An antiangiogenic antibiotic
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Borrelidin

Item No. 14436

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R)-2R-[7-cyano-8R,16S-dihydroxy-9S,11R,13S,15S-tetramethyl-18-oxooxacyclooctadeca-4E,6Z-dien-2S-yl]-cyclopentanecarboxylic acid
CAS Number
7184-60-3
Synonyms
  • NSC 216128
  • Treponemycin
Molecular Formula
C28H43NO6
Formula Weight
489.6
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
Chloroform: SolubleDMSO: SolubleMethanol: Soluble
SMILES
O=C1C[C@H](O)[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])O1
InChi Code
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
InChi Key
OJCKRNPLOZHAOU-TVHKGLGPSA-N
Origin
Bacterium/Streptomyces sp.
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

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    Product Description

    Borrelidin is a secondary metabolite produced by Streptomyces and other bacteria. It displays potent antiangiogenic activity, preventing tube formation in rat aorta explants (IC50 = 0.8 nM) and inducing apoptosis in endothelial cells.1,2 Borrelidin also alters the splicing of VEGF mRNA, producing an antiangiogenic isoform of the growth factor.3 It has long been known as a powerful inhibitor of both eukaryotic and bacterial threonyl tRNA synthetase.4 Borrelidin is also an effective anti-malarial drug, as it kills P. falciparum with an IC50 value of 1.8 nM.5 At higher doses, it inhibits cyclin-dependent kinase in yeast (IC50 = 24 μM), resulting in growth arrest in the G1 phase.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wakabayashi, T., Kageyama, R., Naruse, N., et al. Borrelidin is an angiogenesis inhibitor; Disruption of angiogenic capillary vessels in a rat aorta matrix culture model. J. Antibiot. (Tokyo) 50(8), 671-676 (1997).

    2. Kawamura, T., Liu, D., Towle, M.J., et al. 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. J. Antibiot. (Tokyo) 56(8), 709-715 (2003).

    3. Woolard, J., Vousden, W., Moss, S.J., et al. Borrelidin modulates the alternative splicing of VEGF in favour of anti-angiogenic isoforms. Chem. Sci. 2011(2), 273-278 (2011).

    4. Paetz, W., and Nass, G. Biochemical and immunological characterization of threonyl-tRNA synthetase of two borrelidin-resistant mutants of Escherichia coli K12. Eur. J. Biochem. 35(2), 331-337 (1973).

    5. Otoguro, K., Ui, H., Ishiyama, A., et al. In vitro and in vivo antimalarial activities of a non-glycosidic 18-membered macrolide antibiotic, borrelidin, against drug-resistant strains of Plasmodia. J. Antibiot. (Tokyo) 56(8), 727-729 (2003).

    6. Tsuchiya, E., Yukawa, M., Miyakawa, T., et al. Borrelidin inhibits a cyclin-dependent kinase (CDK), Cdc28/Cln2, of Saccharomyces cerevisiae. J. Antibiot. (Tokyo) 54(1), 84-90 (2001).