Identification of an alcohol binding site in the first cysteine-rich domain of protein kinase C δ

Protein Science

Volumn 15, Issue 9, 2006, Pages 2107-2119

  Das, Joydip ^a,b   Zhou, Xiaojuan ^a   Miller, Keith W ^a,b  

^a MASSACHUSETTS GENERAL HOSPITAL   (United States)

^b HARVARD MEDICAL SCHOOL   (United States)

Author keywords

Anesthesia; Binding site; Diazirine; Fluorescence; Mass spectrometry; Photolabeling; Protein kinase C

Indexed keywords

3 AZIBUTANOL; 3 AZIOCTANOL; 7 AZIOCTANOL; ALCOHOL; ALKANOL; BUTANOL; CYSTEINE; GLUTAMIC ACID; LYSINE; OCTANOL; PROTEIN KINASE C DELTA; TRYPSIN; TYROSINE; UNCLASSIFIED DRUG;

ALKYLATION; AMINO ACID SEQUENCE; ARTICLE; BINDING SITE; CONTROLLED STUDY; ENZYME ANALYSIS; ENZYME BINDING; ENZYME PURIFICATION; ESCHERICHIA COLI; FLUORESCENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MOLECULAR CLONING; NONHUMAN; PHOTOAFFINITY LABELING; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN DOMAIN; PROTEIN EXPRESSION; PROTEIN PURIFICATION; STOICHIOMETRY;

ALCOHOLS; AMINO ACID SEQUENCE; ANIMALS; BINDING SITES; CIRCULAR DICHROISM; DIAZOMETHANE; DIGLYCERIDES; MASS SPECTROMETRY; MICE; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PHORBOL ESTERS; PROTEIN BINDING; PROTEIN KINASE C-DELTA; PROTEIN STRUCTURE, TERTIARY; SEQUENCE HOMOLOGY, AMINO ACID; STAINING AND LABELING;

ESCHERICHIA COLI;

EID: 33748155296     PISSN: 09618368     EISSN: 1469896X     Source Type: Journal    
DOI: 10.1110/ps.062237606     Document Type: Article

References (40)

1. Addona, G.H., Husain, S.S., Stehle, T., and Miller, K.W. 2002. Geometric isomers of a photoactivable general anesthetic delineate a binding site on adenylate kinase. J. Biol. Chem. 277: 25685-25691.
2. Alifimoff, J.K., Firestone, L.L., and Miller, K.W. 1989. Anaesthetic potencies of primary alkanols: Implications for the molecular dimensions of the anesthetic site. Br. J. Pharmacol. 96: 9-16.
3. Bohm, G., Muhr, R., and Jaenicke, R. 1992. Quantitative analysis of protein far UV circular dichroism spectra by neural networks. Protein Eng. 5: 191-195.
4. Brunner, J. 1993. New photolabeling and crosslinking methods. Annu. Rev. Biochem. 62: 483-514.
5. Canagarajah, B., Leskow, F.C., Ho, J.Y., Mischak, H., Saidi, L.F., Kazanietz, M.G., and Hurley, J.H. 2004. Structural mechanism for lipid activation of the Rac-specific GAP, β2-chimaerin. Cell 119: 407-418.
6. Cho, W. 2001. Membrane targeting by C1 and C2 domains. J. Biol. Chem. 276: 32407-32410.
7. Church, R.F.R. and Weiss, M.J. 1970. Diazirines. II. Synthesis and properties of small functionalized diazirine molecules. Some observations on the reaction of a diazirine with the iodine-iodide ion system. J. Org. Chem. 35: 2465-2471.
8. Das, J., Addona, G.H., Sandberg, W.S., Husain, S.S., Stehle, T., and Miller, K.W. 2004a. Identification of a general anesthetic binding site in the diacylglycerol-binding domain of protein kinase Cδ. J. Biol. Chem. 279: 37964-37972.
9. Das, J., Stehle, T., and Miller, K.W. 2004b. Identification of an alcohol-binding site in the second cysteine-rich domain of protein kinase Cδ by X-ray crystallography. Biophys. J. 86: 508a.
10. Dodson, B.A., Braswell, L.M., and Miller, K.W. 1987. Barbiturates bind to an allosteric regulatory site on nicotinic acetylcholine receptor-rich membranes. Mol. Pharmacol. 32: 119-126.
11. Eng, J.K., McCormack, A.L., and Yates, J.R. 1994. An approach to correlate tandem mass spectral data of peptides with amino acid sequences in a protein database. J. Am. Soc. Mass Spectrom. 5: 976-989.
12. Hemmings Jr., H.C. and Adamo, A.I. 1994. Effects of halothane and propofol on purified brain protein kinase C activation. Anesthesiology 81: 147-155.
13. Husain, S.S., Forman, S.A., Kloczewiak, M.A., Addona, G.H., Olsen, R.W., Pratt, M.B., Cohen, J.B., and Miller, K.W. 1999. Synthesis and properties of 3-(2-hydroxyethyl)-3-n-pentyldiazirine, a photoactivable general anesthetic. J. Med. Chem. 42: 3300-3307.
14. Husain, S.S., Ziebell, M.R., Ruesch, D., Hong, F., Arevalo, E., Kosterlitz, J.A., Olsen, R.W., Forman, S.A., Cohen, J.B., and Miller, K.W. 2003. (3-Methyl-3H-diaziren-3-yl)ethyl 1-(1-phenylethyl)-1H-imidazole-5-carboxylate: A derivative of the stereoselective general anesthetic etomidate for photolabeling ligand-gated ion channels. J. Med. Chem 46: 1257-1265.
15. Irie, K., Oie, K., Nakahara, A., Yanai, Y., Ohigashi, H., Wender, P.A., Fukuda, H., Konishi, H., and Kikkawa, U. 1998. Molecular basis for protein kinase C isozyme-selective binding: The systhesis, folding, and phorbol ester binding of the cysteine-rich domains of all protein kinase C isozymes. J. Am. Chem. Soc. 120: 9159-9167.
16. Kinter, M. and Sherman, N.E. 2000. Protein sequencing and identification using tandem mass spectrometry. Wiley-Interscience, New York.
17. Laskowski, R.A., MacArthur, W., Moss, D., and Thornton, J.M. 1993. PROCHECK: A program to check the stereochemical quality of protein structures. J. Appl. Crystallogr. 26: 283-291.
18. Levitt, M. 1992. Accurate modeling of protein conformation by automatic segment matching. J. Mol. Biol. 226: 507-533.
19. Levitt, M., Hirshberg, M., Sharon, R., and Daggett, V. 1995. Potential energy function and parameters for simulations of the molecular dynamics of proteins and nucleic acids in solution. Comput. Phys. Commun. 91: 215-231.
20. Lund, O., Nielsen, M., Lundegaard, C., and Worning, P. 2002. X3M: A computer program to extract 3D models. In CASP5 methods abstracts, p. A102. CASP5, Asilomar, CA.
21. Luthy, R., Bowie, J.U., and Eisenberg, D. 1992. Assessment of protein models with three-dimensional profiles. Nature 5: 583-585.
22. Newton, A.C. 2001. Protein kinase C: Structural and spatial regulation by phosphorylation, cofactors, and macromolecular interactions. Chem. Rev. 101: 2353-2364.
23. Peng, J. and Gygi, S.P. 2001. Proteomics: The move to mixtures. J. Mass Spectrom. 36: 1083-1091.
24. Perczel, A., Park, K., and Fasman, G.D. 1992. Analysis of the circular dichroism spectrum of proteins using the convex constraint algorithm: A practical guide. Anal. Biochem. 203: 83-93.
25. Pettersen, E.F., Goddard, T.D., Huang, C.C., Couch, G.S., Greenblatt, D.M., Meng, E.C., and Ferrin, T.E. 2004. UCSF Chimera-A visualization system for exploratory research and analysis. J. Comput. Chem. 25: 1605-1612.
26. Pu, Y., Perry, N.A., Yang, D., Lewin, N.E., Kedei, N., Braun, D.C., Choi, S.H., Blumberg, P.M., Garfield, S.H., Stone, J.C., et al. 2005. A novel diacylglycerol-lactone shows marked selectivity in vitro among C1 domains of protein kinase C (PKC) isoforms α and δ as well as selectivity for RasGRP compared with PKCα. J. Biol. Chem. 280: 27329-27338.
27. Quest, A.F., Bardes, E.S., Xie, W.Q., Willott, E., Borchardt, R.A., and Bell, R.M. 1995. Expression of protein kinase C γ regulatory domain elements containing cysteine-rich zinc-coordinating regions as glutathione S-transferase fusion proteins. Methods Enzymol. 252: 153-167.
28. Rappsilber, J., Ishihama, Y., and Mann, M. 2003. Stop and go extraction tips for matrix-assisted laser desorption/ionization, nanoelectrospray, and LC/MS sample pretreatment in proteomics. Anal. Chem. 75: 663-670.
29. Rebecchi, M.J. and Pentyala, S.N. 2002. Anaesthetic actions on other targets: Protein kinase C and guanine nucleotide-binding proteins. Br. J. Anaesth. 89: 62-78.
30. Shen, N., Guryev, O., and Rizo, J. 2005. Intramolecular occlusion of the diacylglycerol-binding site in the C1 domain of munc13-1. Biochemistry 44: 1089-1096.
31. Sigrist, H., Muhlemann, M., and And Dolder, M. 1990. Philicity of amino acid side-chains for photogenerated carbenes. J. Photochem. Photobiol. B 7: 277-287.
32. Slater, S.J., Cox, K.J., Lombardi, J.V., Ho, C., Kelly, M.B., Rubin, E., and Stubbs, C.D. 1993. Inhibition of protein kinase C by alcohols and anaesthetics. Nature 364: 82-84.
33. Slater, S.J., Ho, C., Kelly, M.B., Larkin, J.D., Taddeo, F.J., Yeager, M.D., and Stubbs, C.D. 1996. Protein kinase Cα contains two activator binding sites that bind phorbol esters and diacylglycerols with opposite affinities. J. Biol. Chem. 271: 4627-4631.
34. Slater, S.J., Kelly, M.B., Larkin, J.D., Ho, C., Mazurek, A., Taddeo, F.J., Yeager, M.D., and Stubbs, C.D. 1997. Interaction of alcohols and anesthetics with protein kinase Cα. J. Biol. Chem. 272: 6167-6173.
35. Slater, S.J., Taddeo, F.J., Mazurek, A., Stagliano, B.A., Milano, S.K., Kelly, M.B., Ho, C., and Stubbs, C.D. 1998. Inhibition of membrane lipid-independent protein kinase Cα activity by phorbol esters, diacylglycerols, and bryostatin-1. J. Biol. Chem. 273: 23160-23168.
36. Slater, S.J., Malinowski, S., and Stubbs, C.D. 2004. The nature of hydrophobic n- alkanol binding site within the C1 domains of protein kinase Cα. Biochemistry 43: 7601-7609.
37. Stahelin, R.V., Digman, M.A., Medkova, M., Ananthanarayanan, B., Rafter, J.D., Melowic, H.R., and Cho, W. 2004. Mechanism of diacylglycerol-induced membrane targeting and activation of protein kinase Cδ. J. Biol. Chem. 279: 29501-29512.
38. Xu, R.X., Pawelczyk, T., Xia, T.H., and Brown, S.C. 1997. NMR structure of a protein kinase C-γ phorbol-binding domain and study of protein-lipid micelle interactions. Biochemistry 36: 10709-10717.
39. Zhang, G., Kazanietz, M.G., Blumberg, P.M., and Hurley, J.H. 1995. Crystal structure of the cys2 activator-binding domain of protein kinase C δ in complex with phorbol ester. Cell 81: 917-924.
40. Ziebell, M.R., Nirthanan, S., Husain, S.S., Miller, K.W., and Cohen, J.B. 2004. Identification of binding sites in the nicotinic acetylcholine receptor for [3H]azietomidate, a photoactivatable general anesthetic. J. Biol. Chem. 279: 17640-17649.