BORRELIDIN
- Product Name
- BORRELIDIN
- CAS No.
- 7184-60-3
- Chemical Name
- BORRELIDIN
- Synonyms
- Aids128115;BORRELIDIN;NSC 216128;Aids-128115;BORRELIDINE;TREPONEMYCIN;Antispirochetin;Quinquangulin K 182;Quinquangulin K 031;BORRELIDIN USP/EP/BP
- CBNumber
- CB1134351
- Molecular Formula
- C28H43NO6
- Formula Weight
- 489.64
- MOL File
- 7184-60-3.mol
BORRELIDIN Property
- 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.
- InChIKey
- OJCKRNPLOZHAOU-UGKRXNSESA-N
- SMILES
- [H][C@]1(CCC[C@H]1C(O)=O)[C@@H]2C\C=C\C=C(C#N)[C@H](O)[C@@H](C)C[C@H](C)C[C@H](C)C[C@H](C)[C@@H](O)CC(=O)O2
Safety
- Safety Statements
- 24/25
- WGK Germany
- 3
- RTECS
- ED8750000
- HS Code
- 29419090
- Storage Class
- 11 - Combustible Solids
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
N-Bromosuccinimide Price
- Product number
- B3061
- Product name
- Borrelidin
- Purity
- from Streptomyces parvulus, ≥98% (HPLC)
- Packaging
- 1mg
- Price
- $714
- Updated
- 2026/04/30
- Product number
- 14436
- Product name
- Borrelidin
- Purity
- ≥98%
- Packaging
- 500μg
- Price
- $90
- Updated
- 2026/04/30
- Product number
- 14436
- Product name
- Borrelidin
- Purity
- ≥98%
- Packaging
- 1mg
- Price
- $135
- Updated
- 2026/04/30
- Product number
- 14436
- Product name
- Borrelidin
- Purity
- ≥98%
- Packaging
- 500μg
- Price
- $81
- Updated
- 2024/03/01
- Product number
- 14436
- Product name
- Borrelidin
- Purity
- ≥98%
- Packaging
- 1mg
- Price
- $122
- Updated
- 2024/03/01
BORRELIDIN Chemical Properties,Usage,Production
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 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.
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.
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.
Synthesis
A small amount of spore powder of Streptomyces ghanaensis (S. ghanaensis) TRM78-24 was inoculated in ISP4 medium and incubated at 28C for 4 d to obtain seed liquid, and 2 mL (8 % of the inoculum) seed liquid was inoculated into millet fermentation medium for fermentation culture, and the fermentation conditions were as follows: 180 rpm, initial pH 7.2-7.4, loading volume of 250 mL, fermentation temperature of 28 , fermentation for 7 d. The fermentation broth was collected, and the fermentation broth was filtered through four layers of gauze, and then wet-sampled on a macroporous resin column (the fermentation filtrate was loaded with 2.0 kg of D101 or AB-8 macroporous resin for every 100 L); the fermentation filtrate was then eluted with 50% ethanol-water and 95% ethanol-water, respectively; and the 95% ethanol eluate was concentrated to remove the solvent and obtain the rich content of the solvent. The 95% ethanol eluent was concentrated to remove the solvent to obtain the 95% ethanol extract rich in spirochetes, and then eluted with 50% methanol-water and 100% methanol by ODS medium-pressure column chromatography, and the 100% methanol eluted part was prepared with 70% methanol-water to obtain the spirochetes in pure form, and the HPLC analysis showed that the spirochetes in the fermentation broth contained 12.0 mg/L, and the actual amount of spirochetes in the fermentation broth was 6.6 mg/L. The actual amount was 6.6 mg/L.
storage
+4°C
References
[1] BENFANG RUAN. A unique hydrophobic cluster near the active site contributes to differences in borrelidin inhibition among threonyl-tRNA synthetases.[J]. The Journal of Biological Chemistry, 2005, 280 1: 571-577. DOI:10.1074/jbc.m411039200
[2] TAKANORI KAWAMURA. 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]. Journal of Antibiotics, 2003, 56 8: 709-715. DOI:10.7164/antibiotics.56.709
[3] WOOLARD J, VOUSDEN W, MOSS S J, et al. Borrelidin modulates the alternative splicing of VEGF in favour of anti-angiogenic isoforms†[J]. Chemical Science, 2010, 2: 273-278. DOI:10.1039/c0sc00297f
[4] DARYA HABIBI. Borrelidin, a small molecule nitrile-containing macrolide inhibitor of threonyl-tRNA synthetase, is a potent inducer of apoptosis in acute lymphoblastic leukemia.[J]. Investigational New Drugs, 2012, 30 4: 1361-1370. DOI:10.1007/s10637-011-9700-y
[5] ALPA SIDHU. Borrelidin Induces the Unfolded Protein Response in Oral Cancer Cells and Chop-Dependent Apoptosis[J]. ACS Medicinal Chemistry Letters, 2015, 6 11: 1122-1127. DOI:10.1021/acsmedchemlett.5b00133
BORRELIDIN Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from BORRELIDIN manufacturers
- Product
- BORRELIDIN 7184-60-3
- Price
- US $1.00/KG
- Min. Order
- 1KG
- Purity
- 99.0%
- Supply Ability
- 100kg
- Release date
- 2020-03-11