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2,3-Dehydro-2-deoxy-N-acetylneuraminic acid (Neu5Ac2en; DANA)

Cat No.:V41078 Purity: ≥98%
N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid (Neu5Ac2en) is a potent neuraminidase inhibitor.
2,3-Dehydro-2-deoxy-N-acetylneuraminic acid (Neu5Ac2en; DANA)
2,3-Dehydro-2-deoxy-N-acetylneuraminic acid (Neu5Ac2en; DANA) Chemical Structure CAS No.: 24967-27-9
Product category: Influenza Virus
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
Other Sizes
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Product Description
N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid (Neu5Ac2en) is a potent neuraminidase inhibitor. N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid exhibits inhibitory effect against human neuraminidase enzyme, with IC50s of 143, 43, 61 and 74 μM for human NEU1, NEU2, NEU3 and NEU4 respectively. N-acetyl-2,3-dehydro-2-Deoxyneuramine Acid has anti-influenza virus activity.
2,3-Dehydro-2-deoxy-N-acetylneuraminic acid (Neu5Ac2en; DANA) (CAS#: 24967-27-9) is a specific endogenous neuraminidase (sialidase) inhibitor used in biochemical and antiviral research. It is a transition-state analog of sialic acid that inhibits viral, bacterial, and mammalian neuraminidases. The compound is used to study the roles of endogenous neuraminidase in neural development, immune function, and other sialylation-dependent processes.
Biological Activity I Assay Protocols (From Reference)
Targets
Neuraminidase (sialidase), including viral (influenza), bacterial, and mammalian neuraminidases. DANA acts as a competitive inhibitor by mimicking the transition state of sialic acid cleavage, binding to the active site of neuraminidase and preventing the removal of sialic acid from glycoproteins and glycolipids.
ln Vitro
N-acetyl-2,3-dehydro-2-Deoxyneuramine Acid (Neu5Ac2en) at concentrations between 10 and 100 μM strongly suppresses the activity of sialidase in INS-1D cells [4].
In vitro, DANA inhibits viral, bacterial, and mammalian neuraminidase activity. It is a specific endogenous neuraminidase inhibitor used to study the roles of endogenous neuraminidase in the development and function of neural processes and pathways, as well as other processes that depend upon sialylation-desialylation cycles. The compound serves as a tool for investigating neuraminidase function in various biological systems.
ln Vivo
In mouse models, N-acetyl-2,3-dehydro-2-Deoxyneuramine Acid (Neu5Ac2en) (10 mg/kg; i.p.; daily) decreases lung fibrosis[3].
In vivo activity data for DANA are available from studies investigating neuraminidase function. As a neuraminidase inhibitor, it has been used to elucidate the roles of sialidases in neural development, immune regulation, and disease processes. However, detailed in vivo efficacy data are not extensively documented in the available literature. The compound is primarily used as a research tool rather than a therapeutic agent.
Enzyme Assay
Neuraminidase inhibition is measured using a fluorometric or colorimetric assay with a fluorogenic sialic acid substrate (e.g., 4-methylumbelliferyl-N-acetylneuraminic acid, MU-NANA). The enzyme (viral, bacterial, or mammalian neuraminidase) is incubated with the substrate and varying concentrations of DANA. The IC50 is determined by measuring the reduction in fluorescence or absorbance upon substrate cleavage.
Cell Assay
DANA is used in cell-based assays to study neuraminidase function. Cells are treated with DANA at varying concentrations, and neuraminidase activity is measured in cell lysates using fluorogenic substrates. The effects of neuraminidase inhibition on cellular processes such as neural development, immune cell function, or viral infection are assessed by appropriate downstream assays (e.g., neurite outgrowth, cytokine production, viral titer).
Animal Protocol
Animal/Disease Models: Mice (Mouse model of pulmonary fibrosis)[3]
Doses: 10 mg/kg
Route of Administration: Ip; daily (starting at day 10 after Bleomycin, and then euthanized at day 21)
Experimental Results: Inhibition of sialidases starting at day 10 after bleomycin attenuates fibrosis.
Specific in vivo protocols for DANA vary depending on the biological question. For neural development studies, DANA may be administered via injection in animal models, and effects on neuronal differentiation or synaptic plasticity are assessed. For viral infection studies, DANA is used as a reference inhibitor to compare with other neuraminidase inhibitors. Dosing regimens are determined based on the specific experimental model.
ADME/Pharmacokinetics
DANA has molecular formula C11H17NO8 and molecular weight 291.25. It is also known as N-acetyl-2,3-didehydro-2-deoxyneuraminic acid (NADNA). CAS number is 24967-27-9. The compound is a transition-state analog of sialic acid. Its pharmacokinetic properties are not extensively characterized as it is primarily used as a research tool. Purity is typically 98-99%.
Toxicity/Toxicokinetics
No comprehensive toxicity data are specifically reported for DANA. As a research-grade neuraminidase inhibitor, its safety profile has not been extensively characterized for therapeutic applications. Standard laboratory safety precautions should be followed when handling the compound. It is not intended for human or veterinary use.
References

[1]. Design, synthesis, and biological evaluation of human sialidase inhibitors. Part 1: selective inhibitors of lysosomal sialidase (NEU1). Bioorg Med Chem Lett. 2008;18(2):532-537.

[2]. Sialidase-catalyzed one-pot multienzyme (OPME) synthesis of sialidase transition-state analogue inhibitors. ACS Catal. 2018;8(1):43-47.

[3]. Sialidase inhibitors attenuate pulmonary fibrosis in a mouse model. Sci Rep. 2017;7(1):15069. Published 2017 Nov 8.

[4]. The sialidase inhibitor 2,3-dehydro-2-deoxy-N-acetylneuraminic acid is a glucose-dependent potentiator of insulin secretion. Sci Rep. 2020;10(1):5198. Published 2020 Mar 23.

Additional Infomation
2-Deoxy-2,3-Dehydro-N-acetylneuraminic acid is a product formed by the reduction of N-acetylneuraminic acid at the 2,3-dicarbon sugar bond, resulting in the loss of the C-2 hydroxyl group. It is present in relatively low amounts in body fluids but abundant in salivary urine. It is the conjugate acid of 2-deoxy-2,3-dehydro-N-acetylneuraminic acid.
2,3-Dehydro-2-deoxy-N-acetylneuraminic acid (Neu5Ac2en, DANA, NADNA) is a specific endogenous neuraminidase (sialidase) inhibitor used in biochemical and antiviral research. It is a transition-state analog of sialic acid that inhibits neuraminidases from viral, bacterial, and mammalian sources. The compound is used to study sialylation-desialylation cycles, neural development, and immune function. It is for research use only and has not entered clinical trials or received FDA approval.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C11H17NO8
Molecular Weight
291.25
Exact Mass
291.095
CAS #
24967-27-9
PubChem CID
65309
Appearance
White to off-white solid powder
Density
1.58g/cm3
Boiling Point
773.4ºC at 760 mmHg
Melting Point
227-228ºC
Flash Point
421.6ºC
Vapour Pressure
1.27E-27mmHg at 25°C
Index of Refraction
1.612
LogP
-2.5
Hydrogen Bond Donor Count
6
Hydrogen Bond Acceptor Count
8
Rotatable Bond Count
5
Heavy Atom Count
20
Complexity
409
Defined Atom Stereocenter Count
5
SMILES
CC(=O)N[C@@H]1[C@H](C=C(O[C@H]1[C@@H]([C@@H](CO)O)O)C(=O)O)O
InChi Key
JINJZWSZQKHCIP-UFGQHTETSA-N
InChi Code
InChI=1S/C11H17NO8/c1-4(14)12-8-5(15)2-7(11(18)19)20-10(8)9(17)6(16)3-13/h2,5-6,8-10,13,15-17H,3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,8+,9+,10+/m0/s1
Chemical Name
(2R,3R,4S)-3-acetamido-4-hydroxy-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid
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

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 : 33.33 mg/mL (114.44 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 3.4335 mL 17.1674 mL 34.3348 mL
5 mM 0.6867 mL 3.4335 mL 6.8670 mL
10 mM 0.3433 mL 1.7167 mL 3.4335 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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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?
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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:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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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