Dehydro-β-proline Containing α4β1 Integrin Antagonists: Stereochemical Recognition in Ligand–Receptor Interplay Article Swipe
Alessandra Tolomelli
,
Monica Baiula
,
Angelo Viola
,
Lucia Ferrazzano
,
Luca Gentilucci
,
Samantha Deianira Dattoli
,
Santi Spampinato
,
Eusebio Juaristi
,
Margarita Escudero‐Casao
·
YOU?
·
· 2015
· Open Access
·
· DOI: https://doi.org/10.1021/acsmedchemlett.5b00125
YOU?
·
· 2015
· Open Access
·
· DOI: https://doi.org/10.1021/acsmedchemlett.5b00125
A novel class of dehydro-β-proline-containing peptidomimetics, designed to be effective as α4β1 integrin ligands, has been developed on the basis of the fundamental requirements for the interactions of these transmembrane receptors with bioactive ligands. Dehydro-β-proline ring has been synthesized through an original pathway, involving ring closing metathesis of a diallylamino derivative. The synthesized products showed to be effective and selective as α4β1 integrin antagonists and displayed IC50 values in the nanomolar range in cell adhesion inhibition assays and in VCAM-1-induced phosphorylation of extracellular-signal-regulated kinases. Significant activity was observed also toward the homologous integrin α4β7, while they did not display any activity toward selected members of β1, β2, and β3 families. A strong dependence on the stereochemistry of the heterocyclic central core could be observed. The great importance of α4β1 integrin in chronic inflammatory and autoimmune diseases suggests a possible exploitation of these ligands as lead compounds for therapeutic tools development.
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Metadata
- Type
- article
- Language
- en
- Landing Page
- https://doi.org/10.1021/acsmedchemlett.5b00125
- OA Status
- green
- Cited By
- 23
- References
- 48
- Related Works
- 10
- OpenAlex ID
- https://openalex.org/W2437850879
All OpenAlex metadata
Raw OpenAlex JSON
- OpenAlex ID
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https://openalex.org/W2437850879Canonical identifier for this work in OpenAlex
- DOI
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https://doi.org/10.1021/acsmedchemlett.5b00125Digital Object Identifier
- Title
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Dehydro-β-proline Containing α4β1 Integrin Antagonists: Stereochemical Recognition in Ligand–Receptor InterplayWork title
- Type
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articleOpenAlex work type
- Language
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enPrimary language
- Publication year
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2015Year of publication
- Publication date
-
2015-05-06Full publication date if available
- Authors
-
Alessandra Tolomelli, Monica Baiula, Angelo Viola, Lucia Ferrazzano, Luca Gentilucci, Samantha Deianira Dattoli, Santi Spampinato, Eusebio Juaristi, Margarita Escudero‐CasaoList of authors in order
- Landing page
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https://doi.org/10.1021/acsmedchemlett.5b00125Publisher landing page
- Open access
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YesWhether a free full text is available
- OA status
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greenOpen access status per OpenAlex
- OA URL
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https://hdl.handle.net/11585/519198Direct OA link when available
- Concepts
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Peptidomimetic, Integrin, Transmembrane protein, Chemistry, Stereochemistry, Receptor, Ligand (biochemistry), Proline, Structure–activity relationship, Biochemistry, In vitro, Amino acid, PeptideTop concepts (fields/topics) attached by OpenAlex
- Cited by
-
23Total citation count in OpenAlex
- Citations by year (recent)
-
2025: 2, 2024: 1, 2023: 2, 2022: 1, 2021: 4Per-year citation counts (last 5 years)
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48Number of works referenced by this work
- Related works (count)
-
10Other works algorithmically related by OpenAlex
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