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Search for "adhesion" in Full Text gives 107 result(s) in Beilstein Journal of Organic Chemistry.
Clicked and long spaced galactosyl- and lactosylcalix[4]arenes: new multivalent galectin-3 ligands
Beilstein J. Org. Chem. 2014, 10, 1672–1680, doi:10.3762/bjoc.10.175
- plasmon resonance; Introduction Lectins are carbohydrate-binding proteins (CBP) [1][2][3] without any catalytic or immunogenic activity. In the latest decades, they attracted an increasing interest due to their involvement in a series of fundamental biological processes such as cell adhesion, cell
- conformations [18][19]. A few years ago we [20][21] reported about the synthesis and inhibitory properties of a small library of lactosylthioureidocalixarenes and found that the cone derivatives I and III (Figure 1) were able to efficiently inhibit the adhesion of Gal-3 to tumor cells in vitro, but not that of
Photoswitchable precision glycooligomers and their lectin binding
Beilstein J. Org. Chem. 2014, 10, 1603–1612, doi:10.3762/bjoc.10.166
- potential perspectives for the sensing and adhesion of bacteriological targets on various substrates. The examples reported so far make use of azobenzene [16], a well-known photochromic compound offering robustness and straightforward preparation. It is able to reversibly isomerize between an extended and
Glycosystems in nanotechnology: Gold glyconanoparticles as carrier for anti-HIV prodrugs
Beilstein J. Org. Chem. 2014, 10, 1339–1346, doi:10.3762/bjoc.10.136
- related to HIV envelope [18]. GNPs coated with oligomannosides of the gp120 (manno-GNPs) were able to inhibit the DC-SIGN-mediated HIV-1 trans-infection of human T-cells [19] and gold glyconanoparticles coated with sulfated ligands showed to interfere with the adhesion/fusion of HIV during its entry [20
Human dendritic cell activation induced by a permannosylated dendron containing an antigenic GM3-lactone mimetic
Beilstein J. Org. Chem. 2014, 10, 1317–1324, doi:10.3762/bjoc.10.133
- (Figure 1) was able to elicit in vivo antimelanoma antibodies [32]. More recently [33], we established that the multivalent presentation of this synthetic mimetic positively interferes with human melanoma cell (A375) adhesion, migration and resistance to apoptosis, showing a clear amplification of the
Continuous flow nitration in miniaturized devices
Beilstein J. Org. Chem. 2014, 10, 405–424, doi:10.3762/bjoc.10.38
Towards a biocompatible artificial lung: Covalent functionalization of poly(4-methylpent-1-ene) (TPX) with cRGD pentapeptide
Beilstein J. Org. Chem. 2013, 9, 270–277, doi:10.3762/bjoc.9.33
- -acid sequence. We chose cRGD pentapeptide 1b derived from lysine precursor 1a, as cRGD’s intensively studied by the Kessler group [6][7][8][9] are well-established cell-recognition motifs that can trigger integrin-mediated cell adhesion [9]. Because of the high potential to stimulate this, these RGD
- ]. Finally, TPX surfaces 8a and 8b functionalized with cRGD behaved differently regarding their cell-adhesion properties (Figure 5e and 5g). These tests strongly indicate that copper-catalyzed attachment of cRGD pentapeptides only provides a minor increase of biocompatibility, despite the fact that the
- copper-free “click” protocols on TPX surfaces. Finally, cRGD-functionalized TPX membrane surfaces showed excellent biocompatibility regarding the adhesion of endothelial cells. These studies pave the way for the development of improved, extracorporeal oxygenators. We believe that the combination of
Synthesis and testing of the first azobenzene mannobioside as photoswitchable ligand for the bacterial lectin FimH
Beilstein J. Org. Chem. 2013, 9, 223–233, doi:10.3762/bjoc.9.26
- control of carbohydrate-specific bacterial adhesion, it has become our goal to synthesise azobenzene mannosides as photoswitchable inhibitors of type 1 fimbriae-mediated adhesion of E. coli. An azobenzene mannobioside 2 was prepared and its photochromic properties were investigated. The E→Z isomerisation
- was found to be highly effective, yielding a long-lived (Z)-isomer. Both isomers, E and Z, show excellent water solubility and were tested as inhibitors of mannoside-specific bacterial adhesion in solution. Their inhibitory potency was found to be equal and almost two orders of magnitude higher than
- adhesive surfaces. Keywords: azobenzene glycosides; bacterial adhesion; E/Z photoisomerisation; FimH antagonists; mannobiosides; molecular switches; sweet switches; Introduction Adhesion of bacteria to surfaces can be a severe problem both in vivo and in vitro. Hence, inhibition of bacterial adhesion by
Efficient synthesis of phenylene-ethynylene rods and their use as rigid spacers in divalent inhibitors
Beilstein J. Org. Chem. 2013, 9, 215–222, doi:10.3762/bjoc.9.25
- obtained after deprotection of the alkyne moieties with K2CO3. Preliminary application As part of our program on bacterial adhesion inhibition by multivalent carbohydrates, the bacterial lectin LecA, a virulence factor of the problematic pathogen Pseudomonas aeruginosa is a target of interest [30][31
Flow photochemistry: Old light through new windows
Beilstein J. Org. Chem. 2012, 8, 2025–2052, doi:10.3762/bjoc.8.229
- reduce the risk of product adhesion. In this way the reactor could be run continuously for over 16 hours. Compared to the batch process the maleic anhydride dimer 88 was formed in a higher purity since over-irradiation is avoided. A higher overall conversion can be achieved by continuous filtering of the
Self-assembled organic–inorganic magnetic hybrid adsorbent ferrite based on cyclodextrin nanoparticles
Beilstein J. Org. Chem. 2012, 8, 1867–1876, doi:10.3762/bjoc.8.215
- available binding sites, to bond or interact through intermolecular forces with the inorganic matrix, and high surface area, which is important to improve the MHM adsorption and adhesion properties. In order to design a MHM based on Fe-Ni/Zn with adsorption properties for environmental use, cyclodextrins
Mannose-decorated cyclodextrin vesicles: The interplay of multivalency and surface density in lectin–carbohydrate recognition
Beilstein J. Org. Chem. 2012, 8, 1543–1551, doi:10.3762/bjoc.8.175
- are proteins that bind to specific carbohydrates on the cell surface and activate biochemical responses [2]. In this way, protein–carbohydrate interactions regulate cell division, protein synthesis, the immune system, and the adhesion of cells. A well-known lectin is concanavalin A (ConA), which can
- guest interaction with the surface of the vesicles has become a useful system to investigate recognition, adhesion and fusion of biological cell membranes [24][25][26]. In this context, amphiphilic cyclodextrins are a promising platform due to their ability to form stable bilayer vesicles that can be
Synthetic glycopeptides and glycoproteins with applications in biological research
Beilstein J. Org. Chem. 2012, 8, 804–818, doi:10.3762/bjoc.8.90
- cell-surface binding events, such as cell growth and differentiation, cell proliferation, cell adhesion, binding of pathogens, fertilization and immune responses [1][2]. Furthermore, glycans assist in intracellular protein folding and transport. Pathogenic processes, such as chronic inflammation, viral
- techniques for glycoprotein synthesis by preparation of a number of GalNAc containing O-glycoproteins, such as the antimicrobial protein diptericin, the cytokine lymphotactin and the leukocyte adhesion molecule ligand GlyCAM-1 [46][47][48]. By repeated NCL couplings of mucin tandem repeats, MUC2 and MUC1
- infection to progress. As a consequence, mutations of the pathogen adhesion proteins, resulting in a loss of cell-surface binding recognition are not very likely to occur. Interference with the microbe binding events by employing an anti-adhesive strategy could therefore be very efficient. In several
An easily accessible sulfated saccharide mimetic inhibits in vitro human tumor cell adhesion and angiogenesis of vascular endothelial cells
Beilstein J. Org. Chem. 2012, 8, 787–803, doi:10.3762/bjoc.8.89
- Kao Germany GmbH, Pfungstädter Str. 92–100, 64297 Darmstadt/Eberstadt, Germany, Biognos AB, Generatorsgatan 1, 41705 Goeteborg, Sweden 10.3762/bjoc.8.89 Abstract Oligosaccharides aberrantly expressed on tumor cells influence processes such as cell adhesion and modulation of the cell’s
- as core structure were synthesized and screened in biological assays for their abilities to interfere in cell adhesion and other steps of the metastatic cascade, such as tumor-induced angiogenesis. The most active compound, (4-{[(β-D-galactopyranosyl)oxy]methyl}furan-3-yl)methyl hydrogen sulfate (GSF
- ), inhibited the activation of matrix-metalloproteinase-2 (MMP-2) as well as migration of the human melanoma cells of the lines WM-115 and WM-266-4 in a two-dimensional migration assay. GSF inhibited completely the adhesion of WM-115 cells to the extracellular matrix (ECM) proteins, fibrinogen and fibronectin
Formation of carbohydrate-functionalised polystyrene and glass slides and their analysis by MALDI-TOF MS
Beilstein J. Org. Chem. 2012, 8, 753–762, doi:10.3762/bjoc.8.86
- groups can be used as simple hydrophobic, noncovalently linked anchors for ligands on surfaces and at the same time facilitate the in situ mass spectrometric analysis of such ligands. Keywords: carbohydrate array; conductive tape; MALDI-TOF MS; nonconductive surface; trityl-mediated adhesion
- be useful in a bacterial adhesion inhibition assay against the bacterial lectin FimH [20][21]. The second glycoside 7 has been used previously for well-established enzymatic surface modifications [22]. Both these compounds can be synthesised by starting from commercially available 11
- slides. After application of trityl samples, the polystyrene and glass slides were gently washed with 1 μL of water (washing procedure 1). Subsequent analysis by MALDI-TOF MS showed no noticeable change to the prewashed samples, confirming the trityl-group-mediated noncovalent adhesion of the ligands to
Metathesis access to monocyclic iminocyclitol-based therapeutic agents
Beilstein J. Org. Chem. 2011, 7, 699–716, doi:10.3762/bjoc.7.81
- ) (129) a natural iminosugar present in buckwheat (widely used in traditional recipes) is an efficient agent for preventing sharp blood glucose peaks after the intake of refined carbohydrates and for positively influencing intestinal microbiota by favouring adhesion of probiotics. It is supposed that
Synthesis of glycoconjugate fragments of mycobacterial phosphatidylinositol mannosides and lipomannan
Beilstein J. Org. Chem. 2011, 7, 369–377, doi:10.3762/bjoc.7.47
- dendritic cell specific intercellular adhesion molecule-grabbing non-integrin (DC-SIGN) [8]. Thus, while total syntheses of many PIM structures have now been reported, the synthesis of substructures remains a worthwhile endeavor as these are useful to clarify fine details of enzymatic substrate recognition
Regioselective ester cleavage during the preparation of bisphosphonate methacrylate monomers
Beilstein J. Org. Chem. 2011, 7, 364–368, doi:10.3762/bjoc.7.46
- ester function without affecting the methacrylate ester. Keywords: bifunctional monomer; phosphonic acid; regioselective ester cleavage; Introduction The potential applications for polymer products containing phosphorus are numerous; dental adhesives, ion-exchange resins and adhesion promotors are
- just three of the more common applications [1][2][3][4][5][6][7]. Compounds containing phosphorous are excellent promotors with respect to adhesion, and thus anti-corrosion. Commercial anti-corrosion polymer compounds are generally formed from Sipomer® or Phosmer® monomers, which are phosphate-type
- many applications such as dental adhesives, ion-exchange resins and adhesion promotors. However, these polymers must be in the acidic form, i.e., with phosphonic acid groups, to function efficiently [26]. The intermediate bisphosphonates were then subjected to a two-step deprotection process to restore
ROMP-Derived cyclooctene-based monolithic polymeric materials reinforced with inorganic nanoparticles for applications in tissue engineering
Beilstein J. Org. Chem. 2010, 6, 1199–1205, doi:10.3762/bjoc.6.137
- biocompatibility of the monolithic hybrid support as well as sufficient cell adhesion on the monolithic material. Conclusion COE-based monolithic scaffolds have been prepared via ROMP in the presence of two different types of inorganic nanoparticles. It was shown that variation of both the nanoparticle type and
Novel 2-(ω-phosphonooxy-2-oxaalkyl)acrylate monomers for self-etching self-priming one part adhesive
Beilstein J. Org. Chem. 2010, 6, 766–772, doi:10.3762/bjoc.6.95
- , comprising of polymerizable acids 3, ranges from 5.8 to 19.3 MPa on enamel and from 8.7 to 16.9 MPa on dentin. Keywords: adhesion to enamel and dentin; hydrolysis stable 2-(ω-phosphonooxy-2-oxaalkyl)acrylates; phosphorylation using POCl3; polymerization enthalpy; shear bond strength; Introduction Dental
- consuming procedure that is prone to failure during the procedure. Therefore, a reduction of the complexity of the adhesives during application was desirable. Furthermore, the adhesion procedure should be more safe, easy and robust. In order to fulfill these demands some generations of adhesives were
- bond conversion of 87.3% at 37 °C. Adhesion of phosphoric acids 3 The shear bond strength of adhesive compositions 4 [11], comprising of polymerizable acids 3, ranges from 5.8 to 19.3 MPa on enamel and from 8.7 to 16.9 MPa on dentin (Table 3, Figure 1). With increasing length of the aliphatic spacers
En route to photoaffinity labeling of the bacterial lectin FimH
Beilstein J. Org. Chem. 2010, 6, 810–822, doi:10.3762/bjoc.6.91
- , Uppsala Biomedical Center, SE-75124 Uppsala, Sweden 10.3762/bjoc.6.91 Abstract Mannose-specific adhesion of Escherichia coli bacteria to cell surfaces, the cause of various infections, is mediated by a fimbrial lectin, called FimH. X-ray studies have revealed a carbohydrate recognition domain (CRD) on
- FimH that can complex α-D-mannosides. However, as the precise nature of the ligand–receptor interactions in mannose-specific adhesion is not yet fully understood, it is of interest to identify carbohydrate recognition domains on the fimbrial lectin also in solution. Photoaffinity labeling serves as an
- -mannoside (pNPMan), respectively (Table 1). When these mannosides were tested as inhibitors of type 1 fimbriae-mediated bacterial adhesion to a mannan-coated surface in an ELISA [21][22], IC50-values were obtained, which reflect the concentration of the derivative employed, that leads to 50% inhibition of
A bivalent glycopeptide to target two putative carbohydrate binding sites on FimH
Beilstein J. Org. Chem. 2010, 6, 801–809, doi:10.3762/bjoc.6.90
- capacity to bridge two putative carbohydrate binding sites on FimH was designed and synthesized. Anti-adhesion assays with the new bivalent ligand and type 1-fimbriated bacteria have revealed, that verification of the number of carbohydrate binding sites on FimH with a tailor-made bivalent glycopeptide
- requires further investigation to be conclusive. Keywords: bacterial adhesion; bivalent ligand; ELISA; FimH; glycopeptides; Introduction Bacterial adhesion is a phenomenon which occurs on the surface of host cells as well as on the surface of surgical implants, where it can lead to the formation of
- persistent biofilms. In all cases of bacterial adhesion and of biofilm formation severe health problems can result for the host organism [1][2]. A number of microbial adhesins are known, that co-operate in the adhesion process [3], such as the fimbriae, which are long filamentous adhesive organells on the
Chromo- and fluorophoric water-soluble polymers and silica particles by nucleophilic substitution reaction of poly(vinyl amine)
Beilstein J. Org. Chem. 2010, 6, No. 79, doi:10.3762/bjoc.6.79
- cationic form leads to a polymer with the highest known charge density along the polymer backbone. Such highly protonated polymers appear to be very interesting compounds for the prevention of bacteria adhesion on surfaces [18]. Non-protonated primary amino groups in the PVAm polymer have a high synthetic
Synthesis, electronic properties and self-assembly on Au{111} of thiolated (oligo)phenothiazines
Beilstein J. Org. Chem. 2010, 6, No. 72, doi:10.3762/bjoc.6.72
- thiols on Au{111}. The ability of the molecules to form SAMs was investigated by solution adsorption of different systems onto gold films of 100 nm thickness thermally evaporated onto Si wafers using 10 nm of Ti as adhesion promoter. This procedure is known to yield polycrystalline gold films with
New amphiphilic glycopolymers by click functionalization of random copolymers – application to the colloidal stabilisation of polymer nanoparticles and their interaction with concanavalin A lectin
Beilstein J. Org. Chem. 2010, 6, No. 58, doi:10.3762/bjoc.6.58
- pyrrolidone) as the starting copolymer. Poly(NVP) is known to be biocompatible and to promote adhesion. NVP-based maleic copolymers have been reported for BSA immobilization [14] as well as for the preparation of polymer nanoparticles [10][15]. The choice of the carbohydrate moieties to be grafted onto the
- biological phenomena such as cell adhesion or cell–cell recognition. The specific binding of a lectin receptor with a carbohydrate ligand (usually called recognition) is obtained, provided that the ligands are orientated in a specific manner that can fit several lectin receptors and is usually referred to as
Synthesis of glycosylated β3-homo-threonine conjugates for mucin-like glycopeptide antigen analogues
Beilstein J. Org. Chem. 2010, 6, No. 47, doi:10.3762/bjoc.6.47
- proteins involved in fundamental biological recognition events of cell adhesion, cell differentiation and cell growth [1][2][3]. As a consequence, synthetic oligosaccharides and their conjugates are recognised as important tools for the expanding field of chemical biology [4]. Aberrant glycosylation of
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