Synthesis and growth inhibitory properties of glycosides of 1-O-hexadecyl-2-O-methyl-sn-glycerol, analogs of the antitumor ether lipid ET-18-OCH3 (edelfosine).

@article{Marinoalbernas1996SynthesisAG,
  title={Synthesis and growth inhibitory properties of glycosides of 1-O-hexadecyl-2-O-methyl-sn-glycerol, analogs of the antitumor ether lipid ET-18-OCH3 (edelfosine).},
  author={J. R. Marino-albernas and Robert Bittman and A Peters and Eric G. Mayhew},
  journal={Journal of medicinal chemistry},
  year={1996},
  volume={39 17},
  pages={
          3241-7
        }
}
Glycosylated antitumor ether lipids (GAELs), analogs of 1-O-octadecyl-2-O-methyl-sn-glycero-3-phosphocholine (1, ET-18-OCH3, edelfosine), were synthesized in good overall yields by glycosylation of 1-O-alkyl-2-O-methyl-sn-glycerol and tested for in vitro antineoplastic activity against a variety of murine and human tumor cell lines. Stereospecific glycosylation was achieved by the use of 2-O-acetyl-3,4,6-tri-O-benzylglucopyranosyl and -mannopyranosyl trichloroacetimidates as donors, with… 
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23 Citations

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The results of the study show that GAELs are taken up by endocytosis and an active endocytic pathway is required for the formation of large acidic vacuoles byGAELs and manifestation of their cytotoxic effects.
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A glycosylated antitumor ether lipid kills cells via paraptosis-like cell death.
TLDR
The data suggest thatGAELs may activate autophagy; however, GAELs do not kill cells by apoptosis orAutophagy but rather by a paraptosis-like cell death mechanism.
Synthetic β-1,2-Mannosyloxymannitol Glycolipid from the Fungus Malassezia pachydermatis Signals through Human Mincle.
TLDR
The total synthesis of a complex β-1,2-mannosyloxymannitol glycolipid from Malassezia pachydermatis 44-2 is reported, which constitutes the first fungal metabolite identified that can signal through the human Mincle receptor, providing new insights into antifungal immunity.
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The Barton-McCombie Reaction
Deoxygenations of alcohols, i.e., processes that replace a hydroxyl group with hydrogen at a saturated carbon, find applications in both total synthesis and the systematic modifications of natural…
Hydrogen Bond Synchronized Dual Activation Enables the Unified β-Selective O-Glycosylation Inside a Molecular Capsule
TLDR
It is demonstrated that a molecular capsule catalyzes the highlychallenging selective formation of b-glycosides independent of the substrate’s substitution pattern and configuration, which is unprecedented for man-made catalysts.
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Glycosidated phospholipids: uncoupling of signalling pathways at the plasma membrane
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The potential of glycosidated phospholipids, especially Ino‐C2‐PAF, as a promising new group of drugs for the treatment of hyperproliferative and migration‐based skin diseases is highlighted.
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