| Synthesis of novel adamantylacetyl derivative of peptidoglycan monomer--biological evaluation of immunomodulatory peptidoglycan monomer and respective derivatives with lipophilic substituents on amino group. | |
| | |
MedLine Citation:
|
PMID: 11058039 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
|
Novel synthetic analogue of immunomodulatory peptidoglycan monomer 1 (PGM), (adamant-1-yl)-CH2CO-PGM (2), was prepared by acylation of epsilon-amino group of diaminopimelic acid with symmetrical (adamant-1-yl)-acetic acid anhydride in the presence of triethylamine. The product was isolated by gel filtration on Sephadex G-25, followed by ion exchange chromatography on SP-Sephadex C-25. The susceptibility of (adamant-1-yl)-CH2CO-PGM to hydrolysis with N-acetylmuramyl-L-alanine amidase was demonstrated, and the product of hydrolysis, (adamant-1-yl) CH2CO-pentapeptide 3, was characterized. Both 2 and 3 are water soluble and non-pyrogenic compounds. Immunomodulatory activity of PGM (adamant-1-yl)-CH2CO-PGM and structurally related derivative Boc-Tyr-PGM was compared in experiments in vivo, in mice, using ovalbumin (OVA) as an antigen. All three tested compounds exhibited comparable immunostimulating effects with respect to the induction of anti-ovalbumin immunoglobulin G. The results of evaluation of biological activity show that the substitution of free amino group in the parent peptidoglycan molecule with bulky lipophilic substituents did not affect the susceptibility to hydrolysis with N-acetylmuramyl-L-alanine amidase and did not alter markedly the immunostimulating activity. The results also indicate that the free amino group in the peptide chain is not a necessary requirement in the mechanism of immunostimulation of tested immunomodulators. |
| | |
Authors:
|
D Ljevaković; J Tomasić; V Sporec; B H Spoljar; I Hanzl-Dujmovic |
Related Documents
:
|
22508409 - Amino-acid-based block copolymers by raft polymerization. 9629469 - Synthesis and radioprotective effects of adamantyl substituted 1,4-dihydropyridine deri... 22138239 - Prediction of pattern recognition receptor family using pseudo-amino acid composition. 12418859 - Dysinosin a: a novel inhibitor of factor viia and thrombin from a new genus and species... 1632829 - New isoflavonoids as inhibitors of porcine 5-lipoxygenase. 11382149 - Synthesis and evaluation of steroidal hydroxamic acids as inhibitors of p450 17 (17 alp... 22367529 - Chitin and l(+)-lactic acid production from crab (callinectes bellicosus) wastes by fer... 6195129 - Affinity chromatographic quantitation of glycosylated hemoglobin in newborn infants. 2161549 - Amino acid patterns in schizophrenia: some new findings. |
Publication Detail:
|
Type: Evaluation Studies; Journal Article; Research Support, U.S. Gov't, Non-P.H.S. |
Journal Detail:
|
Title: Bioorganic & medicinal chemistry Volume: 8 ISSN: 0968-0896 ISO Abbreviation: Bioorg. Med. Chem. Publication Date: 2000 Oct |
Date Detail:
|
Created Date: 2001-01-24 Completed Date: 2001-02-22 Revised Date: 2006-11-15 |
Medline Journal Info:
|
Nlm Unique ID: 9413298 Medline TA: Bioorg Med Chem Country: ENGLAND |
Other Details:
|
Languages: eng Pagination: 2441-9 Citation Subset: IM |
Affiliation:
|
Institute of Immunology, Inc., Zagreb, Croatia. |
Export Citation:
|
APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
|
Adamantane
/
analogs & derivatives*,
analysis,
chemical synthesis* Adjuvants, Immunologic / pharmacology* Amidohydrolases / metabolism Animals Chromatography, Thin Layer Enzyme-Linked Immunosorbent Assay Immunization Lipids / chemistry Mice Mice, Inbred C57BL Molecular Structure Peptidoglycan / metabolism* |
| Chemical | |
Reg. No./Substance:
|
0/Adjuvants, Immunologic; 0/Lipids; 0/Peptidoglycan; 281-23-2/Adamantane; EC 3.5.-/Amidohydrolases |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
Previous Document: Synthesis of a triply phosphorylated pentapeptide from human tau-protein.
Next Document: Investigating the role of the geminal dimethyl groups of coenzyme A: synthesis and studies of a dide...