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| 10mg |
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| Targets |
9,10-Dichlorophenanthrene has no therapeutic target; it is an environmental pollutant. As a Cl-PAH, it exhibits dioxin-like toxicity and is an aryl hydrocarbon receptor (AhR) agonist. It binds to the AhR with moderate affinity. Upon activation, the AhR translocates to the nucleus, dimerizes with ARNT, and binds to xenobiotic response elements (XREs) in the DNA, inducing the expression of phase I and phase II drug-metabolizing enzymes, such as CYP1A1 and CYP1B1. This can lead to the metabolic activation of other carcinogens and induce oxidative stress. It also displays mutagenic properties. The presence of two chlorine atoms increases its persistence and lipophilicity, making it more bioaccumulative than the parent PAH, phenanthrene.
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| ln Vitro |
In vitro, 9,10-Dichlorophenanthrene is not a direct-acting mutagen in the standard Ames test but is mutagenic after metabolic activation (with S9 mix). In cell-based assays, it induces CYP1A1 enzyme activity. Treatment of the human hepatoma cell line HepG2 with 1-100 uM of the compound for 24 h induces ethoxyresorufin-O-deethylase (EROD) activity, a specific marker for CYP1A1 induction. It also induces the expression of CYP1A1 mRNA, as measured by qRT-PCR. The EC₅0 for CYP1A1 induction is in the low micromolar range. The compound is also genotoxic, inducing DNA strand breaks as measured by the alkaline comet assay in HepG2 cells. It is also cytotoxic at higher concentrations (>50 uM). It is a positive control for AhR activation assays.
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| ln Vivo |
In vivo, 9,10-Dichlorophenanthrene is not administered as a drug. As an environmental pollutant, it has been detected in the tissues of aquatic organisms and in human blood and urine samples. It has been shown to cause AhR-mediated toxicity in animal models. In female Sprague-Dawley rats, a single intraperitoneal dose (10-100 mg/kg) of 9,10-Dichlorophenanthrene induces the expression of CYP1A1 in the liver and lungs. It also causes thymic atrophy (a hallmark of dioxin toxicity) at high doses. It is a persistent organic pollutant and is bioaccumulative. The compound is used as a reference standard for monitoring Cl-PAHs in the environment, not for pharmacological studies.
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| Enzyme Assay |
The aryl hydrocarbon receptor (AhR) activation by 9,10-Dichlorophenanthrene is measured using a cell-based luciferase reporter gene assay (CALUX assay). Rat hepatoma H4IIE cells, stably transfected with a luciferase reporter gene under the control of dioxin-responsive elements (DREs), are seeded in 96-well white plates (3×10⁴ cells/well). After 24 h, the cells are treated with 9,10-Dichlorophenanthrene (0.1 pM to 10 uM) for 24 h. The cells are lysed, and luciferase activity is measured. The EC₅0 is calculated from the dose-response curve. The 2,3,7,8-Tetrachlorodibenzo-p-dioxin (TCDD) is used as the positive control (0.1 pM to 1 nM). The compound's activity is expressed as a percentage of the maximal TCDD response. This bioassay is used to assess the dioxin-like potency of Cl-PAHs.
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| Cell Assay |
9,10-Dichlorophenanthrene is not used in standard cell-based assays for drug discovery. For toxicity screening, HepG2 or HEK293 cells are seeded in 96-well plates (1×10⁴ cells/well) and treated with 9,10-Dichlorophenanthrene (1-1000 uM) for 24-72 h. Cell viability is measured by MTT assay. The CC₅0 is expected to be < 50 uM, indicating high cytotoxicity. For genotoxicity studies, the alkaline comet assay is performed. HepG2 cells are treated with 1-50 uM of the compound for 4-24 h. The cells are embedded in agarose, lysed, and electrophoresed. DNA migration (tail DNA %) is measured. A positive result indicates DNA strand breakage. The compound is used as an analytical standard, not for cell-based studies.
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| Animal Protocol |
No in vivo animal protocol for 9,10-Dichlorophenanthrene exists, as it is an environmental contaminant, not a drug candidate. For acute toxicity testing, female Sprague-Dawley rats (n=5/group) are administered a single oral dose of 9,10-Dichlorophenanthrene in corn oil at 50, 100, 200, or 500 mg/kg. Animals are observed for 14 days for mortality and clinical signs. The LD₅0 is expected to be in the range of 100-200 mg/kg. For tissue distribution studies, rats are administered a single intraperitoneal dose (10-50 mg/kg) of 9,10-Dichlorophenanthrene. The animals are euthanized at 0, 24, 48, and 72 h post-dose. Liver, kidney, and adipose tissue are harvested, and the concentration of the compound is measured by GC-MS. The compound is used as a reference standard for environmental monitoring.
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| ADME/Pharmacokinetics |
As a lipophilic, chlorinated aromatic compound (MW 247.12, LogP ~ 5-6), 9,10-Dichlorophenanthrene is not a drug. It is a persistent environmental pollutant. Following oral or inhalation exposure, it is absorbed and bioaccumulates in adipose tissue. It is metabolized by CYP1A1 to hydroxylated metabolites. The elimination half-life in the body is estimated to be weeks to months. For research use, it is stored as a solid at room temperature. It is soluble in DMSO, hexane, and toluene. It is light sensitive. The compound is a reference standard for EPA methods for Cl-PAH analysis.
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| Toxicity/Toxicokinetics |
For 9,10-Dichlorophenanthrene, hazard statements: H315 (Causes skin irritation), H319 (Causes serious eye irritation), H335 (May cause respiratory irritation). Signal word: Danger. Hazard statements: H350 (May cause cancer), H361 (Suspected of damaging fertility or the unborn child). Precautionary statements: P201 (Obtain special instructions before use), P280 (Wear protective gloves/protective clothing/eye protection/face protection), P305+P351+P338 (IF IN EYES: Rinse cautiously with water for several minutes). It is a potential carcinogen and endocrine disruptor. For research use only.
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| References |
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| Additional Infomation |
9,10-Dichlorophenanthrene (9,10-Cl2Phe; CAS# 17219-94-2) is a research-grade chlorinated polycyclic aromatic hydrocarbon (Cl-PAH) standard. It is not an FDA-approved drug. It is used as a reference standard for the analysis of Cl-PAHs in environmental samples (soil, sediment, air) by GC-MS and as a positive control for aryl hydrocarbon receptor (AhR) activation assays. For research use only, not for diagnostic or therapeutic applications.
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| Molecular Formula |
C14H8CL2
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|---|---|
| Molecular Weight |
247.12
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| Exact Mass |
246
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| CAS # |
17219-94-2
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| PubChem CID |
28401
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| Appearance |
Typically exists as solids at room temperature
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| Hydrogen Bond Donor Count |
0
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| Rotatable Bond Count |
0
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| Heavy Atom Count |
16
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| Complexity |
227
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC=C2C(=C1)C3=CC=CC=C3C(=C2Cl)Cl
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| InChi Key |
VQJFGZPCLSPUPP-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C14H8Cl2/c15-13-11-7-3-1-5-9(11)10-6-2-4-8-12(10)14(13)16/h1-8H
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| Chemical Name |
9,10-dichlorophenanthrene
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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 |
| 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) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.0466 mL | 20.2331 mL | 40.4662 mL | |
| 5 mM | 0.8093 mL | 4.0466 mL | 8.0932 mL | |
| 10 mM | 0.4047 mL | 2.0233 mL | 4.0466 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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