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Merck

A2411

Amphotericin B from Streptomyces sp.

solid, suitable for cell culture, BioReagent

Synonym(s):

Fungizone

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About This Item

Empirical Formula (Hill Notation):
C47H73NO17
CAS Number:
1397-89-3
Molecular Weight:
924.08
NACRES:
NA.76
PubChem Substance ID:
24890655
UNSPSC Code:
12352207
EC Number:
215-742-2
MDL number:
MFCD00877763
Beilstein/REAXYS Number:
78342

Product Name

Amphotericin B from Streptomyces sp., BioReagent, suitable for cell culture, ~80% (HPLC)

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.

product line

BioReagent

assay

~80% (HPLC)

form

solid

potency

>750.00 μg per mg (Dry basis)

technique(s)

cell culture | mammalian: suitable

color

yellow to yellow-orange

solubility

H2O: slightly soluble

antibiotic activity spectrum

fungi
yeast

mode of action

cell membrane | interferes

storage temp.

2-8°C

Quality Level

300

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Application

Amphotericin B is a polyene antifungal antibiotic from Streptomyce sp. It has a high affinity for sterols, especially ergosterols, of both fungal and bacterial cell membranes. Normal usage in maintenance of antifungal cell cultures is 2.5 mg/L with penicillin and streptomycin used in the medium.

Biochem/physiol Actions

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.

Disclaimer

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.

General description

Chemical structure: polyene

Other Notes

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

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.

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H372

Hazard Classifications

STOT RE 1

Storage Class

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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Certificates of Analysis (COA)

Lot/Batch Number
0000471018
0000471018
0000471019
0000471019
0000379913

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Daniel J Mullen et al.
PLoS genetics, 16(9), e1009023-e1009023 (2020-09-15)
Lung cancer is the leading cause of cancer-related death and lung adenocarcinoma is its most common subtype. Although genetic alterations have been identified as drivers in subsets of lung adenocarcinoma, they do not fully explain tumor development. Epigenetic alterations have
Shannon M Reilly et al.
The Journal of clinical investigation, 131(10) (2021-04-07)
The protein kinases IKKε and TBK1 are activated in liver and fat in mouse models of obesity. We have previously demonstrated that treatment with the IKKε/TBK1 inhibitor amlexanox produces weight loss and relieves insulin resistance in obese animals and patients.
Anna-Maria Dietl et al.
Microorganisms, 9(3) (2021-04-04)
Fungal infections due to Aspergillus species have become a major cause of morbidity and mortality among immunocompromised patients. At the Medical University of Innsbruck, A. terreus and related species are the second most common causative agents of aspergillosis. In this
Manica Balasegaram et al.
Expert opinion on emerging drugs, 17(4), 493-510 (2012-11-22)
Leishmaniasis is a parasitic disease transmitted by phlebotomine sandflies. Between 700,000 and 1.2 million cases of cutaneous leishmaniasis and between 200,000 and 400,000 cases of visceral leishmaniasis (VL), which is fatal if left untreated, occur annually worldwide. Liposomal amphotericin B
Richard J Hamill
Drugs, 73(9), 919-934 (2013-06-04)
Because of the increasing prevalence and changing microbiological spectrum of invasive fungal infections, some form of amphotericin B still provides the most reliable and broad spectrum therapeutic alternative. However, the use of amphotericin B deoxycholate is accompanied by dose-limited toxicities
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Data Sheet - A2411

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