Biologically active biotin derivatives of schweinfurthin F.

@article{Ulrich2010BiologicallyAB,
  title={Biologically active biotin derivatives of schweinfurthin F.},
  author={Natalie Christine Ulrich and Craig Heath Kuder and Raymond J. Hohl and David F. Wiemer},
  journal={Bioorganic \& medicinal chemistry letters},
  year={2010},
  volume={20 22},
  pages={
          6716-20
        }
}
As a prelude to efforts to identify schweinfurthin binding proteins, an ester conjugate and an amide conjugate of schweinfurthin F and biotin have been prepared by chemical synthesis. These compounds maintain activity in SF-295 cells comparable to the parent system, and display the lower potency in A549 cells that is a characteristic of the schweinfurthin pattern of activity. 
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References

SHOWING 1-10 OF 47 REFERENCES
Synthesis and biological activity of a fluorescent schweinfurthin analogue.
TLDR
Development of a fluorescent schweinfurthin analogue that retains the differential activity of the natural products, and yet has properties that facilitate its visualization within cells. Expand
Schweinfurthin D, A Cytotoxic Stilbene from Macaranga schweinfurthii
Abstract A novel cytotoxic stilbene, schweinfurthin D, was isolated from Macaranga schweinfurthii (Euphorbiaceae) and its structure was determined by spectroscopic methods. Schweinfurthin D showedExpand
Schweinfurthins I and J from Macaranga schweinfurthii.
TLDR
During chromatographic purification of the organic solvent extract, analytical UPLC-PDA-TOFMS of stilbene-enriched fractions revealed the presence of six known schweinfurthins and two previously unknown stilbenes. Expand
Cytotoxic geranyl stilbenes from Macaranga schweinfurthii.
TLDR
The cytot toxicity profile of the schweinfurthins tested in the NCI 60-cell screen was similar to that of the stelletins and cephalostatins, suggesting that these structurally diverse natural products may share similar mechanisms of cytotoxicity. Expand
CHAPTER 22 THE SCHWEINFURTHINS Issues in development of a plant-derived anticancer lead
The development of a natural product into a pharmaceutical drug product can follow a long and tortuous path in the best of cases. This chapter highlights issues that have arisen in the development ofExpand
Structural analogues of schweinfurthin F: probing the steric, electronic, and hydrophobic properties of the D-ring substructure.
TLDR
Chemical synthesis of analogues modified in different olefinic positions, and preliminary results from studies of their biological activity, are reported. Expand
Total synthesis of (+)-schweinfurthins B and E.
TLDR
The first total synthesis of (+)-schweinfurthin B, a potent and differentially active cytotoxic agent, has been accomplished and established for the first time the absolute stereochemistry of the natural product, and provides access to material on a scale that will advance biological studies. Expand
Polyproline-rod approach to isolating protein targets of bioactive small molecules: isolation of a new target of indomethacin.
TLDR
The results indicate that insertion of a long, rigid polyproline helix between a small-molecule bait and a biotin tag boosts the capacity of affinity purification and thereby permits isolation of low-abundance or low-affinity proteins. Expand
The cephalostatin way of apoptosis.
TLDR
It is found that endoplasmic reticulum stress-associated caspase-4 contributes to nonclassical cephalostatin-mediated casp enzyme activation, additionally pointing out the unusual pathway used by this substance. Expand
Synthesis and evaluation of caffeic acid amides as antioxidants.
TLDR
A series of amides of caffeic acid has been synthesised and their antioxidant properties evaluated as lipid peroxidation inhibitors and found to be very efficient antioxidants with IC50's of 0.3 microM. Expand
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