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N2286

Sigma-Aldrich

Nonactin

from Streptomyces griseus, ≥98.0% (Total homologs, HPLC)

Sinonimo/i:

Ammonium ionophore I, Ammonium ionophore

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About This Item

Formula empirica (notazione di Hill):
C40H64O12
Numero CAS:
6833-84-7
Peso molecolare:
736.93
Beilstein:
76434
Numero CE:
229-911-3
Codice UNSPSC:
51102829
ID PubChem:
24897566
NACRES:
NA.76

Origine biologica

Streptomyces griseus

Livello qualitativo

300

Descrizione

Natural macrotetrolide, may contain homologues (like monactin and dinactin)

Saggio

≥98.0% (Total homologs, HPLC)

Forma fisica

powder

Solubilità

chloroform: soluble 10 mg/mL

Spettro attività antibiotica

Gram-positive bacteria

Modalità d’azione

DNA synthesis | interferes
cell membrane | interferes

Temperatura di conservazione

2-8°C

Stringa SMILE

C[C@H]1C[C@@H]2CC[C@@H](O2)[C@@H](C)C(=O)O[C@H](C)C[C@H]3CC[C@H](O3)[C@H](C)C(=O)O[C@@H](C)C[C@@H]4CC[C@@H](O4)[C@@H](C)C(=O)O[C@H](C)C[C@H]5CC[C@H](O5)[C@H](C)C(=O)O1

InChI

1S/C40H64O12/c1-21-17-29-9-13-34(49-29)26(6)38(42)46-23(3)19-31-11-15-36(51-31)28(8)40(44)48-24(4)20-32-12-16-35(52-32)27(7)39(43)47-22(2)18-30-10-14-33(50-30)25(5)37(41)45-21/h21-36H,9-20H2,1-8H3/t21-,22+,23+,24-,25-,26+,27+,28-,29-,30+,31+,32-,33-,34+,35+,36-
RMIXHJPMNBXMBU-QIIXEHPYSA-N

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Categorie correlate

Descrizione generale

Chemical structure: macrolide

Applicazioni

Nonactin is a macrotetrolide that forms complexes with alkali cations, such as potassium and sodium. Nonactin has been reported to inhibit the processing of cytoplasmic precursor proteins destined for the mitochondria. Nonactin is an uncoupler of oxidative phosphorylation .

Azioni biochim/fisiol

Nonactin is used as a neutral lipid membrane soluble ammonium (and potassium) ionophore, and to inhibit surface expression of certain heat shock proteins (HSP60) .

Altre note

Keep container tightly closed in a dry and well-ventilated place.Keep in a dry place.

Applicazioni

N° Catalogo
Descrizione
Determinazione del prezzo

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)

Certificati d'analisi (COA)

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Total synthesis of nonactin.
Ju Y.L.; Byeang H.K.
ChemInform, 52, 571-571 (1996)
Pei-Ji Zhao et al.
Archives of pharmacal research, 28(11), 1228-1232 (2005-12-15)
Four compounds, including two novel macrolides, were isolated from an endophyte Streptomyces sp. Is9131 of Maytenus hookeri. Spectral data indicated that these compounds were dimeric dinactin (1), dimeric nonactin (2), cyclo-homononactic acid (3), and cyclo-nonactic acid (4). Bioassay results showed
S Krasne et al.
Science (New York, N.Y.), 174(4007), 412-415 (1971-10-22)
An abrupt loss of effectiveness of the presumed carriers, nonactin and valinomycin, in mediating ion conductance occurred at the same temperature as the membrane fluidity, judged visually, was lost. By contrast, the effects of the presumed channel-former, gramicidin, were the
Svetlana S Efimova et al.
Langmuir : the ACS journal of surfaces and colloids, 28(26), 9908-9914 (2012-06-19)
The effects of various subclasses of flavonoids, Rose Bengal, and different styrylpyridinium dyes on the magnitude of the dipole potential of membranes composed of pure phospholipids and sterol-containing bilayers were investigated. Changes in the steady-state membrane conductance induced by cation-ionophore
Peter Jani et al.
Biotechnology journal, 3(2), 202-208 (2007-12-08)
The optimization of the biosynthetic pathways is highly attractive for the large-scale preparation of macrotetrolides, because overall yields in the chemical synthesis of compounds like nonactin have been very low. A key success factor determining the outcome of such optimizations
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