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207132 Concanamycin A (Olimycin, Antibiotic TAN 1323B, Antibiotic X4357B) 98+% CAS: 80890-47-7

Specifications
References
CAS Number
80890-47-7
Grade
Highly Purified
Molecular Formula
C46H75NO14
Molecular Weight
866.1
EU Commodity Code
38220090
Shipping Temp
Blue Ice
Storage Temp
-20°C
Olimycin; Folimycin, Antibiotic TAN 1323B; (3Z,5E,7R,8R,9S,10S,11R,13E,15E,17S,18R)-18-[(1S,2R,3S)-3-[(2R,4R,5S,6R)-4-[[4-O-(Aminocarbonyl)-2,6-dideoxy-β-D-arabino-hexopyranosyl]oxy]tetrahydro-2-hydroxy-5-methyl-6-(1E)-1-propenyl-2H-pyran-2-yl]-2-hydroxy-1-methylbutyl]-9-ethyl-8,10-dihydroxy-3,17-dimethoxy-5,7,11,13-tetramethyloxacyclooctadeca-3,5,13,15-tetraen-2-one

Concanamycin A is the major analogue of the concanamycin complex produced by Streptomyces sp. It has has been shown to act as a potent and specific vacuolar-APTase inhibitor. Concanamycin A inhibits the acidification of organelles and blocks cell surface expression of viral envelope glycoproteins without affecting their synthesis. It also interferes with intracellular protein trafficking and inhibits perforin- and Fas-based lytic pathways in cell-mediated cytotoxicity. Concanamycins are structurally related to the bafilomycins.

Source
Streptomyces sp.
Synonyms
Folimycin, Antibiotic TAN 1323B; (3Z,5E,7R,8R,9S,10S,11R,13E,15E,17S,18R)-18-[(1S,2R,3S)-3-[(2R,4R,5S,6R)-4-[[4-O-(Aminocarbonyl)-2,6-dideoxy-β-D-arabino-hexopyranosyl]oxy]tetrahydro-2-hydroxy-5-methyl-6-(1E)-1-propenyl-2H-pyran-2-yl]-2-hydroxy-1-methylbutyl]-9-ethyl-8,10-dihydroxy-3,17-dimethoxy-5,7,11,13-tetramethyloxacyclooctadeca-3,5,13,15-tetraen-2-one
CAS No
80890-47-7
Molecular Formula
C46H75NO14
Molecular Weight
866.09
Appearance
White lyophilized powder
Purity
≥98% (HPLC)
Method for Determining Identity
Proton NMR
Related to
Bafilomycin A1, Bafilomycin B1, Bafilomycin C1
Solubility
Ethanol, Methanol, DMF, DMSO
Storage and Stability
Lyophilized powder may be stored at -20°C. Stable for 12 months at -20°C. Reconstitute with ethanol, methanol, DMF or DMSO. Aliquot to avoid repeated freezing and thawing. Store at -20°C. For maximum recovery of product, centrifuge the original vial after thawing and prior to removing the cap. Further dilutions can be made in assay buffer.
References
1. Isolation and characterization of concanamycins A, B and C: H. Kinashi, et al.; J. Antibiot. 37: 1333 (1984). 2. Folimycin (concanamycin A), a specific inhibitor of V-ATPase, blocks intracellular translocation of the glyco- protein of vesicular stomatitis virus before arrival to the Golgi apparatus: M. Muroi, et al.; Cell Struct. Funct. 18: 139 (1993). 3. Folimycin (concanamycin A), an inhibitor of V-type H(+)-ATPase, blocks cell-surface expression of virus- envelope glycoproteins: M. Muroi, et al.; BBRC 193: 999 (1993). 4. Inhibitory effect of modified bafilomycins and concanamycins on P- and V-type adenosinetriphosphatases: S. Drose, et al.; Biochemistry 32: 3902 (1993). 5. Involvement of the vacuolar H(+)-ATPases in the secretory pathway of HepG2 cells: M. Yilla, et al.; J. Biol. Chem. 268: 19092 (1993). 6. Characterization of the ATPase activity of P-glycoprotein from multidrug-resistant Chinese hamster ovary cells: F.J. Sharom, et al.; Biochem. J. 308 (Pt2): 381 (1995). 7. Specific inhibitors of vacuolar type H(+)-ATPases induce apoptotic cell death: T. Nishihara, et al.; BBRC 212: 255 (1995). 8. Concanamycin A, the specific inhibitor of V-ATPases, binds to the V(o) subunit c: M. Huss, et al.; J. Biol. Chem. 277: 40544 (2002). 9. Nitric oxide production by the vacuolar-type (H+)-ATPase inhibitors bafilomycin A1 and concanamycin A and its possible role in apoptosis in RAW 264.7 cells: J. Hong, et al.; J. Pharmacol. Exp. Ther. 319: 672 (2006). 10. Degradation of oxidized proteins by autophagy during oxidative stress in Arabidopsis: Y. Xiong, et al.; Plant Physiol. 143: 291 (2007). 11. Inhibitors of the V0 subunit of the vacuolar H+-ATPase prevent segregation of lysosomal- and secretory- pathway proteins: J.A. Sobota, et al.; J. Cell Sci. 122: 3542 (2009). 12. Inhibitors of V-ATPase: old and new players: M. Huss, et al.; J. Exp. Biol. 212: 341 (2009).
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