Fluorescent carbon dots from mono- and polysaccharides: synthesis, properties and applications

• Stephen Hill and
• M. Carmen Galan

Beilstein J. Org. Chem. 2017, 13, 675–693, doi:10.3762/bjoc.13.67

• via the adhesion of Ag+ to the CD surface, followed by reduction in the presence of sunlight, which promotes the excitation of the reducing electron to a higher energetic state (Scheme 23). Through UV–vis absorbance and TEM measurements it was evident that a surface layer of plasmonic Ag existed on

Brønsted acid-mediated cyclization–dehydrosulfonylation/reduction sequences: An easy access to pyrazinoisoquinolines and pyridopyrazines

• Ramana Sreenivasa Rao and
• Chinnasamy Ramaraj Ramanathan

Beilstein J. Org. Chem. 2017, 13, 428–440, doi:10.3762/bjoc.13.46

• anticancer [2][3], antifungal [4], amoebiasis, trypanosomiasis, bilharziasis [5][6], and schistosomiasis [7][8]. Some are cell adhesion inhibitors [9] brandykinin receptor antagonists [10][11] and chymase inhibitors [12]. Quinoxaline derivatives are known to act as aldose reductase (ALR2) inhibitors and are

The digital code driven autonomous synthesis of ibuprofen automated in a 3D-printer-based robot

• Philip J. Kitson,
• Stefan Glatzel and
• Leroy Cronin

Beilstein J. Org. Chem. 2016, 12, 2776–2783, doi:10.3762/bjoc.12.276

• , respectively. In order to effectively print the PP reaction vessels it was necessary to replace the standard carbon fibre or glass-printing bed of the RepRap with a PP plate leading to better adhesion of the PP during printing. The print settings were adjusted such that the reaction vessels could be readily

Interactions between cyclodextrins and cellular components: Towards greener medical applications?

• Loïc Leclercq

Beilstein J. Org. Chem. 2016, 12, 2644–2662, doi:10.3762/bjoc.12.261

• . proposed to prevent the activation/expression of monocyte adhesion [130]. For this cell adhesion, molecules such as CD11b are required. Therefore, the authors reported that β-CD, but not its cholesterol complex, inhibits CD11b activation. As the cholesterol content of lipid rafts diminished after treatment

Synthesis and in vitro cytotoxicity of acetylated 3-fluoro, 4-fluoro and 3,4-difluoro analogs of D-glucosamine and D-galactosamine

• Štěpán Horník,
• Lucie Červenková Šťastná,
• Petra Cuřínová,
• Jan Sýkora,
• Kateřina Káňová,
• Roman Hrstka,
• Ivana Císařová,
• Martin Dračínský and
• Jindřich Karban

Beilstein J. Org. Chem. 2016, 12, 750–759, doi:10.3762/bjoc.12.75

• glycoproteins, glycolipids and proteoglycans. As such, they participate in functions performed by cell-surface glycans including cell adhesion and signaling [1]. Unnatural analogs of these amino sugars prepared by a selective replacement of a hydroxy group by fluorine have proved valuable tools to perturb

• ]. The resulting disruption of protein–(glycosamino)glycan interactions had important biomedical consequences such as reduced selectin-mediated tumor cell adhesion [12][13], suppressed selectin-mediated leukocyte migration [11][14][15], reduced angiogenesis [3], or inhibition of tumor growth by decreased

Synthesis, structure, and mechanical properties of silica nanocomposite polyrotaxane gels

• Kazuaki Kato,
• Daisuke Matsui,
• Koichi Mayumi and
• Kohzo Ito

Beilstein J. Org. Chem. 2015, 11, 2194–2201, doi:10.3762/bjoc.11.238

• nanoparticles such as carbon black and silica for practical use as tire materials. Because of adhesion of polymer chains to the nanoparticle surfaces, the chain mobility at the interface is considerably suppressed, thereby increasing the elastic modulus of the nanocomposite [2][3][4][5][6]. Although the

• were not only free from adhesion to the silica surface but can also slide through the immobilized cyclic components, the nanocomposite gel achieved low Young’s modulus and high toughness without any detectable fracture or recombination of network structure under 80% compression. These results suggest

Are D-manno-configured Amadori products ligands of the bacterial lectin FimH?

• Tobias-Elias Gloe,
• Insa Stamer,
• Cornelia Hojnik,
• Tanja M. Wrodnigg and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2015, 11, 1096–1104, doi:10.3762/bjoc.11.123

• E. coli bacteria by means of molecular docking and bacterial adhesion studies. It turns out that Amadori rearrangement products have a limited activity as inhibitors of bacterial adhesion because the β-C-glycosidically linked aglycone considerably hampers complexation within the carbohydrate binding

• site of the type 1-fimbrial lectin FimH. Keywords: Amadori rearrangement; bacterial adhesion; C-mannosides; docking studies; FimH ligands; Introduction The Amadori rearrangement (AR) is the reaction in which aldohexoses react with suitable amines under acidic catalysis to 1-amino-1-deoxyketohexoses

• investigation of ligands for the bacterial lectin FimH [4] it has been our goal to investigate the Amadori rearrangement as a method to approach new FimH ligands. These are especially relevant in the context of an anti-adhesion therapy against bacterial infections [5][6]. As FimH-mediated adhesion to the

Adsorption mechanism and valency of catechol-functionalized hyperbranched polyglycerols

• Stefanie Krysiak,
• Qiang Wei,
• Klaus Rischka,
• Andreas Hartwig,
• Rainer Haag and
• Thorsten Hugel

Beilstein J. Org. Chem. 2015, 11, 828–836, doi:10.3762/bjoc.11.92

• adhesives are promising candidates. Understanding the mechanism of the extraordinarily strong adhesive bonds of the catechol group will likely aid in the development of adhesives. With this aim, we study the adhesion of catechol-based adhesives to metal oxides on the molecular level using atomic force

• concluded that hyperbranched polyglycerols with added catechol end groups are promising candidates for durable surface coatings. Keywords: adhesion; atomic force microscopy; catechol; hyperbranched polyglycerols; valency; Introduction While underwater glues are still a challenge for industrial adhesive

• development, mussels, barnacles and numerous other animals and plants have found a way for strong, long-term adhesion to wet surfaces [1]. Wet hydrophilic surfaces are difficult to be wetted by glues since the adhesive competes with the surface water layer [2]. Mussels can easily adhere to hydrophilic metal

Mechanical stability of bivalent transition metal complexes analyzed by single-molecule force spectroscopy

• Manuel Gensler,
• Christian Eidamshaus,
• Maurice Taszarek,
• Hans-Ulrich Reissig and
• Jürgen P. Rabe

Beilstein J. Org. Chem. 2015, 11, 817–827, doi:10.3762/bjoc.11.91

• rb [6]. In natural environments, hydrodynamic effects may cause forces competing with biomolecular interactions, such as the leukocyte adhesion to endothelial cells [7] or the Escherichia coli adhesion to uroepithelium cells [8]. The latter has been well analyzed by single-molecule force spectroscopy

• [9], showing unfolding of a very malleable, helical PapA-domain in p-pili, which plays an important role for the adhesion. This process consumes a large amount of energy, whilst adhesion forces are kept at a low force of 27 pN, in order not to break the adhesive glycolipid–ligand interaction. In

• contrast, cellulosome–adhesion complexes tighten under load, leading to rupture forces of 600–750 pN, one of the strongest biomolecular interactions discovered until now [10]. Another fascinating biological example is the von Willebrand factor, where nature utilizes shear forces on an ultra large protein

Regulation of integrin and growth factor signaling in biomaterials for osteodifferentiation

• Qiang Wei,
• Theresa L. M. Pohl,
• Anja Seckinger,
• Joachim P. Spatz and
• Elisabetta A. Cavalcanti-Adam

Beilstein J. Org. Chem. 2015, 11, 773–783, doi:10.3762/bjoc.11.87

• synthetic integrin ligands were developed to control the interaction between biomaterials and stem cells. The effect of the topography and the distribution of the ligands on cell adhesion, proliferation, and differentiation were intensively studied as well [7]. Besides integrin ligands, growth factors

• signaling of integrins and growth factor receptors are discussed. Integrin ligands for cell adhesion and stem cell fate In order to enhance the effectiveness of cell-based bone therapy, it is important to understand the signals from integrin–ligand interactions. New technologies have been employed to

• adhesion proteins, on the other hand, bind to multiple integrin receptors (Figure 2b) [18]. A set of receptor–ligand combinations with high-affinity interaction has even been identified. The best characterized and most widely used ligand is the arginine-glycine-aspartic acid (RGD) sequence. RGD motifs are

Glycodendrimers: tools to explore multivalent galectin-1 interactions

• Jonathan M. Cousin and
• Mary J. Cloninger

Beilstein J. Org. Chem. 2015, 11, 739–747, doi:10.3762/bjoc.11.84

• residues were present at each stage in the assay irrespective of the scaffold generation number, dose-responsive inhibition of galectin-1 mediated cancer cell adhesion was only observed with lactose functionalized G(3)-dendrimer 2 at these concentrations (Figure 7b, and representative images 7e–h, the dose

• of glycoconjugates (TF antigen Mucin-1) on adjacent cells which directly facilitates aggregation; and (ii) clustering of receptors (TF antigen Mucin-1) which exposes adhesion molecules that interact with adhesion molecules on neighboring cells to cause aggregation. All four generations of the

• )-PAMAM 1 was the most potent inhibitor of galectin-1 induced cellular aggregation, exhibiting complete inhibition of cancer cell adhesion at low dosage (Figure 4). Galectin-1/1 nanoparticles were not detected by DLS or fluorescence microscopy. Because galectin-1 is known to bind these glycodendrimers, it

Probing multivalency in ligand–receptor-mediated adhesion of soft, biomimetic interfaces

• Stephan Schmidt,
• Hanqing Wang,
• Daniel Pussak,
• Simone Mosca and
• Laura Hartmann

Beilstein J. Org. Chem. 2015, 11, 720–729, doi:10.3762/bjoc.11.82

• protein receptors are formed to control cell–cell recognition, cell adhesion and related processes. The aim of this work is to shed light on the principles of complex formation between surface anchored carbohydrates and receptor surfaces by measuring the specific adhesion between surface bound mannose on

• a concanavalin A (ConA) layer via poly(ethylene glycol)-(PEG)-based soft colloidal probes (SCPs). Special emphasis is on the dependence of multivalent presentation and density of carbohydrate units on specific adhesion. Consequently, we first present a synthetic strategy that allows for controlled

• synthetic strategy allows for straightforward variation in grafting density and grafting length enabling the controlled presentation of mannose units on the PEG network. Finally we determined the specific adhesion of PEG-network-conjugated mannose units on ConA surfaces as a function of density and grafting

Synthesis of tripodal catecholates and their immobilization on zinc oxide nanoparticles

• Franziska Klitsche,
• Julian Ramcke,
• Julia Migenda,
• Andreas Hensel,
• Tobias Vossmeyer,
• Horst Weller,
• Silvia Gross and
• Wolfgang Maison

Beilstein J. Org. Chem. 2015, 11, 678–686, doi:10.3762/bjoc.11.77

• of new tripodal catecholates as valuable multivalent anchor molecules for immobilization on metal surfaces and nanoparticles. These catecholate anchors make use of a biomimetic covalent immobilization concept as found for example in mussel adhesion proteins. Our tripodal catecholate anchors are

Synthesis of carbohydrate-scaffolded thymine glycoconjugates to organize multivalency

• Anna K. Ciuk and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2015, 11, 668–674, doi:10.3762/bjoc.11.75

• influence their recognition by lectins [7]. Recently, we have introduced a photoswitchable glycoazobenzene-covered surface, in which alteration of ligand orientation allowed to switch cell adhesion without changing the recognition quality or the valency of the ligand itself [6]. It is also well-known that

Synthesis of a hexasaccharide partial sequence of hyaluronan for click chemistry and more

• Marina Bantzi,
• Stephan Rigol and
• Athanassios Giannis

Beilstein J. Org. Chem. 2015, 11, 604–607, doi:10.3762/bjoc.11.67

• addition, HA is able to interact with three major classes of cell surface receptors, namely CD44 (cluster of differentiation 44), RHAMM (receptor for HA-mediated motility) and ICAM-1 (intracellular adhesion molecule-1) [10][11]. CD44 is a heterogeneous, transmembrane glycoprotein which is overexpressed on

IR and electrochemical synthesis and characterization of thin films of PEDOT grown on platinum single crystal electrodes in [EMMIM]Tf₂N ionic liquid

• Andrea P. Sandoval,
• Marco F. Suárez-Herrera and
• Juan M. Feliu

Beilstein J. Org. Chem. 2015, 11, 348–357, doi:10.3762/bjoc.11.40

• ) < Pt(110) < Pt(111) [6]. The synthesis of other conducting polymers on well-defined surfaces [7][8][9][10] and templates [11] also has shown how the surface affects their adhesion, coverage, morphology and redox kinetics. On the other hand, the synthesis of conducting polymers in ionic liquids (ILs

Functionalized branched EDOT-terthiophene copolymer films by electropolymerization and post-polymerization “click”-reactions

• Miriam Goll,
• Adrian Ruff,
• Erna Muks,
• Felix Goerigk,
• Beatrice Omiecienski,
• Ines Ruff,
• Rafael C. González-Cano,
• Juan T. Lopez Navarrete,
• M. Carmen Ruiz Delgado and
• Sabine Ludwigs

Beilstein J. Org. Chem. 2015, 11, 335–347, doi:10.3762/bjoc.11.39

• layer)-coated Si wafers (with a 5 nm Cr adhesion layer between the Si wafer and the Au layer) or ITO-coated glass (≤50 Ω/sq, PGO, Germany) slides (approximately 1 cm2) were used. The gold working electrodes were fabricated by the physical vapor deposition of Cr and Au on rotating Si wafers. The gold

Natural phenolic metabolites with anti-angiogenic properties – a review from the chemical point of view

• Qiu Sun,
• Jörg Heilmann and
• Burkhard König

Beilstein J. Org. Chem. 2015, 11, 249–264, doi:10.3762/bjoc.11.28

• the ability to prevent apoptosis, it also stimulates angiogenesis, mitogenesis, cell migration, as well as modulates cell adhesion. The presence of the 3-galloyl moiety in catechins led to higher biological activity [63][64][65], but an increasing number of aromatic hydroxy groups result in low

• )flavanone (69, Figure 8) is a prenylated flavanone isolated from Sophora flavescens by Wang and Yuan et al. in 2013 [101]. It displays inhibitory effects on cell proliferation, cell migration, cell adhesion and tube formation in the human umbilical vein endothelial cell line ECV304. These four steps are

Formulation development, stability and anticancer efficacy of core-shell cyclodextrin nanocapsules for oral chemotherapy with camptothecin

• Hale Ünal,
• Naile Öztürk and
• Erem Bilensoy

Beilstein J. Org. Chem. 2015, 11, 204–212, doi:10.3762/bjoc.11.22

• to higher cellular adhesion and increasing residence time at the cell surface provided by CS molecules. This finding suggests that with chitosan-coated cationic NCs, electrostatic interactions between positively charged CS amino groups and the negatively charged cell membrane occurred. Therefore, the

Effects of RAMEA-complexed polyunsaturated fatty acids on the response of human dendritic cells to inflammatory signals

• Éva Rajnavölgyi,
• Renáta Laczik,
• Viktor Kun,
• Lajos Szente and
• Éva Fenyvesi

Beilstein J. Org. Chem. 2014, 10, 3152–3160, doi:10.3762/bjoc.10.332

• via inhibition of the expression of cytokine-induced adhesion molecules in primary human retinal vascular endothelial (hRVE) cells, the target tissue affected by diabetic retinopathy [23]. To study whether the lipid rafts were involved in the mechanism of action, methylated β-CD was used for both the

Cyclodextrin–polysaccharide-based, in situ-gelled system for ocular antifungal delivery

• Anxo Fernández-Ferreiro,
• Noelia Fernández Bargiela,
• María Santiago Varela,
• Maria Gil Martínez,
• Maria Pardo,
• Antonio Piñeiro Ces,
• José Blanco Méndez,
• Miguel González Barcia,
• Maria Jesus Lamas and
• Francisco.J. Otero-Espinar

Beilstein J. Org. Chem. 2014, 10, 2903–2911, doi:10.3762/bjoc.10.308

• strength and duration of the adhesion. However, the specific interactions in the polymer/biological substrate interface are governed by both the properties of the polymer and the nature of the substrate [27]. Figure 6 shows the bioadhesive behavior of the ion-sensitive gels in tanned leather in the

Detonation nanodiamonds biofunctionalization and immobilization to titanium alloy surfaces as first steps towards medical application

• Juliana P. L. Gonçalves,
• Afnan Q. Shaikh,
• Manuela Reitzig,
• Daria A. Kovalenko,
• Jan Michael,
• René Beutner,
• Gianaurelio Cuniberti,
• Dieter Scharnweber and
• Jörg Opitz

Beilstein J. Org. Chem. 2014, 10, 2765–2773, doi:10.3762/bjoc.10.293

• on chemical modification of the nanodiamond surface with phosphate groups and their electrochemically assisted immobilization on titanium-based materials to increase adhesion at biomaterial surfaces. The starting material is detonation nanodiamond, which exhibits a heterogeneous surface due to the

• material properties towards biomedical applications the authors aim to increase adhesion to bone material by incorporating nanodiamonds into the implant surface, namely the anodically grown titanium dioxide layer. Differently functionalized nanodiamonds are characterized by infrared spectroscopy and the

• ]. Others worked on collagenous matrix coatings on titanium implants modified with decorin and chondroitin sulfate that enhanced osteoblast adhesion and increased expression of osteopontin (a bone-specific marker) [19]. Immobilization of biologically active molecules, by using tripartite molecules (linker

Towards the sequence-specific multivalent molecular recognition of cyclodextrin oligomers

• Michael Kurlemann and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2014, 10, 2428–2440, doi:10.3762/bjoc.10.253

• binding partner [1]. In recent years multivalency has been recognized to play a major role in almost all biological processes, e.g., the recognition of cells by other cells, bacteria or viruses, the adhesion of cells or signal transduction pathways [2]. By the combination of multiple, rather weak non

Synthesis of novel conjugates of a saccharide, amino acids, nucleobase and the evaluation of their cell compatibility

• Dan Yuan,
• Xuewen Du,
• Junfeng Shi,
• Ning Zhou,
• Abdulgader Ahmed Baoum and
• Bing Xu

Beilstein J. Org. Chem. 2014, 10, 2406–2413, doi:10.3762/bjoc.10.250

• exploration [26]. As an amino acid, Phe or naphthAla increases molecular aromatic–aromatic interactions [19][21][27]. Arg-Gly-Asp, which is a well-established tripeptidic epitope, that modulates mammalian cell adhesion through binding with integrins on the cell membrane [28][29]. Thymine or adenine, as a

Expeditive synthesis of trithiotriazine-cored glycoclusters and inhibition of Pseudomonas aeruginosa biofilm formation

• Meriem Smadhi,
• Sophie de Bentzmann,
• Anne Imberty,
• Marc Gingras,
• Raoudha Abderrahim and
• Peter G. Goekjian

Beilstein J. Org. Chem. 2014, 10, 1981–1990, doi:10.3762/bjoc.10.206

• bioactivity of these lectins in host recognition and adhesion in biofilm formation represents an attractive antibacterial strategy, as multivalent carbohydrate motifs on cell surfaces are known to mediate a broad range of cellular and tissue adhesion processes. Carbohydrate recognition in biological systems