PHASE; CONTROLLED STUDY; DRUG MECHANISM; DRUG POTENCY; DRUG SYNTHESIS; ENZYME ACTIVATION; FLOW CYTOMETRY; HUMAN; HUMAN CELL; LEUKEMIA CELL LINE; MEMBRANE POTENTIAL; MITOCHONDRIAL MEMBRANE;

AMINO ALCOHOLS; APOPTOSIS; CASPASE 3; CASPASES; DIAMINES; G1 PHASE; HUMANS; JURKAT CELLS; S PHASE;

EID: 0037119698     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(02)00476-6     Document Type: Article

References (40)

1. Kerr J.F.R., Wyllie A.H., Currie A.R. Apoptosis. 26:1972;239.
2. (a) Newmeyer D.D., Farschon D.M., Reed J.C. Cell. 79:1994;353.
3. (b) Kroemer G., Zamzami N., Susín S.A. Immunol. Today. 18:1997;44.
4. (a) Vayssière J.L., Petit P.X., Risler Y., Mignotte B. Proc. Natl. Acad. Sci. U.S.A. 91:1994;11752.
5. (b) Zamzami N., Marchetti P., Castedo M., Decaudin D., Macho A., Hirsch T., Susín S.A., Petit P.X., Mignotte B., Kroemer G. J. Exp. Med. 182:1995;367.
6. (c) Macho A., Decaudin D., Castedo M., Hirsch T., Susín S.A., Zamzami N., Kroemer G. Cytometry. 25:1996;333.
7. (a) Susin S.A., Zamzami N., Castedo M., Hirsch T., Marchetti P., Macho A., Daugas E., Geuskens M., Kroemer G. J. Exp. Med. 184:1996;1331.
8. (b) Yang J., Liu X.S., Bhalla K., Kim C.N., Ibrado A.M., Cai J.Y., Peng T.I., Jones D.P., Wang X.D. Science. 275:1997;1129.
9. (c) Kluck R.M., Bossywetzel E., Green D.R., Newmeyer D.D. Science. 275:1997;1132.
10. (a) Nicholson D.W. Cell Death Differ. 6:1999;1028.
11. (b) Thornberry N.A., Lazebnik Y. Science. 281:1998;1312.
12. (c) Hengartner M.O. Nature. 407:2000;770.
13. (a) Castedo M., Macho A., Zamzami N., Hirsch T., Marchetti P., Uriel J., Kroemer G. Eur, J. Immunol. 25:1996;3277.
14. (b) Zamzami N., Marchetti P., Castedo M., Zanin C., Vayssière J.L., Petit P.X., Kroemer G. J. Exp. Med. 181:1995;1661.
15. (c) Quillet-Mary A., Jaffrezou J.P., Mansat V., Bordier C., Naval J., Laurent G. J. Biol. Chem. 272:1997;21388.
16. (a) Krammer P.H. Nature. 407:2000;789.
17. (b) Susin S.A., Zamzami N., Castedo M., Daugas E., Wang H.G., Geley S., Fassy F., Reed J.C., Kroemer G. J. Exp. Med. 186:1997;25.
18. (a) France-Lanord V., Brugg B., Michel P.P., Agid Y., Ruberg M. J. Neurochem. 69:1997;1612.
19. (b) Mignotte B., Vayssière J.L. Eur. J. Biochem. 252:1998;1.
20. (c) Macho A., Calzado M.A., Muñoz Blanco J., Gómez Díaz C., Gajate C., Mollinedo F., Navas P., Muñoz E. Cell Death Differ. 6:1999;155.
21. (a) Padron J.M., Martin V.S., Hadjipavlou-Litina D., Noula C., Constantinou-Kokotou V., Peters G.J., Kokotos G. Bioorg. Med. Chem. Lett. 9:1999;821.
22. (b) Lucas R., Ubeda A., Payá M., Alves M., del Olmo E., López J.L., San Feliciano A. Bioorg. Med. Chem. Lett. 10:2000;285.
23. (a) Kokotos G., Theodorou V., Constantinou-Kokotou V., Gibbons W.A., Roussakis C. Bioorg. Med. Chem. Lett. 8:1998;1525.
24. (b) Constantinou-Kokotou V., Kokotos G., Roussakis C. Anticancer Res. 18:1998;3439. See ref 9(a).
25. Karikas G.A., Constantinuo-Kokotou V., Kokotos G. J. Liq. Chrom. Rel. Technol. 20:1997;1789.
26. Gibbons W.A., Hughes R.H., Charalambous M., Christodoulou M., Szeto A., Aulabauh A.E., Mascagni P., Toth I. Liebigs Ann. Chem. 1990;1175.
27. Kokotos G. Synthesis. 1990;299.
28. Kokotos, G.; Constantinou-Kokotou, V. J. Chem. Res. (S) 1992, 391. Kokotos, G.; Constantinou-Kokotou, V. J. Chem. Res. (M) 1992, 3117.
29. Kokotos, G.; Constantinou-Kokotou, V. J. Chem. Res. (S) 1992, 391. Kokotos, G.; Constantinou-Kokotou, V. J. Chem. Res. (M) 1992, 3117.
30. Otherwise indicated, all reagents were from Sigma Chemical Co. (St. Louis, MO, USA). Flow cytofluorimetric analyses were carried out on an Epics XL Analyzer (Coulter, Hialeah, FL, USA).
31. 1 fraction).
32. 3,3′-Dihexyloxacarbocyanine iodide, (Molecular Probes, Eugene, OR, USA).
33. In this method, fixation in formaldehyde prevents extraction of low molecular weight DNA from apoptotic cells and thus the cell cycle distribution estimates both apoptotic and non-apoptotic cells.
34. The AMC liberated was measured using a spectrofluorometer (Hitachi F-2500 model, Hitachi Ltd., Tokyo, Japan) with an excitation wavelength of 380 nm and an emission wavelength range of 400-550 nm. Data were collected as the integer of relative fluorescence intensity minus the background fluorescence. As a control, the cell-permeable caspase-3 inhibitor zDEVD-fmk (Bachem, Bubendorf, Switzerland) was used.
35. hlow (preapoptotic cells, top-left compartment). Results are representative of five independent experiments.
36. 50 apoptotic concentrations of compounds 2a, 3a, and 4b for 6 h, lysed and 30 μg of protein from cell extracts were incubated with the specific caspase-3 substrate Ac-DEVD-AMC for 1 h at 37°C. Results represent the integer of relative fluorescence intensity from the AMC liberated from reaction minus the background fluorescence. The activation of caspase-3 by compounds 2a was inhibited in the presence of zDEVD-fmk (20 μM). Values are means±SE of three independent experiments.
37. Hartley A., Stone J.M., Heron C., Cooper J.M., Schapira A.H.V. J. Neurochem. 63:1994;1987.
38. (a) Marzo I., Brenner C., Zamzami N., Susin S.A., Beutner G., Brdiczka D., Remy R., Xie Z.H., Reed J.C., Kroemer G. J. Exp. Med. 187:1998;1261.
39. (b) Nicolli A., Basso E., Petronilli V., Wenger R.M., Bernardi P. J. Biol. Chem. 271:1996;2185.
40. 2/M phases separated by vertical lines and the DNA strand breaks (Y-axis) analysed by flow cytometry. Results are representative of three different experiments.