1,2-Dihydroxynaphthalene
Based on 1 Customer Validation
1,2-Dihydroxynaphthalene is a metabolic intermediate of Naphthalene and a precursor for the formation of 1,2-Naphthoquinone, and is also the most sensitive biomarker of Naphthalene exposure in humans. 1,2-Dihydroxynaphthalene inhibits the AMPK/SIRT3 pathway and activates acetylated p53 and NF-κB by inducing oxidative stress, leading to G2/M cell cycle arrest, senescence, and apoptosis, while also damaging DNA through the formation of depurination adducts, thereby causing mutations. 1,2-Dihydroxynaphthalene can be used in research on cancer and cataracts.
For research use only. We do not sell to patients.
- Purity : 98.88%
- CAS No.: 574-00-5
- Formula: C10H8O2
- Molecular Weight:160.17
-
Storage:
-20°C, stored under nitrogen
* In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen)
To place orders, for customer services and technical support, please contact: MedChemExpress USA
Tel: 609-228-6898 E-mail: [email protected] [email protected]
-
Biological Activity
-
Chemical Information
-
Solvent & Solubility
- Protocols
- Purity & Documentation
- References
-
Help & FAQs
Biological Activity
Description
Cellular Effect
|
Cell Line
|
Type | Value | Description | References |
|---|---|---|---|---|
| HFL1 | ED50 |
25 μM
Compound: 7a
|
Antiproliferative activity against human fibroblast HFL1 cells
Antiproliferative activity against human fibroblast HFL1 cells
|
[PMID: 16539380] |
| T-24 | ED50 |
13 μM
Compound: 7a
|
Antiproliferative activity against human bladder carcinoma T24 cells
Antiproliferative activity against human bladder carcinoma T24 cells
|
[PMID: 16539380] |
In Vitro
1,2-Dihydroxynaphthalene (10 μM) inhibits AMPK phosphorylation and SIRT3 expression, and promotes p53 acetylation and total p53 protein expression in ARPE-19 cells[2].
1,2-Dihydroxynaphthalene (10 μM) increases the expression of the DNA damage marker γH2Ax, decreases LaminB1 expression, and promotes the secretion of the senescence-associated secretory phenotype (including IL-6, IL-1B, IL-18, MCP-1) through activation of the NF-κB signaling pathway in ARPE-19 cells[2].
1,2-Dihydroxynaphthalene (1-500 μM; 24 h) decreases hLEC viability in a concentration-dependent manner, with significant cytotoxicity observed starting at 10 μM[4].
1,2-Dihydroxynaphthalene (50 μM; 12-36 h) causes a modest increase in Akt phosphorylation in hLECs[4].
1,2-Dihydroxynaphthalene (50 μM; 24 h) exposure is associated with p-Akt immunofluorescence in SRA01/04 hLECs, and Sodium Selenite (HY-W686381) preincubation promotes nuclear translocation of p-Akt in 1,2-Dihydroxynaphthalene-exposed cells[4].
1,2-Dihydroxynaphthalene (1 mM; 1-2 min) is cleaved by an Fe2+-dependent oxygenase in naphthalene-grown Pseudomonas extracts, consuming 1 mol O2/mol with no release of CO2[5].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
-
Cell Line:ARPE-19 cells
-
Concentration:10 μM
-
Incubation Time:24 h
-
Result:Decreased ARPE-19 cell viability.
-
Cell Line:human lens epithelial cells (hLECs, SRA01/04)
-
Concentration:1, 5, 10, 50, 100, 500 μM
-
Incubation Time:24 h
-
Result:Cell viabilities started decreasing when the 1,2-DHN concentration reached 10 μM.
At 50 μM, cell viabilities were significantly decreased, but not many cells were killed at this concentration.
-
Cell Line:hLECs
-
Concentration:50, 100 μM
-
Incubation Time:24 h
-
Result:Induced cell death at high concentrations was apparent after 24 h of incubation.
Morphological changes were visible in hLECs.
-
Cell Line:hLECs
-
Concentration:50 μM
-
Incubation Time:24 h
-
Result:The cell apoptosis ratio was 25.4% after exposure to 50 μM 1,2-DHN for 24 h.
-
Cell Line:hLECs
-
Concentration:50 μM
-
Incubation Time:12, 24, and 36 h
-
Result:Akt phosphorylation was only slightly increased after exposure to 50 μM 1,2-DHN for 24 h.
-
Cell Line:human lens epithelial cells (hLECs, SRA01/04)
-
Concentration:50 μM
-
Incubation Time:24 h
-
Result:Promoted Akt phosphorylation and nuclear translocation.
In Vivo
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
-
Animal Model:SENCAR (female, 6 weeks old at housing, 8 weeks old at application)[1]
-
Dosage:500 mM
-
Administration:topical skin application; single application; 4 h
-
Result:Possesseed the activity to form DNA damage adducts.
- Detection of Apoptosis
- TUNEL staining for apoptotic DNA fragmentation
- Flow cytometric DNA-content cell-cycle staining
- Annexin V plus membrane-impermeant dye apoptosis staining
- ROS/oxidative-stress fluorescent staining
- BrdU Incorporation Assay
- Apoptosis Solutions
- Protocol for Cell Cycle
- Research Protocol for Inflammation-related Diseases
- Senescence-associated β-galactosidase staining
Chemical Information
-
CAS No. 574-00-5
-
Appearance Solid
-
Molecular Weight 160.17
-
Formula C10H8O2
-
Color Off-white to light yellow
-
SMILES
OC1=C2C=CC=CC2=CC=C1O
-
Synonyms
1,2-Naphthalenediol
-
Structure Classification
-
Shipping
Room temperature in continental US; may vary elsewhere.
-
Storage
-20°C, stored under nitrogen
* In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen)
Solvent & Solubility
In Vitro:
DMSO : 50 mg/mL (312.17 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Purity & Documentation
-
Data Sheet (293 KB)
-
SDS (394 KB)
- English - EN (394 KB)
- Français - FR (394 KB)
- Deutsch - DE (394 KB)
- Norwegian - NO (394 KB)
- Español - ES (394 KB)
- Swedish - SV (394 KB)
- Italian - IT (394 KB)
- Korean - KR (394 KB)
- Portuguese - PT (394 KB)
-
Handling Instructions (2659 KB)
References
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month (stored under nitrogen). When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO | 1 mM | 6.2434 mL | 31.2168 mL | 62.4337 mL | 156.0842 mL |
| 5 mM | 1.2487 mL | 6.2434 mL | 12.4867 mL | 31.2168 mL | |
| 10 mM | 0.6243 mL | 3.1217 mL | 6.2434 mL | 15.6084 mL | |
| 15 mM | 0.4162 mL | 2.0811 mL | 4.1622 mL | 10.4056 mL | |
| 20 mM | 0.3122 mL | 1.5608 mL | 3.1217 mL | 7.8042 mL | |
| 25 mM | 0.2497 mL | 1.2487 mL | 2.4973 mL | 6.2434 mL | |
| 30 mM | 0.2081 mL | 1.0406 mL | 2.0811 mL | 5.2028 mL | |
| 40 mM | 0.1561 mL | 0.7804 mL | 1.5608 mL | 3.9021 mL | |
| 50 mM | 0.1249 mL | 0.6243 mL | 1.2487 mL | 3.1217 mL | |
| 60 mM | 0.1041 mL | 0.5203 mL | 1.0406 mL | 2.6014 mL | |
| 80 mM | 0.0780 mL | 0.3902 mL | 0.7804 mL | 1.9511 mL | |
| 100 mM | 0.0624 mL | 0.3122 mL | 0.6243 mL | 1.5608 mL |
1,2-Dihydroxynaphthalene Related Classifications
HY-128105 Related Classifications
Powered by Bioz
Keywords