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Merck

N6261

Nystatin

powder, suitable for cell culture, BioReagent

Sinónimos:

Fungicidin, Mycostatin

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Número CAS:
1400-61-9
NACRES:
NA.76
PubChem Substance ID:
24897778
UNSPSC Code:
12352207
EC Number:
215-749-0
MDL number:
MFCD25541651

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Nombre del producto

Nystatin, powder, BioReagent, suitable for cell culture

InChI key

VQOXZBDYSJBXMA-QEKUPDCNSA-N

InChI

1S/C47H75NO17/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)25-36(53)35(52)20-19-31(49)21-32(50)22-33(51)23-39(55)62-29(3)28(2)42(27)56/h5-6,8,10-18,27-38,40-44,46,49-54,56-58,61H,7,9,19-26,48H2,1-4H3,(H,59,60)/b6-5+,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

O[C@@H]([C@H](C)[C@H](C)O1)[C@@H](C)/C=C/C=C/CC/C=C/C=C/C=C/C=C/[C@H](O[C@@H]2O[C@H](C)[C@@H](O)[C@H](N)[C@@H]2O)C[C@@]3([H])[C@H](C(O)=O)[C@@H](O)C[C@](O)(O3)C[C@@H](O)[C@H](O)CC[C@@H](O)C[C@@H](O)C[C@@H](O)CC1=O

product line

BioReagent

form

powder

potency

≥4,400 per mg

technique(s)

cell culture | mammalian: suitable

solubility

H2O: insoluble

antibiotic activity spectrum

fungi, yeast

mode of action

cell membrane | interferes

storage temp.

2-8°C

Quality Level

200

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Application

Nystatin has been used -
  • for the treatment of human macrophage cell line U937, to study the effect of nystatin on the production of IL-8 (interleukin 8) by silver nanoparticle-treated U937 cell line
  • to determine its effect on intracellular accumulation of OxLDL (oxidized low density lipoprotein) mediated by SR-BI (scavenger receptor class B type I) in COS-7 cell line
  • as a lipid raft modulator on mice macrophages to study the relationship between increased number of lipid rafts and the heightened response of TNF-α (tumor necrosis factor)
Nystatin is a polyene antibiotic. Its uses include preventing cell culture contamination and inducing interleukin (IL)-1, IL-8, and tumor necrosis factor α secretion in TLR2-expressing THP1 cells. This product is recommended for use in cell culture applications at 50 mg/L.

Biochem/physiol Actions

Mode of Action: Nystatin acts by binding to ergosterols in fungal cell membranes, increasing permeability of the membrane, and creating nystatin/ergosterol based ion channels. It also functions as a lipid raft-inhibiting reagent and as membrane associated cholesterol.

Antimicrobial spectrum: Nystatin acts against fungi, yeasts and molds.
Studies in severely burned patients have shown that treatment with nystatin powder is effective for the treatment of massive angioinvasive fungal infection, without side-effects on wound healing.

Disclaimer

Nystatin in tissue culuture media is stable at 37°C for three days. It is also stable in moderately alkaline media. Solutions and aqueous suspensions begin to lose activity soon after preparation, with heat, light, and oxygen accelerating the decomposition. Aqueous suspensions are stable for 10 minutes when heating to 100°C at pH 7.

General description

Chemical structure: polyene
Nystatin is a polyene macrolide antifungal, which is a polyketide produced by Streptomyces noursei ATCC 11455. This antibiotic contains a macrolactone ring, and its natural synthesis is initiated with acetyl CoA, which is followed by the condensation of three ethylmalonyl-CoA and 15 malonyl-CoA extender moieties.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.Store under inert gas. Air and light sensitive. Keep in a dry place.

Preparation Note

Nystatin is soluble at 28°C in methanol (11.2 mg/mL), ethanol (1.2 mg/mL), carbon tetrachloride (1.23 mg/mL), chloroform (0.48 mg/mL), benzene (0.28 mg/mL), and ethylene glycol (8.75 mg/mL). It is also soluble in DMSO at 5 mg/mL and freely soluble in DMF and formamide. It is not recommended to autoclave or sterile filter solutions of Nystatin. Nystatin is also effective as a suspension, stable at 37°C for 3 days. Prepare 50 mg/mL stock suspensions in water and store at -20°C.

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
SLCL5194
SLCG1944
SLCC2044
SLBC7148V
SLBC2021V

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Seungjae Kim et al.
Yonsei medical journal, 53(3), 654-657 (2012-04-06)
Phagocytosis or endocytosis by macrophages is critical to the uptake of fine particles, including nanoparticles, in order to initiate toxic effects in cells. Here, our data enhance the understanding of the process of internalization of silver nanoparticles by macrophages. When
J P Barret et al.
Burns : journal of the International Society for Burn Injuries, 25(6), 505-508 (1999-09-25)
Angioinvasive fungal infections have a significant morbidity and mortality in the immunocompromised host. Massive burns produce a profound derangement in cellular immunity along with a loss of cutaneous barrier function. Treatment of fungal burn wound infections poses a difficult therapeutic
Bing Sun et al.
Journal of lipid research, 48(12), 2560-2570 (2007-09-19)
Modified forms of LDL, including oxidized low density lipoprotein (OxLDL), contribute to macrophage lipid accumulation in the vessel wall. Despite the pathophysiological importance of uptake pathways for OxLDL, the molecular details of OxLDL endocytosis by macrophages are not well understood.
T Brautaset et al.
Chemistry & biology, 7(6), 395-403 (2000-06-30)
The polyene macrolide antibiotic nystatin produced by Streptomyces noursei ATCC 11455 is an important antifungal agent. The nystatin molecule contains a polyketide moiety represented by a 38-membered macrolactone ring to which the deoxysugar mycosamine is attached. Molecular cloning and characterization
Masahiro Koseki et al.
Journal of lipid research, 48(2), 299-306 (2006-11-03)
Lipid rafts on the cell surface are believed to be very important as platforms for various cellular functions. The aim of this study was to know whether defective lipid efflux may influence lipid rafts on the cell surface and their
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