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F4767

Filipin III from Streptomyces filipinensis

≥85% (HPLC)

Synonym(s):

Filimarisin

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About This Item

Empirical Formula (Hill Notation):
C35H58O11
CAS Number:
480-49-9
Molecular Weight:
654.83
NACRES:
NA.77
PubChem Substance ID:
24894871
UNSPSC Code:
12352202
MDL number:
MFCD00466923
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Quality Level

300

assay

≥85% (HPLC)

form

powder

mp

163-180  °C

solubility

methanol: 9.80-10.20 mg/mL, clear, colorless to yellow

antibiotic activity spectrum

fungi, yeast

mode of action

cell membrane | interferes

storage temp.

−20°C

SMILES string

CCCCCC(O)C1C(O)CC(O)CC(O)CC(O)CC(O)CC(O)CC(O)C(C)=C\C=C\C=C\C=C\C=C\C(O)C(C)OC1=O

InChI

1S/C35H58O11/c1-4-5-11-16-31(42)34-33(44)22-29(40)20-27(38)18-25(36)17-26(37)19-28(39)21-32(43)23(2)14-12-9-7-6-8-10-13-15-30(41)24(3)46-35(34)45/h6-10,12-15,24-34,36-44H,4-5,11,16-22H2,1-3H3/b7-6+,10-8+,12-9+,15-13+,23-14-

InChI key

IMQSIXYSKPIGPD-BWJOQPJXSA-N

Application

Filipin has been used in a double staining procedure as a probe for the detection of lipoproteins in polyacrylamide gel and immobilized on nitrocellulose membranes.
Filipin has been used in a double staining procedure as a probe for the detection of lipoproteins in polyacrylamide gel and immobilized on nitrocellulose membranes. It is also widely used to localize and quantitate unesterified cholesterol by virtue of a specific fluorescent complex.

Biochem/physiol Actions

Filipin is a polyene macrolide antibiotic and antifungal. The antifungal mechanism of action may be due to altering membrane permeability and associated functions by binding to membrane sterols. Filipin inhibits prion protein (PrP) endocytosis and causes the release of PrP from the plasma membrane.

Other Notes

Filipin III is the major component of 8 isomeric components in filipin.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

涉药品监管产品

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Certificates of Analysis (COA)

Lot/Batch Number
068M4045V
039M4005V
14190708
14180102
018M4035V

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Jiangli Dou et al.
Biochimica et biophysica acta, 1821(6), 934-942 (2012-04-10)
Ejaculated mammalian sperm must acquire fertilization capacity after residing into the female reproductive tract, a process collectively known as capacitation. Cholesterol efflux was required for sperm maturation. Different from flagellated sperm, C. elegans sperm are crawling cells. C. elegans sperm
Henrik Tjellström et al.
FASEB journal : official publication of the Federation of American Societies for Experimental Biology, 24(4), 1128-1138 (2009-12-08)
As in other eukaryotes, plant plasma membranes contain sphingolipids, phospholipids, and free sterols. In addition, plant plasma membranes also contain sterol derivatives and usually <5 mol% of a galactolipid, digalactosyldiacylglycerol (DGDG). We earlier reported that compared to fully fertilized oats
Kari Fine-Coulson et al.
PloS one, 7(9), e45028-e45028 (2012-10-02)
Dynamic, cholesterol-dense regions of the plasma membrane, known as lipid rafts (LR), have been observed to develop during and may be directly involved in infection of host cells by various pathogens. This study focuses on LR aggregation induced in alveolar
View All Related Papers

Global Trade Item Number

SKUGTIN
F4767-1MG04061838446060
F4767-5MG04061832947563