420120

Juglone

A highly selective cell-permeable, irreversible inhibitor of PPlases (peptidyl-prolyl cis/trans isomerases of the parvulin family).

• Sinónimos: Juglone, 5-Hydroxy-1,4-naphthlenedione, 5-Hydroxy- p-naphthoquinone
• Fórmula empírica (notación de Hill): C₁₀H₆O₃
• Número de CAS: 481-39-0
• Peso molecular: 174.15
• Número MDL: MFCD00001684
• Código UNSPSC: 51111800
• NACRES: NA.77

Propiedades

• Nivel de calidad: 100
• descripción: Merck USA index - 14, 5269
• Ensayo: ≥95% (HPLC)
• Formulario: solid
• fabricante / nombre comercial: Calbiochem^®
• condiciones de almacenamiento: OK to freeze; protect from light
• color: orange
• solubilidad: DMSO: 10 mg/mL; ethanol: 10 mg/mL
• Condiciones de envío: ambient
• temp. de almacenamiento: 2-8°C
• cadena SMILES: Oc1c2c(ccc1)C(=O)C=CC2=O
• InChI: 1S/C10H6O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-5,12H
• Clave InChI: KQPYUDDGWXQXHS-UHFFFAOYSA-N

Descripción

Descripción general

A highly selective cell-permeable, irreversible inhibitor of PPlases (peptidyl-prolyl cis/trans isomerases of the parvulin family). Other known PPlase inhibitors such as cyclosporin A, FK506, and rapamycin are not reported to inhibit the parvulin family of PPlases. The inactivation is shown to occur via the addition of thiol groups to juglone and not by any redox process. Exhibits bacteriostatic and fungistatic effects. Reported to be cytotoxic towards eukaryotic cells and to block transcription by RNA polymerase II.

Originally isolated from the fruit shells and leaves of walnut trees, juglone is a highly selective, cell permeable, irreversible inhibitor of the parvulin family of peptidyl-prolyl cis/trans isomerases (PPIase). Functions by covalently modifying sulfhydryl groups in the target enzymes. Exhibits bacteriostatic and fungistatic properties as well as cytotoxicity in eukaryotic cells. Also reported to directly block transcription in eukaryotic cells by RNA polymerase I, II, and III as determined by nuclear run-off (IC50 = 7 µM, 7 µM, and 2 µM, respectively). Disrupts formation of functional pre-initiation complexes via modification of sulhydryl groups, but does not significantly affect initiation or elongation. Does not inhibit restriction endonucleases or T7 RNA polymerase.

Acciones bioquímicas o fisiológicas

Cell permeable: yes

Primary Target
PPlases (peptidyl-prolyl cis/trans isomerases of the parvulin family)

Product does not compete with ATP.

Reversible: no

Envase

Packaged under inert gas

Advertencia

Toxicity: Toxic (F)

Reconstitución

Following reconstitution aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Otras notas

Chao, S.H., et al. 2001. Nucleic Acids Res.29, 767.
Hennig, L., et al. 1998. Biochemistry37, 5953.

Due to the nature of the Hazardous Materials in this shipment, additional shipping charges may be applied to your order. Certain sizes may be exempt from the additional hazardous materials shipping charges. Please contact your local sales office for more information regarding these charges.

Información legal

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Información de seguridad

• Pictogramas: GHS06
• Palabra de señalización: Danger
• Frases de peligro: H301
• Consejos de prudencia: P264 - P270 - P301 + P310 - P405 - P501
• Clasificaciones de peligro: Acute Tox. 3 Oral
• Código de clase de almacenamiento: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Clase de riesgo para el agua (WGK): WGK 3