Sodium hyaluronate-g-2-((N-(6-aminohexyl)-4-methoxyphenyl)sulfonamido)-N-hydroxyacetamide with enhanced affinity towards MMP12 catalytic domain to be used as visco-supplement with increased degradation resistance.

Catalytic Domain Chondrocytes / drug effects Hyaluronic Acid / chemical synthesis Hydroxamic Acids / chemical synthesis Matrix Metalloproteinase 12 / chemistry Matrix Metalloproteinase Inhibitors / chemical synthesis Protein Binding Sulfonamides / chemical synthesis Viscoelastic Substances / chemical synthesis
Degradation Hyaluronic acid MMP inhibitors Synovial fluid Viscosupplementation

Journal

Carbohydrate polymers
ISSN: 1879-1344
Titre abrégé: Carbohydr Polym
Pays: England
ID NLM: 8307156

Informations de publication

Date de publication:
01 Nov 2021
Historique:
received: 03 05 2021
revised: 13 07 2021
accepted: 14 07 2021
entrez: 8 8 2021
pubmed: 9 8 2021
medline: 6 1 2022
Statut: ppublish

Résumé

The present paper describes the functionalization of sodium hyaluronate (NaHA) with a small molecule (2-((N-(6-aminohexyl)-4-methoxyphenyl)sulfonamido)-N-hydroxyacetamide) (MMPI) having proven inhibitory activity against membrane metalloproteins involved in inflammatory processes (i.e. MMP12). The obtained derivative (HA-MMPI) demonstrated an increased resistance to the in-vitro degradation by hyaluronidase, viscoelastic properties close to those of healthy human synovial fluid, cytocompatibility towards human chondrocytes and nanomolar affinity towards MMP 12. Thus, HA-MMPI can be considered a good candidate as viscosupplement in the treatment of knee osteoarticular disease.

Identifiants

DOI: 10.1016/j.carbpol.2021.118452 PMID: 34364546
pubmed: 34364546
pii: S0144-8617(21)00839-0
doi: 10.1016/j.carbpol.2021.118452
pii:
doi:

Substances chimiques

Hydroxamic Acids 0
Matrix Metalloproteinase Inhibitors 0
Sulfonamides 0
Viscoelastic Substances 0
Hyaluronic Acid 9004-61-9
Matrix Metalloproteinase 12 EC 3.4.24.65

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

IM

Pagination

118452

Informations de copyright

Copyright © 2021 Elsevier Ltd. All rights reserved.

Auteurs

Gemma Leone (G)

Department of Biotechnology, Chemistry and Pharmacy, University of Siena, Via A. Moro 2, 53100 Siena, Italy; National Interuniversity Consortium of Materials Science and Technology (INSTM), Via Giusti 9, 50121 Firenze, Italy.

Simone Pepi (S)

Department of Biotechnology, Chemistry and Pharmacy, University of Siena, Via A. Moro 2, 53100 Siena, Italy; National Interuniversity Consortium of Materials Science and Technology (INSTM), Via Giusti 9, 50121 Firenze, Italy.

Marco Consumi (M)

Department of Biotechnology, Chemistry and Pharmacy, University of Siena, Via A. Moro 2, 53100 Siena, Italy; National Interuniversity Consortium of Materials Science and Technology (INSTM), Via Giusti 9, 50121 Firenze, Italy.

Stefania Lamponi (S)

Department of Biotechnology, Chemistry and Pharmacy, University of Siena, Via A. Moro 2, 53100 Siena, Italy; National Interuniversity Consortium of Materials Science and Technology (INSTM), Via Giusti 9, 50121 Firenze, Italy.

Marco Fragai (M)

Department of Chemistry, "Ugo Schiff" - University of Florence - Via della Lastruccia 13, 50019 Sesto Fiorentino, FI, Italy; Cerm, University of Florence, via L. Sacconi 6, 50019 Sesto Fiorentino, FI, Italy.

Marco Martinucci (M)

Department of Chemistry, "Ugo Schiff" - University of Florence - Via della Lastruccia 13, 50019 Sesto Fiorentino, FI, Italy.

Veronica Baldoneschi (V)

Department of Chemistry, "Ugo Schiff" - University of Florence - Via della Lastruccia 13, 50019 Sesto Fiorentino, FI, Italy; National Interuniversity Consortium of Materials Science and Technology (INSTM), Via Giusti 9, 50121 Firenze, Italy.

Oscar Francesconi (O)

Department of Chemistry, "Ugo Schiff" - University of Florence - Via della Lastruccia 13, 50019 Sesto Fiorentino, FI, Italy; National Interuniversity Consortium of Materials Science and Technology (INSTM), Via Giusti 9, 50121 Firenze, Italy.

Cristina Nativi (C)

Department of Chemistry, "Ugo Schiff" - University of Florence - Via della Lastruccia 13, 50019 Sesto Fiorentino, FI, Italy; National Interuniversity Consortium of Materials Science and Technology (INSTM), Via Giusti 9, 50121 Firenze, Italy.

Agnese Magnani (A)

Department of Biotechnology, Chemistry and Pharmacy, University of Siena, Via A. Moro 2, 53100 Siena, Italy; National Interuniversity Consortium of Materials Science and Technology (INSTM), Via Giusti 9, 50121 Firenze, Italy. Electronic address: agnese.magnani@unisi.it.

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Classifications MeSH

questionsmedicales.fr › Phénomènes chimiques › Phénomènes biochimiques › Conformation moléculaire › Conformation des protéines › Éléments structuraux des protéines › Domaine catalytique › Sodium...
questionsmedicales.fr › Cellules › Cellules du tissu conjonctif › Chondrocytes › Sodium...
questionsmedicales.fr › Glucides › Polyosides › Glycosaminoglycanes › Acide hyaluronique › Sodium...
questionsmedicales.fr › Composés chimiques organiques › Acides carboxyliques › Hydroxyacides › Acides hydroxamiques › Sodium...
questionsmedicales.fr › Acides aminés, peptides et protéines › Protéines › Secreted matrix metalloproteinases › Matrix metalloproteinase 12 › Sodium...
questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Mécanismes moléculaires de l'action pharmacologique › Antienzymes › Inhibiteurs de protéases › Inhibiteurs de métalloprotéinases matricielles › Sodium...
questionsmedicales.fr › Métabolisme › Liaison aux protéines › Sodium...
questionsmedicales.fr › Composés chimiques organiques › Composés du soufre › Sulfones › Sulfonamides › Sodium...
questionsmedicales.fr › Actions chimiques et utilisations › Utilisations spécialisées de produits chimiques › Substances viscoélastiques › Sodium...