Influence of Mannosylation on Immunostimulating Activity of Adamant‐1‐yl Tripeptide

Ribić, Rosana; Habjanec, Lidija; Frkanec, Ruža; Vranešić, Branka; Tomić, Srđanka

doi:10.1002/cbdv.201200008

Cited by 12 publications

(20 citation statements)

References 21 publications

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“…In continuation of our interest in the influence of chemical modification of carbohydrates on biological activity, we synthesized mannose derivatives of 1-aminoadamantane and adamant-2-yl-tripeptides ( Figure 2 ). The mannose conjugates of adamantyl tripeptides have been prepared in order to target the mannose receptors present on the cell surface of different immunocompetent cells such as macrophages and dendritic cells, which are considered to be pattern recognition receptors [ 43 , 44 , 45 ]. Mannosylated adamantyl tripeptides were tested in vivo and their influence on specific immune responses was evaluated.…”

Section: Adamantane Derivatives In Liposomesmentioning

confidence: 99%

Adamantane in Drug Delivery Systems and Surface Recognition

et al. 2017

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The adamantane moiety is widely applied in design and synthesis of new drug delivery systems and in surface recognition studies. This review focuses on liposomes, cyclodextrins, and dendrimers based on or incorporating adamantane derivatives. Our recent concept of adamantane as an anchor in the lipid bilayer of liposomes has promising applications in the field of targeted drug delivery and surface recognition. The results reported here encourage the development of novel adamantane-based structures and self-assembled supramolecular systems for basic chemical investigations as well as for biomedical application.

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Section: Adamantane Derivatives In Liposomesmentioning

confidence: 99%

Adamantane in Drug Delivery Systems and Surface Recognition

et al. 2017

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“…The binding affinity of β‐CD towards adamantane‐based compounds can be enhanced by attaching neutral, “solubilizing” functionalities (e.g., sugar subunits) . Such glycoconjugates (mannosides) were reported to be efficient immunostimulators and potential vaccine adjuvants . This class of compounds was also incorporated into liposomes, which exhibited promising carrier properties .…”

Section: Introductionmentioning

confidence: 99%

Solvophobically Driven Complexation of Adamantyl Mannoside with β‐Cyclodextrin in Water and Structured Organic Solvents

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Hanževački

Brkljača

et al. 2020

Chemistry A European J

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The effects of solventa nd temperature on the complexation of adamantyl mannoside with b-cyclodextrin and 6-O-monotosyl-6-deoxy-b-cyclodextrinw ere explored experimentally and by means of molecular dynamics simulations. Efficientb inding was observedo nly in hydrogenbondeds olvents, which indicated solvophobically driven complexation. Thes tability of the inclusion complex was considerably higheri na queous media. Ap ronouncedt emperature dependence of D r H * and D r S * ,r esulting in perfect enthalpy-entropy compensation, was observedi nw ater.The complexation thermodynamicsw as in line with classical rationale for the hydrophobic effect at lower temperatures and the nonclassical explanation at higher temperatures. This finding linked cyclodextrinc omplexation thermodynam-ics with insights regarding the effecto ft emperature on the hydration water structure. The complexation enthalpies and entropies were weakly dependent on temperature in organic media. The signs of D r H * and D r S * were in accordance with the nonclassicalh ydrophobic (solvophobic) effect.T he structures of the optimized product corresponded to those deduceds pectroscopically,a nd the calculated and experimentally obtained values of D r G * were in very good agreement. This investigation clearly demonstrated that solvophobically drivenf ormation of cyclodextrin complexes could be anticipated in structured solvents in general. However,u nlike in water, adamantane and the host cavity behaved solely as structure breakers in the organic media explored so far.[a] SE = standard error of the mean (N = 3o r4). Figure 6. Relative a) conformation and b) solvation contribution to the hydration enthalpies of reactantsand the complex over the studied temperature range.

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“…In this study we established an alternative methodology for testing the immune modulatory properties of peptidoglycan-based adjuvant candidates. While in vivo investigations in mice models [12,18,19] are invaluable in proving adjuvant properties, they are also expensive, time consuming, and require special facilities. The presented in vitro assays are simple, fast, cheaper, and can be performed in a simpler laboratory setting for the detection of the immune response induced by these compounds.…”

Section: Discussionmentioning

confidence: 99%

Adamantane Containing Peptidoglycan Fragments Enhance RANTES and IL-6 Production in Lipopolysaccharide-Induced Macrophages

et al. 2020

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We report the enhancement of the lipopolysaccharide-induced immune response by adamantane containing peptidoglycan fragments in vitro. The immune stimulation was detected by Il-6 (interleukine 6) and RANTES (regulated on activation, normal T cell expressed and secreted) chemokine expression using cell assays on immortalized mouse bone-marrow derived macrophages. The most active compound was a α-D-mannosyl derivative of an adamantylated tripeptide with L-chirality at the adamantyl group attachment, whereby the mannose moiety assumed to target mannose receptors expressed on macrophage cell surfaces. The immune co-stimulatory effect was also influenced by the configuration of the adamantyl center, revealing the importance of specific molecular recognition event taking place with its receptor. The immunostimulating activities of these compounds were further enhanced upon their incorporation into lipid bilayers, which is likely related to the presence of the adamantyl group that helps anchor the peptidoglycan fragment into lipid nanoparticles. We concluded that the proposed adamantane containing peptidoglycan fragments act as co-stimulatory agents and are also suitable for the preparation of lipid nanoparticle-based delivery of peptidoglycan fragments.

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Influence of Mannosylation on Immunostimulating Activity of Adamant‐1‐yl Tripeptide

Cited by 12 publications

References 21 publications

Adamantane in Drug Delivery Systems and Surface Recognition

Adamantane in Drug Delivery Systems and Surface Recognition

Solvophobically Driven Complexation of Adamantyl Mannoside with β‐Cyclodextrin in Water and Structured Organic Solvents

Adamantane Containing Peptidoglycan Fragments Enhance RANTES and IL-6 Production in Lipopolysaccharide-Induced Macrophages

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