BioViotica

Borrelidin

CHF 95.00
In stock
BVT-0098-C500500 µgCHF 95.00
BVT-0098-M0011 mgCHF 145.00
BVT-0098-M0055 mgCHF 480.00
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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
  1. 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)
  2. Genetic analysis of mutations causing borrelidin resistance by overproduction of threonyl-transfer ribonucleic acid synthetase: J. Frohler, et al.; J. Bacteriol. 143, 1135 (1980)
  3. Increased levels of threonyl-tRNA synthetase in a borrelidin-resistant Chinese hamster ovary cell line: J.S. Gantt, et al.; PNAS 78, 5367 (1981)
  4. Chinese hamster ovary cells resistant to borrelidin overproduce threonyl-tRNA synthetase: S.C. Gerken and S.M. Arfin; J. Biol. Chem. 259, 9202 (1984)
  5. 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)
  6. 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)
  7. 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)
  8. Borrelidin inhibits a cyclin-dependent kinase (CDK), Cdc28/Cln2, of Saccharomyces cerevisiae: E. Tsuchiya, et al.; J. Antibiot. 54, 84 (2001)
  9. 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)
  10. 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)
  11. 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)
  12. Borrelidin, a potent antimalarial: stage-specific inhibition profile of synchronized cultures of Plasmodium falciparum: A. Ishiyama, et al.; J. Antibiotics 64, 381 (2011)
  13. A study on the effects of borrelidin on cardiovascular and intestinal smooth muscles: D. V. Bhikshapathi, et al.; Pharm. Lett. 5, 83 (2013)
  14. Insights into the preclinical treatment of blood-stage malaria by the antibiotic borrelidin: I. G. Azcarate, et al.; Br. J. Pharmacol. 169, 645 (2013)
  15. Identification of borrelidin binding site on threonyl-tRNA synthetase: M. Li, et al; Biochem. Biophys. Res. Comm. 451, 485 (2014)
  16. Analogs of natural aminoacyl-tRNA synthetase inhibitors clear malaria in vivo: E. M. Novoa, et al.; PNAS (USA) 111, E5508 (2014)
  17. 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)
  18. Borrelidin or microorganism which produces it as inhibitor of potato scab disease: Y. Kobayashi, et al.; Jap. Kokai Tokkyo Koho JP 2014224102 (2014)
  19. 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)
  20. Effect of borrelidin on hepatocellular carcinoma cells in vitro and in vivo: X. Gao, et al.; RSC Adv. 7, 44401 (2017)
  21. Liposomal borrelidin for treatment of metastatic breast cancer: M. Jeong, et al.; Drug Deliv. Transl. Res. 8, 1380 (2018)
  22. 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)
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