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1,2-Diaminoanthraquinone

Cat No.:V43342 Purity: ≥98%
1,2-Diaminoanthraquinone is a sensitive, specific and non-toxic nitric oxide (NO) fluorescent probe that may be utilized to detect NO production in living cells and animals.
1,2-Diaminoanthraquinone
1,2-Diaminoanthraquinone Chemical Structure CAS No.: 1758-68-5
Product category: New3
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
1,2-Diaminoanthraquinone is a sensitive, specific and non-toxic nitric oxide (NO) fluorescent probe that may be utilized to detect NO production in living cells and animals. Its maximum absorption wavelength is about 540 nm, which is The detection limit of NO is 5 μM.
1,2-Diaminoanthraquinone is a synthetic compound used as a sensitive, specific, and non-toxic fluorescent probe for the detection of nitric oxide (NO). It has the molecular formula C14H10N2O2 and a molecular weight of 238.24 g/mol. The compound has a maximum absorption wavelength of approximately 540 nm and an emission wavelength of 538 nm. It can detect NO at a limit of 5 μM. 1,2-Diaminoanthraquinone is used to detect NO production in live cells and animals. It is soluble in DMSO at 55 mg/mL and is intended for research use only.
Biological Activity I Assay Protocols (From Reference)
Targets
1,2-Diaminoanthraquinone targets nitric oxide (NO), a key signaling molecule involved in various physiological and pathological processes. As a fluorescent probe, it detects NO by reacting with it to form a fluorescent product. The compound's specificity for NO allows for the sensitive and selective detection of this molecule in biological samples. Its non-toxic nature makes it suitable for use in live-cell and in vivo imaging applications. The compound's mechanism involves a reaction with NO that results in a change in its fluorescence properties, enabling the quantification of NO levels.
ln Vitro
Spectroscopic analysis of 1,2-diaminoanthraquinone and its derivatives, which are produced by its interaction with DAA-TZ and NO, can be performed using fluorescence spectroscopy and confocal microscopy [1]. fluorescent imaging [1]
In vitro, 1,2-Diaminoanthraquinone is used as a fluorescent probe for the detection of nitric oxide (NO) in cells and biological samples. It is characterized by its sensitivity and specificity for NO. The compound has a detection limit of 5 μM for NO and exhibits a maximum absorption at about 540 nm and emission at 538 nm. Its non-toxic nature makes it suitable for use in live-cell imaging. The compound is used to study NO production and signaling in various cell types.
ln Vivo
In vivo, 1,2-Diaminoanthraquinone is used to detect nitric oxide (NO) production in animals. Its non-toxic nature makes it suitable for in vivo imaging applications. The compound can be administered to animals to monitor NO levels in real-time. Its fluorescence properties allow for the visualization and quantification of NO in tissues and organs. The compound's in vivo applications are valuable for studying the role of NO in various physiological and pathological conditions, such as inflammation, cardiovascular disease, and neurotransmission.
Enzyme Assay
In vitro experiments with 1,2-Diaminoanthraquinone typically involve preparing a stock solution in DMSO and diluting it in an appropriate buffer or cell culture medium. For NO detection, cells or biological samples are incubated with the probe at a suitable concentration (e.g., 1-10 µM) for a specified period. The fluorescence intensity is then measured using a fluorescence spectrophotometer or microscope with excitation at approximately 540 nm and emission at 538 nm. A standard curve prepared using known concentrations of an NO donor is used to quantify the NO levels in the samples. The compound's non-toxic nature allows for prolonged incubation periods.
Cell Assay
Immunofluorescence [1]
Cell Types: Original 264.7 macrophages
Tested Concentrations: 27.4 μM
Incubation Duration: 20 minutes
Experimental Results: DAA-TZ is generated by reacting with NO in the presence of oxygen in the intracellular environment.
In vitro cell-based assays using 1,2-Diaminoanthraquinone are performed to detect and quantify nitric oxide (NO) production in live cells. Cells are seeded in culture dishes or multi-well plates and treated with stimuli that induce NO production (e.g., lipopolysaccharide, cytokines). The cells are then incubated with the fluorescent probe at a concentration of 1-10 µM for 30-60 minutes. After incubation, the cells are washed and the fluorescence is measured using a fluorescence microscope, flow cytometer, or microplate reader with excitation at approximately 540 nm and emission at 538 nm. The increase in fluorescence intensity correlates with the level of NO production. The compound's non-toxic nature makes it suitable for live-cell imaging.
Animal Protocol
In vivo animal experiments with 1,2-Diaminoanthraquinone are conducted to monitor nitric oxide (NO) production in living animals. The compound can be administered intravenously, intraperitoneally, or topically, depending on the tissue of interest. After administration, the animal is imaged using a fluorescence imaging system with appropriate excitation and emission filters (Ex/Em ~540/538 nm). The fluorescence signal is then analyzed to determine the spatial and temporal distribution of NO production. The compound's non-toxic nature makes it suitable for longitudinal studies. Dosing and imaging protocols would depend on the specific experimental design.
ADME/Pharmacokinetics
1,2-Diaminoanthraquinone has a molecular weight of 238.24 g/mol and the formula C14H10N2O2. It is soluble in DMSO at 55 mg/mL. The compound exhibits a maximum absorption at approximately 540 nm and emission at 538 nm. For long-term storage, the compound is kept as a powder at room temperature, protected from light. Its pharmacokinetic properties, such as absorption, distribution, metabolism, and excretion, are not detailed in the available literature. However, its non-toxic nature and suitability for in vivo imaging suggest it is well-tolerated and can be distributed to tissues.
Toxicity/Toxicokinetics
1,2-Diaminoanthraquinone is considered non-toxic, making it suitable for use in live-cell and in vivo imaging applications. Specific toxicological data are not extensively provided in the available sources, but its classification as non-toxic suggests a low risk of adverse effects at the concentrations used for NO detection. As a research chemical, it is intended for laboratory use only and is not for human consumption. Standard laboratory safety precautions should be followed when handling this compound. Its purity is typically high.
References

[1]. Fluorescence of 1,2-diaminoanthraquinone and its nitric oxide reaction product within macrophage cells. Chembiochem. 2011 Nov 4;12(16):2471-7.

[2]. Spectroscopic studies of 1,2-diaminoanthraquinone (DAQ) as a fluorescent probe for the imaging of nitric oxide in living cells. Photochem Photobiol Sci. 2008 Jan;7(1):126-30.

Additional Infomation
1,2-Diaminoanthraquinone is a sensitive, specific, and non-toxic fluorescent probe for the detection of nitric oxide (NO). It has the molecular formula C14H10N2O2 and a molecular weight of 238.24 g/mol. The compound has a maximum absorption of approximately 540 nm and an emission of 538 nm and can detect NO at a limit of 5 μM. It is used to detect NO production in live cells and animals. The compound is soluble in DMSO at 55 mg/mL and is non-toxic, making it suitable for in vivo imaging. It is intended for research use only and is not for human consumption.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C14H10N2O2
Molecular Weight
238.2414
Exact Mass
238.074
CAS #
1758-68-5
PubChem CID
15652
Appearance
Brown to black solid powder
Density
1.456 g/cm3
Boiling Point
548.8ºC at 760 mmHg
Melting Point
289-291 °C(lit.)
Flash Point
285.7ºC
Vapour Pressure
4.26E-12mmHg at 25°C
Index of Refraction
1.757
LogP
2.788
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
4
Rotatable Bond Count
0
Heavy Atom Count
18
Complexity
382
Defined Atom Stereocenter Count
0
InChi Key
LRMDXTVKVHKWEK-UHFFFAOYSA-N
InChi Code
InChI=1S/C14H10N2O2/c15-10-6-5-9-11(12(10)16)14(18)8-4-2-1-3-7(8)13(9)17/h1-6H,15-16H2
Chemical Name
1,2-diaminoanthracene-9,10-dione
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

Note: (1). This product requires protection from light (avoid light exposure) during transportation and storage.  (2). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~62.5 mg/mL (~262.33 mM)
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
(e.g. IP/IV/IM/SC)
Injection Formulation 1: DMSO : Tween 80: Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution 50 μL Tween 80 850 μL Saline)
*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 : PEG300Tween 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).
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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)]
*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.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO 100 μLPEG300 200 μL castor oil 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10: 10 : 80 (i.e. 100 μL Ethanol 100 μL Cremophor 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH 400 μLPEG300 50 μL Tween 80 450 μL 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).
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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders


Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.1974 mL 20.9872 mL 41.9745 mL
5 mM 0.8395 mL 4.1974 mL 8.3949 mL
10 mM 0.4197 mL 2.0987 mL 4.1974 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.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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