Macbecin IAn ansamycin antibiotic inhibitor of Hsp90 activity

Macbecin I (CAS 73341-72-7)

Macbecin I | CAS 73341-72-7 is rated 5.0 out of 5 by 1.
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Synonym: (15R)-6,17-Didemethoxy-15-methoxy-6 -methyl-11-O-methyl-geldanamycin
Application: An ansamycin antibiotic inhibitor of Hsp90 activity
CAS Number: 73341-72-7
Molecular Weight: 558.67
Molecular Formula: C30H42N2O8
* Refer to Certificate of Analysis for lot specific data (including water content).
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Macbecin I is an ansamycin antibiotic compound that inhibits Hsp90 activity (IC50 = 2 μM) by binding to the ATP-binding site. Macbecin I exhibits antitumor and cytocidal activities (IC50 ~ 0.4 μM) by causing degradation of key oncogenic client proteins such as ErbB2 and cRaf1. Macbecin I displays higher potency and affinity than geldanamycin.


References

Ono et al (1982) Antitumor and cytocidal activities of a newly isolated benzenoid ansamycin, macbecin I. Gann. 73 938. Uehara et al (2003) Natural product origins of Hsp90 inhibitors. Curr.Cancer Drug Targets 3 325. Martin et al (2008) Molecular characterization of macbecin as an Hsp90 inhibitor. J.Med.Chem. 51 2853.

Physical State :
Solid
Solubility :
Soluble in water (partly), and DMSO.
Storage :
Desiccate at -20° C
Boiling Point :
736.2° C at 760 mmHg (Predicted)
Density :
1.2 g/cm3 (Predicted)
Refractive Index :
n20D 1.55 (Predicted)
IC50 :
LXF 629L cells: IC50 = 8.95 nM (human); PRXF LNCAP cells: IC50 = 14.32 nM (human); PRXF PC3M cells: IC50 = 16.11 nM (human); Hsp90 activity: IC50 = ~0.4 µM; Antitumor and cytocidal activities: IC50 = 2 µM
pK Values :
pKa: 8.63 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
RTECS :
OL9055000
PubChem CID :
6436263
SMILES :
CC1CC(C(C(/C=C(\\C(C(/C=C\\C=C(\\C(=O)NC2=CC(=O)C=C(C1OC)C2=O)/C)C)OC(=O)N)/C)C)OC)OC

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Certificate of Analysis

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Macbecin I  Product Citations

See how others have used Macbecin I. Click on the entry to view the PubMed entry .

Citations 1 to 1 of 1 total

PMID: # 9446597  Goldfarb, A.N. et al. 1998. J. Biol. Chem. 273: 2866-2873.

Citations 1 to 1 of 1 total
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Rated 5 out of 5 by from Goldfarb Goldfarb, A.N. et al. (PubMed 9446597) used macbecin I, a potent inhibitor of Hsp90, to determine if Hsp90 plays a role in HLH dimerization in yeast. -SCBT Publication Review
Date published: 2015-05-15
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