A4888

Anfotericina B from Streptomyces sp.

Name: Anfotericina B from <I>Streptomyces</I> sp.
Brand: SIGMA

~80% (HPLC), powder

Sinónimos:

Fungizona

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About This Item

Fórmula empírica (notación de Hill):

C₄₇H₇₃NO₁₇

Número CAS:

1397-89-3

Peso molecular:

924.08

UNSPSC Code:

51102829

NACRES:

NA.85

PubChem Substance ID:

57653841

EC Number:

215-742-2

Beilstein/REAXYS Number:

78342

MDL number:

MFCD00877763

Nombre del producto

Anfotericina B from Streptomyces sp., ~80% (HPLC), powder

InChI key

APKFDSVGJQXUKY-INPOYWNPSA-N

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

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

biological source

Streptomyces sp.

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

Quality Level

300

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Categorías relacionadas

Suplementos y reactivos para cultivo celular

Biochem/physiol Actions

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.

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

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

Features and Benefits

High quality antibiotic suitable for mulitple research applications

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.

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.

Preparation Note

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

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.

pictograms

GHS08

signalword

Danger

hcodes

H372

pcodes

P260 - P264 - P270 - P314 - P501

Hazard Classifications

STOT RE 1

Clase de almacenamiento

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

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Susceptibilities of phospholipid vesicles containing different sterols to amphotericin B-loaded lysophosphatidylcholine micelles.

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.

The activity of amphotericin B against Candida albicans is not directly associated with extracellular calcium concentration.

P David Rogers et al.

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

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)

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)

Chemical composition and antimicrobial and antioxidant activities of the essential oil and methanol extract of Hippomarathrum microcarpum (Bieb.) from Turkey.

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

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Contenido relacionado

Data Sheet - A4888

Instructions

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