Sialylated lactosylceramides

Prokazova, N. V.; Dyatlovitskaya, É. V.; Bergel'son, L. D.

doi:10.1111/j.1432-1033.1988.tb13847.x

Cited by 24 publications

(8 citation statements)

References 47 publications

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“…2D NOE spectra were measured in the phase-sensitive mode by applying time-proportional phase incrementation [9], and in each case the radio-frequency carrier was placed in the middle of the spectrum. The spectra Of G M~ were measured at 310 K with mixing times of 55 ms, 100 ms and 200 ms. For a mixing time of 55 ms, 256 spectra with 128 scans each were accumulated; total accumulation time was about 54 h. The spectra for 100 ms and 200 ms were recorded with 512 tl increments and 32 scans were collected for each t l .…”

Section: ' H -N M R Spectroscopymentioning

confidence: 99%

“…In some instances, to reach a more uniform distribution of magnetization of selectively irradiated protons over the coupled spins, the mixing time was additionally varied, as originally proposed by Braunschweiler and Ernst [8]. Simulated spectra were calculated with the aid of the Bruker PANIC programme.2D NOE spectra were measured in the phase-sensitive mode by applying time-proportional phase incrementation [9], and in each case the radio-frequency carrier was placed in the middle of the spectrum. The spectra Of G M~ were measured at 310 K with mixing times of 55 ms, 100 ms and 200 ms. For a mixing time of 55 ms, 256 spectra with 128 scans each were accumulated; total accumulation time was about 54 h. The spectra for 100 ms and 200 ms were recorded with 512 tl increments and 32 scans were collected for each t l .…”

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confidence: 99%

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Solution conformation of sialosylcerebroside (G_M4) and its NeuAc(α2→3)Galβ sugar component

Poppe

Dąbrowski

Lieth

et al. 1989

European Journal of Biochemistry

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The solution conformations of GM4 ganglioside [NeuAc(a2+3)Gal(Pl -+l)Cer] in (ZH3C)zS0 and its component disaccharide in 'HzO were investigated with the aid of 'H-nuclear magnetic resonance spectroscopy (nuclear Overhauser effect, analysis of coupling constants) and by energy-minimum calculations. The existence of three low-energy conformers obtained by theoretical calculations was supported by experimental findings in the case of GM4, whereas the disaccharide appears to exist as a mixture of two conformers.The sialic-acid-containing glycolipids of cell membranes play an important role as binding sites for various toxins, hormones and viruses, e. g. cholera toxin, thyrotropin, polyoma virus, etc. [ 11. Recent studies concerning the binding affinity of a murine monoclonal antibody to various gangliosides have shown that the antibody recognizes only the NeuAc(a2+3)Galp fragment of monosialogangliosides, regardless of the structure of the remaining part of the molecule [2]. The conformation of different oligosaccharides containing this fragment has been investigated by several research groups [3 -51. Since the results obtained differed considerably, it was of interest to elucidate the conformation of the simplest ganglioside containing this disaccharide unit alone, ( 3~4 . Incidentally, this ganglioside showed the highest binding affinity to the murine monoclonal antibody [2]. Unfortunately, intact gangliosides form micelles under physiological conditions and thus cannot be investigated by high-resolution NMR. It is possible however, that the conformation of the water-solvated sugar moiety of a ganglioside, dispersed in a cell membrane, does not differ significantly from the conformation of the same sugar devoid of ceramide and dissolved in water. There is no direct way of proving this, but it would become more probable if the sugar dissolved in water could be shown to have a conformation similar to that adopted by the sugar moiety within the ganglioside dissolved in a solvent suitable for NMR, e.g. (CH3)zS0. To approach this problem, we investigated GM4 and NeuAc(a2-+3)Galp, both with the aid of nuclear Overhauser enhancement (NOE) and by energyminimum calculations. MATERIALS AND METHODSThe preparation of GM4 and NeuAc(a2-3)Galp was described previously [6]. For IH-NMR measurements, deuterium-exchanged GM4 (2 mg) and NeuAc(a2-+3)Galp (2 mg) were dissolved in 0.4 ml (C2H3)zS0 containing 2% 'HzO, and 0.4 ml 'HZ0 containing 0.1% (CH&CO, respectively. The solutions were then degassed by several freezepump-thaw cycles, flushed with argon and sealed. ' H -N M R spectroscopySpectra were obtained at a frequency of 500 MHz using a Bruker AM-500 spectrometer equipped with an Aspect 3000 computer, a process controller and an array processor. Chemical shifts were referenced indirectly to (CH3)& by setting the 'H signal of residual (CH2Hz)zS0 at 2.49 ppm and the 'H signal of (CH3)'C0 at 2.225 ppm.One-dimensional hoinonuclear Hartmann-Hahn spectroscopy (1 D-HOHAHA) experiments were performed in the reverse mode, by using the pu...

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Section: ' H -N M R Spectroscopymentioning

confidence: 99%

mentioning

confidence: 99%

Solution conformation of sialosylcerebroside (G_M4) and its NeuAc(α2→3)Galβ sugar component

Poppe

Dąbrowski

Lieth

et al. 1989

European Journal of Biochemistry

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“…Structures (Hakomori, 1989;Yu and Saito, 1989), functions (Prokazova et al, 1988;Igarashi et al, 1989;Saito, 1989;Hakomori, 1990;Schnaar, 1991;Zeller and Marchase, 1992;Hakomori and Igarashi, 1995), and metabolism of GSLs (Ledeen, 1989;Schwarzmann and Sandhoff, 1990;van Echten and Sandhoff, 1993) have been widely reviewed. Gangliosides are characterized by the presence of one or more sialic acid units in the oligosaccharide chain.…”

Section: Introductionmentioning

confidence: 99%

Isolation and structural characterization of glycosphingolipids of in vitro propagated bovine aortic endothelial cells

Duvar¹,

Peter‐Katalinić²,

Hanisch

et al. 1997

Glycobiology

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Neutral glycosphingolipids and gangliosides were isolated from 3.7 x 10 9 primary bovine aortic endothelial cells and structurally characterized by immunological and chemical methods. Glucosyl-and lactosylceramide were detected as the main neutral glycosphingolipids (28% and 40% of total orcinol stain, respectively); LcOse 3 Cer and nLcOse 4 Cer were expressed to somewhat minor amounts (16% and 10% of total orcinol stain, respectively), and nLcOse 6 Cer occurred only in trace quantities. No neutral glycosphingolipids of the ganglio-series (GgOse 3 Cer and GgOse 4 Cer) and the globo-series (GbOse 4 Cer and the Forssman antigen) have been detected; only traces of GbOse 3 Cer were identified by TLC immunostaining. Positive CD15 bands obtained by TLC overlay with anti-Gaipi-4(Fucal-3)GlcNAcpi-R antibody indicated the presence of lipid bound Lewis" antigen, whereas the isomeric Lewis 3 structure (Gaipi-3(Fuccd-4)GlcNAcpi-R) was not detectable. G M3 substituted with Neu5Gc and Neu5Ac in a 2:1 ratio was the major ganglioside comprising about 95% within the whole ganglioside fraction. G M3 -structures were further characterized by FAB-MS and GC-MS of the native compounds and their permethylated derivatives. C 18 -sphingosine was the only long chain base, whereas variation occurred due to C^o^a and C 16 fatty acids. Terminally a2-3 sialylated neolacto-series gangliosides with nLcOse 4 -and nLcOse 6 Cer (<5% of total resorcinol stain) were found in almost equal quantities, whereas no a.2-6 sialylated counterparts were detected.

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“…Ganglioside GM3 inhibited growth stimulation by fibro blast growth factor [1], regulated receptor function of epi dermal growth factor [2] and integrin receptor function [3,4], Concerning the effect of the modulation of immune function, ganglioside GM3 showed an inhibitory effect on natural killer cytotoxicity and an enhancement of T sup pressor cell activity [5,6], Moreover, suppresion of interleu kin-2 (IL-2) activity and inhibition of IL-2-and interleu kin-4 (IL-4)-dependent T cell proliferation were observed by the addition of exogenous GM3 [7][8][9]. Thus, these things suggested that GM3 may play a role in the regulation of T lymphocyte functions.…”

Section: Introductionmentioning

confidence: 99%

Ganglioside GM3 Inhibits lnterleukin-3-Dependent Bone Marrow-Derived Mast Cell Proliferation

Fujimaki¹,

Nohara²,

Katayama³

et al. 1995

Int Arch Allergy Immunol

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To investigate the modulated proliferation of an interleukin-3 (IL-3)-dependent cell by exogenous ganglioside GM3, mouse bone marrow-derived mast cells (BMMC) were cultured with various concentrations of GM3 in the presence of IL-3. By 4 weeks of culture, most of the nonadherent cells were alcian blue-positive mast cells. Culturing 2-week-cultured BMMC with GM3 for 1 week reduced the number of alcian blue-positive cells, but the increased total histamine content of BMMC was observed. To examine the effect of GM3 on the synergistic response by IL-3 and interleukin-4 (IL-4), 3-week-cultured BMMC were cultured with GM3 in the presence of IL-3 and IL-4 for 1 week. Although the addition of IL-4 to culture medium increased the number of BMMC, treatment with GM3 reduced its proliferative activity. Concerning the effect of GM3 on cell membrane, there are no changes in the expression of IgE receptors on BMMC treated with GM3 though a low concentration of GM3 increased it. However, the production of tumor necrosis factor-α from BMMC treated with GM3 was significantly suppressed. These results indicate that in vitro treatment with exogenous GM3 inhibited the proliferative response of IL-3-dependent mast cell populations and modulated its characteristics.

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Sialylated lactosylceramides

Cited by 24 publications

References 47 publications

Solution conformation of sialosylcerebroside (G_M4) and its NeuAc(α2→3)Galβ sugar component

Solution conformation of sialosylcerebroside (G_M4) and its NeuAc(α2→3)Galβ sugar component

Isolation and structural characterization of glycosphingolipids of in vitro propagated bovine aortic endothelial cells

Ganglioside GM3 Inhibits lnterleukin-3-Dependent Bone Marrow-Derived Mast Cell Proliferation

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Sialylated lactosylceramides

Cited by 24 publications

References 47 publications

Solution conformation of sialosylcerebroside (GM4) and its NeuAc(α2→3)Galβ sugar component

Solution conformation of sialosylcerebroside (GM4) and its NeuAc(α2→3)Galβ sugar component

Isolation and structural characterization of glycosphingolipids of in vitro propagated bovine aortic endothelial cells

Ganglioside GM3 Inhibits lnterleukin-3-Dependent Bone Marrow-Derived Mast Cell Proliferation

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Solution conformation of sialosylcerebroside (G_M4) and its NeuAc(α2→3)Galβ sugar component

Solution conformation of sialosylcerebroside (G_M4) and its NeuAc(α2→3)Galβ sugar component