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Article ; Online: Glycomimetic ligands block the interaction of SARS-CoV-2 spike protein with C-type lectin co-receptors.

Pollastri, Sara / Delaunay, Clara / Thépaut, Michel / Fieschi, Franck / Bernardi, Anna

Chemical communications (Cambridge, England)

2022 Volume 58, Issue 33, Page(s) 5136–5139

Abstract: The C-type lectin receptors DC-SIGN and L-SIGN bind to glycans on the SARS-CoV-2 spike glycoprotein and promote trans-infection of ACE2-expressing cells. We tested C2 triazole-modified mono- and pseudo-di-mannosides as inhibitors of DC/L-SIGN binding to ... ...

Abstract	The C-type lectin receptors DC-SIGN and L-SIGN bind to glycans on the SARS-CoV-2 spike glycoprotein and promote trans-infection of ACE2-expressing cells. We tested C2 triazole-modified mono- and pseudo-di-mannosides as inhibitors of DC/L-SIGN binding to a model mannosylated protein (Man-BSA) and to SARS-CoV2 spike, finding that they inhibit the interaction of both lectins with the spike glycoprotein in a Surface Plasmon Resonance (SPR) assay and are more potent than mannose by up to 36-fold (DC-SIGN) and 10-fold (L-SIGN). The molecules described here are the first known glycomimetic ligands of L-SIGN.
MeSH term(s)	COVID-19 ; Humans ; Lectins, C-Type/metabolism ; Ligands ; Protein Binding ; RNA, Viral/metabolism ; SARS-CoV-2 ; Spike Glycoprotein, Coronavirus/metabolism
Chemical Substances	Lectins, C-Type ; Ligands ; RNA, Viral ; Spike Glycoprotein, Coronavirus ; spike protein, SARS-CoV-2
Language	English
Publishing date	2022-04-21
Publishing country	England
Document type	Journal Article
ZDB-ID	1472881-3
ISSN	1364-548X ; 1359-7345 ; 0009-241X
ISSN (online)	1364-548X
ISSN	1359-7345 ; 0009-241X
DOI	10.1039/d2cc00121g
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article ; Online: Molecular recognition of

Nieto-Fabregat, Ferran / Marseglia, Angela / Thépaut, Michel / Kleman, Jean-Philippe / Abbas, Massilia / Le Roy, Aline / Ebel, Christine / Maalej, Meriem / Simorre, Jean-Pierre / Laguri, Cedric / Molinaro, Antonio / Silipo, Alba / Fieschi, Franck / Marchetti, Roberta

iScience

2024 Volume 27, Issue 2, Page(s) 108792

Abstract: Due to their ability to recognize carbohydrate structures, lectins emerged as potential receptors for bacterial lipopolysaccharides (LPS). Despite growing interest in investigating the association between host receptor lectins and exogenous glycan ... ...

Abstract	Due to their ability to recognize carbohydrate structures, lectins emerged as potential receptors for bacterial lipopolysaccharides (LPS). Despite growing interest in investigating the association between host receptor lectins and exogenous glycan ligands, the molecular mechanisms underlying bacterial recognition by human lectins are still not fully understood. We contributed to fill this gap by unveiling the molecular basis of the interaction between the lipooligosaccharide of
Language	English
Publishing date	2024-01-04
Publishing country	United States
Document type	Journal Article
ISSN	2589-0042
ISSN (online)	2589-0042
DOI	10.1016/j.isci.2024.108792
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Article ; Online: Atomic-Level Dissection of DC-SIGN Recognition of

Nieto-Fabregat, Ferran / Zhu, Qian / Vivès, Corinne / Zhang, Yunqin / Marseglia, Angela / Chiodo, Fabrizio / Thépaut, Michel / Rai, Diksha / Kulkarni, Suvarn S / Di Lorenzo, Flaviana / Molinaro, Antonio / Marchetti, Roberta / Fieschi, Franck / Xiao, Guozhi / Yu, Biao / Silipo, Alba

JACS Au

2024 Volume 4, Issue 2, Page(s) 697–712

Abstract: The evaluation ... ...

Abstract	The evaluation of
Language	English
Publishing date	2024-02-12
Publishing country	United States
Document type	Journal Article
ISSN	2691-3704
ISSN (online)	2691-3704
DOI	10.1021/jacsau.3c00748
Database	MEDical Literature Analysis and Retrieval System OnLINE

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Article ; Online: Rapid On-Chip Synthesis of Complex Glycomimetics from N-Glycan Scaffolds for Improved Lectin Targeting.

Cioce, Anna / Thépaut, Michel / Fieschi, Franck / Reichardt, Niels-Christian

Chemistry (Weinheim an der Bergstrasse, Germany)

2020 Volume 26, Issue 56, Page(s) 12809–12817

Abstract: C-type lectin receptor (CLR) carbohydrate binding proteins found on immune cells with important functions in pathogen recognition as well as self and non-self-differentiation are increasingly moving into the focus of drug developers as targets for the ... ...

Abstract	C-type lectin receptor (CLR) carbohydrate binding proteins found on immune cells with important functions in pathogen recognition as well as self and non-self-differentiation are increasingly moving into the focus of drug developers as targets for the immune therapy of cancer autoimmune diseases and inflammation and to improve the efficacy of vaccines. The development of molecules with increased affinity and selectivity over the natural glycan binders has largely focused on the synthesis of mono and disaccharide mimetics but glycan array binding experiments have shown increased binding selectivity and affinity for selected larger oligosaccharides that are able to engage in additional favorable interactions beyond the primary binding site. Here, a platform for the rapid preparation and screening of N-glycan mimetics on microarrays is presented that turns a panel of complex glycan core structures into structurally diverse glycomimetics by a combination of enzymatic glycosylation with a nonnatural donor and subsequent cycloaddition with a collection of alkynes. All surface-based reactions were monitored by MALDI-TOF MS to assess conversion and purity of spot compositions. Screening the collection of 374 N-glycomimetics against the plant lectin WFA and the 2 human immune lectins MGL ECD and Langerin ECD produced a number of high affinity binders as lead structures for more selective lectin targeting probes.
MeSH term(s)	Glycosylation ; Humans ; Lectins, C-Type/metabolism ; Microarray Analysis ; Oligosaccharides ; Polysaccharides/chemical synthesis
Chemical Substances	Lectins, C-Type ; Oligosaccharides ; Polysaccharides
Language	English
Publishing date	2020-09-11
Publishing country	Germany
Document type	Journal Article
ZDB-ID	1478547-X
ISSN	1521-3765 ; 0947-6539
ISSN (online)	1521-3765
ISSN	0947-6539
DOI	10.1002/chem.202000026
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Article ; Online: PBPK modeling to support risk assessment of pyrethroid exposure in French pregnant women.

Thépaut, Elisa / Bisson, Michèle / Brochot, Céline / Personne, Stéphane / Appenzeller, Brice M R / Zaros, Cécile / Chardon, Karen / Zeman, Florence

Environmental research

2024 Volume 251, Issue Pt 1, Page(s) 118606

Abstract: Background: Pyrethroids are widely used pesticides and are suspected to affect children's neurodevelopment. The characterization of pyrethroid exposure during critical windows of development, such as fetal development and prenatal life, is essential to ... ...

Abstract	Background: Pyrethroids are widely used pesticides and are suspected to affect children's neurodevelopment. The characterization of pyrethroid exposure during critical windows of development, such as fetal development and prenatal life, is essential to ensure a better understanding of pyrethroids potential effects within the concept of Developmental Origins of Health and Disease. Objective: The aim of this study was to estimate maternal exposure of French pregnant women from biomonitoring data and simulate maternal and fetal internal concentrations of 3 pyrethroids (permethrin, cypermethrin and deltamethrin) using a multi-substance pregnancy-PBPK (physiologically based pharmacokinetics) model. The estimated maternal exposures were compared to newly proposed toxicological reference values (TRV) children specific also called draft child-specific reference value to assess pyrethroid exposure risk during pregnancy i.e. during the in utero exposure period. Methods: A pregnancy-PBPK model was developed based on an existing adult pyrethroids model. The maternal exposure to each parent compound of pregnant women of the Elfe (French Longitudinal Study since Childhood) cohort was estimated by reverse dosimetry based on urinary biomonitoring data. To identify permethrin and cypermethrin contribution to their common urinary biomarkers of exposure, an exposure ratio based on biomarkers in hair was tested. Finally, exposure estimates were compared to current and draft child-specific reference values derived from rodent prenatal and postnatal exposure studies. Results: The main contributor to maternal pyrethroid diet intake is cis-permethrin. In blood, total internal concentrations main contributor is deltamethrin. In brain, the major contributors to internal pyrethroid exposure are deltamethrin for fetuses and cis-permethrin for mothers. Risk is identified only for permethrin when referring to the draft child-specific reference value. 2.5% of the population exceeded permethrin draft child-specific reference value. Conclusions: A new reverse dosimetry approach using PBPK model combined with human biomonitoring data in urine and hair was proposed to estimate Elfe pregnant population exposure to a pyrethroids mixture with common metabolites.
Language	English
Publishing date	2024-03-08
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	205699-9
ISSN	1096-0953 ; 0013-9351
ISSN (online)	1096-0953
ISSN	0013-9351
DOI	10.1016/j.envres.2024.118606
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Article ; Online: The unique 3D arrangement of macrophage galactose lectin enables

Abbas, Massilia / Maalej, Meriem / Nieto-Fabregat, Ferran / Thépaut, Michel / Kleman, Jean-Philippe / Ayala, Isabel / Molinaro, Antonio / Simorre, Jean-Pierre / Marchetti, Roberta / Fieschi, Franck / Laguri, Cedric

PNAS nexus

2023 Volume 2, Issue 9, Page(s) pgad310

Abstract: Lipopolysaccharides are a hallmark of gram-negative bacteria, and their presence at the cell surface is key for bacterial integrity. As surface-exposed components, they are recognized by immunity C-type lectin receptors present on antigen-presenting ... ...

Abstract	Lipopolysaccharides are a hallmark of gram-negative bacteria, and their presence at the cell surface is key for bacterial integrity. As surface-exposed components, they are recognized by immunity C-type lectin receptors present on antigen-presenting cells. Human macrophage galactose lectin binds
Language	English
Publishing date	2023-09-20
Publishing country	England
Document type	Journal Article
ISSN	2752-6542
ISSN (online)	2752-6542
DOI	10.1093/pnasnexus/pgad310
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Article ; Online: High-Mannose Oligosaccharide Hemimimetics that Recapitulate the Conformation and Binding Mode to Concanavalin A, DC-SIGN and Langerin.

Herrera-González, Irene / González-Cuesta, Manuel / Thépaut, Michel / Laigre, Eugénie / Goyard, David / Rojo, Javier / García Fernández, José M / Fieschi, Franck / Renaudet, Olivier / Nieto, Pedro M / Ortiz Mellet, Carmen

Chemistry (Weinheim an der Bergstrasse, Germany)

2023 Volume 30, Issue 2, Page(s) e202303041

Abstract: The "carbohydrate chemical mimicry" exhibited by ... ...

Abstract	The "carbohydrate chemical mimicry" exhibited by sp
MeSH term(s)	Humans ; Concanavalin A/metabolism ; Mannose/chemistry ; Lectins, C-Type/metabolism ; Oligosaccharides/chemistry ; Binding Sites ; Mannose-Binding Lectins/chemistry
Chemical Substances	DC-specific ICAM-3 grabbing nonintegrin ; Concanavalin A (11028-71-0) ; Mannose (PHA4727WTP) ; Lectins, C-Type ; Oligosaccharides ; Mannose-Binding Lectins
Language	English
Publishing date	2023-11-14
Publishing country	Germany
Document type	Journal Article
ZDB-ID	1478547-X
ISSN	1521-3765 ; 0947-6539
ISSN (online)	1521-3765
ISSN	0947-6539
DOI	10.1002/chem.202303041
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Article: Glycomimetic ligands block the interaction of SARS-CoV-2 spike protein with C-type lectin co-receptors

Pollastri, Sara / Delaunay, Clara / Thépaut, Michel / Fieschi, Franck / Bernardi, Anna

Chemical communications. 2022 Apr. 21, v. 58, no. 33

2022

Abstract	The C-type lectin receptors DC-SIGN and L-SIGN bind to glycans on the SARS-CoV-2 spike glycoprotein and promote trans-infection of ACE2-expressing cells. We tested C2 triazole-modified mono- and pseudo-di-mannosides as inhibitors of DC/L-SIGN binding to a model mannosylated protein (Man-BSA) and to SARS-CoV2 spike, finding that they inhibit the interaction of both lectins with the spike glycoprotein in a Surface Plasmon Resonance (SPR) assay and are more potent than mannose by up to 36-fold (DC-SIGN) and 10-fold (L-SIGN). The molecules described here are the first known glycomimetic ligands of L-SIGN.
Keywords	Severe acute respiratory syndrome coronavirus 2 ; glycoproteins ; lectins ; ligands ; mannose ; polysaccharides ; surface plasmon resonance
Language	English
Dates of publication	2022-0421
Size	p. 5136-5139.
Publishing place	The Royal Society of Chemistry
Document type	Article
ZDB-ID	1472881-3
ISSN	1364-548X ; 1359-7345 ; 0009-241X
ISSN (online)	1364-548X
ISSN	1359-7345 ; 0009-241X
DOI	10.1039/d2cc00121g
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Molecular recognition of Escherichia coli R1-type core lipooligosaccharide by DC-SIGN

Ferran Nieto-Fabregat / Angela Marseglia / Michel Thépaut / Jean-Philippe Kleman / Massilia Abbas / Aline Le Roy / Christine Ebel / Meriem Maalej / Jean-Pierre Simorre / Cedric Laguri / Antonio Molinaro / Alba Silipo / Franck Fieschi / Roberta Marchetti

iScience, Vol 27, Iss 2, Pp 108792- (2024)

2024

Abstract: Summary: Due to their ability to recognize carbohydrate structures, lectins emerged as potential receptors for bacterial lipopolysaccharides (LPS). Despite growing interest in investigating the association between host receptor lectins and exogenous ... ...

Abstract	Summary: Due to their ability to recognize carbohydrate structures, lectins emerged as potential receptors for bacterial lipopolysaccharides (LPS). Despite growing interest in investigating the association between host receptor lectins and exogenous glycan ligands, the molecular mechanisms underlying bacterial recognition by human lectins are still not fully understood. We contributed to fill this gap by unveiling the molecular basis of the interaction between the lipooligosaccharide of Escherichia coli and the dendritic cell-specific intracellular adhesion molecules (ICAM)-3 grabbing non-integrin (DC-SIGN). Specifically, a combination of different techniques, including fluorescence microscopy, surface plasmon resonance, NMR spectroscopy, and computational studies, demonstrated that DC-SIGN binds to the purified deacylated R1 lipooligosaccharide mainly through the recognition of its outer core pentasaccharide, which acts as a crosslinker between two different tetrameric units of DC-SIGN. Our results contribute to a better understanding of DC-SIGN-LPS interaction and may support the development of pharmacological and immunostimulatory strategies for bacterial infections, prevention, and therapy.
Keywords	Microbiology ; Structural biology ; Science ; Q
Language	English
Publishing date	2024-02-01T00:00:00Z
Publisher	Elsevier
Document type	Article ; Online
Database	BASE - Bielefeld Academic Search Engine (life sciences selection)

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Article ; Online: Fluorinated Man

Silva-Díaz, Adrián / Ramírez-Cárdenas, Jonathan / Muñoz-García, Juan C / de la Fuente, M Carmen / Thépaut, Michel / Fieschi, Franck / Ramos-Soriano, Javier / Angulo, Jesús / Rojo, Javier

Journal of the American Chemical Society

2023 Volume 145, Issue 48, Page(s) 26009–26015

Abstract: Lectins are capable of reading out the structural information contained in carbohydrates through specific recognition processes. Determining the binding epitope of the sugar is fundamental to understanding this recognition event. Nuclear magnetic ... ...

Abstract	Lectins are capable of reading out the structural information contained in carbohydrates through specific recognition processes. Determining the binding epitope of the sugar is fundamental to understanding this recognition event. Nuclear magnetic resonance (NMR) is a powerful tool to obtain this structural information in solution; however, when the sugar involved is a complex oligosaccharide, such as high mannose, the signal overlap found in the NMR spectra precludes an accurate analysis of the interaction. The introduction of tags into these complex oligosaccharides could overcome these problems and facilitate NMR studies. Here, we show the preparation of the Man
MeSH term(s)	Humans ; Mannose/chemistry ; Lectins, C-Type/metabolism ; Oligosaccharides/chemistry ; Sugars ; Magnetic Resonance Spectroscopy ; Epitopes ; Dendritic Cells
Chemical Substances	DC-specific ICAM-3 grabbing nonintegrin ; Mannose (PHA4727WTP) ; Lectins, C-Type ; Oligosaccharides ; Sugars ; Epitopes
Language	English
Publishing date	2023-11-18
Publishing country	United States
Document type	Journal Article ; Research Support, Non-U.S. Gov't
ZDB-ID	3155-0
ISSN	1520-5126 ; 0002-7863
ISSN (online)	1520-5126
ISSN	0002-7863
DOI	10.1021/jacs.3c06204
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