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A4888

Sigma-Aldrich

Amphotericin B from Streptomyces sp.

~80% (HPLC), powder

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Synonym(s):
LNS-AmB, NSC 527017, Fungizone
Empirical Formula (Hill Notation):
C47H73NO17
CAS Number:
Molecular Weight:
924.08
Beilstein:
78342
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.85

biological source

Streptomyces sp.

Quality Level

Assay

~80% (HPLC)

form

powder

storage condition

(Tightly closed. Dry. Keep in a well -ventilated place. Keep locked up or in an area accessible )

color

yellow to orange

solubility

DMF: 2-4 mg/mL
DMSO: 30-40 mg/mL
H2O: insoluble
water: 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

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This Item
A2411A9528A2942
assay

~80% (HPLC)

assay

~80% (HPLC)

assay

-

assay

-

form

powder

form

solid

form

powder

form

liquid

storage condition

(Tightly closed. Dry. Keep in a well -ventilated place. Keep locked up or in an area accessible )

storage condition

-

storage condition

-

storage condition

-

color

yellow to orange

color

yellow to yellow-orange

color

-

color

yellow

solubility

DMF: 2-4 mg/mL, DMSO: 30-40 mg/mL, H2O: insoluble, water: insoluble

solubility

H2O: slightly soluble

solubility

-

solubility

-

General description

Amphotericin B is a polyene antifungal antibiotic from Streptomyces sp. and has a high affinity for sterols, especially ergosterols, of both fungal and bacterial cell membranes.

Application

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.
Amphotericin B from Streptomyces sp. has been used-
  • for amphotericin perforated patch technique
  • as a reference antifungal drug during MIC (minimum inhibitory concentration) agar dilution assay
  • as a component of Arcobacter selective isolation broth

Biochem/physiol Actions

Mode of Action: Amphotericin B binds to sterols, forming pores in the membrane, and causing small molecules to leak out.

Antimicrobial spectrum: Includes fungi and yeast
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.

Features and Benefits

High quality antibiotic suitable for mulitple research applications

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.

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.

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.

Pictograms

Health hazard

Signal Word

Danger

Hazard Statements

Precautionary Statements

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

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The interaction of amphotericin B (AmB) with cholesterol was investigated in monolayers, aqueous solutions, and phospholipid vesicles. When AmB was mixed with cholesterol, it formed a stable monolayer, implying complex formation in which the stoichiometry was primarily 1:1 AmB:cholesterol. However
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The Journal of antimicrobial chemotherapy, 51(2), 305-312 (2003-02-04)
The ability of amphotericin B to increase intracellular calcium concentrations in human cells is associated with the toxicity of this antifungal agent. The present study was performed to determine whether amphotericin B affects the influx or efflux of calcium in

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