CONCANAMYCIN A Chemical Properties

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

pka

12.46±0.70(Predicted)

form 

Lyophilized solid

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.

Safety Information

Hazard Codes 

T+

Risk Statements 

26/27/28-36

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3462 6.1/PG 2

WGK Germany 

3

RTECS 

CB9732000

F 

10-21

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

2941900000

MSDS

• Language:English Provider:SigmaAldrich

CONCANAMYCIN A Usage And Synthesis

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.

Uses

Concanamycin A has been used:

• as a lysosomal inhibitor in young and old fibroblasts
• as a vacuolar-type H⁺-ATPase inhibitor in presynaptic vesicles
• as a lysosomal acidification blocker in HepG2 hepatocytes cells

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

CONCANAMYCIN A(80890-47-7)Related Product Information

• BUTYL SORBATE
• 2,4-DECADIEN-1-OL
• 2,4-NONADIEN-1-OL
• ETHYL SORBATE
• ISODECYL ACRYLATE
• (E,E)-2,4-Dodecadienal
• CONCANAMYCIN A
• trans,trans-2,4-undecadienal
• CONCANAMYCIN A,CONCANAMYCIN A, STREPTOMYCES SP
• 2-methoxyethyl carbamate
• 2,4-DECADIENOIC ACID METHYL ESTER
• 2,4-UNDECADIEN-1-OL
• viranamycin B
• concanamycin G
• concanamycin E
• concanamycin D
• Ethyl-2,4-decadienoate
• hedonal