Synthesis and biological evaluation of novel 2-azido muramyl dipeptide as NOD2 agonistic adjuvants.

Acetylmuramyl-Alanyl-Isoglutamine / pharmacology Adjuvants, Immunologic / chemistry Adjuvants, Pharmaceutic Hydrophobic and Hydrophilic Interactions Nod2 Signaling Adaptor Protein
2-AZMDP(1-5) Bio-isosters CD4 CD8 DENV MDP NOD2 agonist

Journal

Bioorganic & medicinal chemistry
ISSN: 1464-3391
Titre abrégé: Bioorg Med Chem
Pays: England
ID NLM: 9413298

Informations de publication

Date de publication:
15 07 2022
Historique:
received: 15 12 2021
revised: 22 04 2022
accepted: 23 04 2022
pubmed: 16 5 2022
medline: 3 6 2022
entrez: 15 5 2022
Statut: ppublish

Résumé

Novel 2-Azido muramyl dipeptide was synthesized by the bio-isosteric replacement of the N-acetyl group of the muramic acid fragment with the azide functionality at the C2 position. In order to examine the effect of hydrophilic-lipophilic balance on the adjuvant activity, derivatives were synthesized by removing protecting groups sequentially to tune the polarity. Amongst five novel azido derivatives of MDP studied here, di- and mono-benzylated azido derivatives 10 and 11 exhibited good DENV specific antibody(IgG) response with Th1 polarization compared to parent compound Muramyl dipeptide (MDP) whereas all five new derivatives responded positively to NOD2 agonistic assays with compound 10 showing highest stimulation.

Identifiants

DOI: 10.1016/j.bmc.2022.116781 PMID: 35569249
pubmed: 35569249
pii: S0968-0896(22)00173-0
doi: 10.1016/j.bmc.2022.116781
pii:
doi:

Substances chimiques

Adjuvants, Immunologic 0
Adjuvants, Pharmaceutic 0
Nod2 Signaling Adaptor Protein 0
Acetylmuramyl-Alanyl-Isoglutamine 53678-77-6

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

116781

Informations de copyright

Copyright © 2022. Published by Elsevier Ltd.

Auteurs

Paturu Rama Subba Reddy (PRS)

Vaccine Immunology Laboratory, OSPC Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, Uttar Pradesh 201 002, India.

Shainy Sambyal (S)

Vaccine Immunology Laboratory, OSPC Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, Uttar Pradesh 201 002, India.

Tukaram B Mhamane (TB)

Vaccine Immunology Laboratory, OSPC Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, Uttar Pradesh 201 002, India.

Vemireddy Sravanthi (V)

Vaccine Immunology Laboratory, OSPC Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.

Syed Shafi (S)

Department of Chemistry, School of Chemical and Life Sciences, Jamia Hamdard, New Delhi, India.

Imran A Khan (IA)

Department of Chemistry, School of Chemical and Life Sciences, Jamia Hamdard, New Delhi, India.

Halmuthur M Sampath Kumar (HM)

Vaccine Immunology Laboratory, OSPC Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India; Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, Uttar Pradesh 201 002, India. Electronic address: sampath.iict@gov.in.

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Classifications MeSH

questionsmedicales.fr › Acides aminés, peptides et protéines › Peptides › Glycopeptides › Acétylmuramyl alanyl isoglutamine › Synthesis and biological evaluation of novel...
questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Effets physiologiques des médicaments › Facteurs immunologiques › Adjuvants immunologiques › Synthesis and biological evaluation of novel...
questionsmedicales.fr › Actions chimiques et utilisations › Utilisations spécialisées de produits chimiques › Excipients pharmaceutiques › Adjuvants pharmaceutiques › Synthesis and biological evaluation of novel...
questionsmedicales.fr › Phénomènes chimiques › Interactions hydrophobes et hydrophiles › Synthesis and biological evaluation of novel...
questionsmedicales.fr › Acides aminés, peptides et protéines › Protéines › Protéines et peptides de signalisation intracellulaire › Protéines régulatrices de l'apoptose › Protéines adaptatrices de signalisation CARD › Protéine adaptatrice de signalisation NOD2 › Synthesis and biological evaluation of novel...