| Identification | Back Directory | [Name]
BORRELIDIN | [CAS]
7184-60-3 | [Synonyms]
BORRELIDIN
Aids128115
NSC 216128
Aids-128115
BORRELIDINE
TREPONEMYCIN
Quinquangulin K 031
Quinquangulin K 182
BORRELIDIN USP/EP/BP
TreponeMycin, U 78548, C2989
Borrelidin, froM StreptoMyces sp.
Borrelidin, 99%, from Streptomyces sp.
NSC 216128 Borrelidin Treponemycin
2-(7-CYANO-8,16-DIHYDROXY-9,11,13,15-TETRAMETHYL-18-OXOOXACYCLOOCTADECA-4,6-DIEN-2-YL)-CYCLOPENTANECARBOXYLIC ACID
Cyclopentanecarboxylic acid, 2-(7-cyano-8, 16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4, 6-dien-2-yl)-
2-(7-Cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl)cyclopentane-1-carboxylic acid
(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
Cyclopentanecarboxylic acid, 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]-, (1R,2R)- | [Molecular Formula]
C28H43NO6 | [MDL Number]
MFCD01740784 | [MOL File]
7184-60-3.mol | [Molecular Weight]
489.64 |
| Chemical Properties | Back Directory | [Melting point ]
143-145℃ | [Boiling point ]
584.45°C (rough estimate) | [density ]
1.1362 (rough estimate) | [refractive index ]
1.6290 (estimate) | [storage temp. ]
−20°C
| [solubility ]
DMSO: 1 mg/mL
| [form ]
White to off-white powder. | [pka]
4.56±0.40(Predicted) | [color ]
Off-white | [biological source]
Streptomyces parvulus | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months. |
| Hazard Information | Back Directory | [Description]
Borrelidin (7184-60-3) ia a novel macrolide which inhibits bacterial and eukaryotic threonyl-tRNA synthetase.1 Displays potent anti-angiogenic activity (IC50=0.8 nM) and induces the collapse of newly formed capillary tubules.2 Modulates alternative splicing of VEGF in favor of anti-angiogenic isoforms.3 Induces apoptosis in ALL cell lines.4 Induces unfolded protein response in oral cancer cells.5 Cell permeable. | [Uses]
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. Borrelidin also alters the splicing of VEGF mRNA, producing an antiangiogenic isoform of the growth factor. It has long been known as a powerful inhibitor of both eukaryotic and bacterial threonyl tRNA synthetase. Borrelidin is also an effective anti-malarial drug, as it kills P. falciparum with an IC50 value of 1.8 nM. At higher doses, it inhibits cyclin-dependent kinase in yeast (IC50 = 24 μM), resulting in growth arrest in the G1 phase. | [Uses]
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. | [Definition]
ChEBI: A macrolide that is isolated from several Streptomyces species and displays antibiotic, antineoplastic and antimalarial properties. | [General Description]
Chemical structure: macrolide | [Biochem/physiol Actions]
Borrelidin is a potent angiogenesis inhibitor that induces apoptosis in capillary tube-forming cells. Also displays antimalarial activity against drug-resistant Plasmodia. Antimicrobial and selective threonyl t-RNA synthetase inhibitor. | [storage]
Store at -20°C | [References]
References/Citations
1) Ruan et al. (2005), A unique hydrophobic cluster near the active site contributes to differences in borrelidin inhibition among threonyl-tRNA synthetases; J. Biol. Chem., 280 571
2) Kawamura et al. (2003), Anti-angiogenesis effects of borrelidin are mediated through distinct pathways: threonyl-tRNA synthase and caspases are independently involved in suppression of proliferation and induction of apoptosis in endothelial cells; J. Antibiot., 56 709
3) Woolard et al. (2011) Borrelidin modulates the alternative splicing of VEGF in favour of anti-angiogenic isoforms; Chem. Soc. 2011 273
4) Habibi et al. (2012), Borrelidin, a small molecule nitrile-containing macrolide inhibitor of threonyl-tRNA synthase, is a potent inducer of apoptosis in acute lymphoblastic leukemia; Invest. New Drugs, 30 1361
5) Sidhu et al. (2015), Borrelidin Induces the Unfolded Protein Response in Oral Cancer Cells and Chop-Dependent Apoptosis; ACS Med. Chem. Lett., 6 1122 |
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Sigma-Aldrich
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