Supramolecular polymerization of sulfated dendritic peptide amphiphiles into multivalent L-selectin binders

• David Straßburger,
• Svenja Herziger,
• Katharina Huth,
• Moritz Urschbach,
• Rainer Haag and
• Pol Besenius

Beilstein J. Org. Chem. 2021, 17, 97–104, doi:10.3762/bjoc.17.10

• of multivalent interactions is the extracellular adhesion protein L-selectin. L-Selectin plays a critical role in inflammation processes by supporting the migration of leukocytes to inflammatory sites via adhesion to endothelial cells [19][20][21]. On a molecular level, a cationic binding site [22

Optical detection of di- and triphosphate anions with mixed monolayer-protected gold nanoparticles containing zinc(II)–dipicolylamine complexes

• Lena Reinke,
• Julia Bartl,
• Marcus Koch and
• Stefan Kubik

Beilstein J. Org. Chem. 2020, 16, 2687–2700, doi:10.3762/bjoc.16.219

• preferred binding mode of zinc(II)–dipicolylamine complexes with phosphate anions which involves binding of the anion between two metal centers. This work thus provided information on how the behavior of mixed monolayer-protected gold nanoparticles is affected by multivalent interactions, at the same time

• other serves to dilute the receptor units on the surface to such an extent that analyte binding to units residing on the same nanoparticle becomes unlikely. The number of receptors should still be high enough to allow nanoparticle crosslinking to benefit from multivalent interactions [19][20][21]. The

1,2,3-Triazolium macrocycles in supramolecular chemistry

• Mastaneh Safarnejad Shad,
• Pulikkal Veettil Santhini and
• Wim Dehaen

Beilstein J. Org. Chem. 2019, 15, 2142–2155, doi:10.3762/bjoc.15.211

• reduced cavity. These conformational changes are reversible in solution with switching pH. 4.3. A multivalent catenane and its motion in diverse pH media Cell signaling, energy transduction, and cargo delivery are some of functions of very complicatedly assembled biomolecular machines. Multivalent

• interactions, compared to monovalent receptor–ligand interactions offer the advantage of multiple and sequential binding within the host–guest systems. These noncovalent interactions which can be controlled in a chemical or physical manner depend on the binding sites in the multivalent assembly [67

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

• years [67]. Some recent highlights have included using polymer backbones to identify GM1 analogues that can give enhanced multivalent interactions [68], evolving glycopolymers using exchangeable ligands [69], and tuning the way the ligands are connected to the polymer backbone for maximum interaction

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

• hydrophobic guest molecules are of special interest, since CDs are readily available bio-based materials and interactions take place under physiological conditions [17]. CDs are ideal candidates for the investigation of multivalent interactions as they combine high affinities with a versatile integrability in

• spectroscopy, quartz crystal microbalance (QCM), surface plasmon resonance (SPR) and atomic force microscopy (AFM) have been employed to quantify the strength of the multivalent interactions [8]. Because binding affinities can be very high for multivalent supramolecular systems, the constituents are commonly

• , synthesized from polymer 8 (Scheme 3) through Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC) with the triethylene glycol linker 11 (N3-TEG-NH2) which had been prepared in a five-step procedure [62][63]. Probing multivalent interactions by AFM The adhesive forces of 12, due to supramolecular interactions

Size-controlled and redox-responsive supramolecular nanoparticles

• Raquel Mejia-Ariza,
• Gavin A. Kronig and
• Jurriaan Huskens

Beilstein J. Org. Chem. 2015, 11, 2388–2399, doi:10.3762/bjoc.11.260

• these SNPs using host–guest interactions between CD and Ad. Tseng et al. studied the formation of SNPs that are assembled solely by host–guest interactions [11][12]. Here, the core is composed of multivalent interactions between positively charged CD-grafted polymers and positively charged poly

Multivalency as a chemical organization and action principle

• Rainer Haag

Beilstein J. Org. Chem. 2015, 11, 848–849, doi:10.3762/bjoc.11.94

• functional molecular architectures and surface structures as well as the controlled interaction of multivalent surfaces. The chemical and biological mechanisms and the influence of scaffold architectures with different dimensions for multivalent interactions have not been comprehensively explored. Thus, the

• , however, is completely different, when several covalently linked ligands of the same or of a similar nature bind to an ensemble of acceptors (multivalent interactions) [1]. Due to the multiple additive (in some cases cooperative) interactions the equilibrium will shift and bond reinforcement occurs

• understanding of multivalent interactions this Thematic Series in the Beilstein Journal of Organic Chemistry puts its focus to unravel new cellular interactions that are highly relevant [2] and systematically combines theoretical exploration of defined multivalent supramolecular interactions [3] as well as new

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

• multivalent interactions for the different surface contact times (see main text for details). D) Peak values of the maximum force histograms for the first and second peak are plotted against the dwell time. The standard deviation of the Gaussian fit is given as the error. Schematics of the different

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

• clamp motifs, as suggested by Sikora et al. [19]. For example, zipper-type unfolding requires less force than shear-type denaturation. However due to the high complexity of biological multivalent interactions less is known about the influence from individual non-covalent interactions. Here, well defined

• mechanical stability. On the other hand, a stepwise rupture processes, possibly combined with an additional release of geometrical folding, results in a very malleable system that is able to deform without breaking. Thus knowledge about backbone properties of bivalent and probably also multivalent

• interactions is crucial for the specific design of ligands. Future studies will address specific backbone properties and higher valencies on the way to a deeper understanding of their influence on multivalency. Experimental Reactions were generally performed under argon in dried flasks. Solvents and reagents

Orthogonal dual-modification of proteins for the engineering of multivalent protein scaffolds

• Michaela Mühlberg,
• Michael G. Hoesl,
• Christian Kuehne,
• Jens Dernedde,
• Nediljko Budisa and
• Christian P. R. Hackenberger

Beilstein J. Org. Chem. 2015, 11, 784–791, doi:10.3762/bjoc.11.88

• paper was the development of a robust synthetic methodology that allows the site-specific attachment of two distinct chemical modifications to a given protein, which can be used to target multivalent interactions. As a protein scaffold we selected the thermophilic lipase from Thermoanaerobacter

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

• factors to induce osteogenic differentiation of stem cells, and discuss the signaling pathways that are initiated by both individual and cooperative parameters. The joint effect of integrin ligands and growth factors is highlighted as the multivalent interactions for bone therapy. Keywords: biomaterials

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

• activity through multivalent interactions with cell surface glycoconjugates [1][2][3][4]. Galectin-1 is a non-covalent homodimer that belongs to a family of β-galactoside binding proteins called galectins [5][6][7]. The monomeric units are oriented such that the two carbohydrate recognition domains are

• carcinoma cells. The studies reported here indicate that the pattern of galectin-1 that is presented to the cells influences their behavior, thus advancing the understanding of the mechanism of action of galectin-1 mediated cellular aggregation processes and indicating that multivalent interactions can be

• glycodendrimer particles must interact to form the 400 nm aggregates, and this is favorable even when the scaffold is ostensibly saturated with galectin-1. The DU145 human prostate carcinoma cell line was chosen to demonstrate that multivalent interactions initiated by a synthetic multivalent system can be used

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

• glycocalyx interacts also with surface anchored membrane receptors. Thus, the interactions between these surfaces are again multivalent interactions, just on a larger scale between two surfaces. Such carbohydrate based multivalent surface–surface interactions represent a large range of crucial biological

• mannose concentration on the particles. This suggests that the surface interactions between mannose and ConA did not lead to multivalent interactions in the sense of a chelate- or subside binding complex. This could be caused by the flexible arrangement of mannose units on the polymer scaffold or

Potential of acylated peptides to target the influenza A virus

• Daniel Lauster,
• Damian Pawolski,
• Julian Storm,
• Kai Ludwig,
• Rudolf Volkmer,
• Henry Memczak,
• Andreas Herrmann and
• Sumati Bhatia

Beilstein J. Org. Chem. 2015, 11, 589–595, doi:10.3762/bjoc.11.65

• supramolecular assembly, which allows multivalent interactions. By that, multivalent inhibitors could be designed with antiviral activity in the low micromolar range. Recently, we identified an antiviral peptide, which we derived from the paratope region of an antibody directed against HA binding to the sialic

Multivalent scaffolds induce galectin-3 aggregation into nanoparticles

• Candace K. Goodman,
• Mark L. Wolfenden,
• Pratima Nangia-Makker,
• Anna K. Michel,
• Avraham Raz and
• Mary J. Cloninger

Beilstein J. Org. Chem. 2014, 10, 1570–1577, doi:10.3762/bjoc.10.162

• were synthesized and characterized. The presence of complex multivalent interactions between galectin-3 and lactose-functionalized dendrimers is indicated by the observation of large aggregates in DLS and epifluorescence experiments. The large and relatively monodisperse nature of the glycodendrimer

Design and synthesis of multivalent neoglycoconjugates by click conjugations

• Feiqing Ding,
• Li Ji,
• Ronny William,
• Hua Chai and
• Xue-Wei Liu

Beilstein J. Org. Chem. 2014, 10, 1325–1332, doi:10.3762/bjoc.10.134

• (Table 3, method B). This result showed that the synthesis of 3-tosylamino-2,3-dideoxyneoglycoconjugates via copper-catalyzed Huisgen cycloaddition is highly efficient under microwave irradiation. In carbohydrate recognition events, higher multivalent interactions are absolutely essential as the

Human dendritic cell activation induced by a permannosylated dendron containing an antigenic GM₃-lactone mimetic

• Renato Ribeiro-Viana,
• Elena Bonechi,
• Javier Rojo,
• Clara Ballerini,
• Giuseppina Comito,
• Barbara Richichi and
• Cristina Nativi

Beilstein J. Org. Chem. 2014, 10, 1317–1324, doi:10.3762/bjoc.10.133

• expression and MHCII. Furthermore, DCs activated by the glycodendron 5 stimulate T lymphocytes to proliferate in a mixed lymphocytes reaction (MLR). Keywords: cancer immunotherapy; DC-SIGN; DC targeting; glycodendron; GM3-lactone mimetic; multivalent glycosystems; multivalent interactions; Introduction

Synthesis of homo- and heteromultivalent carbohydrate-functionalized oligo(amidoamines) using novel glyco-building blocks

• Felix Wojcik,
• Sinaida Lel,
• Alexander G. O’Brien,
• Peter H. Seeberger and
• Laura Hartmann

Beilstein J. Org. Chem. 2013, 9, 2395–2403, doi:10.3762/bjoc.9.276

• oligonucleotides [14]. Such constructs have contributed to our current understanding of multivalent interactions [5]. Nevertheless, binding studies on multivalent compounds with different scaffold architectures or combinations of different sugar ligands are limited due to the often undefined chemical composition

Synthesis of heteroglycoclusters by using orthogonal chemoselective ligations

• Baptiste Thomas,
• Michele Fiore,
• Isabelle Bossu,
• Pascal Dumy and
• Olivier Renaudet

Beilstein J. Org. Chem. 2012, 8, 421–427, doi:10.3762/bjoc.8.47

• : chemoselective ligation; click chemistry; cyclopeptide; heteroglycocluster; oxime; Introduction Multivalent interactions between carbohydrates and proteins play key roles in diverse biological events, including fertilization, cell–cell communication, host–pathogen interactions, immune response and cancer

Thematic series on supramolecular chemistry

• Christoph A. Schalley

Beilstein J. Org. Chem. 2009, 5, No. 76, doi:10.3762/bjoc.5.76

• successfully transferred to neutral and anionic hosts. Nowadays, multivalent interactions start to play a significant role for host-guest chemistry. But supramolecular chemistry is much more than molecular recognition. Concepts such as templated synthesis, (hierarchical) self-assembly, and self-sorting have