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BioViotica
Borrelidin
95
CHF
CHF 95.00
In stock
BVT-0098-C500500 µgCHF 95.00
BVT-0098-M0011 mgCHF 145.00
BVT-0098-M0055 mgCHF 480.00
Product Details | |
---|---|
Synonyms | Treponemycin; U 78548; C2989 |
Product Type | Chemical |
Properties | |
Formula |
C28H43NO6 |
MW | 489.6 |
CAS | 7184-60-3 |
RTECS | ED8750000 |
Source/Host Chemicals | Isolated from Streptomyces sp. |
Purity Chemicals | ≥98% (HPLC) |
Appearance | White to off-white powder. |
Solubility | Soluble in DMSO or methanol. |
Identity | Determined by 1H-NMR. |
Declaration | Manufactured by BioViotica. |
InChi Key | OJCKRNPLOZHAOU-TVHKGLGPSA-N |
Smiles | [H][C@]1(CCC[C@H]1C(O)=O)[C@]1([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)CC(=O)O1 |
Shipping and Handling | |
Shipping | AMBIENT |
Short Term Storage | +4°C |
Long Term Storage | -20°C |
Handling Advice | Protect from light when in solution. |
Use/Stability |
Stable for at least 1 year after receipt when stored at -20°C. After reconstitution protect from light at -20°C. |
Documents | |
MSDS | Download PDF |
Product Specification Sheet | |
Datasheet | Download PDF |
Description
- Macrolide antibiotic.
- Bacterial, protozoan and mammalian threonyl-tRNA synthetase (THrRS) inhibitor.
- Antiangiogenic (IC50 = 0.8 nM) and anticancer agent.
- Induces the collapse of formed capillary tubes in a dose-dependent fashion. In HUVECs, the capillary tube collapsing activity is mediated by the activation of caspases-3 and -8 and induction of apoptosis.
- Blocks the formation of spontaneous lung metastases of B16-BL6 melanoma cells.
- Cyclin-dependent kinase (CDK) inhibitor.
- Antiviral.
- Potent antimalarial agent (IC50 = 0.97 nM).
- Inhibitor of potato scab disease.
Product References
- Isolation of vivomycin and borrelidin, two antibiotics with anti-viral activity, from a species of Streptomyces (C2989): M. Lumb, et al.; Nature 206, 263 (1965)
- Genetic analysis of mutations causing borrelidin resistance by overproduction of threonyl-transfer ribonucleic acid synthetase: J. Frohler, et al.; J. Bacteriol. 143, 1135 (1980)
- Increased levels of threonyl-tRNA synthetase in a borrelidin-resistant Chinese hamster ovary cell line: J.S. Gantt, et al.; PNAS 78, 5367 (1981)
- Chinese hamster ovary cells resistant to borrelidin overproduce threonyl-tRNA synthetase: S.C. Gerken and S.M. Arfin; J. Biol. Chem. 259, 9202 (1984)
- Isolation of a cDNA clone for human threonyl-tRNA synthetase: amplification of the structural gene in borrelidin-resistant cell lines: K.J. Kontis and S.M. Arfin; Mol. Cell. Biol. 9, 1832 (1989)
- Borrelidin is an angiogenesis inhibitor; disruption of angiogenic capillary vessels in a rat aorta matrix culture model: T. Wakabayashi, et al.; J. Antibiot. 50, 671 (1997)
- Establishment of a quantitative mouse dorsal air sac model and its application to evaluate a new angiogenesis inhibitor: Y. Funahashi, et al.; Oncol. Res. 11, 319 (1999)
- Borrelidin inhibits a cyclin-dependent kinase (CDK), Cdc28/Cln2, of Saccharomyces cerevisiae: E. Tsuchiya, et al.; J. Antibiot. 54, 84 (2001)
- 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: T. Kawamura, et al.; J. Antibiot. 56, 709 (2003)
- Borrelidin induces the transcription of amino acid biosynthetic enzymes via a GCN4-dependent pathway: E.L. Eastwood & S.E. Schaus; Bioorg. Med. Chem. Lett. 13, 2235 (2003)
- A unique hydrophobic cluster near the active site contributes to differences in borrelidin inhibition among threonyl-tRNA synthetases: B. Ruan, et al.; J. Biol. Chem. 280, 571 (2005)
- Borrelidin, a potent antimalarial: stage-specific inhibition profile of synchronized cultures of Plasmodium falciparum: A. Ishiyama, et al.; J. Antibiotics 64, 381 (2011)
- A study on the effects of borrelidin on cardiovascular and intestinal smooth muscles: D. V. Bhikshapathi, et al.; Pharm. Lett. 5, 83 (2013)
- Insights into the preclinical treatment of blood-stage malaria by the antibiotic borrelidin: I. G. Azcarate, et al.; Br. J. Pharmacol. 169, 645 (2013)
- Identification of borrelidin binding site on threonyl-tRNA synthetase: M. Li, et al; Biochem. Biophys. Res. Comm. 451, 485 (2014)
- Analogs of natural aminoacyl-tRNA synthetase inhibitors clear malaria in vivo: E. M. Novoa, et al.; PNAS (USA) 111, E5508 (2014)
- Borrelidin has limited anti-cancer effects in bcl-2 overexpressing breast cancer and leukemia cells and reveals toxicity in non-malignant breast epithelial cells: D. Gafiuc, et al.; J. Appl. Toxicol. 34, 1109 (2014)
- Borrelidin or microorganism which produces it as inhibitor of potato scab disease: Y. Kobayashi, et al.; Jap. Kokai Tokkyo Koho JP 2014224102 (2014)
- Borrelidin Induces the Unfolded Protein Response in Oral Cancer Cells and Chop-Dependent Apoptosis: A. Sidhu, et al.; ACS Med. Chem. Lett. 6, 1122 (2015)
- Effect of borrelidin on hepatocellular carcinoma cells in vitro and in vivo: X. Gao, et al.; RSC Adv. 7, 44401 (2017)
- Liposomal borrelidin for treatment of metastatic breast cancer: M. Jeong, et al.; Drug Deliv. Transl. Res. 8, 1380 (2018)
- Aminoacyl-tRNA synthetase inhibition activates a pathway that branches from the canonical amino acid response in mammalian cells: Y. Kim, et al.; PNAS 117, 8900 (2020)