[CAS NO. 7184-60-3] Borrelidin
PRODUCTS SPECIFICATIONS [7184-60-3]
DESCRIPTION [7184-60-3]
Overview
| MDL | MFCD08276914 |
|---|---|
| Molecular Weight | 489.64 |
| Molecular Formula | C28H43NO6 |
| SMILES | O=C([C@H]1[C@H]([C@H](C/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)C2)OC2=O)CCC1)O |
Summary
Borrelidin (Treponemycin) is a bacterial and eukaryal threonyl-tRNA synthetase inhibitor which is a nitrile-containing macrolide antibiotic isolated from Streptomyces rochei [1] . Borrelidin is an inhibitor of Cdc28/Cln2 of the budding yeast, with an IC 50 of 24 μM [2] . Borrelidin is a potent angiogenesis inhibitor, with an IC 50 of 0.8 nM. Borrelidin induces apoptosis in the tube-forming cells [3] . Borrelidin has strong antimalarial activities, with IC 50 s of 1.9 nM and 1.8 nM against K1 and FCR3 strains of Plasmodium falciparum , respectively [4] .
IC50 & Target
|
Plasmodium |
Macrolide |
In Vitro
Borrelidin can target ALL cell lines and induce apoptosis and mediating G
1
arrest
[1]
.
MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Appearance
Solid
Source
Streptomyces rochei
Shipping
Room temperature in continental US; may vary elsewhere.
Storage
-20°C, sealed storage, away from moisture
* In solvent : -80°C, 6 months; -20°C, 1 month (sealed storage, away from moisture)
Solvent & Solubility
Ethanol : ≥ 100 mg/mL ( 204.23 mM )
* "≥" means soluble, but saturation unknown.
Stock Solutions
| Concentration Solvent Mass | 1 mg | 5 mg | 10 mg |
|---|
| 1 mM | 2.0423 mL | 10.2116 mL | 20.4232 mL |
| 5 mM | 0.4085 mL | 2.0423 mL | 4.0846 mL |
| 10 mM | 0.2042 mL | 1.0212 mL | 2.0423 mL |
-
1.
-
2.
Add each solvent one by one: 10% EtOH >> 90% corn oil
Solubility: ≥ 2.5 mg/mL (5.11 mM); Clear solution
References
- [1] Habibi D, et al. Borrelidin, a small molecule nitrile-containing macrolide inhibitor of threonyl-tRNA synthetase, is a potent inducer of apoptosis in acute lymphoblastic leukemia. Invest New Drugs. 2012 Aug;30(4):1361-70.
- [2] Tsuchiya E, et al. Borrelidin inhibits a cyclin-dependent kinase (CDK), Cdc28/Cln2, of Saccharomyces cerevisiae. J Antibiot (Tokyo). 2001 Jan;54(1):84-90.
- [3] Wakabayashi T, et al. Borrelidin is an angiogenesis inhibitor; disruption of angiogenic capillary vessels in a rat aorta matrix culture model. J Antibiot (Tokyo). 1997 Aug;50(8):671-6.
- [4] Otoguro K, 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). 2003 Aug;56(8):727-9.
Synonyms