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P9703 Sigma-Aldrich

Pimaricin

from Streptomyces chattanoogensis, ≥95% (HPLC)

Synonym: Natamycin

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Properties

Related Categories Analytical Standards, Analytical/Chromatography, Antibiotics, Antibiotics A to Z, Antibiotics N-S,
Quality Level   300
biological source   Streptomyces chattanoogensis
assay   ≥95% (HPLC)
form   lyophilized powder
  powder
solubility   0.1% formic acid in methanol: soluble 1 mg/mL
Featured Industry   Agriculture
Environmental
Mode of action   cell membrane | interferes
antibiotic activity spectrum   fungi
storage temp.   2-8°C
SMILES string   C[C@@H]1C\C=C\C=C\C=C\C=C\[C@@H](C[C@@H]2O[C@](O)(C[C@@H](O)C[C@H]3O[C@@H]3\C=C\C(=O)O1)C[C@H](O)[C@H]2C(O)=O)O[C@@H]4O[C@H](C)[C@@H](O)[C@H](N)[C@@H]4O
InChI   1S/C33H47NO13/c1-18-10-8-6-4-3-5-7-9-11-21(45-32-30(39)28(34)29(38)19(2)44-32)15-25-27(31(40)41)22(36)17-33(42,47-25)16-20(35)14-24-23(46-24)12-13-26(37)43-18/h3-9,11-13,18-25,27-30,32,35-36,38-39,42H,10,14-17,34H2,1-2H3,(H,40,41)/b4-3+,7-5+,8-6+,11-9+,13-12+/t18-,19-,20+,21+,22+,23-,24-,25+,27-,28+,29-,30+,32+,33-/m1/s1
InChI key   NCXMLFZGDNKEPB-FFPOYIOWSA-N

Description

General description

Chemical structure: macrolide

Application

Pimaricin is an amphoteric antibiotic from Streptomyces chattanoogensis. It is used for a variety of fungal infections, mainly topically. It is used as an ergosterol and cholesterol binding agent to study lipid bilayer dynamics, especially in fungal cells. Pimaricin is used as a fungicide in agar media. It is used to study the pleitropic regulator AdpAch and the gamma-butyrolactone regulatory system of Streptomyces chattanoogensis.

Packaging

25 mg in poly bottle

50, 100 mg in glass bottle

Biochem/physiol Actions

An antifungal polyene macrolide that binds specifically to ergosterol and blocks fungal growth. However, unlike nysatin and filipin, pimaricin does not change the permeability of the plasma membrane

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Recommended storage temperature: 2 - 8 °C. Light sensitive.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
TK3325000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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