Design, synthesis and biological evaluation of novel lipoamino acid-based glycolipids for oral drug delivery.

@article{Falconer2007DesignSA,
  title={Design, synthesis and biological evaluation of novel lipoamino acid-based glycolipids for oral drug delivery.},
  author={R. Falconer and I. Toth},
  journal={Bioorganic \& medicinal chemistry},
  year={2007},
  volume={15 22},
  pages={
          7012-20
        }
}
A series of lipoamino acid-based glycolipids were synthesised. Suitably derivatised lipoamino acid derivatives were prepared and conjugated to monosaccharides (including glycosyl azides, isothiocyanates, thiols and sulphones) to yield novel O-, N-, S- and C-linked glycolipids in good yields. Their potential to improve the oral absorption of piperacillin is reported. 
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References

SHOWING 1-10 OF 27 REFERENCES
Novel liposaccharide conjugates for drug and peptide delivery.
TLDR
These preliminary experiments have demonstrated the ability of the liposaccharides to form particulate systems per se and also their ability to be incorporated into conventional liposomal systems. Expand
Lipid, sugar and liposaccharide based delivery systems 2.
TLDR
The progress in the development of chemical systems to improve the metabolic stability, absorption and physicochemical properties of potential drugs, as well as novel methods of conjugation of these groups to drugs are discussed. Expand
Design, synthesis, and evaluation of a liposaccharide drug delivery agent: application to the gastrointestinal absorption of gentamicin.
TLDR
The design, synthesis, and evaluation of a liposaccharide for use as an agent to enhance the gastrointestinal absorption of charged, hydrophilic drugs with poor membrane permeability suggests that the molar ratio of 1:11 may be critical in optimizing the delivery system. Expand
Synthesis and in vitro evaluation of lipoamino acid and carbohydrate-modified enkephalins as potential antinociceptive agents
Abstract The principal hindrance to drug uptake into central nervous tissue is the blood–brain barrier (BBB). In addition, potential peptide-based neuropharmaceuticals are rapidly destroyed by intra-Expand
Lipidic peptides. IV. Penicillin and cephalosporin amide conjugates with lipidic amino acids and their oligomers
Abstract A series lipidic amide conjugates ( 2b, c, 3b, c, 4b-d, 5b and c ) of β-lactam antibiotics were synthesised using mixed anhydride methods to couple the Boc-protected lipidic amino acids ( 1aExpand
Efficient synthesis of thioglycosides via a Mitsunobu condensation.
Abstract Thioglycosides were synthesised from 1-thiosugars and a series of alcohols under Mitsunobu conditions using 1,1′-(azodicarbonyl)dipiperidine and trimethylphosphine. The conditions were foundExpand
Synthesis of C-terminal glycopeptides from resin-bound glycosyl azides via a modified Staudinger reaction.
TLDR
The solid-phase synthesis of glycopeptides containing the sugar at the C-terminus is reported, generally applicable to most peptide sequences and is compatible with both Boc- and Fmoc- synthetic strategies on a variety of resins. Expand
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
Carbohydrate mimetics-based glycosyltransferase inhibitors.
TLDR
The purpose of this account is to foster a synergy between the two expanding research areas of glycomimetics and glycosyltransferases. Expand
Lipidic peptides. III: Lipidic amino acid and oligomer conjugates of morphine.
TLDR
A series of lipidic morphine esters 1b-1f with enhanced membrane-like character were synthesized by coupling the lipidic amino acids 2a-2e to the phenolic hydroxyl group of the opioid analgesic morphine, with a potency similar to that of the parent compound 1a. Expand
...
1
2
3
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