Mechanism of inhibition of LDL phospholipase A2 by monocyclic-β- lactams. Burst kinetics and the effect of stereochemistry

Biochemistry

Volumn 37, Issue 28, 1998, Pages 10087-10093

  Tew, David G ^a   Boyd, Helen F ^a   Ashman, Stephen ^a   Theobald, Colin ^a   Leach, Colin A ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

4 (PHENYLTHIO) N (4 PHENYL 2 OXOBUTYL)AZETIDIN 2 ONE; BETA LACTAM; LOW DENSITY LIPOPROTEIN PHOSPHOLIPASE A2; SERINE PROTEINASE; THROMBOCYTE ACTIVATING FACTOR; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CONFORMATIONAL TRANSITION; DEACYLATION; DRUG HYDROLYSIS; ENANTIOMER; ENZYME INHIBITION; INHIBITION KINETICS; MASS SPECTROMETRY; PHOTOREACTIVATION; PRIORITY JOURNAL; STEREOCHEMISTRY; STOICHIOMETRY;

1-ALKYL-2-ACETYLGLYCEROPHOSPHOCHOLINE ESTERASE; AZETIDINES; BETA-LACTAMS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ENZYME ACTIVATION; KINETICS; LACTAMS; LIPOPROTEINS, LDL; PHOSPHOLIPASES A; SPECTRUM ANALYSIS; STEREOISOMERISM; SUBSTRATE SPECIFICITY;

EID: 0032516463     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi9801412     Document Type: Article

References (27)

1. Tew, D. G., Southan, C., Rice, S. Q., Lawrence, M. P., Li, H., Boyd, H. F., Moores, K., Gloger, I. S., and Macphee, C. H. (1996) Arterioscler. Thromb. Vasc. Biol. 16, 591-599.
2. Tjoelker, L. W., Wilder, C., Eberhardt, C., Stafforini, D. M., Dietsch, G., Schimpf, B., Hooper, S., Trong, H. L., Cousens, L. S., Zimmerman, G. A., Yamada, Y., McIntyre, T. M., Prescott, S. M., and Gray, P. W. (1995) Nature 374, 549-552.
3. Stremler, K. E., Stafforini, D. M., Prescott, S. M., and McIntyre, T. M. (1991) J. Biol. Chem. 266, 11095-11103.
4. Parthasarathy, S., Steinbrecher, U. P., Barnett, J., Witzum, J. L., and Steinberg, D. (1985) Proc. Natl. Acad. Sci. U.S.A. 82, 3000-3004.
5. Quinn, M. T., Parthasarathy, S., and Steinberg, D. (1988) Proc. Natl. Acad. Sci. U.S.A. 85, 2805-2809.
6. Kume, N., Cybulsky, M. I., and Gimbrone, N. A. (1992) J. Clin. Invest. 90, 1138-1144.
7. Liu, S.-Y., Lu, X., Choy, S., Dembinski, T. C., Hatch, G. M., Mymin, D., Shen, X., Angel, A., Choy, P. C., and Man, R. Y. K. (1994) Cardiovasc. Res. 28, 1476-1481.
8. Svendsen, A. (1994) in Lipases, Their Structure Biochemistry and Application (Woolley, P., and Petersen, S. B., Eds.) pp 1-21.
9. Derewenda, U., Brzozowski, A. M., Lawson, D. M., and Derewenda, Z. S. (1992) Biochemistry 31, 1532-1541.
10. Leuveling Tjeenk, M., Bulsink, Y. B., Slotboom, A. J., Verheij, H. M., de Haas, G. H., Demleitner, G., and Gotz, F. (1994) Protein Eng. 7, 579-583.
11. Bartoli, F., Lin, H. K., Ghomashchi, F., Gelb, M. H., Jain, M. K., and Apitz-Castro, R. (1994) J. Biol. Chem. 269, 15625-15630.
12. Imanaka, T., Moriyama, Y., Ecsedi, G. G., Aoyagi, T., Amanuma-Muto, K., Ohkuma, S., and Takano, Y. (1983) J. Biochem. 94, 1017-1020.
13. Hadvarry, P., Lengsfield, H., and Wolfer, H. (1988) Biochem. J. 256, 357-361.
14. Washburn, W. N., and Dennis, E. A. (1991) J. Biol. Chem. 266, 5042-5048.
15. Leatherbarrow, R. J. (1992) Grafit Version 3.0, Erithacus Software Ltd., Staines, U.K.
16. Iwata-Reuyl, D., Basak, A., Silverman, L. S., Engle, C. A., and Townsend, A. A. (1993) J. Nat. Prod. 56, 1373-1396.
17. Basak, A. (1993) Synth. Commun. 23, 1985-1989.
18. Gaudry, M., and Marquet, A. (1970) Tetrahedron 26, 5611-5615.
19. Knowles, J. R. (1985) Acc. Chem. Res. 18, 97-104.
20. Firestone, R. A., Barker, P. L., Pisano, J. M., Ashe, B. M., and Dahlgren, M. E. (1990) Tetrahedron 46, 2255-2262.
21. Knight, W. B., Chabin, R., and Green, B. (1992) Arch. Biochem. Biophys. 296, 704-708.
22. Hartley, B. S., and Kilby, B. A. (1954) Biochem. J. 56, 288-297.
23. Page, M. G. P. (1993) Biochem. J. 295, 295-304.
24. Waley, S. G. (1991) Biochem. J. 279, 87-94.
25. Ledent, P., and Frere, J.-M. (1993) Biochem. J. 295, 871-878.
26. Charnas, R. L., Fisher, J., and Knowles, J. R. (1978) Biochemistry 17, 2185-2190.
27. Chabin, R., Green, B. G., Gale, P., Maycock, A. L., Weston, H., Dorn, C. P., Finke, P. E., Hagmann, W. K., Hale, J. J., MacCoss, M., Shah, S. K., Underwood, D., Doherty, J. B., and Knight, W. B. (1993) Biochemistry 32, 8970-8980.