ChemicalBook >> CAS DataBase List >>BORRELIDIN

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
Molecular Weight:
489.64
MDL Number:
MFCD08276914
MOL File:
7184-60-3.mol
Last updated:2023-06-30 15:45:59

BORRELIDIN Properties

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
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.
EWG's Food Scores 1
FDA UNII PWC22KGM2P

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P271-P280
Safety Statements  24/25
WGK Germany  3
RTECS  ED8750000
HS Code  29419090
NFPA 704
0
2 0

BORRELIDIN price More Price(18)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich B3061 Borrelidin from Streptomyces parvulus, ≥98% (HPLC) 7184-60-3 1mg $648 2024-03-01 Buy
Cayman Chemical 14436 Borrelidin ≥98% 7184-60-3 500μg $81 2024-03-01 Buy
Cayman Chemical 14436 Borrelidin ≥98% 7184-60-3 1mg $122 2024-03-01 Buy
Tocris 4706 Borrelidin ≥98%(HPLC) 7184-60-3 1 $316 2021-12-16 Buy
TRC B675390 Borrelidin 7184-60-3 1mg $370 2021-12-16 Buy
Product number Packaging Price Buy
B3061 1mg $648 Buy
14436 500μg $81 Buy
14436 1mg $122 Buy
4706 1 $316 Buy
B675390 1mg $370 Buy

BORRELIDIN Chemical Properties,Uses,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 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

+4°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

35079-19-7
7184-60-3
Synthesis of BORRELIDIN from 1,2-Cyclopentanedicarboxylic acid, 4-oxo-, 1,2-diMethyl ester, (1R,2R)-
Global( 73)Suppliers
Supplier Tel Email Country ProdList Advantage
career henan chemical co
+86-0371-86658258 15093356674; factory@coreychem.com China 29826 58
Shaanxi Dideu Medichem Co. Ltd
+86-029-81138252 +86-18789408387 1057@dideu.com China 3537 58
TargetMol Chemicals Inc.
+1-781-999-5354 +1-00000000000 marketing@targetmol.com United States 19892 58
Shaanxi Dideu Medichem Co. Ltd
+86-029-89586680 +86-18192503167 1026@dideu.com China 9320 58
BOC Sciences
+16314854226 inquiry@bocsci.com United States 19743 58
Shanghai Acmec Biochemical Technology Co., Ltd.
+undefined18621343501 product@acmec-e.com China 33349 58
Shaanxi Cuikang Pharmaceutical Technology Co., Ltd
+86-19164747840 +86-13119157289 13119157289@163.com China 2971 58
J & K SCIENTIFIC LTD. 010-82848833 400-666-7788 jkinfo@jkchemical.com China 96815 76
ChemStrong Scientific Co.,Ltd 0755-66853366 13670046396 sales@chem-strong.com China 17982 56
Sigma-Aldrich 021-61415566 800-8193336 orderCN@merckgroup.com China 51471 80

View Lastest Price from BORRELIDIN manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Borrelidin  pictures 2020-05-10 Borrelidin
7184-60-3
US $1.00 / KG 1KG 99% 20T Shaanxi Dideu Medichem Co. Ltd
BORRELIDIN pictures 2020-03-12 BORRELIDIN
7184-60-3
US $1.00 / KG 1KG 99.0% 100kg Career Henan Chemical Co
  • Borrelidin  pictures
  • Borrelidin
    7184-60-3
  • US $1.00 / KG
  • 99%
  • Shaanxi Dideu Medichem Co. Ltd
  • BORRELIDIN pictures
  • BORRELIDIN
    7184-60-3
  • US $1.00 / KG
  • 99.0%
  • Career Henan Chemical Co
2-(7-CYANO-8,16-DIHYDROXY-9,11,13,15-TETRAMETHYL-18-OXOOXACYCLOOCTADECA-4,6-DIEN-2-YL)-CYCLOPENTANECARBOXYLIC ACID BORRELIDIN BORRELIDINE 2-(7-Cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxo-1-oxacyclooctadeca-4,6-dien-2-yl)cyclopentane-1-carboxylic acid Aids128115 Aids-128115 Cyclopentanecarboxylic acid, 2-(7-cyano-8, 16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclooctadeca-4, 6-dien-2-yl)- Quinquangulin K 031 Quinquangulin K 182 NSC 216128 TREPONEMYCIN TreponeMycin, U 78548, C2989 Borrelidin, froM StreptoMyces sp. NSC 216128 Borrelidin Treponemycin (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 Borrelidin, 99%, from Streptomyces sp. 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)- BORRELIDIN USP/EP/BP Antispirochetin 7184-60-3 C28H43NO6 Antibiotics Antibiotics A to Z Antibiotics A-F BioChemical