Divalent cation-mediated interaction between cerebroside sulfate and cerebrosides: An investigation of the effect of structural variations of lipids by electrospray ionization mass spectrometry

Biophysical Journal

Volumn 77, Issue 1, 1999, Pages 306-318

  Koshy, Kalavelil M ^a   Wang, Jianyao ^b,c   Boggs, Joan M ^a,b  

^a HOSPITAL FOR SICK CHILDREN RESEARCH INSTITUTE   (Canada)

^b UNIVERSITY OF TORONTO   (Canada)

^c Apotex Inc   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CALCIUM ION; CEREBROSIDE; DIVALENT CATION; FATTY ACID; GALACTOSYLCERAMIDE; GALACTOSYLTRANSFERASE; GLYCOLIPID; METHANOL; MYELIN; POTASSIUM ION; SULFATIDE; ZINC ION;

ANIMAL EXPERIMENT; ARTICLE; CENTRAL NERVOUS SYSTEM; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONTROLLED STUDY; HYDROXYLATION; LIPID ANALYSIS; MASS SPECTROMETRY; MOUSE; MYELIN SHEATH; MYELINATION; NONHUMAN; PERIPHERAL NERVOUS SYSTEM;

EID: 0032975041     PISSN: 00063495     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-3495(99)76891-8     Document Type: Article

References (56)

1. Angyal, S. J. 1989. Complexes of metal cations with carbohydrates in solution. Adv. Carbohydr. Chem. Biochem. 47:1-43.
2. 13C-NMR studies of D-glucose and D-galactose monosulphates. Carbohydr. Res. 93:177-190.
3. Baca, M., and S. B. H. Kent. 1992. Direct observation of a ternary complex between the dimeric enzyme HIV-1 protease and a substrate based inhibitor. J. Am. Chem. Soc. 114:3992-3993.
4. Boison, D., and W. Stoffel. 1994. Disruption of the compacted myelin sheath of axons of the CNS in PLP-deficient mice. Proc. Natl. Acad. Sci. USA. 91:11709-11713.
5. Bosio, A., E. Binczek, W. F. Haupt, and W. Stoffel. 1998. Composition and biophysical properties of myelin lipid define the neurological defects in galactocerebroside and sulfatide-deficient mice. J. Neurochem. 70: 308-315.
6. Bosio, A., E. Binczek, and W. Stoffel. 1996. Functional breakdown of the lipid bilayer of the myelin membrane in central and peripheral nervous system by disrupted galactocerebroside synthesis. Proc. Natl. Acad. Sci. USA. 93:13280-13285.
7. Bourre, J. M., I. Cloez, M. Galliot, A. Buisine, O. Dumont, M. Picotti, F. Prouillet, and R. Bourdon. 1987. Occurrence of manganese, copper and zinc in myelin. Alterations in the peripheral nervous system of dysmyelinating trembler mutant are at variance with brain mutants (quaking and shiverer). Neurochem. Int. 10:281-286.
8. Bovin, N. V. 1996. Carbohydrate-carbohydrate interactions: a review. Biochemistry (Moscow). 61:694-704.
9. Bugg, C. E. 1973. Calcium binding to carbohydrates. Crystal structure of a hydrated calcium bromide complex of lactose. J. Am. Chem. Soc. 95:908-913.
10. Cadotte, J. E., F. Smith, and D. Spriestersbach. 1952. A new synthesis of glycosides. J. Am. Chem. Soc. 74:1501-1503.
11. Coetzee, T., N. Fujita, J. Dupree, R. Shi, A. Blight, K. Suzuki, and B. Popko. 1996. Myelination in the absence of galactocerebroside and sulfatide: normal structure with abnormal function and regional instability. Cell. 86:209-219.
12. Coetzee, T., K. Suzuki, and B. Popko. 1998. New perspectives on the function of myelin galactolipids. Trends Neurosci. 21:126-130.
13. Cook, W. J., and C. E. Bugg. 1977. Structure of calcium carbohydrate complexes. In Metal Ligand Interactions in Organic Chemistry and Biochemistry, Part 2. B. Pullman and N. Goldblum, editors. Reidel Publishing, Dordrecht, the Netherlands. 231-256.
14. Crook, S. J., J. M. Boggs, A. I. Vistnes, and K. M. Koshy. 1986. Factors affecting surface expression of glycolipids: influence of lipid environment and ceramide composition on antibody recognition of cerebroside sulfate in liposomes. Biochemistry. 25:7488-7494.
15. Dammer, U., O. Popescu, P. Wagner, D. Anselmetti, H.-J. Guntherodt, and G. N. Misevic. 1995. Binding strength between cell adhesion proteoglycans measured by atomic force microscopy. Science. 267:1173-1175.
16. Douglas, B. E., D. H. McDaniel, and J. J. Alexander. 1994. Coordination chemistry. In Concepts and Models of Inorganic Chemistry, 3rd Ed. John Wiley and Sons, New York. 386-401.
17. Dupree, J. L., T. Coetzee, A. Blight, K. Suzuki, and B. Popko. 1998. Myelin galactolipids are essential for proper node of Ranvier formation in the CNS. J. Neurosci. 18:1642-1649.
18. D'Urso, D., P. J. Brophy, S. M. Staugaitis, C. S. Gillespie, A. B. Frey, J. G. Stempak, and D. R. Colman. 1990. Protein zero of peripheral nerve meylin: biosynthesis, membrane insertion and evidence for homotypic interaction. Neuron. 2:449-460.
19. x determinants. A possible basis for cell recognition in preimplantation embryos and in embryonal carcinoma cells. J. Biol. Chem. 264:9476-9484.
20. 2+-coordinated branched trisaccharide isomers: an electrospray ionization and tandem mass spectrometry study. Anal. Chem. 65:2805-2811.
21. Hakomori, S. 1991. Carbohydrate-carbohydrate interaction as an initial step in cell recognition. Pure Appl. Chem. 63:473-482.
22. Huang, R. T. C. 1978. Cell adhesion mediated by glycolipids. Nature. 276:624-626.
23. Jackobs, J. J., R. R. Bumb, and B. Zaslow. 1968. Crystalline structure in oriented fibers of KBr-amylose. Biopolymers. 6:1659-1670.
24. Jorgensen, T. J. D., P. Roepstorff, and A. J. R. Heck. 1998. Direct determination of solution binding constants for noncovalent complexes between bacterial cell wall peptide analogues and vancomycin group antibiotics by electrospray ionization mass spectrometry. Anal. Chem. 70:4427-4432.
25. Kojima, N., and S. Hakomori. 1989. Specific interaction between gangliotriaosylceramide (Gg3) and sialosyllactosylceramide (GM3) as a basis for specific cellular recognition between lymphoma and melanoma cells. J. Biol. Chem. 264:20159-20162.
26. Kojima, N., and S. Hakomori. 1991. Cell adhesion, spreading, and motility of GM3-expressing cells based on glycolipid-glycolipid interaction. J. Biol. Chem. 266:17552-17558.
27. Kojima, N., M. Shiota, Y. Sadahira, K. Handa, and S. Hakomori. 1992. Cell adhesion in a dynamic flow system as compared to static system. J. Biol. Chem. 267:17264-17270.
28. Kopaczyk, K. C., and N. S. Radin. 1965. In vivo conversion of cerebroside and ceramide in rat brain. J. Lipid Res. 6:140-145.
29. 3-sulphate. Lipids. 17:998-1000.
30. Koshy, K. M., and J. M. Boggs. 1983. Partial synthesis and physical properties of cerebroside sulfate containing palmitic or α-hydroxy palmitic acid. Chem. Phys. Lipids. 34:41-53.
31. 3 sulfate by electrospray ionization mass spectrometry. J. Biol. Chem. 271:3496-3499.
32. Langley, J. G., E. Hecquet, I. P. Morris, and D. G. Hamilton. 1997. Direct observation of associative behaviour by electrospray ionization: self-assembly - fact or fiction? Rapid Commun. Mass Spectrom. 11: 165-170.
33. Lee, D. C., I. R. Miller, and D. Chapman. 1986. An infrared spectroscopic study of metastable and stable forms of hydrated cerebroside bilayers. Biochim. Biophys. Acta. 856:266-270.
34. +2 with hydroxy and non-hydroxy fatty acid species of cerebroside sulfate by Fourier transform infrared spectroscopy and molecular modeling. Biochemistry. 36:3438-3447.
35. Misevic, G. N., and M. M. Burger. 1993. Carbohydrate-carbohydrate interactions of a novel acidic glycan can mediate sponge cell adhesion. J. Biol. Chem. 268:4922-4929.
36. Misevic, G. N., J. Finne, and M. M. Burger. 1987. Involvement of carbohydrates as multiple low affinity interaction sites in the self-association of the aggregation factor from the marine sponge Microciona prolifera. J. Biol. Chem. 262:5870-5877.
37. Norton, W. T. 1977. Isolation and characterization of myelin. In Myelin. P. Morell, Ed. Plenum Press, New York. 161-199.
38. Padron, R., L. Mateu, and D. A. Kirschner. 1979. X-ray diffraction study of the kinetics of myelin lattice swelling. Biophys. J. 28:231-240.
39. Polvorinos, A. J., R. R. Contreras, D. Martin-Ramos, J. Romero, and M. A. Hidalgo. 1994. Crystal and molecular structure of methyl α-D-galactopyranoside 3-(sodium sulfate) monohydrate. Carbohydr. Res. 257:1-10.
40. Rendleman, J. A., Jr. 1966. Complexes of alkali metals and alkaline-earth metals with carbohydrates. Adv. Carbohydr. Chem. Biochem. 21: 209-271.
41. Robinson, C. V., E. W. Chung, B. B. Kragelund, J. Knudsen, R. T. Aplin, F. M. Poulsen, and C. M. Dobsen. 1996. Probing the nature of noncovalent interactions by mass spectrometry. A study of protein-CoA ligand binding and assembly. J. Am. Chem. Soc. 118:8646-8653.
42. 2+-dependent carbohydrate association through ion spray mass spectrometry. J. Am. Chem. Soc. 115: 2877-2881.
43. Siuzdak, G., Z. Zheng, J. Y. Ramphal, Y. Ichikawa, K. C. Nicolau, F. C. A. Gaeta, K. S. Chatman, and C.-H. Wong. 1994. Examination of the sialyl Lewis X-calcium complex by electrospray mass spectrometry. Bioorg. Med. Chem. Lett. 4:2863-2866.
44. Smith, R. D., and K. J. Light-Wahi. 1993. The observation of non-covalent interactions in solution by electrospray ionization mass spectrometry: promise, pitfalls and prognosis. Biol. Mass Spectrom. 22:493-501.
45. Spillman, D. 1994. Carbohydrates in cellular recognition: from leucine-zipper to sugar-zipper? Glycoconj. J. 11:169-171.
46. Spillman, D., K. Hard, J. Thomas-Oates, F. G. Vliegenthart, G. Misevic, M. M. Burger, and J. Finne. 1993. Characterization of a novel pyruvylated carbohydrate unit implicated in the cell aggregation of the marine sponge Microciona prolifera. J. Biol. Chem. 268:13378-13387.
47. Spillmann, D., J. Thomas-Oates, A. J. van Kuik, F. G. Vliegenthart, G. N Misevic, M. M. Burger, and J. Finne. 1995. Characterization of a novel sulfated carbohydrate unit implicated in the carbohydrate-carbohydrate-mediated cell aggregation of the marine sponge Microciona prolifera. J. Biol. Chem. 270:5089-5097.
48. Stewart, R. J., and J. M. Boggs. 1993a. The carbohydrate-carbohydrate interaction between galactosylceramide-containing liposomes and cerebroside sulfate-containing liposomes: dependence on the glycolipid ceramide composition. Biochemistry. 32:10666-10674.
49. Stewart, R. J., and J. M. Boggs. 1993b. Exposure of galactosyl-ceramide to galactose oxidase in liposomes: dependence on lipid environment and ceramide composition. Biochemistry. 32:5605-5614.
50. Stoffel, W., and A. Bosio. 1997. Myelin glycolipids and their functions. Curr. Opin. Neurobiol. 7:654-661.
51. Svennerholm, L., and S. Stallberg-Stenhagen. 1968. Changes in the fatty acid composition of cerebrosides and sulfatides of human nervous tissue with age. J. Lipid Res. 9:215-225.
52. Symons, M. C. R., J. A. Benbow, and H. Pelmore. 1984. Interactions between calcium ions and a range of monosaccharides studied by hydroxy-proton resonance spectroscopy. J. Chem. Soc. Faraday Trans. 1:1999-2016.
53. Webb, M. S., C. P. S. Tilcock, and B. R. Green. 1988. Salt-mediated interactions between vesicles of the thylakoid lipid digalactosyldiacyl-glycerol. Biochim. Biophys. Acta. 938:323-333.
54. Whitfield, D. M., S. Stojkovski, and B. Sarkar. 1993. Metal coordination to carbohydrates. Structures and function. Coord. Chem. Rev. 122: 171-225.
55. Yu, Z. W., T. L. Calvert, and D. Leckband. 1998. Molecular forces between membranes displaying neutral glycosphingolipids: evidence for carbohydrate attraction. Biochemistry. 37:1540-1550.
56. Zimmerman, J. W., J. Lindermuth, P. A. Fish, G. P. Palace, T. T. Stevenson, and D. E. De Mong. 1998. A novel carbohydrate-glycosphingolipid interaction between a β-(1-3)-glucan immunomodulator, PGG-glucan, and lactosylceramide of human leukocytes. J. Biol. Chem. 273: 22014-22020.