Borrelidin (CAS 7184-60-3)

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Alternate Names: Quinquangulin K 031; Quinquangulin K 182; oxacyclooctadeca-4, 6-dien-2-yl)-

Application: Borrelidin is an anti-angiogenic and anti-microbial compound

CAS Number: 7184-60-3

Purity: 98%

Molecular Weight: 489.64

Molecular Formula: C₂₈H₄₃NO₆

* Refer to Certificate of Analysis for lot specific data (including water content).

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Borrelidin is derived from Streptomyces rochei and has anti-angiogenic and anti-microbial activity. The compound has been shown to inhibit both eukaryal and bacterial threonyl-tRNA synthetase (ThrRS). It also stimulate apoptosis of tube-forming cells in capillary tubes with the activation of caspase-3 and caspase-8. Research shows that Borreldin also disrupts formed capillary tubes and inhibits proliferation of human umbilical vein endothelial cell (HUVEC) proliferation. Borrelidin is an inhibitor of Cdk.

References

Borrelidin inhibits a cyclin-dependent kinase (CDK), Cdc28/Cln2, of Saccharomyces cerevisiae. | Tsuchiya, E., et al. 2001. J Antibiot (Tokyo). 54: 84-90. PMID: 11269718
Borrelidin induces the transcription of amino acid biosynthetic enzymes via a GCN4-dependent pathway. | Eastwood, EL. and Schaus, SE. 2003. Bioorg Med Chem Lett. 13: 2235-7. PMID: 12798341
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. 2003. J Antibiot (Tokyo). 56: 709-15. PMID: 14563161
Biosynthesis of the angiogenesis inhibitor borrelidin by Streptomyces parvulus Tü4055: insights into nitrile formation. | Olano, C., et al. 2004. Mol Microbiol. 52: 1745-56. PMID: 15186422
A unique hydrophobic cluster near the active site contributes to differences in borrelidin inhibition among threonyl-tRNA synthetases. | Ruan, B., et al. 2005. J Biol Chem. 280: 571-7. PMID: 15507440
Isolation of borrelidin as a phytotoxic compound from a potato pathogenic streptomyces strain. | Cao, Z., et al. 2012. Biosci Biotechnol Biochem. 76: 353-7. PMID: 22313786
Borrelidin modulates the alternative splicing of VEGF in favour of anti-angiogenic isoforms. | Woolard, J., et al. 2011. Chem Sci. 2011: 273-278. PMID: 22822423
Insights into the preclinical treatment of blood-stage malaria by the antibiotic borrelidin. | Azcárate, IG., et al. 2013. Br J Pharmacol. 169: 645-58. PMID: 23488671
Borrelidin has limited anti-cancer effects in bcl-2 overexpressing breast cancer and leukemia cells and reveals toxicity in non-malignant breast epithelial cells. | Gafiuc, D., et al. 2014. J Appl Toxicol. 34: 1109-13. PMID: 24155182
Synthesis of complex intermediates for the study of a dehydratase from borrelidin biosynthesis. | Hahn, F., et al. 2014. Beilstein J Org Chem. 10: 634-640. PMID: 24778714
Borrelidin Induces the Unfolded Protein Response in Oral Cancer Cells and Chop-Dependent Apoptosis. | Sidhu, A., et al. 2015. ACS Med Chem Lett. 6: 1122-7. PMID: 26617965
Design, synthesis and antifungal evaluation of borrelidin derivatives. | Hu, C., et al. 2018. Bioorg Med Chem. 26: 6035-6049. PMID: 30442507
Structural insights into dehydratase substrate selection for the borrelidin and fluvirucin polyketide synthases. | Barajas, JF., et al. 2019. J Ind Microbiol Biotechnol. 46: 1225-1235. PMID: 31115703
A semisynthetic borrelidin analogue BN-3b exerts potent antifungal activity against Candida albicans through ROS-mediated oxidative damage. | Su, H., et al. 2020. Sci Rep. 10: 5081. PMID: 32193473
Borrelidin is an angiogenesis inhibitor; disruption of angiogenic capillary vessels in a rat aorta matrix culture model. | Wakabayashi, T., et al. 1997. J Antibiot (Tokyo). 50: 671-6. PMID: 9315080

Physical State :

Solid

Solubility :

Soluble in ethanol, methanol (1 mg/ml), DMSO (1 mg/ml), DMF, and ethyl acetate.

Storage :

Store at -20° C

Boiling Point :

710.30° C at 760 mmHg (Predicted)

Density :

1.15 g/cm³ (Predicted)

Refractive Index :

n²⁰_D 1.54 (Predicted)

IC50 :

Cyclin-dependent kinase Cdc28/Cln2: IC₅₀ = 24 µM; Antiangiogenic activity: IC₅₀ = 0.8 nM; HUVEC₅₀ (Umbilical vein endothelial cells): IC₅₀ = 0.5 nM (human); Antiproliferative activity against NCI60 cell line: IC₅₀ = 20 nM

pK Values :

pK_a: 4.56 (Predicted)

WGK Germany :

RTECS :

ED8750000

PubChem CID :

23724539

MDL Number :

MFCD01740784

SMILES :

C[[email protected]]1C[[email protected]](C[[email protected]@H]([[email protected]](/C(=C\\C=C\\C[[email protected]@H](OC(=O)C[[email protected]@H]([[email protected]](C1)C)O)[[email protected]@H]2CCC[[email protected]]2C(=O)O)/C#N)O)C)C

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SAMPLE Certificate of Analysis (COA)

Borrelidin | CAS 7184-60-3 SAMPLE Certificate of Analysis

Certificate of Analysis

SAMPLE Certificate of Analysis (COA)

Catalog Number:sc-200379

Lot Number:SAMPLE

Product Name:Borrelidin

Molecular Formula:C₂₈H₄₃NO₆

Molecular Weight:489.64

Native Source:Streptomyces sp. MST-AS5347

Test	Specification	Results
Appearance		White Lyophilistate
Purity (HPLC)		> 99%