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Different binding properties of three monoclonal antibodies to sialyl Le(x) glycolipids in a gastric cancer cell line and normal stomach tissue.

We established a mouse monoclonal antibody (Mab) KM93 which recognized sialyl Le(x)-carbohydrate epitope determined by solid phase radioimmunoassay using a panel of authentic glycolipids. The specificity of KM93 was similar to another anti-sialyl Le(x) Mab CSLEX-1 established previously, and different from that of Mab FH6 which recognized sialyl Le(x)-i (sialyl dimeric Le(x)). In a further study, however, we found that KM93 reacted with some glycolipids much more strongly than CSLEX-1 did on thin-layer chromatography (TLC) plates. We purified two gangliosides named K-1 and K-2 from gastric cancer cell line KATOIII, and three gangliosides named H-1, H-2, and H-3 from human stomach. KM93 reacted with all of these glycolipids. CSLEX-1 reacted with K-1 and K-2 with less intensity than KM93 did, and faintly reacted with H-1, but not at all with H-2 or H-3. FH6 did not react with K-1, K-2 or H-1, while it stained H-2 and H-3. In spite of this different reactivity with Mabs, analysis by proton nuclear magnetic resonance (1H NMR) proved that carbohydrate structure of K-1 and H-2 were the same: NeuAc alpha 2-->3Ga1 beta 1-->4 [Fuc alpha 1-->3] G1cNAc beta 1-->3 Ga1 beta 1-->4G1c beta 1-->1Cer. The H1 NMR spectrum of H-3 also indicated that H-3 consisted of the same sugars as K-1. These results indicated that KM93 had wider reactivity than CSLEX-1, and that the distinct reactivity of KM93 from CSLEX-1 was not caused by sugar moiety. It was also shown that the interaction of sialyl Le(x) sugar determinant with MAb depended on the tissue origin of molecules carrying carbohydrate.

Amino Acid Sequence↗
PubMed2000

Characterisation of membrane phospholipids and glycolipids from a halophilic archaebacterium by high-performance liquid chromatography/electrospray mass spectrometry.

Combined high-performance liquid chromatography and electrospray mass spectrometry (LC/ES-MS) has been used for direct characterisation of the polar membrane lipids in total lipid extracts from Halobacterium salinarium, a species of halophilic archaebacterium. The principle phospholipids found were the diphytanyl archaeol phosphatidylglycerol and diphytanyl archaeol phosphatidylglycerolphosphate methyl ester. The application of LC/ES-MS revealed the additional presence of diphytanyl archaeol phosphatidylglycerol sulphate The extracts also contained an archaeol glycolipid, initially detected in preliminary offline ES-MS studies, which was further characterised by LC/ES-MS and by product ion tandem mass spectrometry (MS/MS) as a sulphate ester of diglycosyl-2,3-di-O-phytanyl-sn-glycerol. Whilst archaeol phospho- and glycolipids containing a (C(20)-C(20))-isopranyl glycerol ether core predominated, LC/ES-MS of the extracts from Halobacterium salinarium indicated the presence of an analogue containing one double bond in its isoprenyl ether core as a minor component of the phosphatidylglycerolphosphate methyl ester fraction, providing a further example of the previously recognised existence of isoprenologues of diphytanyl archaeols which occur as minor components of archaebacterial membrane lipids. The value of these techniques in compositional analysis of archaebacterial lipid extracts is discussed.

Archaea↗
PubMed2002

Supramolecular self-assembling properties of membrane-spanning archaeal tetraether glycolipid analogues.

The self-assembling properties of a new series of archaeal tetraether glycolipid analogues 1-6 that are characterized by a bipolar architecture with two similar or different glycosidic and/or phosphate polar heads and a lipid core possessing a cyclopentane unit and/or branched chains were studied by means of differential scanning calorimetry, optical microscopy, X-ray scattering, freeze-fracture electron microscopy and dynamic light scattering. Unsymmetrical phosphate derivatives 1 and 2 spontaneously formed thermostable multilamellar and unilamellar vesicles in which most of the bipolar lipids adopted a trans-membrane conformation, as revealed by freeze-fracture electron microscopy. Supramolecular aggregates of neutral glycolipids 3-6 were found to depend on both the saccharidic polar heads and the chain composition. The presence of one glycosidic residue with rather marked hydrophilic properties, such as the lactosyl moiety, was required to allow the formation of multilamellar vesicles. Surprisingly, the introduction of a cyclopentane unit in the bridging chain was able to induce an apparent two-by-two membrane association: this unusual behaviour might be the result of unsymmetrical interfacial properties of the lipid layer caused by the presence of the cyclopentane unit.

Archaea↗
PubMed1993

Rostrocaudal expression of antibody HNK-1-reactive glycolipids in mouse cerebellum: relationship to developmental compartments and leaner mutation.

Sulfoglucuronylglycolipids (SGGLs) and glycoproteins, reacting with monoclonal antibody HNK-1, are developmentally and spatially regulated in the mammalian cortex and cerebellum. It has been proposed that the HNK-1 carbohydrate epitope is involved in intercellular adhesion and cell-cell interactions. Biochemical analysis and immunocytochemical localization of SGGLs and other neolacto series glycolipids were studied in the leaner mutant mouse cerebellum, where a slow and progressive rostral to caudal degeneration occurs with a gradual loss of both granule cells and Purkinje cells. Biochemical analyses showed that SGGLs and other neolacto series of glycolipids were significantly decreased in the adult leaner cerebellum; however, HNK-1-reactive glycoproteins were not affected. By an immunocytochemical method which selectively localizes the lipid antigens, it is shown that SGGLs are primarily associated with Purkinje cell bodies and their dendrites in the molecular layer and in cerebellar nuclei where Purkinje cell axons terminate. At postnatal day 30 (P30), SGGL immunoreactivity (SGGL-ir) in the leaner cerebellum was reduced moderately compared to normal littermates, which correlated with the minimal degree of Purkinje cell degeneration at this age in leaner and with the biochemical data. At P67 and P90, the SGGL-ir was significantly more reduced in the leaner as Purkinje cell degeneration proceeded. There was a direct correlation between loss of Purkinje cells and SGGL-ir in the cerebellar molecular layer. In both normal and young leaner cerebella, the SGGL-ir in different lobules was not uniform; there were distinct rostrocaudal and mediolateral differences. SGGL-ir was markedly more intense in rostral than in caudal lobules in the vermis, the dividing line being the region immediately caudal to the primary fissure and rostral to the declival sulcus. In the lateral cerebellum, the SGGL-ir was less intense than in the vermis and the rostrocaudal difference was not as pronounced. There was also nonuniformity in the intensity of staining in different folia. The rostrocaudal as well as mediolateral differences in the intensity of SGGL-ir were confirmed independently by biochemical analysis. The differential phenotypic expression of SGGLs and the selective susceptibility to Purkinje cell death in leaner mutant are discussed in relation to the known embryologic and ontogenetic compartmentation of cerebellum.

Animals↗
PubMed1985

Induction of cell differentiation in Burkitt lymphoma lines. BLA: a glycolipid marker of B-cell differentiation.

We have previously described an MAb referred to as 38.13 which reacts with a glycolipid membrane antigen (named BLA) on Burkitt lymphoma (BL) lines. The BLA antigen and other B-cell differentiation markers have been studied on BL lines treated with sodium butyrate, agents from the phorbol-diester series (with or without differentiating properties) and teleocidin. With all differentiation inducers tested, expression of BLA as well as of surface IgM decreased on the induced cells whereas that of BI increased and that of HLA DR remained stable. No BL cells studied reacted with anti-IgD, with B2 or with LBI MAbs, either before or after induction. An EBV-negative line (BJAB) was compared to its Epstein-Barr virus (EBV)-converted subline (BJAB/B95). Both EBV-positive and EBV-negative lines gave comparable results. These data demonstrate that BL cells could be moved along their differentiation pathway by chemical inducers and suggest that BLA represents a new glycolipid marker of early B-cell differentiation.

Antibodies, Monoclonal↗
PubMed1992

Glycolipids carrying Le(y) are preferentially expressed on small-cell lung cancer cells as detected by the monoclonal antibody MLuC1.

The monoclonal antibody MLuC1, which reacts strongly with a high percentage of small-cell lung cancers (SCLC), as well as with various human carcinomas, has been used to immunochemically characterize the recognized epitope (CaMLuC1). To this aim 3 different approaches were adopted: (1) immunoblotting/immunostaining of extracts from various tumor-cell lines; (2) inhibition of binding by purified oligosaccharides; (3) direct binding to oligosaccharide-protein conjugates. All of these experiments indicate that CaMLuC1 is present on the Le(y) blood-group structure heterogeneously expressed on various glycoproteins and glycolipids. The expression of the glycoconjugates carrying Le(y) was then analyzed on breast and lung cancers and on their normal counterparts. Our overall results suggest that SCLC produce Le(y)-active glycolipids in higher amounts compared to other tumors of the same or of a different oncotype, as well as normal lung cells, thus indicating an SCLC-specific modification of the glycosylation pathways.

Antibodies, Monoclonal↗
PubMed2003

Mannosylerythritol lipids, yeast glycolipid biosurfactants, are potential affinity ligand materials for human immunoglobulin G.

Three mannosylerythritol lipids (MEL-A, -B, and -C), yeast glycolipid biosurfactants, were independently attached to poly (2-hydroxyethyl methacrylate) beads (PHEMA), and the three obtained MEL-PHEMA composites were examined for their binding affinity to human immunoglobulin G (HIgG). Of the three composites, the composite bearing MEL-A exhibited the highest binding capacity for HIgG. The binding amount of HIgG increased with increased applied concentration, reaching 106 mg HIgG (per g of composite), with a binding yield of 81%. Interestingly, the protein binding to the composite appeared to follow two different modes (Langmuir type and Freundlich type) depending on the applied concentration. The binding amount of human serum albumin to the composite was much smaller than that of HIgG. The bound human serum albumin, however, had minimal effect on the subsequent binding of HIgG, indicating that the two proteins have different binding sites onto the composite. More significantly, the bound HIgG was efficiently recovered under significantly mild elution conditions: Approximately 90% of the protein was eluted from the composite with phosphate buffer at pH 7. These results indicate that the glycolipid biosurfactant may have great potential as an affinity ligand material for HIgG.

Binding Sites↗
PubMed1994

Capping and receptor-mediated endocytosis of cell-bound verotoxin (Shiga-like toxin). 1: Chemical identification of an amino acid in the B subunit necessary for efficient receptor glycolipid binding and cellular internalization.

The glycolipid globotriaosylceramide (Gb3) is the plasma membrane receptor that mediates the internalization of verotoxin (VT1) into susceptible cells by capping and receptor-mediated endocytosis (RME). Internalization of fluorescein isothiocyanate-conjugated holotoxin into Daudi lymphoma cells was found to be slower than the pentameric receptor binding B subunit alone, suggesting that the A subunit may interact with the membrane to compromise the lateral mobility of the receptor bound B subunit. 3-D reconstruction of fluorescent images by confocal microscopy confirmed the complete internalization of holotoxin. VT1 internalization and cytotoxicity was inhibited by monodansyl cadavarine, which supports a role for clathrin coated pits in the RME of VT1. Biotinylation of the B subunit (in contrast to fluorescein labelling) was found to prevent toxin internalization. This effect correlated with reduced binding of Gb3 and reduced cytotoxicity in vitro. By cleavage of the B subunit at the single tryptophan residue, the reduced Gb3 binding and lack of cellular internalization was shown to be due to the biotinylation of lysine 53 in the VT1 B subunit. This residue was not labelled with fluorescein isothiocyanate in the native protein. This conclusion was confirmed by the finding that biotinylation of VT2c (which contains lys 53) prevented glycolipid receptor binding, whereas biotinylation of VT2e (in which lys 53 is substituted by ile) had no effect.

Amino Acid Sequence↗
PubMed1987

Characterization of human sperm plasma membrane: glycolipids and polypeptides.

The plasma membranes from ejaculated human spermatozoa were removed by nitrogen cavitation (600 PSI for 10 min) and isolated by centrifugation followed by a discontinuous sucrose density gradient centrifugation. Glycolipid analysis of the plasma membrane revealed a three-fold enrichment in gangliosides: GM3 and GD1a/GD1b and neutral glycolipids: globoside and sulfatide as compared to that of whole human sperm. Two dimensional electrophoresis of human sperm plasma membranes revealed about 75 polypeptides. Several of these polypeptides were similar in migration and in display of shape and color to that found in boar sperm plasma membranes.

Cell Membrane↗
PubMed1988

Glycolipid-directed FH6 monoclonal antibody recognizes high molecular weight glycoprotein antigen carrying sialyl Lex-i determinant in the culture supernatant of PC-9 cells.

The properties of the antigen recognized by monoclonal antibody FH6 have been analyzed. FH6 was originally generated against a glycolipid, i.e. a difucoganglioside isolated from human colonic adenocarcinoma, and specifically reacts with sialyl Lex-i determinant. Several culture supernatants of human carcinoma cell line cells were found to have high levels of FH6-reactive antigen, and PC-9, a human lung carcinoma cell line was used for the analysis. A solid-phase sandwich radioimmunoassay was performed to detect the antigen. The antigenic activity was extractable in 0.6 M PCA or 7% TCA, and was sensitive to mild alkaline treatment and to Pronase digestion. Most of the antigen was eluted in the void volume of a Sepharose CL-2B column, which indicates that its molecular weight is greater than several million. It was eluted from a DEAE-cellulose column at a NaCl concentration in the range of 0.2-0.25 M. The immunoaffinity-purified antigen has a high carbohydrate content of more than 80%. These data indicate that the antigen recognized by FH6 in the culture supernatant of PC-9 is not a glycolipid, but a high molecular weight glycoprotein which could be referred to as a mucin, or a proteoglycan, which contains keratan-sulfate like glycosaminoglycan chains, as judged from the results of the glycosidase treatments.

Antibodies, Monoclonal↗
PubMed1990

Sulfate incorporation into peripheral nerve endoneurial glycolipids after crush and permanent transection injury.

The sulfation of peripheral nerve glycolipids was examined at 35 days after both crush injury or permanent transection of the adult rat sciatic nerve by in vitro incorporation of [35S]sulfate into endoneurial slices. These experimental models of neuropathy are characterized by the presence and absence of both axonal regeneration and subsequent myelin assembly. Although the sulfo-glucuronosyl glycosphingolipids (SGGLs) were not detected by alpha-napthol reagent after HPTLC separation of the total acidic lipid extract, fluorographic analysis after sulfate incorporation revealed a 4.7-fold increase in [35S]sulfate in the sulfo-glucuronosyl paragloboside (SGPG) and a 3.5-fold increase in the sulfo-glucuronosyl-lactosaminosyl paragloboside (SGLPG) after the crush injury compared to permanent transection. These [35S]sulfate-labeled lipids were identified by comigration after HPTLC separation by immunostaining with specific IgM monoclonal antibodies from a patient with demyelinating neuropathy and plasma cell dyscrasia. Enhanced incorporation of sulfate in the crushed nerves was also observed in the sulfatides and in several unknown lipids migrating between GM2 and GM3, between GM1, and GM2, slightly above the origin, and at the origin. Since previous studies (Yao and Poduslo: J Neurochem 50:630-638, 1988) have shown [35S]sulfate incorporation, but not [3H]Gal or [3H]Glc, into sulfatides at 35 days after transection, it is possible that the sulfation observed in the present studies does not represent de novo biosynthesis but rather sulfation of an endogenous pool of glycolipids that results from the nerve injury.(ABSTRACT TRUNCATED AT 250 WORDS)

Amino Sugars↗
PubMed1992

Specific binding of cytotactin to sulfated glycolipids.

The binding of the glial glycoprotein, cytotactin, to a variety of purified glycolipids was examined. Clear-cut evidence was found for binding of radiolabeled cytotactin to sulfatides purified from bovine brain, but the molecule did not bind to gangliosides or cerebrosides. The sulfatide binding was sensitive to pH and ionic strength and was dependent on the presence of divalent cations. Binding was inhibited by purified unlabeled cytotactin, by polyclonal antibodies to cytotactin, and by several monosaccharides and polysaccharides. It was not inhibited by fibronectin, a chondroitin sulfate proteoglycan, or the HNK-1 monoclonal antibody, all of which are known to bind to cytotactin. These findings raise the possibilities that sulfated glycolipids may function as cellular receptors for cytotactin and that binding by sulfatides may modulate the varied effects of cytotactin on cellular processes.

Animals↗
PubMed1994

Patterns of reactivity with anti-glycolipid antibodies in human primary brain tumors.

Antibodies against carbohydrates of three glycolipids were used to determine patterns of immunohistochemical reactivity of histologically identifiable cell subpopulations in 101 human primary brain tumors. For all tumor types fibrillary cells, polar cells, and gemistocytes (commonly seen in astrocytomas and ependymomas) stained more frequently for galactosylcerebroside with mAbO1 than small tumor cells and macrophages. Frequency of staining for sulfatide with mAbO4 was fibrillary > polar > small cells = macrophages. Gemistocytes stained more frequently with mAbO4 than polar cells in all tumors except low grade astrocytomas. These data indicate that tumors classified on histological grounds as astrocytic are often stained with antibodies that recognize oligodendrocytes and their progenitors. Thus, anti-glycolipid antibodies used in the study of developmental lineage may offer useful tools for classification of human brain tumors. Staining of fibrillary cells, polar cells, and gemistocytes for paragloboside directly with mAb F1H11 was much less common than with mAbO1, but this increased by pretreatment of the tissues with neuraminidase (F1H11 + N). Of particular note was the finding that small tumor cells frequently stained with F1H11 + N. Evidence that these were not macrophages was obtained using double immunostaining with F1H11 + N and anti-macrophage antibodies. In astrocytomas the frequency of small tumor cells immunostained with F1H11 + N was high grade > anaplastic > low grade, demonstrating a correlation of this tumor cell population with more aggressive astrocytomas. Thus, immunostaining with F1H11 + N may be of value in identifying small, anaplastic tumor cells, especially in small biopsies or tissue taken adjacent to the main tumor mass.

Animals↗
PubMed1978

Glycolipids as indicators of tumorigenesis.

Hyperplastic liver nodules and hepatocellular carcinomas were induced in rats by oral administration of the carcinogen N-2-fluorenylacetamide. Neoplastic tissue was compared with control, fetal, neonatal, and precancerous liver tissues. The development of the tumors was slow, such that temporal changes in the biochemical and morphologic development of carcinogenesis could be identified. Ganglioside sialic acid levels were elevated in all but the most poorly differentiated tumors. Experiments to monitor individual enzymes suggested that the alterations in glycolipid composition were a direct effect of alterations in biosynthetic activities. The pattern during tumorigenesis was the inverse of that during normal development. Also, ganglioside patterns showed a progressive simplification from hyperplastic nodules to well-differentiated hepatomas and through two grades of poorly differentiated hepatomas. An increase in the activity of the branchpoint enzyme of ganglioside biosynthesis preceded both a decrease in the branchpoint enzyme of the disialoganglioside pathway and a marked increase in the galactosyltranferase of GM1 formation. The results indicate that ganglioside deletions are the end result of a cascade of events in the tumorigenic transformation. The onset of ganglioside deletions but not of the cascade per se may correlate with the onset of malignancy. Glycolipid levels are elevated early in certain surrounding tissues especially in the blood. In rats bearing transplantable hepatomas, serum levels of lipid-bound sialic acid were elevated 2.5-fold. Similar results were obtained with sera of mice bearing transplantable mammary carcinomas and of cancer patients. These findings provide new emphasis for gangliosides in both cancer detection and as regulatory signals for growth and multiplication of cells.

Animals↗
PubMed1992

Glycoconjugates are stage- and position-specific cell surface molecules in the developing olfactory system, 1: The CC1 immunoreactive glycolipid defines a rostrocaudal gradient in the rat vomeronasal system.

Primary sensory neurons in the vomeronasal organ (VNO) project axons to the glomeruli of the accessory olfactory bulb (AOB) where they form connections with mitral cell dendrites. We demonstrate here that monoclonal antibodies to specific carbohydrate antigens define stage- and position-specific events during the development of the vomeronasal system (VN). CC1 monoclonal antibodies react with specific N-acetyl galactosamine containing glycolipids. In the embryo, CC1 antigens are expressed throughout the VNO and on vomeronasal nerves. Beginning approximately at birth and continuing into adults, CC1 expression is spatially restricted in the VNO to centrally located cell bodies. In the postnatal AOB, CC1 is expressed in the nerve layer and glomeruli, but only in the rostral half of the AOB. These data suggest that CC1 antigens may participate in the targeting of axons from centrally located VNO neurons to rostral glomeruli in the AOB. In contrast, CC2 monoclonal antibodies, which recognize complex alpha-galactosyl and alpha-fucosyl glycoproteins and glycolipids, react with all VNO cell bodies and VN nerves from embryonic (E) day 15 to adults. CC2 antibodies do not distinguish rostral from caudal regions of the AOB, nor are the CC2 glycoconjugates developmentally regulated. P-Path monoclonal antibodies, which recognize 9-O-acetyl sialic acid, react with cell bodies in the VNO and nerve fibers from E13 to postnatal (P) day 2. P-Path immunoreactivity disappears from the VNO system almost completely by P14, when only a few P-Path reactive nerve fibers can be seen. These studies suggest that specific cell surface glycoconjugates may participate in spatially and temporally selective cell-cell interactions during development and maintenance of vomeronasal connections.

Animals↗
PubMed1995

Accumulation of a novel glycolipid and a betaine lipid in cells of Rhodobacter sphaeroides grown under phosphate limitation.

Cells of the photosynthetic bacterium Rhodobacter sphaeroides grown under phosphate-limiting conditions accumulated nonphosphorous glycolipids and lipids carrying head groups derived from amino acids. Concomitantly, the relative amount of phosphoglycerolipids decreased from 90 to 22 mol% of total polar lipids in the membranes. Two lipids, not detectable in cells grown under standard conditions, were synthesized during phosphate-limited growth. Fast atom bombardment mass spectroscopy, exact mass measurements, 1H NMR spectroscopy, sugar composition analysis, and methylation analysis of the predominant glycolipid led to the identification of the novel compound 1,2-di-O-acyl-3-O-[alpha-D-glucopyranosyl-(1-->4)-O-beta-D-galactopyr anosyl]glycerol. The second lipid was identified as the betaine lipid 1,2-di-O-acyl-[4'-(N,N,N-trimethyl)-homoserine]glycerol by cochromatography employing an authentic standard from Chlamydomonas reinhardtii, fast atom bombardment mass spectroscopy, exact mass measurements, and 1H NMR spectroscopy. Prior to this observation, the occurrence of this lipid was thought to be restricted to lower plants and algae. Apparently, these newly synthesized nonphosphorous lipids, in addition to the sulfo- and the ornithine lipid also found in R. sphaeroides grown under optimal conditions, take over the role of phosphoglycerolipids in phosphate-deprived cells.

Betaine↗
PubMed1999

A fluorescence resonance energy transfer approach for monitoring protein-mediated glycolipid transfer between vesicle membranes.

A lipid transfer protein, purified from bovine brain (23.7 kDa, 208 amino acids) and specific for glycolipids, has been used to develop a fluorescence resonance energy transfer assay (anthrylvinyl-labeled lipids; energy donors and perylenoyl-labeled lipids; energy acceptors) for monitoring the transfer of lipids between membranes. Small unilamellar vesicles composed of 1 mol% anthrylvinyl-galactosylceramide, 1.5 mol% perylenoyl-triglyceride, and 97.5% 1-palmitoyl-2-oleoyl phosphatidylcholine (POPC) served as donor membranes. Acceptor membranes were 100% POPC vesicles. Addition of glycolipid transfer protein to mixtures of donor and acceptor vesicles resulted in increasing emission intensity of anthrylvinyl-galactosylceramide and decreasing emission intensity of the nontransferable perylenoyl-triglyceride as a function of time. The behavior was consistent with anthrylvinyl-galactosylceramide being transferred from donor to acceptor vesicles. The anthrylvinyl and perylenoyl energy transfer pair offers advantages over frequently used energy transfer pairs such as NBD and rhodamine. The anthrylvinyl emission overlaps effectively the perylenoyl excitation spectrum and the fluorescence parameters of the anthrylvinyl fluorophore are nearly independent of the medium polarity. The nonpolar fluorophores are localized in the hydrophobic region of the bilayer thus producing minimal disturbance of the bilayer polar region. Our results indicate that this method is suitable for assay of lipid transfer proteins including mechanistic studies of transfer protein function.

Animals↗
PubMed1999

Adamantyl globotriaosyl ceramide: a monovalent soluble mimic which inhibits verotoxin binding to its glycolipid receptor.

The globotriaosylceramide (Gb3) verotoxin (VT) interaction is one of several examples of glycolipid receptors where the ceramide (or lipid) free oligosaccharides fail to show the expected binding parameters. We present a novel, yet simple strategy to synthesize monovalent, water soluble glycosphingolipid mimics which retain receptor function. Replacing the fatty acid chain with rigid, three dimensional hydrocarbon frames, such as adamantane, gives a novel class of neohydrocarbon glycoconjugates. Such adamantyl conjugates derived from Gb3 showed significantly enhanced solubility in water compared to natural Gb3. Adamantyl-Gb3 showed a thousand fold enhanced inhibitory activity (IC50 = 1 microM) for VT-Gb3 binding as compared to a lipid free Gb3 oligosaccharide derivative, alphaGal1-4betaGal1-4betaGlc1-O-CH2CH(CH2SO2C 4H9)2 (IC50 > 2 mM). This represents a new approach to the generation of antagonists of glycolipid receptors.

Adamantane↗