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8-Aminopyrene-1,3,6-trisulfonic acid trisodium

Cat No.:V46010 Purity: ≥98%
8-Aminopyrene-1,3,6-trisulfonic acid trisodium is a water-soluble (H2O-soluble) anionic fluorescent dye.
8-Aminopyrene-1,3,6-trisulfonic acid trisodium
8-Aminopyrene-1,3,6-trisulfonic acid trisodium Chemical Structure CAS No.: 196504-57-1
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
8-Aminopyrene-1,3,6-trisulfonic acid trisodium is a water-soluble (H2O-soluble) anionic fluorescent dye. The fluorescence intensity of 8-Aminopyrene-1,3,6-trisulfonic acid trisodium remains stable at pH 4~10.
8-Aminopyrene-1,3,6-trisulfonic acid trisodium (CAS 196504-57-1), also known as APTS, is a water-soluble anionic fluorescent dye. Its molecular formula is C16H8NNa3O9S3 and molecular weight is 523.40 g/mol. The dye features a pyrene backbone with three sulfonic acid groups and an amino group. Its fluorescence intensity remains stable at pH 4-10. APTS has excitation/emission maxima of 425/503 nm in pH 7.4 PBS. It is widely used for detecting carbohydrates and labeling glycoproteins in electrophoresis.
Biological Activity I Assay Protocols (From Reference)
Targets
APTS does not have a specific biological target as a drug. Its primary application is as a fluorescent labeling reagent for carbohydrates and glycoproteins. The amino group on the pyrene core can be used to label reducing sugars via reductive amination. The sulfonic acid groups confer water solubility and anionic character, preventing the dye from crossing biological membranes and reducing nonspecific binding. Its fluorescence properties, including a large Stokes shift and stability over a wide pH range, make it suitable for various analytical applications.
ln Vitro
In vitro, APTS is used as an anionic fluorescent dye for detecting carbohydrates and labeling glycoproteins in electrophoresis. It is also used to modify other carbonyl-containing biomolecules such as aldehydes and ketones. Its fluorescence intensity remains stable at pH 4-10. The dye is widely used in capillary electrophoresis for the analysis of carbohydrates, as the negative charge of the dye helps to separate the labeled carbohydrates based on their charge-to-mass ratio.
ln Vivo
In vivo activity of APTS is not typically studied, as it is a fluorescent labeling reagent rather than a bioactive drug. However, labeled biomolecules (e.g., labeled glycoproteins) could be used in vivo for imaging or tracking purposes. The dye's water solubility and anionic nature limit its ability to cross cell membranes, which may restrict its use to extracellular or ex vivo applications.
Enzyme Assay
In vitro enzyme/receptor binding (non-cell) assays using APTS typically involve the dye as a label for carbohydrates or glycoproteins, rather than as a binding agent itself. A standard protocol for labeling carbohydrates: a carbohydrate sample is incubated with APTS in the presence of a reducing agent (e.g., sodium cyanoborohydride) in an acetic acid solution. The reaction mixture is incubated at 37°C for several hours. The labeled carbohydrate is then analyzed by capillary electrophoresis or HPLC with fluorescence detection. The fluorescence of the APTS-labeled carbohydrate allows for sensitive detection and quantification.
Cell Assay
In vitro cell-based assays using APTS are not common, as it is primarily used for labeling and detecting biomolecules in solution. However, it could be used to label cell surface glycoproteins. A standard protocol: cells are harvested and incubated with a solution containing APTS and a reducing agent. The APTS reacts with the aldehyde groups on glycoproteins (after periodate oxidation) to form fluorescently labeled glycoproteins. The labeled cells can be analyzed by flow cytometry to assess the expression of specific glycoproteins on the cell surface.
Animal Protocol
In vivo animal experiments using APTS are not typically performed, as it is a fluorescent dye for in vitro labeling. However, APTS-labeled biomolecules could be administered to animals for tracking purposes. For example, an APTS-labeled glycoprotein could be injected intravenously, and its distribution in the body could be monitored by measuring the fluorescence in blood and tissues. Such studies would require careful consideration of the dye's properties and the stability of the labeled molecule.
ADME/Pharmacokinetics
Pharmacokinetic properties of APTS are not a primary focus of study. The compound is a highly water-soluble, anionic dye with a large molecular weight (523.40 g/mol). It is not expected to readily cross biological membranes due to its negative charge and size. The dye is stable at pH 4-10, making it suitable for various experimental conditions. Its fluorescence properties, including a large Stokes shift, are advantageous for detection in complex biological samples.
Toxicity/Toxicokinetics
Toxicity data for APTS is limited. As a fluorescent dye, it is generally considered to have low toxicity at the concentrations used for labeling and detection. The compound is water-soluble and anionic, which limits its ability to interact with cellular membranes and reduces its potential for cytotoxicity. However, standard laboratory safety precautions should be followed when handling the compound.
References

[1]. Exploring the use of APTS as a fluorescent reporter dye for continuous glucose sensing. Org Biomol Chem. 2009 Apr 7;7(7):1461-70.

Additional Infomation
APTS is a water-soluble anionic fluorescent dye with stable fluorescence intensity at pH 4-10. It is widely used for detecting carbohydrates and labeling glycoproteins in electrophoresis. The dye has strong green fluorescence with a great Stokes shift. It is also used to modify carbonyl-containing biomolecules. It is not a drug and has no clinical use or approval status. It is commercially available from chemical suppliers for research purposes only.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C16H8NNA3O9S3
Molecular Weight
523.4003
Exact Mass
522.905
CAS #
196504-57-1
PubChem CID
9849652
Appearance
Light brown to brown solid powder
Melting Point
≥250ºC(lit.)
LogP
4.702
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
10
Rotatable Bond Count
0
Heavy Atom Count
32
Complexity
936
Defined Atom Stereocenter Count
0
InChi Key
XSTNYACEWLNWPY-UHFFFAOYSA-K
InChi Code
InChI=1S/C16H11NO9S3.3Na/c17-11-5-12(27(18,19)20)8-3-4-10-14(29(24,25)26)6-13(28(21,22)23)9-2-1-7(11)15(8)16(9)10;;;/h1-6H,17H2,(H,18,19,20)(H,21,22,23)(H,24,25,26);;;/q;3*+1/p-3
Chemical Name
trisodium;8-aminopyrene-1,3,6-trisulfonate
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: This product requires protection from light (avoid light exposure) during transportation and storage.
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)
H2O : ~25 mg/mL (~47.76 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 1.9106 mL 9.5529 mL 19.1058 mL
5 mM 0.3821 mL 1.9106 mL 3.8212 mL
10 mM 0.1911 mL 0.9553 mL 1.9106 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
  • Calculate the Volume of solution required to dissolve a compound of known mass to a desired concentration
  • Calculate the Concentration of a solution resulting from a known mass of compound in a specific volume
An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
  • To calculate molar mass of a chemical compound, please enter the chemical/molecular formula and click the “Calculate’ button.
Definitions of molecular mass, molecular weight, molar mass and molar weight:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
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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