A4888

Amphotericin B from Streptomyces sp.

~80% (HPLC), powder

• Synonym(s): Fungizone
• Empirical Formula (Hill Notation): C₄₇H₇₃NO₁₇
• CAS Number: 1397-89-3
• Molecular Weight: 924.08
• Beilstein: 78342
• EC Number: 215-742-2
• MDL number: MFCD00877763
• PubChem Substance ID: 57653841
• NACRES: NA.85

Properties

• biological source: Streptomyces sp.
• Quality Level: 300
• assay: ~80% (HPLC)
• form: powder
• color: yellow to orange
• solubility: DMF: 2-4 mg/mL; DMSO: 30-40 mg/mL; H₂O: insoluble
• antibiotic activity spectrum: fungi; yeast
• Mode of action: cell membrane | interferes
• storage temp.: 2-8°C
• SMILES string: C[C@H]1O[C@@H](O[C@@H]2C[C@@H]3O[C@](O)(C[C@@H](O)C[C@@H](O)[C@H](O)CC[C@@H](O)C[C@@H](O)CC(=O)O[C@@H](C)[C@H](C)[C@H](O)[C@@H](C)\C=C\C=C\C=C\C=C\C=C\C=C\C=C\2)C[C@H](O)[C@H]3C(O)=O)[C@@H](O)[C@@H](N)[C@@H]1O
• InChI: 1S/C47H73NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-34(64-46-44(58)41(48)43(57)30(4)63-46)24-38-40(45(59)60)37(54)26-47(61,65-38)25-33(51)22-36(53)35(52)20-19-31(49)21-32(50)23-39(55)62-29(3)28(2)42(27)56/h5-18,27-38,40-44,46,49-54,56-58,61H,19-26,48H2,1-4H3,(H,59,60)/b6-5+,9-7+,10-8+,13-11+,14-12+,17-15+,18-16+/t27-,28-,29-,30+,31+,32+,33-,34-,35+,36+,37-,38-,40+,41-,42+,43+,44-,46-,47+/m0/s1
• InChI key: APKFDSVGJQXUKY-INPOYWNPSA-N

Description

General description

Chemical structure: polyene

Application

Amphotericin B is used to study the affects of the influx of calcium on antifungal activity, [1] and to study the binding and kinetics of Amphotericin B to sterols in monolayers, aqueous solutions, and phospholipid bilayers [2][3]. It is also commonly used in tissue culture as an antifungal supplement.
Amphotericin B from Streptomyces sp. has been used-

• for amphotericin perforated patch technique[4]
• as a reference antifungal drug during MIC (minimum inhibitory concentration) agar dilution assay[5][6][7]
• as a component of Arcobacter selective isolation broth[8]

Packaging

100, 250, 500 mg in glass bottle

1, 5, 100 g in glass bottle

Biochem/physiol Actions

Amphotericin B binds to sterols, forming pores in the membrane, and causing small molecules to leak out. The product is most effective against fungi and yeast.

Caution

Amphotericin B remains active for 3 days in culture at 37°C. At -20°C, and with protection from air and light, the product remains active for 5 years.

Preparation Note

Amphotericin B is insoluble in water at pH 6 to 7, but soluble in water at pH 2 or 11. It is soluble in DMSO (30-40 mg/mL) and in dimethylformamide (2-4 mg/mL). Aqueous solutions cannot be sterile filtered due to poor solubility.

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Product is sensitive to light and moisture. Keep in a dry place.

Safety Information

• Pictograms: GHS08
• Signal Word: Danger
• Hazard Statements: H372
• Precautionary Statements: P260 - P264 - P270 - P314 - P501
• Hazard Classifications: STOT RE 1
• Storage Class Code: 6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves