Borrelidin

• CAT Number: R027584
• CAS Number: 7184-60-3
• PubChem Substance ID: 6436801
• Molecular Formula: C₂₈H₄₃NO₆
• Molecular Weight: 489.64
• Purity: 99%
• Synonyms: (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; [2S-[2R*(1S*,2S*),4E,6Z,8S*,9R*,11S*,13R*,15R*,16R*]]-2-(7-Cyano-8,16-dihydroxy-9,11,13,15-te
• Target: Synthases/Synthetases
• Solubility: Limited solubility
• Storage: Store at -20C
• Analysis method: HPLC
• InChI: InChI=1S/C28H43NO6/c1-17-12-18(2)14-20(4)27(32)21(16-29)8-5-6-11-25(22-9-7-10-23(22)28(33)34)35-26(31)15-24(30)19(3)13-17/h5-6,8,17-20,22-25,27,30,32H,7,9-15H2,1-4H3,(H,33,34)/b6-5+,21-8-/t17-,18+,19-,20-,22+,23+,24-,25-,27+/m0/s1
• InChIKey: OJCKRNPLOZHAOU-UGKRXNSESA-N
• SMILES: CC1CC(CC(C(C(=CC=CCC(OC(=O)CC(C(C1)C)O)C2CCCC2C(=O)O)C#N)O)C)C

Borrelidin is an unusual nitrile-containing metabolite isolated from Streptomyces. Originally discovered as active against
Borrelia species, borrelidin has since found a role as a selective inhibitor of bacterial and eukaryal threonyl-tRNA synthetase.
More recent research has found that borrelidin is a very potent angiogenesis inhibitor and induces apoptosis of the capillary
tube-forming cells. Borrelidin is an important lead for antimalarial discovery, displaying activity against drug-resistant
Plasmodia.

Reference

A unique hydrophobic cluster near the active site contributes to differences in borrelidin inhibition among threonyl-tRNA synthetases. Ruan T. et al. , J. Biol. Chem. 2005, 280, 571. 

Borrelidin is an angiogenesis inhibitor; disruption of angiogenic capillary vessels in a rat aorta matrix culture model. Wakabayashi T. et al. , J. Antibiot. 1997, 50, 671.

Anti-angiogenesis effects 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. Kawamura T. et al. , J. Antibiot. 2003, 56, 709.