NONACTIN

NONACTIN Basic information
Product Name:NONACTIN
Synonyms:ta-25-m-i;NONACTIN;NONACTIN, STREPTOMYCES GRISEUS;POLYNACTIN;NONACTIN FROM STREPTOMYCES GRISEUS;NONACTINE, FROM STREPTOMYCES SP.;NONACTIN FROM STREPTOMYCES TSUSIMAENSIS;nonactinfromstreptomycessp.
CAS:6833-84-7
MF:C40H64O12
MW:736.93
EINECS:229-911-3
Product Categories:inhibitor
Mol File:6833-84-7.mol
NONACTIN Structure
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
10-21
HS Code 29321900
ToxicityLD50 intravenous in mouse: 246mg/kg
MSDS Information
ProviderLanguage
SigmaAldrich English
NONACTIN Usage And Synthesis
DescriptionNonactin (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 PropertiesLight yellow powder
UsesNonactin 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.
UsesNonactin is an ionophore antiobiotic that selectively binds K+?and NH4+.
DefinitionChEBI: Nonactin is a macrotetrolide.
Biological ActivityMonovalent 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 MethodsThis 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.]
References1) 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
NONACTIN Preparation Products And Raw materials
Butyl isobutyrate TETRAHYDROFURAN-2-ACETIC ACID ETHYL ESTER DL-B-HYDROXYCAPRYLIC ACID METHYL ESTER (-)-METHYL (R)-3-HYDROXYPENTANOATE Hexyl isobutyrate AMYL-2-METHYLBUTYRATE (R)-ETHYL 3-HYDROXYPENTANOATE ETHYL 6-HYDROXYHEXANOATE NONACTIN OCTYL ISOBUTYRATE ISOBUTYRIC ACID ISOPROPYL ESTER Hexyl 2-methylbutyrate N-PROPYL-2-METHYL BUTYRATE DI(PROPYLENE GLYCOL) PROPYL ETHER 3-HYDROXYNONANOIC ACID ETHYL (S)-3-HYDROXYHEXANOATE BUTYL-2-METHYLVALERATE FEMA 3604

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