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A4888

Sigma-Aldrich

Amphotericin B from Streptomyces sp.

~80% (HPLC), powder

Sinônimo(s):
Fungizone
Empirical Formula (Hill Notation):
C47H73NO17
Número CAS:
Peso molecular:
924.08
Beilstein:
78342
Número EC:
Número MDL:
ID de substância PubChem:
NACRES:
NA.85

Nível de qualidade

300

fonte biológica

Streptomyces sp.

teor

~80% (HPLC)

forma

powder

cor

yellow to orange

solubilidade

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

Modo de ação

cell membrane | interferes

espectro de atividade do antibiótico

fungi
yeast

temperatura de armazenamento

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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Categorias relacionadas

Descrição geral

Chemical structure: polyene

Aplicação

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

Embalagem

1, 5, 100 g in glass bottle
100, 250, 500 mg in glass bottle

Ações bioquímicas/fisiológicas

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.

Atenção

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.

Nota de preparo

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.

Outras notas

Keep container tightly closed in a dry and well-ventilated place. Product is sensitive to light and moisture. Keep in a dry place.

Pictogramas

Health hazard

Palavra indicadora

Danger

Frases de perigo

Declarações de precaução

Classificações de perigo

STOT RE 1

Código de classe de armazenamento

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

WGK

WGK 3

Ponto de fulgor (ºF)

Not applicable

Ponto de fulgor (ºC)

Not applicable

Equipamento de proteção individual

dust mask type N95 (US), Eyeshields, Gloves

Certificado de análise

Certificado de origem

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
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

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