Synthesis of a series of novel heteroglycoclusters and homoglycoclusters and the study of their anti-adhesion activities

Jiang, Shan; Niu, Shan; Zhao, Zhihui; Li, Zhongjun; Li, Qing

doi:10.1016/j.carres.2015.06.002

Cited by 10 publications

(4 citation statements)

References 30 publications

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“…been described [30]. Structure 6 with either probes or immunogenic peptides are useful as MRI contrast agents [31] or as vaccine candidates [32,33], respectively.…”

Section: Introductionmentioning

confidence: 99%

“…Additional cases of heterofunctional glycodendrimers have been disclosed using an “onion peel” approach that has provided precise alternating glycans ( 4 ) [ 26 , 27 , 28 , 29 ] instead of random distribution and numbers. Janus glycodendrimers possessing other aromatic scaffolds ( 5 ) have also been described [ 30 ]. Structure 6 with either probes or immunogenic peptides are useful as MRI contrast agents [ 31 ] or as vaccine candidates [ 32 , 33 ], respectively.…”

Section: Introductionmentioning

confidence: 99%

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Design, Synthetic Strategies, and Therapeutic Applications of Heterofunctional Glycodendrimers

Mousavifar

Roy

2021

Molecules

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Glycodendrimers have attracted considerable interest in the field of dendrimer sciences owing to their plethora of implications in biomedical applications. This is primarily due to the fact that cell surfaces expose a wide range of highly diversified glycan architectures varying by the nature of the sugars, their number, and their natural multiantennary structures. This particular situation has led to cancer cell metastasis, pathogen recognition and adhesion, and immune cell communications that are implicated in vaccine development. The diverse nature and complexity of multivalent carbohydrate–protein interactions have been the impetus toward the syntheses of glycodendrimers. Since their inception in 1993, chemical strategies toward glycodendrimers have constantly evolved into highly sophisticated methodologies. This review constitutes the first part of a series of papers dedicated to the design, synthesis, and biological applications of heterofunctional glycodendrimers. Herein, we highlight the most common synthetic approaches toward these complex molecular architectures and present modern applications in nanomolecular therapeutics and synthetic vaccines.

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“…been described [30]. Structure 6 with either probes or immunogenic peptides are useful as MRI contrast agents [31] or as vaccine candidates [32,33], respectively.…”

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Design, Synthetic Strategies, and Therapeutic Applications of Heterofunctional Glycodendrimers

Mousavifar

Roy

2021

Molecules

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“…[18][19][20][21] Among these is the use of a multifunctional scaffold tailored for sequential grafting of various sugars. [22][23][24] Despite the promise of this concept, its exploitation is as yet limited and it remains a methodological challenge that warrants further development.…”

Section: Introductionmentioning

confidence: 99%

New synthesis of heteroglycoclusters from p-t-butylcalix[4]arene tetraalkoxyheterohalides as key intermediates

Taouai¹,

Chakroun²,

Vallin-Butruille³

et al. 2018

Arkivoc

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A straightforward synthesis of heteroglycoclusters based p-t-butylcalix [4]arene has been achieved. The key step is the formation of hetero-halopentyloxy-p-t-butylcalix [4]arene mixture via haloalkylation with 1-bromo-5-chloropentane as asymmetric alkylating reagent. Subsequent selective exchange of bromide by azide under mild conditions provides selectively azido-chloro species suitable for click reaction with first propargylglycoside. The products here can then be subjected to further azidation to enable attachment of different glycosides via click chemistry reaction.

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“…On the one hand, it has been demonstrated that glycoheterogeneityh as an impact on carbohydrate-protein recognition events, [8][9][10][11][12] ac oncept that has been termed" the heterocluster effect". [13,14] On the other hand, clusterization of ac arbohydrate-processing-enzymei nhibitory moiety (inhitope), generally an iminosugar-type glycomimetic, has been shownt omodulate and eventually amplify the ability of inhibiting certaing lycosidases [15][16][17][18][19][20] and glycosyltransferases, [21] ac ounterintuitive phenomenon named "multivalent enzymei nhibition" or "multivalent inhibition effect". [22,23] Similar to the classical multivalent or cluster effect operating in homogeneous glycoligand-lectin interactions, the heterocluster and multivalent inhibition effects depend on the interacting partnersa nd on architectural parameters.…”

Section: Introductionmentioning

confidence: 99%

The Impact of Heteromultivalency in Lectin Recognition and Glycosidase Inhibition: An Integrated Mechanistic Study

García‐Moreno

Ortega‐Caballero

Rísquez‐Cuadro

et al. 2017

Chemistry A European J

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The vision of multivalency as a strategy limited to achieve affinity enhancements between a protein receptor and its putative sugar ligand (glycotope) has proven too simplistic. On the one hand, binding of a glycotope in a dense glycocalix-like construct to a lectin partner has been shown to be sensitive to the presence of a third sugar entity (heterocluster effect). On the other hand, several carbohydrate processing enzymes (glycosidases and glycosyltransferases) have been found to be also responsive to multivalent presentations of binding partners (multivalent enzyme inhibition), a phenomenon first discovered for iminosugar-type inhibitory species (inhitopes) and recently demonstrated for multivalent carbohydrate constructs. By assessing a series of homo- and heteroclusters combining α-d-glucopyranosyl-related glycotopes and inhitopes, it was shown that multivalency and heteromultivalency govern both kinds of events, allowing for activation, deactivation or enhancement of specific recognition phenomena towards a spectrum of lectin and glycosidase partners in a multimodal manner. This unified scenario originates from the ability of (hetero)multivalent architectures to trigger glycosidase binding modes that are reminiscent of those harnessed by lectins, which should be considered when profiling the biological activity of multivalent architectures.

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Synthesis of a series of novel heteroglycoclusters and homoglycoclusters and the study of their anti-adhesion activities

Cited by 10 publications

References 30 publications

Design, Synthetic Strategies, and Therapeutic Applications of Heterofunctional Glycodendrimers

Design, Synthetic Strategies, and Therapeutic Applications of Heterofunctional Glycodendrimers

New synthesis of heteroglycoclusters from p-t-butylcalix[4]arene tetraalkoxyheterohalides as key intermediates

The Impact of Heteromultivalency in Lectin Recognition and Glycosidase Inhibition: An Integrated Mechanistic Study

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