Synthesis of novel adamantylacetyl derivative of peptidoglycan monomer—biological evaluation of immunomodulatory peptidoglycan monomer and respective derivatives with lipophilic substituents on amino group

Ljevaković, Đurđica; Tomašić, Jelka; Šporec, Vesna; Halassy, Beata; Hanzl-Dujmović, Ivana

doi:10.1016/s0968-0896(00)00172-3

Cited by 21 publications

(7 citation statements)

References 22 publications

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“…33 Despite numerous synthetic problems encountered in transformations of larger molecules several successful attempts to synthetically modify PGM monomer 1 as a parent compound were made. The previous reports describe the synthesis of PGM modified with Boc-tyrosine, 34 adamant-1-yl, 35 as well as with mannopyranosyl 22 residues. This was possible because the preferential conformation of PGM in aqueous and dimethylsulfoxide solutions showed that the amino group of meso-diaminopimelic acid is exposed and can therefore be manipulated without the interference of other reactive groups.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Evaluation of New Mannose Derived Immunomodulating Adamantyltripeptides

et al. 2011

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Abstract. A novel class of mannosylated adamantyltripeptides, general formula of which is α-Man-OCH 2 CH(CH 3 )CO-AdGly-L-Ala-D-isoGln, were prepared, characterized, and their possible immunomodulatory properties investigated in some preliminary tests in vivo. All newly synthesized glycopeptides comprise in their structure the adamantylglycyl moiety linked to the dipeptide L-Ala-D-isoGln, as well as mannose. Adjuvant activity of mannosylated adamant-2-yl tripeptides was tested in the mouse model using ovalbumin as an antigen and in comparison to the peptidoglycan monomer (PGM, β-D-GlcNAc-(1→4)-D-MurNAc-L-Ala-D-isoGln-mesoDAP(εNH 2 )-D-Ala-D-Ala).

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Section: Resultsmentioning

confidence: 99%

Synthesis and Biological Evaluation of New Mannose Derived Immunomodulating Adamantyltripeptides

et al. 2011

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“…On the other hand, lipophilic substituents attached to MDP resulted in modulation of the activity of the parent molecule in various ways as mentioned above. Their immunostimulating activities were, however, comparable to that of PGM [65]. PGM enhanced the immunogenicity of peptides of measles virus origin [61]; co-administration with liposomes increased the adjuvant activity and induced a switch from Th1 to Th2 type of immune response [62].…”

Section: Muropeptidesmentioning

confidence: 89%

Structural Aspects of Peptides with Immunomodulating Activity

Szilágyi

Pristovšek²

2007

MRMC

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The main function of the innate immune system from insects to mammals is to detect the presence of and act against invading microorganisms by recognizing their unique molecular signatures, most importantly, components of bacterial cell walls. A large number of peptides and derivatives, both synthetic and of natural origin, are known to influence immune responses in mammals by interacting with the conserved microbial structures, making the former attractive targets for drug development. This review focuses on structural aspects of the immunomodulating peptides and their receptors, including primary constitution, stereochemistry, conformation, binding and hydrophobic properties.

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“…The syntheses of peptidoglycan monomer analogues, Boc-Tyr-PGM and (Adamant-1-yl)-acetyl-PGM, were performed according previously reported articles (30)(31)(32). [ 14 C]-PGM was prepared using [ 14 C]-acetate as a precursor as described in (27).…”

Section: Peptidoglycans and Adamantyltripeptidesmentioning

confidence: 99%

“…Two PGM analogs were synthesized in order to investigate their structure-activity relationship. PGM analogs were completely chemically characterized and it was shown that both compounds exhibit immunostimulating activity similar to the activity of the parent molecule, PGM (30)(31)(32). Synthetic adamantyltripeptides, D-(adamant-2-yl)-Gly-L-Ala-D-isoGln (AdTP1) and L-(adamant-2-yl)-Gly-L-Ala-D-isoGln (AdTP2) (33) linked to the dipeptide L-Ala-D-isoGln which is the structural element of the natural peptidoglycans.…”

Section: Introductionmentioning

confidence: 99%

Entrapment of Peptidoglycans and Adamantyltripeptides into Liposomes: An HPLC Assay for Determination of Encapsulation Efficiency

Frkanec¹,

Travaš²,

Krstanović³

et al. 2003

Journal of Liposome Research

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The encapsulation of different immunomodulating peptides, the peptidoglycan monomer, its semisynthetic derivatives (Adamant-1-yl)-acetyl-peptidoglycan monomer and Boc-Tyr-peptidoglycan monomer, respectively, and of two diastereoisomers of adamantyltripeptides into the large negatively charged multilamellar liposomes was investigated. The reproducible quantitative method using HPLC was established for the determination of the entrapped compounds. It was shown that the tested compounds could be efficiently incorporated into liposomes using either the film or modified film method. The results confirmed that the peptidoglycans with lipophilic substituents and particularly the adamantyltripeptides were incorporated into liposomes with higher efficiency than the peptidoglycan monomer using either of the described methods. Liposome preparations were stable at 4 degrees C up to seven days as shown by minimal leaking of the entrapped material.

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Synthesis of novel adamantylacetyl derivative of peptidoglycan monomer—biological evaluation of immunomodulatory peptidoglycan monomer and respective derivatives with lipophilic substituents on amino group

Cited by 21 publications

References 22 publications

Synthesis and Biological Evaluation of New Mannose Derived Immunomodulating Adamantyltripeptides

Synthesis and Biological Evaluation of New Mannose Derived Immunomodulating Adamantyltripeptides

Structural Aspects of Peptides with Immunomodulating Activity

Entrapment of Peptidoglycans and Adamantyltripeptides into Liposomes: An HPLC Assay for Determination of Encapsulation Efficiency

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