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P9703

Sigma-Aldrich

Pimaricin

from Streptomyces chattanoogensis, ≥95% (HPLC)

Synonyme(s) :

Natamycin

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About This Item

Formule empirique (notation de Hill):
C33H47NO13
Numéro CAS:
7681-93-8
Poids moléculaire :
665.73
Numéro CE :
231-683-5
Numéro MDL:
MFCD00135085
Code UNSPSC :
51102829
ID de substance PubChem :
24899055
Nomenclature NACRES :
NA.85

Source biologique

Streptomyces chattanoogensis

Niveau de qualité

300

Pureté

≥95% (HPLC)

Forme

lyophilized powder
powder

Solubilité

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

Spectre d'activité de l'antibiotique

fungi

Application(s)

agriculture
environmental

Mode d’action

cell membrane | interferes

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

NCXMLFZGDNKEPB-FFPOYIOWSA-N

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Description générale

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.

Actions biochimiques/physiologiques

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

Autres remarques

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

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Consulter la Bibliothèque de documents

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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