| Size | Price | |
|---|---|---|
| Other Sizes |
| Targets |
Tropolone acts as a metal chelator, particularly binding to copper and iron, which disrupts metalloenzymes and generates ROS. It also inhibits tyrosinase and other polyphenol oxidases. It may induce apoptosis by activating caspases and disrupting mitochondrial function. It also inhibits bacterial DNA gyrase.
|
|---|---|
| ln Vitro |
In vitro, tropolone exhibits antibacterial activity against S. aureus and E. coli with MIC values of 32-64 µg/mL. It inhibits tyrosinase with an IC50 of 5 µM. It shows moderate cytotoxicity against cancer cells (HeLa IC50 ~ 15 µM). It scavenges DPPH radicals with an IC50 of 30 µM.
|
| ln Vivo |
In vivo, tropolone has shown antitumor activity in mouse models of melanoma. Intraperitoneal injection of 20 mg/kg daily for 10 days reduced tumor size by 40%. It also showed anti-inflammatory effects in a carrageenan-induced paw edema model (50 mg/kg, p.o.). However, its toxicity limits further development.
|
| Enzyme Assay |
The in vitro tyrosinase inhibition assay uses mushroom tyrosinase and L-DOPA as substrate. Tropolone (0.1-10 µM) is incubated with enzyme and substrate, and dopamine chrome formation is measured at 475 nm. IC50 is calculated. For antibacterial assays, broth microdilution is used.
|
| Cell Assay |
For in vitro cell-based assays, HeLa or B16 melanoma cells are seeded in 96-well plates and treated with tropolone (1-50 µM) for 48 h. Cell viability is measured by MTT. Apoptosis is evaluated by Hoechst staining and caspase-3 activity. ROS production is measured using DCFH-DA.
|
| Animal Protocol |
In vivo antitumor studies in C57BL/6 mice: mice are inoculated with B16 melanoma cells. When tumors are palpable, tropolone is administered i.p. at 10, 20, 40 mg/kg daily for 10 days. Tumor volumes are measured. Body weight and survival are monitored. For anti-inflammatory, rats are given tropolone orally before carrageenan injection.
|
| ADME/Pharmacokinetics |
Pharmacokinetic data: in rats, after oral administration (50 mg/kg), Tmax is 1 h, Cmax is 2 µg/mL, half-life is 1.5 h. Bioavailability is about 20%. The compound is metabolized by glucuronidation. Plasma protein binding ~60%. Excretion is via urine.
|
| Toxicity/Toxicokinetics |
Tropolone has moderate toxicity (LD50 in mice ~ 200 mg/kg, i.p.; oral LD50 ~ 800 mg/kg). It is irritating to skin and eyes. At high doses, hepatotoxicity and nephrotoxicity occur. It is not mutagenic.
|
| References | |
| Additional Infomation |
Tolphenone is a cyclic ketone, a compound in which a hydroxyl group is substituted at the 2-position of a cyclohepta-2,4,6-trien-1-one. It is a toxin produced by the agricultural pathogen Burkholderia phytotoxicum. It is both a bacterial metabolite and a toxin and fungicide. Tolphenone is a cyclic ketone, enol, and α-hydroxy ketone. It is derived from the hydride of cyclohepta-1,3,5-triene. It is a seven-membered aromatic ring compound. Its structure is related to many naturally occurring antifungal compounds (antifungal agents).
Tropolone is a versatile chemical used in coordination chemistry and as an inhibitor of tyrosinase and other enzymes. Its potential as an anticancer and antimicrobial agent has been explored. However, its toxicity limits therapeutic use. No clinical trials have been reported. |
| Molecular Formula |
C7H6O2
|
|---|---|
| Molecular Weight |
122.12
|
| Exact Mass |
122.036
|
| CAS # |
533-75-5
|
| PubChem CID |
10789
|
| Appearance |
Light yellow to brown solid powder
|
| Density |
1.3±0.1 g/cm3
|
| Boiling Point |
290.1±33.0 °C at 760 mmHg
|
| Melting Point |
50-52 °C(lit.)
|
| Flash Point |
122.0±18.0 °C
|
| Vapour Pressure |
0.0±1.4 mmHg at 25°C
|
| Index of Refraction |
1.603
|
| LogP |
0.42
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
2
|
| Rotatable Bond Count |
0
|
| Heavy Atom Count |
9
|
| Complexity |
209
|
| Defined Atom Stereocenter Count |
0
|
| InChi Key |
MDYOLVRUBBJPFM-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9)
|
| Chemical Name |
2-hydroxycyclohepta-2,4,6-trien-1-one
|
| HS Tariff Code |
2934.99.9001
|
| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ≥ 100 mg/mL (~818.87 mM)
H2O : ~25 mg/mL (~204.72 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (20.47 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 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 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to 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: ≥ 2.5 mg/mL (20.47 mM) (saturation unknown) in 10% DMSO + 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 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (20.47 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. Solubility in Formulation 4: 20 mg/mL (163.77 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 8.1887 mL | 40.9433 mL | 81.8867 mL | |
| 5 mM | 1.6377 mL | 8.1887 mL | 16.3773 mL | |
| 10 mM | 0.8189 mL | 4.0943 mL | 8.1887 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.
Products are for research use only; We do not sell to patients
Copyright 2020 InvivoChem LLC | All Rights Reserved
