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P9703

Sigma-Aldrich

Pimaricin

from Streptomyces chattanoogensis, ≥95% (HPLC)

Synonym(s):

Natamycin

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About This Item

Empirical Formula (Hill Notation):
C33H47NO13
CAS Number:
7681-93-8
Molecular Weight:
665.73
EC Number:
231-683-5
MDL number:
MFCD00135085
UNSPSC Code:
51102829
PubChem Substance ID:
24899055
NACRES:
NA.85

biological source

Streptomyces chattanoogensis

Quality Level

300

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

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

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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.

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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)
Prajna Lalitha et al.
Cornea, 31(6), 662-667 (2012-02-16)
To analyze the minimum inhibitory concentration (MIC) of isolates from fungal keratitis to natamycin and voriconazole and to assess the relationship between organism, MIC, and clinical outcome. Data were collected as part of a randomized, controlled, double-masked clinical trial. Main
F N Arroyo-López et al.
International journal of food microbiology, 155(3), 257-262 (2012-03-01)
The present work uses a logistic/probabilistic model to obtain the growth/no growth interfaces of Saccharomyces cerevisiae, Wickerhamomyces anomalus and Candida boidinii (three yeast species commonly isolated from table olives) as a function of the diverse combinations of natamycin (0-30 mg/L)
Javier Santos-Aberturas et al.
PloS one, 7(6), e38536-e38536 (2012-06-14)
Control of polyene macrolide production in Streptomyces natalensis is mediated by the transcriptional activator PimR. This regulator combines an N-terminal domain corresponding to the Streptomyces antibiotic regulatory protein (SARP) family of transcriptional activators with a C-terminal half homologous to guanylate
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