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Merck

A4888

Sigma-Aldrich

Anfotericina B from Streptomyces sp.

~80% (HPLC), powder

Sinónimos:

Fungizona

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About This Item

Fórmula empírica (notación de Hill):
C47H73NO17
Número de CAS:
Peso molecular:
924.08
Beilstein/REAXYS Number:
78342
EC Number:
MDL number:
UNSPSC Code:
51102829
PubChem Substance ID:
NACRES:
NA.85

biological source

Streptomyces sp.

Quality Level

assay

~80% (HPLC)

form

powder

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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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
La anfotericina B se une a los esteroles formando poros en la membrana y provocando la salida de moléculas pequeñas. La máxima eficacia del producto es contra hongos y levaduras.

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.

Storage and Stability

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

Other Notes

For additional information on our range of Biochemicals, please complete this form.
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

signalword

Danger

hcodes

Hazard Classifications

STOT RE 1

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Visite la Librería de documentos

Biological activities of the essential oils and methanol extract of Origanum vulgare ssp. vulgare in the Eastern Anatolia region of Turkey.
Sahin F, et al.
Food Control, 15, 549-557 (2004)
Y Saka et al.
Journal of biochemistry, 123(5), 798-805 (1998-06-19)
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
Screening of antimicrobial activity of essential oil and methanol extract of Satureja hortensis on foodborne bacteria and fungi.
Adiguzel A, et al.
Czech Journal of Food Sciences, 25, 81-81 (2007)
Hakan Ozer et al.
Journal of agricultural and food chemistry, 55(3), 937-942 (2007-02-01)
Hippomarathrum microcarpum grows wild in eastern Anatolia, Turkey, and is a plant utilized as food by people. In this study, the in vitro antimicrobial and antioxidant activities of the essential oil and methanol extract from H. microcarpum and its essential
Maki Onda et al.
Journal of biochemistry, 134(1), 121-128 (2003-08-29)
To investigate the susceptibilities of fungal and mammalian cells to amphotericin B (AmB), AmB-loaded lysophosphatidylcholine (LPC)micelles as drug delivery vehicles were incubated at 37 degrees C with phosphatidylcholine vesicles containing different sterols as model systems for fungal and mammalian cells.

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