420120
Juglone
A highly selective cell-permeable, irreversible inhibitor of PPlases (peptidyl-prolyl cis/trans isomerases of the parvulin family).
Synonyme(s) :
Juglone, 5-Hydroxy-1,4-naphthlenedione, 5-Hydroxy- p-naphthoquinone
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About This Item
Formule empirique (notation de Hill):
C10H6O3
Numéro CAS:
Poids moléculaire :
174.15
Numéro MDL:
Code UNSPSC :
51111800
Nomenclature NACRES :
NA.77
Produits recommandés
Niveau de qualité
Pureté
≥95% (HPLC)
Forme
solid
Fabricant/nom de marque
Calbiochem®
Conditions de stockage
OK to freeze
protect from light
Couleur
orange
Solubilité
DMSO: 10 mg/mL
ethanol: 10 mg/mL
Conditions d'expédition
ambient
Température de stockage
2-8°C
InChI
1S/C10H6O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-5,12H
Clé InChI
KQPYUDDGWXQXHS-UHFFFAOYSA-N
Description générale
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.
Actions biochimiques/physiologiques
Cell permeable: yes
Primary Target
PPlases (peptidyl-prolyl cis/trans isomerases of the parvulin family)
PPlases (peptidyl-prolyl cis/trans isomerases of the parvulin family)
Product does not compete with ATP.
Reversible: no
Conditionnement
Packaged under inert gas
Avertissement
Toxicity: Toxic (F)
Reconstitution
Following reconstitution aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
Autres remarques
Chao, S.H., et al. 2001. Nucleic Acids Res.29, 767.
Hennig, L., et al. 1998. Biochemistry37, 5953.
Hennig, L., et al. 1998. Biochemistry37, 5953.
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Informations légales
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Mention d'avertissement
Danger
Mentions de danger
Conseils de prudence
Classification des risques
Acute Tox. 3 Oral
Code de la classe de stockage
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
Classe de danger pour l'eau (WGK)
WGK 3
Certificats d'analyse (COA)
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Insights and future directions of potential genetic therapy for Apert syndrome: A systematic review.
Nisreen Mohammed Al-Namnam et al.
Gene therapy, 28(10-11), 620-633 (2021-02-24)
Apert syndrome is a genetic disorder characterised by craniosynostosis and structural discrepancy of the craniofacial region as well as the hands and feet. This condition is closely linked with fibroblast growth factor receptor-2 (FGFR2) gene mutations. Gene therapies are progressively
Caixia Wu et al.
American journal of translational research, 13(10), 11162-11177 (2021-11-18)
Peptidyl-prolyl isomerase Pin1 is crucial for cell proliferation, but its role in pulmonary artery remodeling (PAR) is unclear. In the present study, we aimed to evaluate the expression and contribution of Pin1 in PAR. Treatment with Pin1 inhibitor Juglone or
Jia-Hua Hu et al.
Nature communications, 11(1), 1567-1567 (2020-03-29)
Voltage-gated K+ channels function in macromolecular complexes with accessory subunits to regulate brain function. Here, we describe a peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (Pin1)-dependent mechanism that regulates the association of the A-type K+ channel subunit Kv4.2 with its auxiliary subunit
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