Amphotericin B (from Streptomyces species)
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Synonyms:
(1R,3S,5R,6R,9R,11R,15S,16R,17R,18S,19E,21E,23E,25E,27E,29E,31E,33R,35S,36R,37S)-33-(((2R,3S,4S,5S,6R)-4-Amino-3,5-dihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-1,3,5,6,9,11,17,37-octahydroxy-15,16,18-trimethyl-13-oxo-14,39-dioxabicyclo[33.3.1]nonatriaconta-19,21,23,25,27,29,31-heptaene-36-carboxylic acid
Amphotericin B is a polyene antifungal antibiotic from Streptomyces. It has an affinity for sterols, primarily ergosterols, of fungal cell membranes. It forms channels in the membranes, causing small molecules to leak out which contributes to cell death.
Antimicrobial spectrum: fungi and yeast. Polyene antifungal antibiotic from Streptomyces. Affinity for sterols, primarily ergosterols, of fungal cell membranes. Forms channels in the membranes, causing small molecules to leak out. Antimicrobial spectrum: fungi and yeast
Amphotericin B is used to study the affects of the influx of calcium on antifungal activity and to study the binding and kinetics of Amphotericin B to sterols in monolayers, aqueous solutions, and phospholipid bilayers. It is also commonly used in tissue culture as an antifungal supplement.
Soluble in acidic water (pH 2) or basic water (pH 11) (about 0,1 mg/ml). Water solubility can be increased with the addition of deoxycholic acid, sodium salt (increasing solubility with increasing concentration of deoxycholic acid). Soluble in Dimethylformamide (DMF) (2 to 4 mg/ml), DMF + 1 M HCl (3:1) (60 to 80 mg/ml), DMSO (30 to 40 mg/ml), propylene glycol; slightly soluble in methanol and methyl alcohol; insoluble in water, anhydrous alcohol, ether, benzene, and toluene.
Soluble in acidic water (pH 2) or basic water (pH 11) (about 0.1 mg/mL). Water solubility can be increased with the addition of deoxycholic acid, sodium salt (increasing solubility with increasing concentration of deoxycholic acid). Soluble in Dimethylformamide (DMF) (2 to 4 mg/mL), DMF + 1 M HCl (3:1) (60 to 80 mg/mL), DMSO (30 to 40 mg/mL), propylene glycol; slightly soluble in methanol and methyl alcohol; insoluble in water, anhydrous alcohol, ether, benzene, and toluene.
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Formula:
C₄₇H₇₃NO₁₇ MW: 924.08 g/mol |
MDL Number:
MFCD00877763 CAS Number: 1397-89-3 |
Specification Test Results
| Physical Appearance | Yellow Powder |
| pKa | 5.5 and 10.0.(Lit.) |
| Sterilization of Solutions | Sterilization of solutions should be by filtration through teflon membrane filters; Amphotericin B should not be gamma irradiated or autoclaved. |
| Typical Working Concentration | recommended concentration of 2.5 ug/L (prepared solution use 10 mL/L) |
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