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SMB01003

Sigma-Aldrich

Cyclopenin

≥90% (LC/MS-ELSD)

Sinônimo(s):

(-)-Cyclopenin, (-)-Cyclopenine, 4-methyl-3′-phenylspiro[1H-1,4-benzodiazepine-3,2′-oxirane]-2,5-dione

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About This Item

Fórmula empírica (Notação de Hill):
C17H14N2O3
Número CAS:
Peso molecular:
294.30
Código UNSPSC:
12352205
NACRES:
NA.25

fonte biológica

plant

Ensaio

≥90% (LC/MS-ELSD)

Formulário

solid

peso molecular

294.3

solubilidade

water: slightly soluble

aplicação(ões)

metabolomics
vitamins, nutraceuticals, and natural products

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

N1(C3(OC3c4ccccc4)C(=O)Nc2c(cccc2)C1=O)C

InChI

1S/C17H14N2O3/c1-19-15(20)12-9-5-6-10-13(12)18-16(21)17(19)14(22-17)11-7-3-2-4-8-11/h2-10,14H,1H3,(H,18,21)

chave InChI

APLKWZASYUZSBL-UHFFFAOYSA-N

Descrição geral

Cyclopenin, a benzodiazepine alkaloid, is a natural product commonly available from strains of Penicillum cyclopium, Penicillium aurantiogriseum and Penicillum corymbiferum. Existing research suggests that this Penicillium metabolite exerts various biological activities, including antibacterial, antiviral, antitumor, anti-inflammatory, and neuroprotective properties.

Aplicação

It is a natural product derived from plant source that finds application in compound screening libraries, metabolomics, phytochemical, and pharmaceutical research.

Ações bioquímicas/fisiológicas

According to existing research, Cyclopenin displays selective inhibition against acetylcholinesterase (AChE). Furthermore, it demonstrates anti-inflammatory properties by inhibiting nitric oxide production, NF-κB activation, and the expression of inflammatory factors such as IL-1β, IL-6, and iNOS in brain macrophages. In an Alzheimer′s disease model, Cyclopenin exhibited the ability to rescue learning deficits induced by amyloid-β42 overexpression in flies, indicating its potential as an anti-inflammatory agent for neurodegenerative diseases. Isolated from Penicillium polonicum MCCC3A00951, Cyclopenin displayed potent inhibition of influenza neuraminidase (NA) with an IC50 value of 5.02μM, suggesting its potential as a candidate for anti-influenza NA therapy. Cyclopenin, identified in the fungus Penicillium auratiogriseum Sp-19, demonstrated cytotoxicity against the tsFT210 cell line at a concentration of 3 μg/mL-1, implying its potential as an antitumor agent.(3)Cyclopenin, isolated from Penicillium polonicum MCCC3A00951, exhibited strong inhibition of influenza neuraminidase (NA) with an IC50 value of 5.02μM. This suggests that Cyclopenin has the potential to be developed as an anti-influenza NA candidate.

Características e benefícios

  • High quality compound suitable for multiple research applications
  • Compatible with HPLC and mass spectrometry techniques

Outras notas

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Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable


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Liyan Wang et al.
The Journal of antibiotics, 73(9), 622-629 (2020-03-27)
In the course of screening lipopolysaccharide (LPS)-induced nitric oxide (NO) production inhibitors, two related benzodiazepine derivatives, cyclopenol and cyclopenin, were isolated from the extract of a deep marine-derived fungal strain, Aspergillus sp. SCSIOW2. Cyclopenol and cyclopenin inhibited the LPS-induced formation

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