Synthesis and convenient functionalization of azide-labeled diacylglycerol analogues for modular access to biologically active lipid probes

Bioconjugate Chemistry

Volumn 19, Issue 9, 2008, Pages 1855-1863

  Smith, Matthew D ^a   Gong, Denghuang ^a   Sudhahar, Christopher G ^b,c   Reno, Justin C ^a   Stahelin, Robert V ^b,c   Best, Michael D ^a  

^a UNIVERSITY OF TENNESSEE   (United States)

^b INDIANA UNIVERSITY SCHOOL OF MEDICINE   (United States)

^c UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CELL MEMBRANES; CELL SIGNALING; CYTOLOGY; GLYCEROL; PHOSPHOLIPIDS; PROTEINS;

ANCHORINGS; BINDING INTERACTION; DIACYLGLYCEROL ANALOGUE; FUNCTIONALIZATIONS; LIPID BINDING; MEMBRANE BINDING; MEMBRANE LIPIDS; MODULARS; PROTEIN MEMBRANE; SITE-SPECIFIC;

BINDING ENERGY;

AZIDE; DIACYLGLYCEROL; GLYCOLIPID; LIPID; PROTEIN KINASE C;

APOPTOSIS; ARTICLE; CELL CYCLE; CYCLOADDITION; DEPROTECTION REACTION; DERIVATIZATION; FLUORESCENCE RESONANCE ENERGY TRANSFER; PROTEIN LIPID INTERACTION; STAUDINGER REACTION; SYNTHESIS;

EID: 52249114702     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc8001002     Document Type: Article

References (66)

1. Cho, W. H., and Stahelin, R. V. (2005) Membrane-protein interactions in cell signaling and membrane trafficking. Annu. Rev. Biophys. Biomol. Struct. 34, 119-151.
2. Colon-Gonzalez, F., and Kazanietz, M. G. (2006) C1 domains exposed: From diacylglycerol binding to protein-protein interactions. Biochim. Biophys. Acta 1761, 827-837.
3. Testerink, C., and Munnik, T. (2005) Phosphatidic acid: a multifunctional stress signaling lipid in plants. Trends Plant Sci. 10, 368-375.
4. Stace, C. L., and Ktistakis, N. T. (2006) Phosphatidic acid-and phosphatidylserine-binding proteins. Biochim. Biophys. Acta 1761, 913-926.
5. McLaughlin, S., Wang, J. Y., Gambhir, A., and Murray, D. (2002) PIP2 and proteins: Interactions, organization, and information flow. Annu. Rev. Biophys. Biomol. Struct. 31, 151-175.
6. Lemmon, M. A. (2003) Phosphoinositide recognition domains. Traffic 4, 201-213.
7. Prestwich, G. D. (2004) Phosphoinositide signaling: From affinity probes to pharmaceutical targets. Chem. Biol. 11, 619-637.
8. Di Paolo, G., and De Camilli, P. (2006) Phosphoinositides in cell regulation and membrane dynamics. Nature 443, 651-657.
9. Lemmon, M. A. (2008) Membrane recognition by phospholipid-binding domains. Nature Rev. Mol. Cell Biol. 9, 99-111.
10. Hurley, J. H. (2006) Membrane binding domains. Biochim. Biophys. Acta 1761, 805-811.
11. Schultz, A., Ling, M., and Larsson, C. (2004) Identification of an amino acid residue in the protein kinase CC1b domain crucial for its localization to the Golgi network. J. Biol. Chem. 279, 31750-31760.
12. Griner, E. M., and Kazanietz, M. G. (2007) Protein kinase C and other diacylglycerol effectors in cancer. Nat. Rev. Cancer 7, 281-294.
13. Mackay, H. J., and Twelves, C. J. (2007) Targeting the protein kinase C family: are we there yet? Nat. Rev. Cancer 7, 554-562.
14. Sampson, S. R., and Cooper, D. R. (2006) Specific protein kinase C isoforms as transducers and modulators of insulin signaling. Mol. Genet. Metab. 89, 32-47.
15. Carrasco, S., and Merida, I. (2007) Diacylglycerol, when simplicity becomes complex. Trends Biochem. Sci. 32, 27-36.
16. Gomez-Fernandez, J. C., and Corbalan-Garcia, S. (2007) Diacylglycerols, multivalent membrane modulators. Chem. Phys. Lipids 148, 1-25.
17. Spitaler, M., and Cantrell, D. A. (2004) Protein kinase C and beyond. Nat. Immunol. 5, 785-790.
18. Gutcher, I., Webb, P. R., and Anderson, N. G. (2003) The isoform-specific regulation of apoptosis by protein kinase C. Cell. Mol. Life Sci. 60, 1061-1070.
19. Wender, P. A., DeBrabander, J., Harran, P. G., Jimenez, J. M., Koehler, M. F. T., Lippa, B., Park, C. M., Siedenbiedel, C., and Pettit, G. R. (1998) The design, computer modeling, solution structure, and biological evaluation of synthetic analogs of bryostatin 1. Proc. Natl. Acad. Sci. U.S.A. 95, 6624-6629.
20. Ghosh, S., Strum, J. C., Sciorra, V. A., Daniel, L., and Bell, R. M. (1996) Raf-1 kinase possesses distinct binding domains for phosphatidylserine and phosphatidic acid - Phosphatidic acid regulates the translocation of Raf-1 in 12-O-tetradecanoylphorbol-13-acetate-stimulated Madin-Darby canine kidney cells. J. Biol. Chem. 271, 8472-8480.
21. Mott, H. R., Carpenter, J. W., Zhong, S., Ghosh, S., Bell, R. M., and Campbell, S. L. (1996) The solution structure of the Raf-1 cysteine-rich domain: A novel Ras and phospholipid binding site. Proc. Natl. Acad. Sci. U.S.A. 93, 8312-8317.
22. Improta-Brears, T., Ghosh, S., and Bell, R. M. (1999) Mutational analysis of Raf-1 cysteine rich domain: Requirement for a cluster of basic aminoacids for interaction with phosphatidylserine. Mol. Cell. Biochem. 198, 171-178.
23. Rizzo, M. A., Shome, K., Vasudevan, C., Stolz, D. B., Sung, T. C., Frohman, M. A., Watkins, S. C., and Romero, G. (1999) Phospholipase D and its product, phosphatidic acid, mediate agonist-dependent Raf-1 translocation to the plasma membrane and the activation of the mitogen-activated protein kinase pathway. J. Biol. Chem. 274, 1131-1139.
24. Rizzo, M. A., Shome, K., Watkins, S. C., and Romero, G. (2000) The recruitment of Raf-1 to membranes is mediated by direct interaction with phosphatidic acid and is independent of association with Ras. J. Biol. Chem. 275, 23911-23918.
25. Andresen, B. T., Rizzo, M. A., Shome, K., and Romero, G. (2002) The role of phosphatidic acid in the regulation of the Ras/MEK/Erk signaling cascade. FEBS Lett. 531, 65-68.
26. Hekman, M., Hamm, H., Villar, A. V., Bader, B., Kuhlmann, J., Nickel, J., and Rapp, U. R. (2002) Associations of B- and C-raf with cholesterol, phosphatidylserine, and lipid second messengers - Preferential binding of Raf to artificial lipid rafts. J. Biol. Chem. 277, 24090-24102.
27. Ghosh, S., Moore, S., Bell, R. M., and Dush, M. (2003) Functional analysis of a phosphatidic acid binding domain in human Raf-1 kinase - Mutations in the phosphatidate binding domain lead to tail and trunk abnormalities in developing zebrafish embryos. J. Biol. Chem. 278, 45690-45696.
28. Wittinghofer, A., and Waldmann, H. (2000) Ras - A molecular switch involved in tumor formation. Angew. Chem., Int. Ed. 39, 4193-4214.
29. Gupta, S., Ramjaun, A. R., Haiko, P., Wang, J., Warne, P. H., Nicke, B., Nye, E., Stamp, G., Alitalo, K., and Downward, J. (2007) Binding of Ras to phosphoinositide 3-kinase p110α is required for Ras-driven tumorigenesis in mice. Cell 129, 957- 968.
30. Overduin, M., and Cheever, M. L. (2001) Signaling with phosphoinositides: better than binary. Mol. Intervent. 1, 150-159.
31. Misra, S., Miller, G. J., and Hurley, J. H. (2001) Recognizing phosphatidylinositol 3-phosphate. Cell 107, 559-562.
32. Pendaries, C., Tronchere, H., Plantavid, M., and Payrastre, B. (2003) Phosphoinositide signaling disorders in human diseases. FEBS Lett. 546, 25-31.
33. Rzepecki, P. W., and Prestwich, G. D. (2002) Synthesis of hybrid lipid probes: Derivatives of phosphatidylethanolamine-extended phosphatidylinositol 4,5-bisphosphate (Pea-PIP2). J. Org. Chem. 67, 5454-5460.
34. Fernandes, R. A. (2007) An efficient synthesis of (-)-posticlure: The sex pheromone of Orgyia postica. Eur. J. Org. Chem. 5064-5070.
35. Wroblewski, A. E., and Glowacka, I. E. (2005) Enantiomerically pure 4-amino-1,2,3-trihydroxybutylphosphonic acids. Tetrahedron 61, 11930-11938.
36. Glacon, V., Benazza, M., El Anzi, A., Beaupere, D., and Demailly, G. (2004) Synthesis of alpha,omega-diazidoalditol derivatives via both bis- or tris-cyclic sulfites and peracetylated alpha,omega-dibromoalditols as bielectrophilic intermediates. J. Carbohydr. Chem. 23, 95-110.
37. Stahelin, R. V., Digman, M. A., Medkova, M., Ananthanarayanan, B., Rafter, J. D., Melowic, H. R., and Cho, W. H. (2004) Mechanism of diacylglycerol-induced membrane targeting and activation of protein kinase C delta. J. Biol. Chem. 279, 29501-29512.
38. Stahelin, R. V., and Cho, W. H. (2001) Differential roles of ionic, aliphatic, and aromatic residues in membrane-protein interactions: A surface plasmon resonance study on phospholipases A(2). Biochemistry 40, 4672-4678.
39. Stahelin, R. V., Long, F., Diraviyam, K., Bruzik, K. S., Murray, D., and Cho, W. H. (2002) Phosphatidylinositol 3-phosphate induces the membrane penetration of the FYVE domains of Vps27p and Hrs. J. Biol. Chem. 277, 26379-26388.
40. Mammen, M., Choi, S. K., and Whitesides, G. M. (1998) n. Polyvalent interactions in biological systems: Implications for design and use of multivalent ligands and inhibitors. Angew. Chem., Int. Ed. 37, 2755-2794.
41. Kiessling, L. L., Gestwicki, J. E., and Strong, L. E. (2006) Synthetic multivalent ligands as probes of signal transduction. Angew. Chem., Int. Ed. 45, 2348-2368.
42. 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 synthesis, folding, and phorbol ester binding of the cysteine-rich domains of all protein kinase C isozymes. J. Am. Chem. Soc. 120, 9159-9167.
43. Prestwich, G. D. (1996) Touching all the bases: Synthesis of inositol polyphosphate and phosphoinositide affinity probes from glucose. Acc. Chem. Res. 29, 503-513.
44. Thum, O., Chen, J., and Prestwich, G. D. (1996) Synthesis of a photoaffinity analogue of phosphatidylinositol 3,4-bisphosphate, an effector in the phosphoinositide 3-kinase signaling pathway. Tetrahedron Lett. 37, 9017-9020.
45. Chaudhary, A., Chen, J., Gu, Q. M., Witke, W., Kwiatkowski, D. J., and Prestwich, G. D. (1998) Probing the phosphoinositide 4,5-bisphosphate binding site of human profilin I. Chem. Biol. 5, 273-281.
46. Manifava, M., Thuring, J., Lim, Z. Y., Packman, L., Holmes, A. B., and Ktistakis, N. T. (2001) Differential binding of traffic-related proteins to phosphatidic acid- or phosphatidylinositol (4,5)-bisphosphate-coupled affinity reagents. J. Biol. Chem. 276, 8987-8994.
47. Lim, Z. Y., Thuring, J. W., Holmes, A. B., Manifava, M., and Ktistakis, N. T. (2002) Synthesis and biological evaluation of a PtdIns(4,5)P-2 and a phosphatidic acid affinity matrix. J. Chem. Soc., Perkin Trans. 1, 1067-1075.
48. Picq, M., Huang, Y., Lagarde, M., Doutheau, A., and Nemoz, G. (2002) Synthesis of photoreactive phosphatidic acid analogues displaying activatory properties on cyclic AMP-phosphodiesterases. Photoaffinity labeling of an isoform of phosphodiesterase. J. Med. Chem. 45, 1678-1685.
49. Chen, J., Profit, A. A., and Prestwich, G. D. (1996) Synthesis of photoactivatable 1,2-O-diacyl-sn-glycerol derivatives of L-phosphatidyl-D-myo-inositol 4,5-bisphosphate (Pt-dInsP(2)) and 3,4,5-trisphosphate (PtdInsP(3)). J. Org. Chem. 61, 6305-6312.
50. Lewis, W. G., Green, L. G., Grynszpan, F., Radic, Z., Carlier, P. R., Taylor, P., Finn, M. G., and Sharpless, K. B. (2002) Click chemistry in situ: Acetylcholinesterase as a reaction vessel for the selective assembly of a femtomolar inhibitor from an array of building blocks. Angew. Chem., Int. Ed. 41, 1053-1057.
51. Kolb, H. C., Finn, M. G., and Sharpless, K. B. (2001) Click chemistry: Diverse chemical function from a few good reactions. Angew. Chem., Int. Ed. 40, 2004-2021.
52. Rostovtsev, V. V., Green, L. G., Fokin, V. V., and Sharpless, K. B. (2002) A stepwise Huisgen cycloaddition process: Coppers-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew. Chem., Int. Ed. 41, 2596-2599.
53. Saxon, E., Armstrong, J. I., and Bertozzi, C. R. (2000) A "traceless" Staudinger ligation for the chemoselective synthesis of amide bonds. Org. Lett. 2, 2141-2143.
54. Saxon, E., and Bertozzi, C. R. (2000) Cell surface engineering by a modified Staudinger reaction. Science 287, 2007-2010.
55. Kohn, M., and Breinbauer, R. (2004) The Staudinger ligation-A gift to chemical biology. Angew. Chem., Int. Ed. 43, 3106-3116.
56. Spencer, T A., Wang, P. Z., Li, D. S., Russel, J. S., Blank, D H., Huuskonen, J., Fielding, P. E., and Fielding, C. J. (2004) Benzophenone- containing cholesterol surrogates: synthesis and biological evaluation. J. Lipid Res. 45; 1510-1518.
57. Smith, M., Khorana, H. G., Rammler, D. H., and Goldberg, I. H. (1962) Studies on polynucleotides 0.14. Specific synthesis of C3′-C5′ interrribonucleotide linkage - syntheses of uridylyl-(3′-5′)-uridine and uridylyl-(3′-5′)-adenosine. J. Am. Chem. Soc. 84, 430.
58. Kodali, D. R., Tercyak, A., Fahey, D. A., and Small, D. M. (1990) Acyl migration in 1,2-dipalmitoyl-sn-glycerol. Chem. Phys. Lipids 52, 163-170.
59. Jiang, G. W., Xu, Y., and Prestwich, G. D. (2006) Practical enantiospecific syntheses of lysobisphosphatidic acid and its analogues. J. Org. Chem. 71, 934-939.
60. Baker, D. C., Haskell, T. H., Putt, S. R., and Sloan, B. J. (1979) Prodrugs of 9-(beta-D-arabinofuranosyl)adenine 0.2. Synthesis and evaluation of a number of 2′,3′-di-O-acyl derivatives and 3′,5′-di-O-acyl derivatives. J. Med. Chem. 22, 273-279.
61. Kubiak, R. J., and Bruzik, K. S. (2003) Comprehensive and uniform synthesis of all naturally occurring phosphorylated phosphatidylinositols. J. Org. Chem. 68, 960-968.
62. Reese, C. B., and Yan, H. B. (2002) Solution phase synthesis of ISIS 2922 (Vitravene) by the modified H-phosphonate approach. J. Chem. Soc., Perkin Trans. 1, 2619-2633.
63. Wu, P., and Brand, L. (1994) Resonance energy transfer: methods and applications. Anal. Biochem. 218, 1-13.
64. Clegg, R. M. (1995) Fluorescence resonance energy transfer. Curr. Opin. Biotechnol. 6, 103-110.
65. Sapsford, K. E., Berti, L., and Medintz, I. L. (2006) Materials for fluorescence resonance energy transfer analysis: Beyond traditional donor-acceptor combinations. Angew. Chem., Int. Ed. 45, 4562-4588.
66. Hatanaka, Y., and Sadakane, Y. (2002) Photoaffinity labeling in drug discovery and developments: Chemical gateway for entering proteomic frontier. Curr. Top. Med. Chem. 2, 271-288.