420120

Juglone

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

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

Propriedades

• Nível de qualidade: 100
• Ensaio: ≥95% (HPLC)
• Formulário: solid
• fabricante/nome comercial: Calbiochem^®
• condição de armazenamento: OK to freeze; protect from light
• cor: orange
• solubilidade: DMSO: 10 mg/mL; ethanol: 10 mg/mL
• Condições de expedição: ambient
• temperatura de armazenamento: 2-8°C
• InChI: 1S/C10H6O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-5,12H
• chave InChI: KQPYUDDGWXQXHS-UHFFFAOYSA-N

Descrição

Descrição geral

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.

Ações bioquímicas/fisiológicas

Cell permeable: yes

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

Product does not compete with ATP.

Reversible: no

Embalagem

Packaged under inert gas

Advertência

Toxicity: Toxic (F)

Reconstituição

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

Outras 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.

Informações legais

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

Informações de segurança

• Pictogramas: GHS06
• Palavra indicadora: Danger
• Frases de perigo: H301
• Declarações de precaução: P264 - P270 - P301 + P310 - P405 - P501
• Classificações de perigo: Acute Tox. 3 Oral
• Código de classe de armazenamento: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe de risco de água (WGK): WGK 3