nonactin

Names

[ Name ]:
nonactin

[Synonym ]:
nonactin
EINECS 229-911-3

Biological Activity

[Description]:

Nonactin is a naturally occurring macrotetrolide antibiotic from Streptomyces griseus. Nonactin acts as an ionophore for monovalent cations, including K+, and NH4+[1]. Nonactin is able to uncouple the oxidative phosphorylation of mitochondria. Nonactin selectively induces apoptosis in cell lines harboring active mutant β-catenin[2]. Nonactin inhibits the surface expression of endogenous HSP60[3].

[Related Catalog]:

Signaling Pathways >> Apoptosis >> Apoptosis

Research Areas >> Cancer

Research Areas >> Infection

[References]

[1]. Martínez-Haya B, et al. On the ionophoric selectivity of nonactin and related macrotetrolide derivatives. Phys Chem Chem Phys. 2017 Jan 4;19(2):1288-1297.

[2]. Shikata Y, et al. Mitochondrial uncoupler exerts a synthetic lethal effect against β-catenin mutant tumor cells. Cancer Sci. 2017 Apr;108(4):772-784.

[3]. Barazi HO, et al. Identification of heat shock protein 60 as a molecular mediator of alpha 3 beta 1 integrin activation. Cancer Res. 2002 Mar 1;62(5):1541-8.

Chemical & Physical Properties

[ Density]:
1.041 g/cm3

[ Boiling Point ]:
890.6ºC at 760 mmHg

[ Melting Point ]:
147-148°

[ Molecular Formula ]:
C₄₀H₆₄O₁₂

[ Molecular Weight ]:
736.92900

[ Flash Point ]:
352.7ºC

[ Exact Mass ]:
736.44000

[ PSA ]:
142.12000

[ LogP ]:
6.02200

[ Appearance of Characters ]:
white to faint yellow

[ Index of Refraction ]:
1.452

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
chloroform: soluble10mg/mL

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi

[ Safety Phrases ]:
S22-S24/25

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
RH1685000

[ HS Code ]:
29321900

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Pilot-plant cultivation of Streptomyces griseus producing homologues of nonactin by precursor-directed biosynthesis and their identification by LC/MS-ESI.

J. Antibiot. 63(8) , 524-9, (2010)

Precursor-directed biogenetic approach was used to produce a range of nonactin homologues in a 50 l fermentor cultivation of strain Streptomyces griseus 34/249 obtained by UV mutagenesis. The producti...

Synthesis of nonactin and the proposed structure of trilactone.

Org. Lett. 8(13) , 2831-4, (2006)

[reaction: see text] An efficient enantioselective route to nonactin using a novel beta-inversion of an Evans syn aldol to construct the THF ring is presented. Through total synthesis, the structure f...

Resolution of methyl nonactate by Rhodococcus erythropolis under aerobic and anaerobic conditions.

Org. Lett. 8(3) , 443-5, (2006)

[reaction: see text]. An efficient resolution of methyl nonactate is reported by biotransformation in shake flask cultures of Rhodococcus erythropolis. The equilibrium of the reaction redox system can...