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A2411

Sigma-Aldrich

Amphotéricine B from Streptomyces sp.

solid, suitable for cell culture, BioReagent

Synonyme(s) :

Fungizone

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About This Item

Formule empirique (notation de Hill):
C47H73NO17
Numéro CAS:
1397-89-3
Poids moléculaire :
924.08
Numéro Beilstein :
78342
Numéro CE :
215-742-2
Numéro MDL:
MFCD00877763
Code UNSPSC :
12352207
ID de substance PubChem :
24890655
Nomenclature NACRES :
NA.76

product name

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

Source biologique

Streptomyces sp.

Niveau de qualité

300

Gamme de produits

BioReagent

Pureté

~80% (HPLC)

Forme

solid

Puissance

>750.00 μg per mg (Dry basis)

Technique(s)

cell culture | mammalian: suitable

Couleur

yellow to yellow-orange

Solubilité

H2O: slightly soluble

Spectre d'activité de l'antibiotique

fungi
yeast

Mode d’action

cell membrane | interferes

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

APKFDSVGJQXUKY-INPOYWNPSA-N

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Catégories apparentées

Description générale

Chemical structure: polyene

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.

Actions biochimiques/physiologiques

L′amphotéricine B se fixe aux stérols, formant ainsi des pores dans la membrane et provoquant la libération de petites molécules. Ce produit est particulièrement efficace contre les champignons et les levures.

Attention

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.

Notes préparatoires

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.

Autres remarques

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

Pictogrammes

Health hazard
GHS08

Mention d'avertissement

Danger

Mentions de danger

H372

Classification des risques

STOT RE 1

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

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.
Malav S Trivedi et al.
The Journal of nutritional biochemistry, 25(10), 1011-1018 (2014-07-16)
Dietary interventions like gluten-free and casein-free diets have been reported to improve intestinal, autoimmune and neurological symptoms in patients with a variety of conditions; however, the underlying mechanism of benefit for such diets remains unclear. Epigenetic programming, including CpG methylation
Hsin-Yun Sun et al.
Transplantation, 96(6), 573-578 (2013-07-12)
Limited data exist regarding echinocandins as antifungal prophylaxis in liver transplant recipients. The efficacy and safety of targeted prophylaxis with micafungin or amphotericin B lipid complex (ABLC) was assessed in a sequential cohort of high-risk patients (posttransplantation dialysis, retransplantation, or
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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