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Merck

P9703

Pimaricin

from Streptomyces chattanoogensis, ≥95% (HPLC)

Sinónimos:

Natamycin

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About This Item

Fórmula empírica (notación de Hill):
C33H47NO13
Número CAS:
7681-93-8
Peso molecular:
665.73
NACRES:
NA.85
PubChem Substance ID:
24899055
UNSPSC Code:
51102829
EC Number:
231-683-5
MDL number:
MFCD00135085

Nombre del producto

Pimaricin, from Streptomyces chattanoogensis, ≥95% (HPLC)

InChI key

NCXMLFZGDNKEPB-FFPOYIOWSA-N

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

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

biological source

Streptomyces chattanoogensis

assay

≥95% (HPLC)

form

lyophilized powder
powder

solubility

0.1% formic acid in methanol: soluble 1 mg/mL

antibiotic activity spectrum

fungi

application(s)

agriculture
environmental

mode of action

cell membrane | interferes

storage temp.

2-8°C

Quality Level

300

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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.

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

General description

Chemical structure: macrolide

Other Notes

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

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
0000447843
0000447844
0000447846
0000447846
0000447844

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Visite la Librería de documentos

Gamma-Butyrolactone Regulatory System of Streptomyces chattanoogensis Links Nutrient Utilization, Metabolism, and Development
Yi-Ling Du, Shan-Zhen Li, et al.
Microbiology, 77, 8415-8426 (2011)
Yi-Ling Du et al.
Microbiology (Reading, England), 157(Pt 5), 1300-1311 (2011-02-19)
The complete natamycin (NTM) biosynthetic gene cluster of Streptomyces chattanoogensis was cloned and confirmed by the disruption of pathway-specific activator genes. Comparative cluster analysis with its counterpart in Streptomyces natalensis revealed different cluster architecture between these two clusters. Compared with
R S Bhatta et al.
International journal of pharmaceutics, 432(1-2), 105-112 (2012-05-10)
The aim of this study was to prepare natamycin encapsulated lecithin/chitosan mucoadhesive nanoparticles (NPs) for prolonged ocular application. These NPs were characterized by their mean particle size 213nm, encapsulation efficiency 73.57%, with a theoretical drug loading 5.09% and zeta potential
Chau-Minh Phan et al.
Eye & contact lens, 39(2), 162-168 (2013-02-09)
To investigate the uptake and release of the antifungal ocular drug, natamycin from commercially available conventional hydrogel (CH) and silicone hydrogel (SH) contact lens (CL) materials and to evaluate the effectiveness of this delivery method. Five commercial SH CLs (balafilcon
Yvonne Maria te Welscher et al.
Proceedings of the National Academy of Sciences of the United States of America, 109(28), 11156-11159 (2012-06-27)
The limited therapeutic arsenal and the increase in reports of fungal resistance to multiple antifungal agents have made fungal infections a major therapeutic challenge. The polyene antibiotics are the only group of antifungal antibiotics that directly target the plasma membrane
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