Amphotericin B

SKU: orb1309878

Description

Amphotericin B is a broad-spectrum polyene antifungal that acts by irreversibly binding to ergosterol, thereby disrupting fungal membrane integrity. It is widely used in both in vitro susceptibility testing and in vivo models of systemic fungal infections such as aspergillosis and candidiasis.

Research Area

Infectious Disease & Virology, Pharmacology & Drug Discovery

Key Properties

• CAS Number: 1397-89-3
• MW: 924.1
• Purity: >90%
• Formula: C₄₇H₇₃NO₁₇
• SMILES: [H][C@]12C[C@@H](O[C@@H]3O[C@H](C)[C@@H](O)[C@H](N)[C@@H]3O)\C=C\C=C\C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]1C(O)=O)O2
• Target: Antibiotic
• Solubility: Soluble in DMSO (up to 18 mg/ml),

Bioactivity

• Target IC50:
  Candida species:2-8 µg/mL (MIC50)|Adherence to plastic:5.1 mg/L (PMNs)|Leishmania donovani:0.06 µg/mL|Trichophyton mentagrophytes:0.02 µg/mL
• In Vivo:
  METHODS: To assay antifungal activity in vivo, Amphotericin B (0.25-4 mg/kg) was administered as a single intraperitoneal injection to C. albicans K-1-infected ICR/Swiss mice. RESULTS: Only the highest single dose of Amphotericin B treatment significantly reduced the number of colonies compared to the number of colonies at the start of treatment.
• In Vitro:
  METHODS: Human normal colon epithelial cells CCD 841 CoTr and human colorectal cancer cells HT-29 were treated with Amphotericin B (0.05-25 µg/mL) for 24 h. Cell viability was measured by Neutral Red method. RESULTS: Higher concentrations of Amphotericin B were toxic to CCD 841 CoTr and HT-29 cells, with IC50 values of 8.7 µg/mL and 21.2 µg/mL, respectively. METHODS: Candida albicans were treated with Amphotericin B (100 µM) for 4-16 min and imaged using the FLIM technique. RESULTS: Amphotericin B preferentially binds to the cell wall and does not efficiently cross the barrier covering the cell membrane.Amphotericin B can more readily pass through the cell wall barrier of young cells during the emergence stage.
• Cell Research:
  Amphotericin B is dissolved in DMSO. The kinetics of cell death induced by AmB against Leishmania promastigotes is followed by using fluorometry with the DNA-binding compound ethidium bromide (EB). Fluorescence measurements are performed on a SPEX Fluorolog II spectrophotometer at 365-580 nm excitation-emission wavelengths. Promastigotes at a final concentration of 25×106 cells/mL are incubated for 5 min with gentle stirring in the fluorescence cuvette with 2 mL of different buffered solutions but always containing 10 mM glucose and EB (50 mM). After signal stabilization is achieved, AmB is added and dissolved in dimethylsulfoxide. Maximal EB incorporation is always obtained by adding digitonin (50 mg/mL). All solutions used are buffered with 75 mM TRIS (pH 4 7.6) and contain 150 mM NaCl (BNa+), 150 mM KCl (BK+), 150 mM choline chloride, and 100 mM sucrose, 100 mM NaCl. The osmolarity of all solutions is always adjusted to 390±5 mOsm using an advanced instrument SW2 osmometer.

Storage & Handling

• Storage: -20°C / protect from light
• Expiration Date: 12 months from date of receipt.
• Disclaimer: For research use only

Alternative Names

NSC 527017

Compound Identifiers

PubChem CID

73438937