Novel liposaccharide conjugates for drug and peptide delivery.

@article{Drouillat1998NovelLC,
  title={Novel liposaccharide conjugates for drug and peptide delivery.},
  author={Bruno Drouillat and Anya M. Hillery and Gyula D{\'e}k{\'a}ny and Robert A Falconer and Karen Wright and Istvan Toth},
  journal={Journal of pharmaceutical sciences},
  year={1998},
  volume={87 1},
  pages={
          25-30
        }
}
Sugar-lipid conjugates with general structure 1-4 were prepared by coupling amino sugars with N-Boc-protected lipoamino acids and oligomers. Conjugates with general structure 5 were also prepared from glucuronic acid and methyl 2-aminohexadecanoate. The physicochemical properties of the conjugates were modified by varying the nature and number of sugars or the number of lipoamino acids or their alkyl chain length. The ability of the liposaccharides to aggregate was examined. These preliminary… Expand
Development and characterization of anionic liposaccharides for enhanced oral drug delivery.
TLDR
The results suggested that the studied liposaccharide with two lipids was safe to apply biologically and may have an absorption enhancing activity on hydrophilic, orally poorly available drugs. Expand
Liposaccharide-based nanoparticulate drug delivery system
Abstract A series of anionic liposaccharide derivatives were synthesized in order to develop a system, which would have the capacity to act as an absorption enhancer and to improve oralExpand
Design, synthesis and biological evaluation of novel lipoamino acid-based glycolipids for oral drug delivery.
TLDR
A series of lipoamino acid-based glycolipids were synthesised and conjugated to monosaccharides to yield novel O-, N, S- and C-linked glycolIPids in good yields, with potential to improve the oral absorption of piperacillin. Expand
Lipophilic methotrexate conjugates with glucose‐lipoamino acid moieties: Synthesis and in vitro antitumor activity
To obtain methotrexate (MTX) derivatives with a balanced hydrolipophilic character, we synthesized a series of conjugates in which the drug was linked to lipoamino acid (LAA)‐glucose residuesExpand
Encapsulation of lipopeptides within liposomes: effect of number of lipid chains, chain length and method of liposome preparation.
TLDR
Investigation of the effect of lipid chain length and number of lipid chains present on lipopeptides on their ability to be incorporated within liposomes found freeze drying of monophase systems is better at maintaining a molecular dispersion of thelipopeptide within the solid phospholipid matrix compared to preparation of lipid film by evaporation. Expand
Oral absorption enhancement of dipeptide L-Glu-L-Trp-OH by lipid and glycosyl conjugation.
TLDR
A library of novel derivatives of the dipeptide L-Glu-L-Trp, a naturally occurring thymic immunomodulator with high hydrophilic character and low membrane permeability, was designed and synthesised to enhance the stability towards enzymatic degradation and the permeability across biological membranes of poorly orally available drugs, including peptides. Expand
Effect of Liposomal Delivery on In Vitro Antitumor Activity of Lipophilic Conjugates of Methotrexate with Lipoamino Acids
Some selected lipophilic conjugates of the antifolate drug methotrexate (MTX) with lipoamino acids (LAA), previously described, were incorporated in liposomes with a different composition and chargeExpand
Design, synthesis and characterisation of mannosylated ovalbumin lipid core peptide self-adjuvanting vaccine delivery system
TLDR
The mannosylated ovalbumin peptides were nontoxic to human erythrocytes in haemolytic assay and showed increased (up to 20-fold) stability in plasma, and incorporated two or four copies of either epitope into the LCP vaccine. Expand
Synthesis and biological evaluation of novel lipoamino acid derivatives.
TLDR
It was found that compound 3b was the most potent antibacterial compound which showed good activity against four Gram positive bacterial strains and also exhibited excellent antifungal activity against a fungal strain. Expand
Synthesis of glycolipopeptidic building blocks for carbohydrate receptor discovery.
TLDR
A class of glycolipopeptides for use as building blocks for a new type of dynamic combinatorial library is reported, providing entities which could be screened in biological assays to find the most potent combination of building blocks in order to identify new bioactive carbohydrate ligands. Expand
...
1
2
3
...

References

SHOWING 1-10 OF 11 REFERENCES
A novel chemical approach to drug delivery: lipidic amino acid conjugates.
  • I. Toth
  • Chemistry, Medicine
  • Journal of drug targeting
  • 1994
TLDR
Conjugation to lipidic amino acids and peptides is a useful approach to improve the absorption of poorly-absorbed drugs. Expand
Oral absorption of lipidic amino acid conjugates
Abstract A series of unlabelled and radiolabelled lipidic peptide conjugates 2a-2f were synthesised by reduction of 1a-1f with NaBH 4 and NaB 3 H 4 , respectively. Initial in vitro experiments usingExpand
Synthesis and oral uptake studies of lipidic and glyco-lipidic conjugates of β-lactam antibiotics
Lipidic and glyco-lipidic cephalosporin conjugates 1c and 1i were synthesised as diastereomeric mixtures to improve their oral absorption. 2-(tert-Butoxycarbonylamino)tetradecanoic acid was condensedExpand
Lipidic peptides X. Synthesis, structural and physico-chemical elucidation of lipidic amino acid conjugates with hydrophilic compounds☆
Lipidic amino acids 1a, c and dimer 1b were coupled to highly hydrophilic compounds, lactic, glycolic and gluconic acids and protected gulonic acid, yielding conjugates 1d,f,h,i,j,l and o. AfterExpand
Liposomes as immunoadjuvants and vaccine carriers: antigen entrapment.
TLDR
Successful use of liposomes as immunological adjuvants in vaccines requires simple, easy to scale up technology capable of high-yield antigen entrapment, which has led to the development of techniques that can generate liposome of various sizes containing soluble antigens. Expand
Lipidic conjugates of luteinizing hormone releasing hormone (LHRH)+ and thyrotropin releasing hormone (TRH)+ that release and protect the native hormones in homogenates of human intestinal epithelial (Caco-2) cells
TLDR
The released LHRH or TRH subsequently demonstrated a longer half-life than when present alone in the incubation mixture, suggesting that the cleaved lipidic peptide is capable of inhibiting enzymes. Expand
Immunological adjuvants: a role for liposomes.
TLDR
The use of liposomes is discussed as an alternative safe, versatile, universal adjuvant that can induce humoral- and cell-mediated immunity to antigens when administered parenterally or enterally. Expand
Factors affecting the oral uptake and translocation of polystyrene nanoparticles: histological and analytical evidence.
TLDR
The ability to decrease and increase uptake is clear evidence of a phenomenon which has the potential for further control to allow it to be exploited fully for drug or vaccine delivery. Expand
Targeting of drugs and vaccines to the gut.
TLDR
The different targeting mechanisms available to the pharmaceutical scientist to provide site-specific delivery in the gastrointestinal tract will be critically assessed. Expand
Intestinal translocation of particulates — implications for drug and antigen delivery
TLDR
It must be concluded that in certain circumstances intestinal translocation of particulates is possible and it is possible that particulate carriers can be exploited successfully to develop more effective oral vaccines for non-replicating antigens. Expand
...
1
2
...