Selective recognition of ATP by multivalent nano-assemblies of bisimidazolium amphiphiles through “turn-on” fluorescence response

• Rakesh Biswas,
• Surya Ghosh,
• Shubhra Kanti Bhaumik and
• Supratim Banerjee

Beilstein J. Org. Chem. 2020, 16, 2728–2738, doi:10.3762/bjoc.16.223

• ]. It is a principle ubiquitously used in biology to achieve high affinity binding events with examples ranging from protein–carbohydrate interactions to host–pathogen interactions or cell surface adhesion [12][13][14]. The high affinity originates from the simultaneous interactions of multiple sites in

Enzyme-instructed morphological transition of the supramolecular assemblies of branched peptides

• Dongsik Yang,
• Hongjian He and
• Bing Xu

Beilstein J. Org. Chem. 2020, 16, 2709–2718, doi:10.3762/bjoc.16.221

• peptides has received limited attention [2][32][33][34][35][36][37]. For example, Stupp et al. reported that a cell adhesion epitope, RGDS, acts as a branch to peptide amphiphiles for making hydrogels via self-assembly [34][36]. Ulijn et al. connected Fmoc-DAARRGG to a lysine side chain for incorporation

Muyocopronones A and B: azaphilones from the endophytic fungus Muyocopron laterale

• Ken-ichi Nakashima,
• Junko Tomida,
• Tomoe Tsuboi,
• Yoshiaki Kawamura and
• Makoto Inoue

Beilstein J. Org. Chem. 2020, 16, 2100–2107, doi:10.3762/bjoc.16.177

• (Dothideomycetes) were reported as intercellular adhesion molecule-1 (ICAM1) expression inhibitors in a patent literature [28]. Therefore, the presence of the 2,4-dimethyl-3-hydroxyhexanoate moiety may be a potential chemical marker for Dothideomycetes, although this is difficult to conclude due to the fact that

Synthesis of novel sulfide-based cyclic peptidomimetic analogues to solonamides

• José Brango-Vanegas,
• Luan A. Martinho,
• Lucinda J. Bessa,
• Andreanne G. Vasconcelos,
• Alexandra Plácido,
• Alex L. Pereira,
• José R. S. A. Leite and
• Angelo H. L. Machado

Beilstein J. Org. Chem. 2019, 15, 2544–2551, doi:10.3762/bjoc.15.247

• . Cyclic thioether peptides have been found in the chemical skeletons of natural products and synthetic ones that display a wide variety of activities, including antibiotics [31], vascular cell adhesion molecule-1 antagonists [32] and anticardiolipin antibodies [33][34]. Two MBH adducts (2) (R = Me, heptyl

Reversible switching of arylazopyrazole within a metal–organic cage

• Anton I. Hanopolskyi,
• Soumen De,
• Michał J. Białek,
• Yael Diskin-Posner,
• Liat Avram,
• Moran Feller and
• Rafal Klajn

Beilstein J. Org. Chem. 2019, 15, 2398–2407, doi:10.3762/bjoc.15.232

• selectivity [35][36][37][38][39][40]. Consequently, arylazopyrazoles have been employed as photoresponsive gelators [41] and adhesives [42] and for controlling antimicrobial response [43][44], cell adhesion to surfaces [45], as well as DNA [46] and microtubule [47] self-assembly using light. Here, we focused

Stereo- and regioselective hydroboration of 1-exo-methylene pyranoses: discovery of aryltriazolylmethyl C-galactopyranosides as selective galectin-1 inhibitors

• Alexander Dahlqvist,
• Axel Furevi,
• Niklas Warlin,
• Hakon Leffler and
• Ulf J. Nilsson

Beilstein J. Org. Chem. 2019, 15, 1046–1060, doi:10.3762/bjoc.15.102

• -linked glycans on the cell surface. Surface proteins such as integrins [6][7], vascular endothelial growth factor receptor [8], and lysosome-associated membrane proteins [9] are known to be crosslinked by galectins, giving galectins a modulating role in cell adhesion, blood vessel growth and cellular

• uptake and breakdown, respectively. The association of galectins to cell signaling and adhesion gives them roles in several different pathological processes, such as pulmonary fibrosis [6][10], pathological lymphangiogenesis [11], inflammation [12] and cancer [13], with galectin inhibitors demonstrated

Diaminoterephthalate–α-lipoic acid conjugates with fluorinated residues

• Leon Buschbeck,
• Aleksandra Markovic,
• Gunther Wittstock and
• Jens Christoffers

Beilstein J. Org. Chem. 2019, 15, 981–991, doi:10.3762/bjoc.15.96

• monolayers (SAMs) can also be triggered electrochemically to perform reactions on the surfaces. These "dynamic" surfaces allow the "turn-on" of active states upon application of electrochemical potentials, for instance, for the addition of compounds to surfaces or for the control of cell adhesion [36][37][38

• cleaned glass slides as the support by depositing 0.5 nm of chromium by electron-beam evaporation as adhesion layer and 200 nm of gold by resistive heating using an evaporation chamber (minicoater, Tectra GmbH, Frankfurt, Germany). The thickness was monitored by means of a quartz crystal microbalance

Towards the preparation of synthetic outer membrane vesicle models with micromolar affinity to wheat germ agglutinin using a dialkyl thioglycoside

• Dimitri Fayolle,
• Nathalie Berthet,
• Bastien Doumeche,
• Olivier Renaudet,
• Peter Strazewski and
• Michele Fiore

Beilstein J. Org. Chem. 2019, 15, 937–946, doi:10.3762/bjoc.15.90

• -phenylacetophenone. Synthesis of the lipophilic scaffold 6; DMAP = N,N-dimethylaminopyridine. Inhibition of the adhesion of WGA-HRP to GlcNAc-coated microtiter plates as determined by ELLAa. Supporting Information Supporting Information File 190: Additional Figures S1–S6 and spectra of synthesized glycolipids and

Adhesion, forces and the stability of interfaces

• Robin Guttmann,
• Johannes Hoja,
• Christoph Lechner,
• Reinhard J. Maurer and
• Alexander F. Sax

Beilstein J. Org. Chem. 2019, 15, 106–129, doi:10.3762/bjoc.15.12

• interaction energies, or by attractive forces between the interacting subsystems; in the case of stabilizing WMIs, one frequently speaks of adhesion energies and adhesive forces. We show that the description of system stability using maximum adhesive forces and the description using adhesion energies are not

• equivalent. The systems discussed are polyaromatic molecules adsorbed to graphene and carbon nanotubes; dimers of alcohols and amines; cellulose crystals; and alcohols adsorbed onto cellulose surfaces. Keywords: adhesion energy; adhesive force; dispersion interaction; weak molecular interaction

• , which are characterized by their own short multipole expansion, together with the short range of attractive induction and dispersion interactions in particular, explains our findings of an approximate additivity of the stabilization energy and the adhesive forces [13][14][15]. Adhesion is the term for

Lectins of Mycobacterium tuberculosis – rarely studied proteins

• Katharina Kolbe,
• Sri Kumar Veleti,
• Norbert Reiling and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2019, 15, 1–15, doi:10.3762/bjoc.15.1

• Abstract The importance of bacterial lectins for adhesion, pathogenicity, and biofilm formation is well established for many Gram-positive and Gram-negative bacteria. However, there is very little information available about lectins of the tuberculosis-causing bacterium, Mycobacterium tuberculosis (Mtb

• ). In this paper we review previous studies on the carbohydrate-binding characteristics of mycobacteria and related Mtb proteins, discussing their potential relevance to Mtb infection and pathogenesis. Keywords: adhesion; carbohydrates; fimbriae; lectins; Mycobacterium tuberculosis; pili; Introduction

• interactions strongly contribute to bacterial adhesion and uptake, and are also associated with the capability of Mtb to survive, replicate, and persist within macrophages [21][22][23][24][25]. Ubiquitous in both eukaryotes and prokaryotes, lectins comprise a subclass of glycan-binding proteins most commonly

Dispersion interactions

• Peter R. Schreiner

Beilstein J. Org. Chem. 2018, 14, 3076–3077, doi:10.3762/bjoc.14.286

• for all matter starting from atoms (e.g., the condensation of helium) over molecules (e.g., aggregation) to materials (e.g., adhesion). It is also difficult to include in theoretical approaches and for the longest time it had been left virtually unnoticed that many density functional theory (DFT

Pathoblockers or antivirulence drugs as a new option for the treatment of bacterial infections

• Matthew B. Calvert,
• Varsha R. Jumde and
• Alexander Titz

Beilstein J. Org. Chem. 2018, 14, 2607–2617, doi:10.3762/bjoc.14.239

• pathogen [10]. 3. Blocking adhesion and biofilm formation Bacterial adhesion to the host’s tissue is the initial step of every infection. In many cases, microbial adhesion is mediated by carbohydrate-binding proteins, so-called lectins, which recognize glycoconjugates on the surface of cells and tissue

• inhibition of this adhesion process using glycomimetics as pathoblockers has developed as an area of active research in the last two decades [11][12]. Uropathogenic Escherichia coli (UPEC) is a major cause for chronic and recurrent urinary tract infections. These bacteria employ lectins in order to attach to

• adhesion in mice [18][19]. These compounds have been extensively optimized in many works published by both groups, culminating in the identification of mannophosphates as prodrugs to increase oral bioavailability [20] and mannose C-glycosides, such as compound 6 , demonstrating enhanced in vivo metabolic

Impact of Pseudomonas aeruginosa quorum sensing signaling molecules on adhesion and inflammatory markers in endothelial cells

• Carmen Curutiu,
• Florin Iordache,
• Veronica Lazar,
• Aurelia Magdalena Pisoschi,
• Aneta Pop,
• Mariana Carmen Chifiriuc and
• Alina Maria Hoban

Beilstein J. Org. Chem. 2018, 14, 2580–2588, doi:10.3762/bjoc.14.235

• infectious process. In this study we evaluate the expression of adhesion and inflammatory molecules in endothelial cells treated with P. aeruginosa QSSMs, in order to bring new insights on the mechanisms involved in the interaction of P. aeruginosa with host cells during the infectious process. Endothelial

• evaluated. The expression of adhesion molecules (VE-cadherin, PECAM-1, ICAM-1, and P-selectin) and inflammatory response molecules (IL-1β, IL-6, TNFα, TGFβ, and eNOS) was assessed by qRT-PCR and flow cytometry. Our results showed that bacterial adherence to inert substratum and biofilm were decreased in the

• presence of all tested QSSMs. The adherence index of PAO1 laboratory strain to host cells was decreased between 10–40% in the presence of QSSMs, as compared to untreated control. Expression of eukaryotic cells adhesion molecules ICAM-1 and P-selectin was stimulated by QSSMs, whereas VE-cadherin and PECAM-1

Comparative cell biological study of in vitro antitumor and antimetastatic activity on melanoma cells of GnRH-III-containing conjugates modified with short-chain fatty acids

• Eszter Lajkó,
• Sarah Spring,
• Rózsa Hegedüs,
• Beáta Biri-Kovács,
• Sven Ingebrandt,
• Gábor Mező and
• László Kőhidai

Beilstein J. Org. Chem. 2018, 14, 2495–2509, doi:10.3762/bjoc.14.226

• -targeting by application of a GnRH analog as a carrier to deliver a covalently linked chemotherapeutic drug directly to the tumor cells. In this study our aim was (i) to analyze the effects of GnRH-drug conjugates on melanoma cell proliferation, adhesion and migration, (ii) to study the mechanisms of tumor

• mediated via a phosphoinositide 3-kinase-dependent signaling. GnRH-III(Dau=Aoa) and [4Lys(Ac)]-GnRH-III(Dau=Aoa) were shown to be blockers of the cell cycle in the G2/M phase, while [4Lys(Bu)]-GnRH-III(Dau=Aoa) rather induced apoptosis. In short-term, the melanoma cell adhesion was significantly increased

• by all the tested conjugates. The modification of the GnRH-III in position 4 was accompanied by an increased cellular uptake, higher cytotoxic and cell adhesion inducer activity. By studying the cell movement of A2058 cells with a holographic microscope, it was found that the migratory behavior of

Diazirine-functionalized mannosides for photoaffinity labeling: trouble with FimH

• Femke Beiroth,
• Tomas Koudelka,
• Thorsten Overath,
• Stefan D. Knight,
• Andreas Tholey and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2018, 14, 1890–1900, doi:10.3762/bjoc.14.163

• ligand–receptor interactions in solution. We have employed an interdisciplinary methodology to achieve facile photolabeling of the lectin FimH, which is a bacterial protein, crucial for adhesion, colonization and infection. Following our earlier work, we have here designed and synthesized diazirine

• with optimized photolabeling conditions and high-end mass spectrometry. Results and Discussion FimH is a fimbrial lectin found at the tips of adhesive organelles (type 1 fimbriae), which are projecting from the surface of enterobacteriaceae such as E. coli. Fimbriae mediate firm attachment (adhesion

• carbohydrate binding site. A more negative value predicts better binding. Scores obtained for mannosides 3 and 4 suggest a high affinity for FimH, surpassing that of pNPMan 1 for both protein conformations tested (Table 1). (Diazirines cannot be tested in bacterial adhesion–inhibition assays due to their light

On the design principles of peptide–drug conjugates for targeted drug delivery to the malignant tumor site

• Eirinaios I. Vrettos,
• Gábor Mező and
• Andreas G. Tzakos

Beilstein J. Org. Chem. 2018, 14, 930–954, doi:10.3762/bjoc.14.80

• general, the ‘integrin’ nomenclature was first used in 1987 to describe a family of receptors, appearing as heterodimers of noncovalently associated α and β subunits, able to link the extracellular matrix (ECM) with the intracellular cytoskeleton to mediate cell adhesion, migration and proliferation [42

Carbohydrate inhibitors of cholera toxin

• Vajinder Kumar and
• W. Bruce Turnbull

Beilstein J. Org. Chem. 2018, 14, 484–498, doi:10.3762/bjoc.14.34

• released by Vibrio cholera in the host’s intestine. The toxin enters intestinal epithelial cells after binding to specific carbohydrates on the cell surface. Over recent years, considerable effort has been invested in developing inhibitors of toxin adhesion that mimic the carbohydrate ligand, with

• driven opportunities for the design of potent inhibitors for these toxins. While some interest has been shown in the possibility of inhibition of cholera toxin assembly and inhibition of the enzymatic activity, most effort has been invested in seeking inhibitors of the adhesion process [29]. Designing

Synthesis and biological evaluation of RGD and isoDGR peptidomimetic-α-amanitin conjugates for tumor-targeting

• Lizeth Bodero,
• Paula López Rivas,
• Barbara Korsak,
• Torsten Hechler,
• Andreas Pahl,
• Christoph Müller,
• Daniela Arosio,
• Luca Pignataro,
• Cesare Gennari and
• Umberto Piarulli

Beilstein J. Org. Chem. 2018, 14, 407–415, doi:10.3762/bjoc.14.29

• -adhesion molecule) monoclonal antibody was prepared by Moldenhauer and co-workers [5]. The cytotoxicity of this conjugate was tested in EpCAM-overexpressing cancer cell lines obtaining IC50 values from 2.5 × 10−10 to 2.0 × 10−12 M. Promising results were also observed in mice bearing BxPc-3 pancreatic

• –34 times, see Table 1). Furthermore, these ligands were shown to inhibit the FAK (focal adhesion kinase) and Akt (protein kinase B) signaling cascade and the tumor cell infiltration process, performing as true integrin antagonists [27]. Ligands 1 and 3 were also functionalized with an aminomethyl

What contributes to an effective mannose recognition domain?

• Christoph P. Sager,
• Deniz Eriş,
• Martin Smieško,
• Rachel Hevey and
• Beat Ernst

Beilstein J. Org. Chem. 2017, 13, 2584–2595, doi:10.3762/bjoc.13.255

• carbohydrate–lectin interactions of the innate immune system but also in bacterial adhesion, a process key for the bacterium’s survival. In an effort to better understand the particular characteristics, which contribute to a successful carbohydrate recognition domain, the mannose-binding sites of six C-type

• ion [1][2][3][4]. CLECs are involved in a wide range of biological processes, such as pathogen recognition and intercellular adhesion [5][6][7]. A large number of CLEC structures, including animal, plant and bacterial lectins, are available in the Protein Data Bank [8]. A second large family of

• of oligomannosides on viral envelop glycoprotein gp120, facilitating stronger adhesion between dendritic cells and HIV-1 [43][75][76]. This multivalent binding interaction results in an enhancement in binding by several orders of magnitude, from a KD of 26 μM for monovalent Man9GlcNAc2, as compared

The chemistry and biology of mycolactones

• Matthias Gehringer and
• Karl-Heinz Altmann

Beilstein J. Org. Chem. 2017, 13, 1596–1660, doi:10.3762/bjoc.13.159

• fibroblasts, which are extremely mycolactone-sensitive. Upon exposure to natural mycolactone A/B concentrations as low as 0.025 ng/mL (0.034 nM), L929 cells show cytoskeletal rearrangements at 12 h, cell rounding within 24 h and a loss of adhesion along with growth arrest after 48 h [32]. At this point, the

• triggering uncontrolled ARP2/3-mediated assembly of actin. As a consequence, mycolactone A/B causes impaired cell adhesion and defects in the migration of epithelial cells (e.g., increased cell motility accompanied by a loss of directionality). Mycolactone binding to WASP was also demonstrated by means of a

• fluorescent mycolactone-derived probe, which co-localized with active WASP to a small but significant extent in Jurkat T cells. At the same time, wiskostatin, a known N-WASP inhibitor [97] was found to counteract some of the effects of mycolactone (e.g., impaired cell adhesion in HeLa cells). Wiskostatin also

BODIPY-based fluorescent liposomes with sesquiterpene lactone trilobolide

• Ludmila Škorpilová,
• Silvie Rimpelová,
• Michal Jurášek,
• Miloš Buděšínský,
• Jana Lokajová,
• Roman Effenberg,
• Petr Slepička,
• Tomáš Ruml,
• Eva Kmoníčková,
• Pavel B. Drašar and
• Zdeněk Wimmer

Beilstein J. Org. Chem. 2017, 13, 1316–1324, doi:10.3762/bjoc.13.128

• in width and 30 nm in height. The larger dimension of the liposomes in width, than expected, was probably caused by their adhesion to the glass surface, which was on the other hand necessary in order to perform the AFM analysis. The values of average roughness described in the Figure 4 for both (2

Biomimetic molecular design tools that learn, evolve, and adapt

• David A Winkler

Beilstein J. Org. Chem. 2017, 13, 1288–1302, doi:10.3762/bjoc.13.125

• identify low adhesion materials for coating medical devices [45]. These data were used to generate a sparse machine learning model for each pathogen (Figure 13) that predicted pathogen attachment and described the relationship between polymer surface chemistry and attachment [46]. The pathogen attachment

Glycoscience@Synchrotron: Synchrotron radiation applied to structural glycoscience

• Serge Pérez and
• Daniele de Sanctis

Beilstein J. Org. Chem. 2017, 13, 1145–1167, doi:10.3762/bjoc.13.114

• can bind to the combining site of lectins at relatively low concentration, and provide sufficient anomalous signals for MAD or SAD methods of phasing to work, as was exemplified by the structure solution of the F17-G fibrial adhesion [54]. This elegant approach was used to elucidate the crystal

Glyco-gold nanoparticles: synthesis and applications

• Federica Compostella,
• Olimpia Pitirollo,
• Alessandro Silvestri and
• Laura Polito

Beilstein J. Org. Chem. 2017, 13, 1008–1021, doi:10.3762/bjoc.13.100

• different bacterial adhesion. Indeed, gold nanorods presented a bacteria detection limit of 0.03 ± 0.01 µg/mL, 80-folds more sensitive than spherical and star shaped AuNPs. This discrepancy has been ascribed to the difference in the relative amount of mannose involved in the NP-bacteria interaction. The

Interactions between shape-persistent macromolecules as probed by AFM

• Johanna Blass,
• Jessica Brunke,
• Franziska Emmerich,
• Cédric Przybylski,
• Vasil M. Garamus,
• Artem Feoktystov,
• Roland Bennewitz,
• Gerhard Wenz and
• Marcel Albrecht

Beilstein J. Org. Chem. 2017, 13, 938–951, doi:10.3762/bjoc.13.95

• configuration of the CD moieties. Depending on the geometrical configuration of attachment anisotropic adhesion characteristics of the polymer system can be distinguished between a peeling and a shearing mechanism. Keywords: AFM; cyclodextrin; inclusion complexes; molecular recognition; polyconjugated polymers

• AFM tip and found enhancement factors up to 2, depending on the force loading rate [46]. We have previously explored the adhesion characteristics of dense CD layers on an AFM tip and a planar silicon surface connected by various ditopic linker molecules. In this system we were able to switch adhesion

• with ditopic guest 9, between a planar silicon surface and an AFM tip both modified with the CD polymer 12 or 6-monoamino-6-deoxy-β-CD were systematically investigated by AFM. While adhesion was very weak in pure water, significant adhesion took place over a wide range of distances in a 10 μM solution