420120
Juglone
A highly selective cell-permeable, irreversible inhibitor of PPlases (peptidyl-prolyl cis/trans isomerases of the parvulin family).
Synonym(s):
Juglone, 5-Hydroxy-1,4-naphthlenedione, 5-Hydroxy- p-naphthoquinone
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About This Item
Empirical Formula (Hill Notation):
C10H6O3
CAS Number:
Molecular Weight:
174.15
MDL number:
UNSPSC Code:
51111800
NACRES:
NA.77
Recommended Products
Quality Level
assay
≥95% (HPLC)
form
solid
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze
protect from light
color
orange
solubility
DMSO: 10 mg/mL
ethanol: 10 mg/mL
shipped in
ambient
storage temp.
2-8°C
InChI
1S/C10H6O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-5,12H
InChI key
KQPYUDDGWXQXHS-UHFFFAOYSA-N
General description
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.
Biochem/physiol Actions
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
Packaging
Packaged under inert gas
Warning
Toxicity: Toxic (F)
Reconstitution
Following reconstitution aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
Other Notes
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.
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.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
signalword
Danger
hcodes
Hazard Classifications
Acute Tox. 3 Oral
Storage Class
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk_germany
WGK 3
Certificates of Analysis (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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