Kendomycin CAS: 183202-73-5
Kendomycin is a broadly efficacious polyketide macrocycle antibiotic.

Kendomycin (CAS 183202-73-5)

Kendomycin | CAS 183202-73-5 is rated 5.0 out of 5 by 1.
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Alternate Names: (−)-TAN 2162
Application: Kendomycin is a broadly efficacious polyketide macrocycle antibiotic
CAS Number: 183202-73-5
Purity: >95%
Molecular Weight: 486.64
Molecular Formula: C29H42O6
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data (including water content).
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Kendomycin is a polyketide macrolide antibiotic isolated from various Streptomyces strains, with demonstrated cytotoxic and antiosteoporotic properties. Structurally intriguing to synthetic chemists, the macrocycle of Kendomycin contains a rare quinone methide chromophore. The antibiotic activity of Kendomycin shows efficacy against a range of bacteria including Methicillin- and Vancomycin-resistant Staphylococcus aureus. Studies correlate the demonstrated cytotoxicity of Kendomycin against multiple tumor cell lines to an inhibition of chymotrypsin-like proteasome activity. Kendomycin is also described to disable the antiapoptotic protein Bcl-xl by blocking protein-protein interaction with Bak, though this finding showed no direct correlation to cytotoxicity. Early reports described Kendomycin as an endothelin receptor antagonist, and the antiosteoporotic effects were correlated to CT-R (calcitonin receptor) agonism. Kendomycin is an inhibitor of ETAR and ETBR.


References

1. Yuan, Y., et al. 2004. J. Am. Chem. Soc. 126: 14720-14721. PMID: 15535687

2. Mulzer, J., et al. 2004. Proc. Natl. Acad. Sci. U.S.A. 101: 11980-11985. PMID: 15277689

3. Elnakady, Y.A., et al. 2007. Chembiochem. 8: 1261-1272. PMID: 17592829

4. Janssen, C.O., et al. 2008. Bioorg. Med. Chem. Lett. 18: 5771-5773. PMID: 18845435

5. Bahnck, K.B., et al. 2008. J. Am. Chem. Soc. 130: 13177-13181. PMID: 18767844

6. Martin, H.J., et al. 2010. Angew. Chem. Int. Ed. Engl. 49: 5614-5626. PMID: 20818753

Physical State :
Solid
Derived From :
Streptomyces sp.
Solubility :
Soluble in DMSO, and methanol.
Storage :
Store at -20° C
Melting Point :
270.93° C (Predicted)
Boiling Point :
678.49° C at 760 mmHg (Predicted)
Density :
1.20 g/cm3 (Predicted)
Refractive Index :
n20D 1.58 (Predicted)
IC50 :
Bcl-x: IC50 = 12.3 µM (human); A549: IC50 = 16 µM (human)
pK Values :
pKa: 8.53 (Predicted)
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
PubChem CID :
MDL Number :
MFCD14635192
SMILES :
CC1CCC2C(C(C(C(O2)C3=C(C(=O)C(=C4C3=CC(O4)(C(CC(CC(=C1)C)C)C)O)C)O)C)O)C

Download SDS (MSDS)

Certificate of Analysis

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Rated 5 out of 5 by from An increase in cleaved caspase An increase in cleaved caspase-3 p17 protein was observed by WB in U-937 cells post treatment with Kendomycin. -SCBT QC
Date published: 2015-05-18
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