420120

Juglone

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

• Sinonimo/i: Juglone, 5-Hydroxy-1,4-naphthlenedione, 5-Hydroxy- p-naphthoquinone
• Formula empirica (notazione di Hill): C₁₀H₆O₃
• Numero CAS: 481-39-0
• Peso molecolare: 174.15
• Numero MDL: MFCD00001684
• Codice UNSPSC: 51111800
• NACRES: NA.77

Proprietà

• Livello qualitativo: 100
• Saggio: ≥95% (HPLC)
• Stato: solid
• Produttore/marchio commerciale: Calbiochem^®
• Condizioni di stoccaggio: OK to freeze; protect from light
• Colore: orange
• Solubilità: DMSO: 10 mg/mL; ethanol: 10 mg/mL
• Condizioni di spedizione: ambient
• Temperatura di conservazione: 2-8°C
• InChI: 1S/C10H6O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-5,12H; KQPYUDDGWXQXHS-UHFFFAOYSA-N

Descrizione

Descrizione generale

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.

Azioni biochim/fisiol

Cell permeable: yes

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

Product does not compete with ATP.

Reversible: no

Confezionamento

Packaged under inert gas

Attenzione

Toxicity: Toxic (F)

Ricostituzione

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

Altre note

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

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Note legali

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

Informazioni sulla sicurezza

• Pittogrammi: GHS06
• Avvertenze: Danger
• Indicazioni di pericolo: H301
• Consigli di prudenza: P264 - P270 - P301 + P310 - P405 - P501
• Classi di pericolo: Acute Tox. 3 Oral
• Codice della classe di stoccaggio: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe di pericolosità dell'acqua (WGK): WGK 3