ChemicalBook--->CAS DataBase List--->7184-60-3

7184-60-3

7184-60-3 Structure

7184-60-3 Structure
IdentificationBack 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 PropertiesBack 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.
Safety DataBack Directory
[Safety Statements ]

24/25
[WGK Germany ]

3
[RTECS ]

ED8750000
[HS Code ]

29419090
Hazard InformationBack 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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