| Size | Price | Stock | Qty |
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| 10mg |
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| 100mg |
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| Targets |
The primary target of Juglone is peptidyl-prolyl cis/trans isomerases (PPlases) of the parvulin family, particularly human Pin1. Pin1 is a phosphorylation-dependent prolyl isomerase that regulates protein conformation and function by catalyzing the cis-trans isomerization of phospho-Ser/Thr-Pro peptide bonds. Pin1 plays a critical role in cell cycle regulation, transcription, and oncogenesis. Juglone acts as an irreversible inhibitor of Pin1 with a Ki of 55.9 nM, covalently modifying sulfhydryl groups in the target enzyme. Juglone also targets NF-κB, Toll-like receptors, and apoptosis pathways.
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| ln Vitro |
In vitro, Juglone is a highly selective, cell-permeable, irreversible inhibitor of PPlases of the parvulin family, including human Pin1, yeast Ess1/Ptf1, and E. coli parvulin, with a Ki of 55.9 nM. It inhibits the transcription of Pol II by modifying sulfhydryl groups and blocking the assembly of the preinitiation complex. Juglone exhibits bacteriostatic and fungistatic properties as well as cytotoxicity in eukaryotic cells. It promotes apoptosis via the mitochondrial-dependent pathway and is an antifibrotic compound.
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| ln Vivo |
In vivo, Juglone disrupts cellular processes by generating reactive oxygen species, making it a useful tool in biochemical research for studying oxidative stress and apoptosis. It exhibits antimicrobial, antifungal, and antioxidant properties. However, Juglone is also considered a potentially toxic natural product. The compound is unstable in solution and is recommended to be prepared and used immediately. Specific in vivo efficacy data is not detailed in the available sources.
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| Enzyme Assay |
For Pin1 inhibitors, standard cell-free assays involve measuring the isomerase activity of recombinant Pin1 using a peptide substrate (e.g., Suc-Ala-Glu-Pro-Phe-pNA). The compound is incubated with the enzyme and substrate, and the isomerization reaction is monitored by the change in absorbance or fluorescence. Inhibition constants (Ki) are determined from the inhibition of enzyme activity.
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| Cell Assay |
For Pin1 inhibitors, standard cellular assays involve treatment of cancer cell lines with the test compound for 24-72 hours. Pin1 activity is assessed by measuring the isomerization of a cell-permeable substrate or by monitoring changes in the phosphorylation status of Pin1 substrates (e.g., Cyclin D1, β-catenin, p53). Cell viability (MTT or CellTiter-Glo) and apoptosis (Annexin V/PI staining, caspase activity) are assessed.
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| Animal Protocol |
For in vivo evaluation of Pin1 inhibitors, standard animal models include tumor xenograft models using cancer cell lines sensitive to Pin1 inhibition. The compound is typically administered orally or intraperitoneally for 2-4 weeks. Tumor growth, Pin1 activity, apoptosis markers, and survival are assessed. Juglone's ability to generate ROS may also be studied in models of oxidative stress.
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| ADME/Pharmacokinetics |
Detailed pharmacokinetic data for Juglone is not extensively provided in the available sources. The compound has a molecular weight of 174.15 and formula C₁₀H₆O₃. It is soluble in DMSO at 10 mg/mL and in ethanol at 10 mg/mL. Juglone is unstable in solution and is recommended to be prepared and used immediately. As a small molecule with moderate lipophilicity, it would be expected to have reasonable cell permeability. Comprehensive PK studies would be required for therapeutic development.
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| Toxicity/Toxicokinetics |
Juglone is a potentially toxic natural product. As a naphthoquinone, it can generate reactive oxygen species and cause oxidative stress. The compound exhibits cytotoxicity in eukaryotic cells. Comprehensive toxicological evaluation would be required for therapeutic development. The compound is unstable in solution and should be prepared and used immediately. It is for research use only and not for therapeutic applications.
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| References |
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| Additional Infomation |
Juglone is a hydroxy-1,4-naphthoquinone, meaning it is a compound in which the hydrogen atom at the 5-position is replaced by a hydroxyl group. It is a plant-derived 1,4-naphthoquinone that has been shown to possess antibacterial and antitumor activities. Juglone can be used as a herbicide, a reactive oxygen species generator, and an anti-aging agent. It has been reported to exist in Talaromyces diversus, Pterocarya fraxinifolia, and several other organisms with relevant data.
Juglone is also known as 5-Hydroxy-1,4-naphthalenedione and has the molecular formula C₁₀H₆O₃. It is a natural naphthoquinone found in the black walnut (Juglans regia). Juglone is a highly selective, cell-permeable, irreversible inhibitor of PPlases of the parvulin family, including human Pin1 (Ki = 55.9 nM). It exhibits antimicrobial, antifungal, antioxidant, and antifibrotic properties. No regulatory approval has been identified. |
| Molecular Formula |
C10H6O3
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|---|---|
| Molecular Weight |
174.15
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| Exact Mass |
174.031
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| CAS # |
481-39-0
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| Related CAS # |
Juglone; 481-39-0
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| PubChem CID |
3806
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| Appearance |
Brown to orange solid powder
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| Density |
1.4±0.1 g/cm3
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| Boiling Point |
385.8±42.0 °C at 760 mmHg
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| Melting Point |
161-163 °C(lit.)
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| Flash Point |
201.3±24.4 °C
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| Vapour Pressure |
0.0±0.9 mmHg at 25°C
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| Index of Refraction |
1.662
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| Source |
Originated from plants: Juglandaceae Juglans regia Linn.
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| LogP |
1.86
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
13
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| Complexity |
280
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C(C1=C2C=CC=C1O)C=CC2=O
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| InChi Key |
KQPYUDDGWXQXHS-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C10H6O3/c11-7-4-5-9(13)10-6(7)2-1-3-8(10)12/h1-5,12H
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| Chemical Name |
5-hydroxynaphthalene-1,4-dione
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| Synonyms |
NSC 153189; Akhnot; Juglone
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage. (2). This product is not stable in solution, please use freshly prepared working solution for optimal results. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
Ethanol : ~10 mg/mL (~57.42 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 0.33 mg/mL (1.89 mM) (saturation unknown) in 10% EtOH + 40% PEG300 + 5% Tween-80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), Clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of ethanol stock solution (3.3 mg/mL) to 400 μL of PEG300 and mix well; then add 50 μL of Tween-80 and mix well; finally add 450 μL of physiological saline and adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 0.33 mg/mL (1.89 mM) (saturation unknown) in 10% EtOH + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), Clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of ethanol stock solution (3.3 mg/mL) to 900 μL of 20% SBE-β-CD physiological saline and mix well. Preparation of 20% SBE-β-CD physiological saline (4°C, store for one week): Dissolve 2 g of SBE-β-CD powder in 10 mL of physiological saline until completely dissolved and clear. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 0.33 mg/mL (1.89 mM) (saturation unknown) in 10% EtOH + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), Clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of EtOH stock solution (3.3 mg/mL) to 900 μL of corn oil and mix well. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.7422 mL | 28.7109 mL | 57.4218 mL | |
| 5 mM | 1.1484 mL | 5.7422 mL | 11.4844 mL | |
| 10 mM | 0.5742 mL | 2.8711 mL | 5.7422 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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