| Identification | Back Directory | [Name]
CONCANAMYCIN A | [CAS]
80890-47-7 | [Synonyms]
S-45A
A661-I
x4357b
FOLIMYCIN
NSC 674620
Concanamycin
A,ConcanaMycin
CONCANAMYCIN A
Antibiotic A661I
Antibiotic S-45A
antibioticx4357b
FoliMycin, TAN 1323B
CONCANAMYCIN A USP/EP/BP
Concanamycin A (Folimycin)
FOLIMYCIN, STREPTOMYCES SP
ConcanaMycin A (high purity)
CONCANAMYCIN A, STREPTOMYCES SP
FOLIMYCIN, STREPTOMYCES SPECIES
concanamycin A from streptomyces species
Folimycin, Streptomyces sp. - CAS 80890-47-7 - Calbiochem
(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-
Oxacyclooctadeca-3,5,13,15-tetraen-2-one, 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-propen-1-yl-2H-pyran-2-yl]-2-hydroxy-1-methylbutyl]-9-ethyl-8,10-dihydroxy-3,17-dimethoxy-5,7,11,13-tetramethyl-, (3Z,5E,...
(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 | [EINECS(EC#)]
620-709-4 | [Molecular Formula]
C46H75NO14 | [MDL Number]
MFCD00210037 | [MOL File]
80890-47-7.mol | [Molecular Weight]
866.09 |
| Chemical Properties | Back Directory | [Melting point ]
179-180℃ (dichloromethane ethanol ) | [Boiling point ]
966.4±65.0 °C(Predicted) | [density ]
1.20±0.1 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
Soluble in DMSO | [form ]
Lyophilized solid | [pka]
12.46±0.70(Predicted) | [color ]
White | [BRN ]
3560277 | [Stability:]
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month. |
| Hazard Information | Back Directory | [Description]
Concanamycin A (80890-47-7) is a potent and specific inhibitor of the vacuolar (V-type) H+-ATPase which can induce apoptotic cell death in various cell lines.1,2?Inhibits cell surface expression of virus envelope glycoproteins.3?Dramatically increases the rate of extracellular vesicle release from a variety of cell types.4?Inhibits autophagy by blocking lysosomal acidification.5 | [Uses]
Concanamycin A is the major analogue of the concanamycin complex produced by Streptomyces sp.. It has been shown to act as a potent and specific vacuolar-ATPase 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. | [Definition]
ChEBI: A concanamycin in which the lactone ring contains 4 double bonds and is substituted by 4 methyl groups, 2 hydroxy groups, 2 methoxy groups and an ethyl group. | [General Description]
Chemical structure: macrolide | [Biological Activity]
Specific inhibitor of V-type (vacuolar) H + -ATPase that displays > 2000-fold selectivity over other H + -ATPases (IC 50 values are 9.2, > 20000, > 20000 and > 20000 nM for yeast V-type, F-type, P-type H + -ATPases and porcine P-type Na + ,K + -ATPase respectively). Blocks cell surface expression of virus envelope glycoproteins without affecting synthesis and exhibits cytotoxicity in several cell lines. | [Biochem/physiol Actions]
Concanamycin A (ConA) inhibits acidification of organelles and perforin-mediated cytotoxicity. It is a vacuolar-type v-ATPase inhibitor. ConA possesses antiprotozoal and antineoplastic properties. It mediates inhibition of the negative factor (Nef) protein of the human immunodeficiency virus. | [storage]
Store at -20°C | [References]
1) Nishihara?et al.?(1995),?Specific inhibitors if vacuolar type H(+)-ATPases induce apoptotic cell death; Biochem. Biophys, Res. Commun.,?212?255
2) Hong?et al. (2006),?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. Pharmacol. Exp. Ther.,?319?672
3) Muroi?et al.?(1993),?Folimycin (concanamycin A), a specific inhibitor of V-ATPase, blocks intracellular translocation of the glycoprotein of vesicular stomatitis virus before arrival to the Golgi apparatus; Cell Struct. Function,?18?139
4) Cashikar and Hanson (1987),?A cell-based assay for CD63-containing extracellular vesicles; PLoS One,?14?e0220007
5) Gradzka?et al.?(2018),?Inhibitor of apoptosis proteins are required for effective fusion of autophagosomes with lysosomes; Cell Death Dis.,?9?529 |
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