A2411

Amphotericin B from Streptomyces sp.

solid, suitable for cell culture, BioReagent

• Synonym(s): Fungizone
• Empirical Formula (Hill Notation): C₄₇H₇₃NO₁₇
• CAS Number: 1397-89-3
• Molecular Weight: 924.08
• NACRES: NA.76
• PubChem Substance ID: 24890655
• UNSPSC Code: 12352207
• EC Number: 215-742-2
• MDL number: MFCD00877763
• Beilstein/REAXYS Number: 78342
• eCl@ss: 34010400

Properties

• Product Name: Amphotericin B from Streptomyces sp., BioReagent, suitable for cell culture, ~80% (HPLC)
• biological source: Streptomyces sp.
• Quality Segment: 300
• product line: BioReagent
• assay: ~80% (HPLC)
• form: solid
• potency: >750.00 μg per mg (Dry basis)
• technique(s): cell culture | mammalian: suitable
• color: yellow to yellow-orange
• solubility: H₂O: slightly soluble
• 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 a polyene antifungal antibiotic from Streptomyce sp. It has a high affinity for sterols, especially ergosterols, of both fungal and bacterial cell membranes. Normal usage in maintenance of antifungal cell cultures is 2.5 mg/L with penicillin and streptomycin used in the medium.

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.

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.

Disclaimer

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.

Safety Information

• pictograms: GHS07
• signalword: Warning
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves
• target_organs: Respiratory system
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Storage Class: 11 - Combustible Solids