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7184-60-3,MFCD08276914
Catalog No.:AA005PKK

7184-60-3 | Borrelidin

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1mg
≥98%
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$175.00   $122.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA005PKK
Chemical Name:
Borrelidin
CAS Number:
7184-60-3
Molecular Formula:
C28H43NO6
Molecular Weight:
489.6441
MDL Number:
MFCD08276914
SMILES:
N#CC1=CC=CCC(OC(=O)CC(C(CC(CC(CC(C1O)C)C)C)C)O)C1CCCC1C(=O)O
Properties
Properties
 
BP:
710.3°C at 760 mmHg  
Form:
Solid  
MP:
143-145℃  

Computed Properties
 
Complexity:
827  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
9  
Defined Bond Stereocenter Count:
2  
Heavy Atom Count:
35  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
2  
XLogP3:
5.6  

Downstream Synthesis Route
39536-61-3    7184-60-3   
(1R,2R)-N-butyl-2-(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetramethyl-18-oxooxacyclo-octadeca-4,6-dien-2-yl-N-pentylcyclopentane-1-carboxamide 

[1]Hu,Caijuan;Su,Hao;Luo,Jinghan;Han,Li;Liu,Qingyin;Wu,Wenxi;Mu,Yu;Guan,Peipei;Sun,Tiemin;Huang,Xueshi[BioorganicandMedicinalChemistry,2018,vol.26,#23-24,p.6035-6049]

2706-56-1    7184-60-3   
(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-N-(2-(pyridin-2-yl)ethyl)cyclopentane-1-carboxamide 

[1]BioorganicandMedicinalChemistry,2018,vol.26,p.6035-6049

1615-14-1    7184-60-3   
2-(1H-imidazol-1-yl)ethyl(1R,2R)-2-(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetra-methyl-18-oxooxacyclooctadeca-4,6-dien-2-ylcyclopentane-1-carboxylate 

[1]BioorganicandMedicinalChemistry,2018,vol.26,p.6035-6049

2955-88-6    7184-60-3   
2-(pyrrolidin-1-yl)ethyl(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-ylcyclopentane-1-carboxylate 

[1]Hu,Caijuan;Su,Hao;Luo,Jinghan;Han,Li;Liu,Qingyin;Wu,Wenxi;Mu,Yu;Guan,Peipei;Sun,Tiemin;Huang,Xueshi[BioorganicandMedicinalChemistry,2018,vol.26,#23-24,p.6035-6049]

5464-12-0    7184-60-3   
2-(4-methylpiperazin-1-yl)ethyl(1R,2R)-2-(2S,4E,6Z,8R,9S,11R,13S,15S,16S)-7-cyano-8,16-dihydroxy-9,11,13,15-tetra-methyl-18-oxooxacyclooctadeca-4,6-dien-2-ylcyclopentane-1-carboxylate 

[1]BioorganicandMedicinalChemistry,2018,vol.26,p.6035-6049

Literature

Title: Structural basis for full-spectrum inhibition of translational functions on a tRNA synthetase.

Journal: Nature communications 20150331

Title: Aminoacyl-tRNA synthetase dependent angiogenesis revealed by a bioengineered macrolide inhibitor.

Journal: Scientific reports 20150101

Title: Analogs of natural aminoacyl-tRNA synthetase inhibitors clear malaria in vivo.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20141223

Title: Borrelidin has limited anti-cancer effects in bcl-2 overexpressing breast cancer and leukemia cells and reveals toxicity in non-malignant breast epithelial cells.

Journal: Journal of applied toxicology : JAT 20141001

Title: Genetic validation of aminoacyl-tRNA synthetases as drug targets in Trypanosoma brucei.

Journal: Eukaryotic cell 20140401

Title: Insights into the preclinical treatment of blood-stage malaria by the antibiotic borrelidin.

Journal: British journal of pharmacology 20130601

Title: Borrelidin analogues with antimalarial activity: design, synthesis and biological evaluation against Plasmodium falciparum parasites.

Journal: Bioorganic & medicinal chemistry letters 20130415

Title: Secreted Threonyl-tRNA synthetase stimulates endothelial cell migration and angiogenesis.

Journal: Scientific reports 20130101

Title: Borrelidin, a potent antifungal agent: insight into the antifungal mechanism against Phytophthora sojae.

Journal: Journal of agricultural and food chemistry 20121003

Title: Borrelidin, a small molecule nitrile-containing macrolide inhibitor of threonyl-tRNA synthetase, is a potent inducer of apoptosis in acute lymphoblastic leukemia.

Journal: Investigational new drugs 20120801

Title: Antifungal activity of borrelidin produced by a Streptomyces strain isolated from soybean.

Journal: Journal of agricultural and food chemistry 20120208

Title: Dual targeting of aminoacyl-tRNA synthetases to the apicoplast and cytosol in Plasmodium falciparum.

Journal: International journal for parasitology 20120201

Title: Isolation of borrelidin as a phytotoxic compound from a potato pathogenic streptomyces strain.

Journal: Bioscience, biotechnology, and biochemistry 20120101

Title: Borrelidin, a potent antimalarial: stage-specific inhibition profile of synchronized cultures of Plasmodium falciparum.

Journal: The Journal of antibiotics 20110501

Title: Susceptibility and mode of binding of the Mycobacterium tuberculosis cysteinyl transferase mycothiol ligase to tRNA synthetase inhibitors.

Journal: Bioorganic & medicinal chemistry letters 20110415

Title: Borrelidin modulates the alternative splicing of VEGF in favour of anti-angiogenic isoforms.

Journal: Chemical science 20110201

Title: Hutchinson's legacy: keeping on polyketide biosynthesis.

Journal: The Journal of antibiotics 20110101

Title: Mutasynthesis - uniting chemistry and genetics for drug discovery.

Journal: Trends in biotechnology 20070401

Title: Iterative deoxypropionate synthesis based on a copper-mediated directed allylic substitution: formal total synthesis of borrelidin (C3-C11 fragment).

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20060825

Title: [Study of drugs against neoplastic metastasis].

Journal: Magyar onkologia 20060101

Title: All-catalytic, efficient, and asymmetric synthesis of alpha,omega-diheterofunctional reduced polypropionates via 'one-pot' Zr-catalyzed asymmetric carboalumination-Pd-catalyzed cross-coupling tandem process.

Journal: Journal of the American Chemical Society 20050309

Title: A unique hydrophobic cluster near the active site contributes to differences in borrelidin inhibition among threonyl-tRNA synthetases.

Journal: The Journal of biological chemistry 20050107

Title: Biosynthesis of the angiogenesis inhibitor borrelidin by Streptomyces parvulus Tü4055: insights into nitrile formation.

Journal: Molecular microbiology 20040601

Title: Application of conformation design in acyclic stereoselection: total synthesis of borrelidin as the crystalline benzene solvate.

Journal: Journal of the American Chemical Society 20031112

Title: 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.

Journal: The Journal of antibiotics 20030801

Title: Enantioselective total synthesis of borrelidin.

Journal: Journal of the American Chemical Society 20030212

Title: Establishment of a quantitative mouse dorsal air sac model and its application to evaluate a new angiogenesis inhibitor.

Journal: Oncology research 19990101

Title: Isolation of a cDNA clone for human threonyl-tRNA synthetase: amplification of the structural gene in borrelidin-resistant cell lines.

Journal: Molecular and cellular biology 19890501

Title: Chinese hamster ovary cells resistant to borrelidin overproduce threonyl-tRNA synthetase.

Journal: The Journal of biological chemistry 19840725

Title: Increased levels of threonyl-tRNA synthetase in a borrelidin-resistant Chinese hamster ovary cell line.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19810901

Title: 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.

Title: 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.

Title: 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.

Title: 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.

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