The recognition of three different epitopes for the H-type 2 human blood group determinant by lections ofUlex europaeus, Galactia tenuiflora andPsophocarpus tetragonolobus (Winged Bean)

Du, Ming-Hui; Spohr, Ulrike; Lemieux, R. U.

doi:10.1007/bf00731281

Cited by 39 publications

(44 citation statements)

References 43 publications

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“…The a(1,2)-linked fucose transferred by FUT1, can be detected by the lectin UEA-I. 24 As shown in Figure 1, HepG2 cells are not stained with UEA-I (Fig. 1a, left panel), indicating that these cells do not express a(1,2)-fucosylated glycoconjugates and suggesting that they are deficient in FUT1 activity.…”

Section: Sugar Analysismentioning

confidence: 92%

Introducing α(1,2)‐linked fucose into hepatocarcinoma cells inhibits vasculogenesis and tumor growth

Mathieu¹,

Gerolami²,

Luis³

et al. 2007

Intl Journal of Cancer

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The glycoantigen sialyl-Lewis x (sLex) and its isomer sialy-Lewis a (sLea) are frequently associated with advanced states of cancer and metastasis. In a previous work, we have shown that hepatocarcinoma cells (HCC) HepG2 interact with the endothelial Eselectin exclusively through sLe x oligosaccharides, the synthesis of which could be completely prevented by the a(1,2)-fucosyltransferase-I (FUT1), thus resulting in a strong inhibition of adhesion and rolling on activated endothelial cells. The purpose of the present study was to evaluate the impact of inhibiting sLex synthesis and the subsequent E-selectin adhesion, on HCC tumor growth in nude mice. Four weeks after subcutaneous transplantation of cells, no FUT1-derived tumor could be detected, whereas 75% of control animals developed large size tumor nodules. Between the 4th and the 8th week postinoculation, 33% tumors arose from FUT1-transduced cells but showed a slow growth (nodule volumes less than 500 mm 3 ), while more than 50% of control tumors reached volumes between 1,500 and 3,000 mm 3 . Several parameters were examined, including cell division and proliferation, apoptosis, adhesion to extracellular matrix components and angiogenesis/vasculogenesis. We provide evidence that among all, vasculogenesis was the most clearly affected by FUT1 expression, suggesting that tumor angiomorphogenesis may, at least partly, depend on Eselectin-mediated interaction between HCC and endothelial cells, the inhibition of which remarkably retards tumor growth. ' 2007 Wiley-Liss, Inc.Key words: a(1,2)-fucosyltransferase-I; E-selectin; sialyl-Lewis; antitumor; vasculogenesisThe sialyl-Lewis antigens (sLex and sLea) are blood grouprelated antigens naturally expressed on leukocytes to initiate leukocyte-endothelium interaction mediated by the cytokine-inducible endothelial adhesion molecule E-selectin. 1,2 In addition to this physiological role in inflammation, sialyl-Lewis antigens are also considered as tumor markers expressed on many cancer cells and therefore, they are thought to be involved in metastasis by initiating tumor cell-endothelium adhesion. 3 Indeed, the expression of sialyl-Lewis antigens on carcinoma cells is frequently associated with advanced states of cancer and a statistically relevant relationship has been established between the postoperative prognosis of patients and the degree of expression of sialyl-Lewis antigens on cancer tissues. 3 Besides, several lines of evidence from selectin-deficient mice studies pointed out the contribution of selectins in facilitating tumor growth and progression. 4,5 In particular, E-selectin and its sLex-containing glycoconjugate ligands have been shown to be involved in the essential events of tumor angiogenesis, 6-9 including the fact that coinjection of tumor cells expressing high level of sLe x together with endothelial cells constitutively expressing E-selectin, has been found to promote tumor angiogenesis and growth. 10 We have recently succeeded in strongly blocking the expression of sLex on digestive cancer cells...

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Section: Sugar Analysismentioning

confidence: 92%

Introducing α(1,2)‐linked fucose into hepatocarcinoma cells inhibits vasculogenesis and tumor growth

Mathieu¹,

Gerolami²,

Luis³

et al. 2007

Intl Journal of Cancer

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“…Although not without precedent (8), the use of fluoride ion to open the stannylene ring formed on reactions of 1 with di-tzbutyltin oxide is noteworthy. Except for the preparation of 47, bromide-ion catalyzed glycosylations (16,17) were used to establish the interunit a-D linkages of the various congeners of methyl a-isomaltoside (29).…”

Section: Synthesismentioning

confidence: 99%

“…Except for 6 and 12, the 2,3,4-trisubstituted derivatives of methyl a-D-glucopyranosides (17-21), reported in Scheme 2, were prepared as previously reported (8). All of the bromides reported in Scheme 3 were prepared from literature compounds.…”

Section: General Procedures For Bromide-ion Catalyzedmentioning

confidence: 99%

“…The protein combining site is normally a shallow cavity (3,4) within which several-attractive polar interactions are established (5). It was reasonable to expect that the acceptance of an oligosaccharide into the active site of an enzyme is a similar event and that our recently established method (6)(7)(8) based on the differential effects on the extent of binding that result from monodeoxygenation and mono-0-methylation would shed light on the epitope that is presented to the enzyme for the recognition and binding that provides the catalysis.…”

Section: Introductionmentioning

confidence: 99%

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Chemical mapping of the active site of the glucoamylase ofAspergillus niger

et al. 1996

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Abstract:A recently developed technique for the probing of the combining sites of lectins and antibodies, to establish the structure of the epitope that is involved in the binding of an oligosaccharide, is used to study the binding of methyl aisomaltoside by the enzyme glucoamylase. The procedure involved the determination of the effects on the kinetics of hydrolysis of both monodeoxygenation and mono-0-methylation at each of the seven hydroxyl groups in order to gain an estimate of the differential changes in the free energies of activation, AAG' . As expected, from previous publications, both deoxygenation and 0-methylation of OH-4 (reducing unit), OH-4', or OH-6' strongly hindered hydrolysis, whereas the kinetics were virtually unaffected by either the substitutions at OH-2 or structural changes at C-I. The substitutions at OH-3 caused increases of 2.1 and 1.9 kcallmol in the AAG'. In contrast, whereas deoxygenation of either OH-2' or OH-3' caused much smaller (0.96 and 0.52 kcallmol) increases in AAG', the mono-0-methylations resulted in severe steric hindrance to the formation of the activated complex. The relatively weak effects of deoxygenation suggest that the hydroxyl groups are replaced by water molecules and thereby participate in the binding by contributing effective complementarity. Methyl a-isomaltoside was docked into the combining site of the X-ray crystal structure at 2.4 A resolution of the complex with the inhibitor acarbose. A fit free of steric interactions with the protein was found that has the methyl a-glucopyranoside unit in the normal "C, conformation and the other glucose unit approachin a half-chair conformation with the interunit fragment defined by the torsion angles +IIJJ/W = 74°/1340/ % 166' (0-5'-C-l'h-64-6%-5-0-5).The model provides a network of hydrogen bonds that appears to well represent the activated complex formed by the glucoamylase with both maltose and isomaltose since the structures appear to provide a sound rationale for both the specificity and catalysis provided by the enzyme.Key war-ds: monodeoxy and mono-0-methyl derivatives of methyl a-isomaltoside, enzyme binding domain, functioning of glucoamylase, differential changes in free energy of activation, characteristics of hydrogen bonding networks. Resum6: Dans le but d'Ctudier la fixation de l'a-isomaltoside de mCthyle par l'enzyme glucoamylase, on a fait appel B une technique, dCveloppCe rCcemment pour I'examen des sites de fixation des lectines et des anticorps, pour Ctablir la structure de I'Cpitope impliqui dans la fixation d'un oligosaccharide. I,a procCdure implique la dktermination des effets, provoquCs sur la cinCtique d'hydrolyse, par la monodCsoxygCnation ainsi que la mono-0-methylation de chacun des sept groupes hydroxyles; on espitre ainsi obtenir une evaluation des changements diffkrentiels dans les Cnergies libres d'activation, AAG'. Tel qu'on peut s'y attendre sur la base des publications antkrieures, tant la dCsoxygCnation que la 0-mtthylation des groupes OH-4 (unit6 rkductrice), OH-4' ou OH-6' empsc...

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“…5) establish the concept of differential conformer selection by lectins [Siebert et al, 1996;Poppe et al, 1997;Gilleron et al, 1998;von der Lieth et al, 1998;Harris et al, 1999]. Not only different sections of functional groups of a carbohydrate ligand are relevant for binding, as documented for example for plant, animal and bacterial galactoside-or plant blood group H (type 2)-trisaccharide-binding lectins by chemical mapping [Rivera-Sagredo et al, 1991;Du et al, 1994;Haataja et al, 1994;Solís et al, 1994;Solís and Díaz-Mauriño, 1997]. Importantly, each of the conformations in solution can be selected by different receptors as bioactive.…”

Section: How Lectins and Carbohydrate Ligands Interactmentioning

confidence: 99%

Towards Defining the Role of Glycans as Hardware in Information Storage and Transfer: Basic Principles, Experimental Approaches and Recent Progress

Solı́s¹,

Jiménez‐Barbero²,

Kaltner³

et al. 2000

Cells Tissues Organs

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The term ‘code’ in biological information transfer appears to be tightly and hitherto exclusively connected with the genetic code based on nucleotides and translated into functional activities via proteins. However, the recent appreciation of the enormous coding capacity of oligosaccharide chains of natural glycoconjugates has spurred to give heed to a new concept: versatile glycan assembly by the genetically encoded glycosyltransferases endows cells with a probably not yet fully catalogued array of meaningful messages. Enciphered by sugar receptors such as endogenous lectins the information of code words established by a series of covalently linked monosaccharides as letters for example guides correct intra- and intercellular routing of glycoproteins, modulates cell proliferation or migration and mediates cell adhesion. Evidently, the elucidation of the structural frameworks and the recognition strategies within the operation of the sugar code poses a fascinating conundrum. The far-reaching impact of this recognition mode on the level of cells, tissues and organs has fueled vigorous investigations to probe the subtleties of protein-carbohydrate interactions. This review presents information on the necessarily concerted approach using X-ray crystallography, molecular modeling, nuclear magnetic resonance spectroscopy, thermodynamic analysis and engineered ligands and receptors. This part of the treatise is flanked by exemplarily chosen insights made possible by these techniques.

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The recognition of three different epitopes for the H-type 2 human blood group determinant by lections ofUlex europaeus, Galactia tenuiflora andPsophocarpus tetragonolobus (Winged Bean)

Cited by 39 publications

References 43 publications

Introducing α(1,2)‐linked fucose into hepatocarcinoma cells inhibits vasculogenesis and tumor growth

Introducing α(1,2)‐linked fucose into hepatocarcinoma cells inhibits vasculogenesis and tumor growth

Chemical mapping of the active site of the glucoamylase ofAspergillus niger

Towards Defining the Role of Glycans as Hardware in Information Storage and Transfer: Basic Principles, Experimental Approaches and Recent Progress

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