Structural Basis for Bile Salt Inhibition of Pancreatic Phospholipase A2

Journal of Molecular Biology

Volumn 369, Issue 2, 2007, Pages 439-450

  Pan, Ying H ^a   Bahnson, Brian J ^a  

^a UNIVERSITY OF DELAWARE   (United States)

Author keywords

bile salt; crystallography; inhibition; interfacial enzyme; lipid homeostasis

Indexed keywords

BILE SALT; CARBOXYL GROUP; CHOLIC ACID; GLYCEROPHOSPHOLIPID; GLYCOCHENODEOXYCHOLIC ACID; GLYCOCHOLIC ACID; HYDROXYL GROUP; LIPID EMULSION; PHOSPHOLIPASE A2; TAUROCHENODEOXYCHOLIC ACID; TAUROCHOLIC ACID;

ARTICLE; CATALYSIS; CONTROLLED STUDY; CRYSTAL STRUCTURE; CRYSTALLOGRAPHY; HUMAN; HYDROGEN BOND; LIGAND BINDING; LIPID METABOLISM; PANCREAS; PRIORITY JOURNAL; STOICHIOMETRY; STRUCTURE ACTIVITY RELATION;

EID: 34247556450     PISSN: 00222836     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jmb.2007.03.034     Document Type: Article

References (31)

1. Homan R., and Krause B.R. Established and emerging strategies for inhibition of cholesterol absorption. Curr. Pharmaceut. Design 3 (1997) 29-44
2. Mansbach C.M., and Tso P. In: Kuksis A. (Ed). Intestinal Lipid Metabolism (2000), Kluwer Academic Press, Plenum Publishers, New York
3. Thomson A.B.R., Kelan R.M., Garg M.L., and Clandinin M.T. Intestinal aspects of lipid absorption: In Review. Can. J. Physiol. Pharmacol. 67 (1989) 179-191
4. Homan R., and Jain M.K. Biology, pathology, and interfacial enzymology of pancreatic phospholipase A2. In: Mansbach C.M. (Ed). Intestinal Lipid Metabolism (2001), Kluwer Academic Press, Plenum Publishers, New York 81-104
5. Nalbone G., Lairon D., Charbonnier-Augeire M., Vigne J.L., Leonardi J., Chabert C., et al. Pancreatic phospholipase A2 hydrolysis of phosphatidylcholines in various physicochemical states. Biochim. Biophys. Acta 620 (1980) 612-625
6. Hoffman W.J., Vahey M., and Hajdu J. Pancreatic porcine phospholipase A2 catalyzed hydrolysis of phosphatidylcholine in lecithin-bile salt mixed micelles: kinetic studies in a lecithin-sodium cholate system. Arch. Biochem. Biophys. 221 (1983) 361-370
7. Davidson F.F., and Dennis E.A. Limitations of phosphatidylcholine/deoxycholate mixtures for the analysis of phospholipase A2 inhibition and activation: illustration with annexins. Biochim. Biophys. Acta 1127 (1992) 270-276
8. Borgstrom B. Phosphatidylcholine as substrate for human pancreatic phospholipase A2. Importance of the physical state of the substrate. Lipids 28 (1993) 371-375
9. Jain M.K., Rogers J., Hendrickson H.S., and Berg O.G. The chemical step is not rate-limiting during the hydrolysis by phospholipase A2 of mixed micelles of phospholipid and detergent. Biochemistry 32 (1993) 8360-8367
10. Jain M.K., Egmond M.R., Verheij H.M., Apitz-Castro R., Dijkman R., and De Haas G.H. Interaction of phospholipase A2 and phospholipid bilayers. Biochim. Biophys. Acta 688 (1982) 341-348
11. Apitz-Castro R., Jain M.K., and De Haas G.H. Origin of the latency phase during the action of phospholipase A2 on unmodified phosphatidylcholine vesicles. Biochim. Biophys. Acta 688 (1982) 349-356
12. Berg O.G., and Jain M.K. Interfacial Enzyme Kinetics (2002), Wiley, London
13. Berg O.G., Gelb M.H., Tsai M.D., and Jain M.K. Interfacial enzymology: the secreted phospholipase A2-paradigm. Chem. Rev. 101 (2001) 2613-2654
14. Jain M.K., Tao W.J., Rogers J., Arenson C., Eibl H., and Yu B.Z. Active-site-directed specific competitive inhibitors of phospholipase A2: novel transition-state analogues. Biochemistry 30 (1991) 10256-10268
15. Chakrabarti P., and Samanta U. CH/pi interaction in the packing of the adenine ring in protein structures. J. Mol. Biol. 251 (1995) 9-14
16. Steiner R.A., Rozeboom H.J., de Vries A., Kalk K.H., Murshudov G.N., Wilson K.S., and Dijkstra B.W. X-ray structure of bovine pancreatic phospholipase A2 at atomic resolution. Acta Crystallog. sect. D 57 (2001) 516-526
17. Pan Y.H., Epstein T.M., Jain M.K., and Bahnson B.J. Five coplanar anion binding sites on one face of phospholipase A2: relationship to interface binding. Biochemistry 40 (2001) 609-617
18. Sekar K., Kumar A., Liu X., Tsai M.D., Gelb M.H., and Sundaralingam M. Structure of the complex of bovine pancreatic phospholipase A2 with a transition-state analogue. Acta Crystallog. sect. D 54 (1998) 334-341
19. Small D.M. The physical chemistry of cholanic acids. In: Nair P.P., and Kritchevsky D. (Eds). The Bile Acids: Chemistry, Physiology, and Metabolism vol. 1 (1971), Plenum Press, New York
20. Subuddhi U., and Mishra A.K. Micellization of bile salts in aqueous medium: a fluorescence study. Colloids Surf. B Biointerfaces (2007) 10.1016/j.colsurfb.2007.01.009
21. Ranganathan R., Tcacenco C.M., Rosseto R., and Hajdu J. Characterization of the kinetics of phospholipase C activity toward mixed micelles of sodium deoxycholate and dimyristoylphosphatidylcholine. Biophys. Chem. 122 (2006) 79-89
22. Huggins K.W., Boileau A.C., and Hui D.Y. Protection against diet-induced obesity and obesity-related insulin resistance in Group 1B PLA2-deficient mice. Am. J. Physiol. Endocrinol. Metab. 283 (2002) E994-E1001
23. Richmond B.L., Boileau A.C., Zheng S., Huggins K.W., Granholm N.A., Tso P., and Hui D.Y. Compensatory phospholipid digestion is required for cholesterol absorption in pancreatic phospholipase A(2)-deficient mice. Gastroenterology 120 (2001) 1193-1202
24. Labonte E.D., Kirby R.J., Schildmeyer N.M., Cannon A.M., Huggins K.W., and Hui D.Y. Group 1B phospholipase A2-mediated lysophospholipid absorption directly contributes to postprandial hyperglycemia. Diabetes 55 (2006) 935-941
25. Pan Y.H., Yu B.Z., Singer A.G., Ghomashchi F., Lambeau G., Gelb M.H., et al. Crystal structure of human group X secreted phospholipase A2. Electrostatically neutral interfacial surface targets zwitterionic membranes. J. Biol. Chem. 277 (2002) 29086-29093
26. Brunger A.T., Adams P.D., Clore G.M., Delano W.L., Gros P., Grosse-Kunstleve R.W., et al. Crystallography and NMR systems (CNS): a new software system for macromolecular structure determination. Acta Crystallog. sect. D 54 (1998) 905-921
27. Otwinowski Z., and Minor W. Processing of x-ray diffraction data collected in oscillation mode. Methods Enzymol. 276 (1997) 307-326
28. Navaza J. Implementation of molecular replacement in AMoRe. Acta Crystallog. sect. D 57 (2001) 1367-1372
29. Kraulis P.J. MOLSCRIPT: a program to produce both detailed and schematic plots of protein structures. J. Appl. Crystallog. 24 (1991) 946-950
30. Fenn T., Ringe D., and Petsko G.A. POVScript+: a program for model and data visualization using persistence of vision ray-tracing. J. Appl. Crystallog. 36 (2003) 944-947
31. Nicholls A., Sharp K.A., and Honig B. Protein folding and association: insights from the interfacial and thermodynamic properties of hydrocarbons. Proteins: Struct. Funct. Genet. 11 (1991) 281-296