Borrelidin

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Cat.No. 4706 - Borrelidin | C28H43NO6 | CAS No. 7184-60-3
Description: Antiangiogenic; inhibits threonyl-tRNA synthetase
Chemical Name: (1R,2R)-2-[(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-Cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4,6-dien-2-yl]cyclopentanecarboxylic acid
Purity: ≥98% (HPLC)
Datasheet
Citations
Literature

Biological Activity

Antibiotic and antiangiogenic. Selectively inhibits threonyl-tRNA synthetase (ThrRS). Exhibits antiangiogenic activity in a mouse model of tumor angiogenesis. Induces apoptosis in capillary tube-forming endothelial cells; disrupts capillary tubes and inhibits their formation (IC50 = 0.8 nM in rat aorta). Induces the unfolded protein response (UPR) and apoptosis in oral cancer cells.

Technical Data

M. Wt 489.64
Formula C28H43NO6
Storage Store at -20°C
Purity ≥98% (HPLC)
CAS Number 7184-60-3
PubChem ID 5357974
InChI Key OJCKRNPLOZHAOU-SLNPHPKOSA-N
Smiles O[C@@H](C1)[C@@H](C)C[C@@H](C)C[C@@H](C)C[C@H](C)[C@@H](O)\C(C#N)=C/C=C/C[C@]([C@]2([H])CCC[C@H]2C(O)=O)([H])OC1=O

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 0.98 2

Preparing Stock Solutions

The following data is based on the product molecular weight 489.64. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.04 mL 10.21 mL 20.42 mL
5 mM 0.41 mL 2.04 mL 4.08 mL
10 mM 0.2 mL 1.02 mL 2.04 mL
50 mM 0.04 mL 0.2 mL 0.41 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

Wakabayashi et al (1997) Borrelidin is an angiogenesis inhibitor; disruption of angiogenic capillary vessels in a rat aorta matrix culture model. J.Antibiot.(Tokyo). 50 671 PMID: 9315080

Kawamura et al (2003) Anti-angiogenesis effect of borrelidin are mediated through distinct pathways: threonyl-tRNA synthetase and caspases are independently involved in suppression of proliferation and induction of apoptosis in endothelial cells. J.Antibiot.(Tokyo). 56 709 PMID: 14563161

Woolard et al (2011) Borrelidin modulates the alterntive splicing of VEGF in favour of anti-antiogenic isoforms. Chem.Sci. 273 PMID: 22822423

Sidhu et al (2015) Borrelidin induces the unfolded protein response in oral cancer cells and Chop-dependent apoptosis. ACS Med.Chem.Lett. 6 1122 PMID: 26617965


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Keywords: antibacterials antibiotics threonyl-tRNA synthetase ThrRS antiangiogenics capillary capillaries formation inhibitors inhibits Other Synthases/Synthetases

Citations for Borrelidin

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Literature in this Area

Cancer

Cancer Research Product Guide

A collection of over 750 products for cancer research, the guide includes research tools for the study of:

  • Cancer Metabolism
  • Epigenetics in Cancer
  • Receptor Signaling
  • Cell Cycle and DNA Damage Repair
  • Angiogenesis
  • Invasion and Metastasis

Pathways for Borrelidin

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