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Merck

SMB01003

Sigma-Aldrich

Cyclopenin

≥90% (LC/MS-ELSD)

Sinónimos:

(-)-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 (notación de Hill):
C17H14N2O3
Número de CAS:
Peso molecular:
294.30
Código UNSPSC:
12352205
NACRES:
NA.25

origen biológico

plant

Ensayo

≥90% (LC/MS-ELSD)

Formulario

solid

mol peso

294.3

solubilidad

water: slightly soluble

aplicaciones

metabolomics
vitamins, nutraceuticals, and natural products

temp. de almacenamiento

−20°C

cadena 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)

Clave InChI

APLKWZASYUZSBL-UHFFFAOYSA-N

Descripción general

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.

Aplicación

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

Acciones bioquímicas o 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 y beneficios

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

Otras notas

For additional information on our range of Biochemicals, please complete this form.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable


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Bioactive compounds derived from the marine-derived fungus MCCC3A00951 and their influenza neuraminidase inhibition activity in vitro and in silico
Liu S Z, et al.
Natural product research, 35, 5621-5628 (2021)
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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