NONACTIN Chemical Properties

Melting point:

147-148°

Boiling point:

890.6±65.0 °C(Predicted)

Density 

1.11-1.15 g/cm3

storage temp. 

2-8°C

solubility 

chloroform: soluble10mg/mL

form 

White to off-white crystalline solid.

color 

white to faint yellow

Sensitive 

Moisture Sensitive

Merck 

13,6709

BRN 

76434

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 2 months.

Safety Information

Hazard Codes 

Xi

Safety Statements 

22-24/25

WGK Germany 

3

RTECS 

RH1685000

F 

10-21

HS Code 

29321900

Toxicity

LD50 intravenous in mouse: 246mg/kg

MSDS

• Language:English Provider:SigmaAldrich

NONACTIN Usage And Synthesis

Description

Nonactin (6833-84-7) is a monovalent cation ionophore with high selectivity for NH4+ and K+ .1 Upregulates levels of mitochondrial stress proteins HSP58 and GRP75.2 Nonactin abolishes mitochondrial membrane potential.3

Chemical Properties

Light yellow powder

Uses

Nonactin is the smallest member of the macrotetrolide complex produced by a range of Streptomyces species. Originally the name, nonactin, reflected the lack of biological activity. The literature is confusing in this respect, as virtually all sources of nonactin are contaminated with small amounts of the much more active monactin. The BioAustralis nonactin has been purified to remove traces of other biologically-active macrotetrolides. Like the other macrotetrolides, nonactin is a monovalent cation ionophore with high selectivity for ammonium and potassium.

Uses

Nonactin is an ionophore antiobiotic that selectively binds K+?and NH4+.

Definition

ChEBI: Nonactin is a macrotetrolide.

Biological Activity

Monovalent cation ionophore that displays selectivity for K + and NH 4 + (K + = NH 4 + > Na + > Mg 2+ > Li + >> Ca 2+ for nonactin-EVA sensor). Induces cation transport across artificial membranes. Also inhibits P-glycoprotein-mediated efflux of chemotherapeutic agents in multiple-drug resistant cancer cells. Antibiotic.

Purification Methods

This macrotetrolide antibiotic crystallises from MeOH as colourless needles and is dried at 90o/20hours/high vacuum. [Cordaz et al. Helv Chim Acta 38 1445 1955, crystal structure: Dobler Helv Chim Acta 55 1371 1972, Gambos et al. Tetrahedron Lett 3391 1975, Beilstein 19/12 V 751.]

References

1) Garcia et al. (2003), Determination of potassium ions in pharmaceutical samples by FIA using a potentiometric electrode based on ionophore nonactin occulded in EVA membrane; J. Pham. Biomed. Anal., 31 11 2) Mizzen et al. (1989), Identification, characterization and purification of two mammalian stress proteins present in mitochondria, grp 75, a member of the hsp 70 family and hsp 58, a homolog of the bacterial groEL protein; J. Biol. Chem., 264 20664 3) Dudani et al. (1990), Effects of antimitotic and antimitochondrial agents on the cellular distribution of microtubules and mitochondria; Cytobios, 63 95

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