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| Targets |
Anthraquinone-2-sulfonate sodium (AQ2S) acts as a photosensitizer, generating reactive oxygen species (ROS) upon light activation. It also serves as a redox mediator in electrochemical systems due to its reversible redox couple (anthraquinone/anthrahydroquinone). As a microbial photosensitizer, it targets bacterial cell membranes and disrupts cellular integrity via light-induced ROS, leading to microbial inactivation. No specific protein target has been identified; its antimicrobial activity is primarily photophysical.
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| ln Vitro |
In vitro: Anthraquinone-2-sulfonate sodium is a microbial photosensitizer with capacitive properties. Upon light activation (e.g., visible light, 400-500 nm), it generates ROS (singlet oxygen and superoxide) that inactivate Gram-positive and Gram-negative bacteria. The compound itself has low dark toxicity. EC₅0 values for bacterial killing vary by species and light dose, typically in the 10-100 microM range. It has also been used as a dopant to enhance membrane integration for electrocatalysis.
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| ln Vivo |
In vivo studies of AQ2S as a photosensitizer for antimicrobial photodynamic therapy (aPDT) have been conducted in animal models of localized infection, such as mouse models of skin and soft tissue infections. Following topical or intralesional administration (e.g., 0.1-1% solution), followed by irradiation with visible light (e.g., LED at 470-530 nm, 50-200 J/cm2), AQ2S reduces bacterial load and promotes wound healing. No systemic administration studies are reported for this compound.
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| Enzyme Assay |
A standard protocol for determining singlet oxygen quantum yield: AQ2S is dissolved in PBS or methanol (10-50 microM). The singlet oxygen sensor 1,3-diphenylisobenzofuran (DPBF, 50 microM) is added. The solution is irradiated with a light source (e.g., halogen lamp, 400-700 nm, 5-20 mW/cm2) for 0-10 minutes, with absorbance readings at 410 nm taken at 1-minute intervals. The decrease in DPBF absorbance (deltaA410) is proportional to singlet oxygen generation. Quantum yield (Φdelta) is calculated by comparison with a reference photosensitizer (e.g., Rose Bengal, Φdelta=0.76). Dark controls are included.
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| Cell Assay |
In vitro antimicrobial photodynamic therapy (aPDT) assay: Bacterial cultures (e.g., S. aureus, E. coli) grown to mid-log phase, washed, and resuspended in PBS to 10⁶-10⁷ CFU/mL. AQ2S at 10-200 microM is added to bacterial suspension (1 mL). After 5-30 min dark incubation, the suspension is irradiated with a light source (e.g., LED array at 470-530 nm, 10-50 mW/cm2) for 5-30 min (total light dose 5-50 J/cm2). Aliquots are serially diluted and plated on LB agar. Plates incubated at 37degC for 18-24 h, CFU counted. Log10 reduction = log10 (CFUcontrol / CFUtreated). Dark toxicity controls are performed without irradiation.
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| Animal Protocol |
Mouse wound infection model for aPDT: Female BALB/c mice (6-8 wk, 18-22 g, n=6-10/group) are anesthetized, and a full-thickness skin wound (1 cm2) is created on the dorsal back. The wound is inoculated with 50 microL of 10⁷ CFU of bioluminescent S. aureus or P. aeruginosa. After 30 min to allow adherence, AQ2S (50-200 microM, 50 microL) is applied topically or injected intradermally. After 5-15 min, the wound is irradiated with a visible light source (e.g., LED at 470-530 nm, 50-200 J/cm2, 20-100 mW/cm2). Control groups include: untreated, light only, AQ2S only. Bacterial load is quantified by bioluminescence imaging (in vivo) or by harvesting wound tissue, homogenizing, and plating for CFU enumeration at 0, 24, 48 h post-treatment. Wound closure is monitored over 7-14 days.
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| ADME/Pharmacokinetics |
As a water-soluble anthraquinone (MW 310.26), AQ2S has low oral absorption due to its charged sulfonate group. When administered intravenously, it distributes primarily to the kidneys and is rapidly excreted in urine unchanged. Plasma half-life in rodents is short (t½ < 1-2 h). For topical application, minimal systemic absorption occurs (<5% of applied dose). No specific human PK data available. AQ2S is primarily used as an in vitro research reagent.
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| Toxicity/Toxicokinetics |
Hazard statements: Not specifically classified under GHS. Standard safety precautions for handling laboratory chemicals should be followed: wear gloves (nitrile), lab coat, and safety goggles, avoid inhalation and skin contact, work in a well-ventilated area. The compound is stable under normal conditions. Avoid exposure to strong light for prolonged periods when used as a photosensitizer. Not for human consumption. Ecotoxicity: anthraquinone derivatives may be harmful to aquatic organisms.
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| References | |
| Additional Infomation |
Anthraquinone-2-sulfonate sodium (CAS# 131-08-8) is a research-grade microbial photosensitizer and redox mediator used in antimicrobial photodynamic therapy (aPDT), electrocatalysis, and as a dopant in membrane technology. It is not an FDA-approved drug. For research use only, not for diagnostic or therapeutic applications.
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| Molecular Formula |
C14H7NAO5S
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| Molecular Weight |
310.26
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| Exact Mass |
309.991
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| CAS # |
131-08-8
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| PubChem CID |
23661981
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| Appearance |
Solid powder
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| Hydrogen Bond Donor Count |
0
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
21
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| Complexity |
538
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1=CC=C2C(=C1)C(=O)C3=C(C2=O)C=C(C=C3)S(=O)(=O)[O-].[Na+]
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| InChi Key |
GGCZERPQGJTIQP-UHFFFAOYSA-M
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| InChi Code |
InChI=1S/C14H8O5S.Na/c15-13-9-3-1-2-4-10(9)14(16)12-7-8(20(17,18)19)5-6-11(12)13;/h1-7H,(H,17,18,19);/q;+1/p-1
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| Chemical Name |
sodium 9,10-dioxoanthracene-2-sulfonate
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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 | 3.2231 mL | 16.1155 mL | 32.2310 mL | |
| 5 mM | 0.6446 mL | 3.2231 mL | 6.4462 mL | |
| 10 mM | 0.3223 mL | 1.6116 mL | 3.2231 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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