2,3-Dehydro-2-deoxy-N-acetylneuraminic acid
Based on 4 publication(s) in Google Scholar
N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid (Neu5Ac2en) is a potent neuraminidase (sialidase) inhibitor. N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid shows inhibitory activities against human neuraminidase enzymes with IC50s of 143, 43, 61, and 74 μM for NEU1, NEU2, NEU3, and NEU4, respectively. Anti-influenza virus activity.
For research use only. We do not sell to patients.
- Purity: 98.0%
- CAS No.: 24967-27-9
- Formula: C11H17NO8
- Molecular Weight:291.25
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Storage:Powder -20°C, 3 years ; In solvent -80°C, 6 months , -20°C, 1 month
Publications Citing Use of MedChemExpress (MCE) 2,3-Dehydro-2-deoxy-N-acetylneuraminic acid
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Biological Activity
Description
Cellular Effect
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| HEK293 | IC50 |
143 μM
Compound: 1, DANA
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Inhibition of human NEU1 expressed in HEK293 cells
Inhibition of human NEU1 expressed in HEK293 cells
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[PMID: 18068975] |
| HEK293 | IC50 |
168 μM
Compound: NeuAc2en
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Inhibition of human NEU1 expressed in HEK293 cells by fluorometric high-performance liquid chromatography using 4MU-NeuAc substrate
Inhibition of human NEU1 expressed in HEK293 cells by fluorometric high-performance liquid chromatography using 4MU-NeuAc substrate
|
[PMID: 18694948] |
| HEK293 | IC50 |
43 μM
Compound: 1, DANA
|
Inhibition of human NEU2 expressed in HEK293 cells
Inhibition of human NEU2 expressed in HEK293 cells
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[PMID: 18068975] |
| HEK293 | IC50 |
45.5 μM
Compound: NeuAc2en
|
Inhibition of human NEU2 expressed in HEK293 cells by fluorometric high-performance liquid chromatography using 4MU-NeuAc substrate
Inhibition of human NEU2 expressed in HEK293 cells by fluorometric high-performance liquid chromatography using 4MU-NeuAc substrate
|
[PMID: 18694948] |
| HEK293 | IC50 |
61 μM
Compound: 1, DANA
|
Inhibition of human NEU3 expressed in HEK293 cells
Inhibition of human NEU3 expressed in HEK293 cells
|
[PMID: 18068975] |
| HEK293 | IC50 |
70.3 μM
Compound: NeuAc2en
|
Inhibition of human NEU3 expressed in HEK293 cells by fluorometric high-performance liquid chromatography using ganglioside GM3 substrate
Inhibition of human NEU3 expressed in HEK293 cells by fluorometric high-performance liquid chromatography using ganglioside GM3 substrate
|
[PMID: 18694948] |
| HEK293 | IC50 |
73.1 μM
Compound: NeuAc2en
|
Inhibition of human NEU4 expressed in HEK293 cells by fluorometric high-performance liquid chromatography using 4MU-NeuAc substrate
Inhibition of human NEU4 expressed in HEK293 cells by fluorometric high-performance liquid chromatography using 4MU-NeuAc substrate
|
[PMID: 18694948] |
| HEK293 | IC50 |
74 μM
Compound: 1, DANA
|
Inhibition of human NEU4 expressed in HEK293 cells
Inhibition of human NEU4 expressed in HEK293 cells
|
[PMID: 18068975] |
| HEK-293T | IC50 |
0.04 mM
Compound: 2, Neu5Ac2en, DANA
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Inhibition of human NEU2 transiently transfected in HEK293T cells by fluorimetric analysis
Inhibition of human NEU2 transiently transfected in HEK293T cells by fluorimetric analysis
|
[PMID: 19450982] |
| HEK-293T | IC50 |
0.06 mM
Compound: 2, Neu5Ac2en, DANA
|
Inhibition of human NEU3 transiently transfected in HEK293T cells by fluorimetric high-performance liquid chromatography
Inhibition of human NEU3 transiently transfected in HEK293T cells by fluorimetric high-performance liquid chromatography
|
[PMID: 19450982] |
| HEK-293T | IC50 |
0.07 mM
Compound: 2, Neu5Ac2en, DANA
|
Inhibition of human NEU4 transiently transfected in HEK293T cells by fluorimetric analysis
Inhibition of human NEU4 transiently transfected in HEK293T cells by fluorimetric analysis
|
[PMID: 19450982] |
| HEK-293T | IC50 |
0.143 mM
Compound: 2, Neu5Ac2en, DANA
|
Inhibition of human NEU1 transiently transfected in HEK293T cells by fluorimetric analysis
Inhibition of human NEU1 transiently transfected in HEK293T cells by fluorimetric analysis
|
[PMID: 19450982] |
| HEK-293T | IC50 |
49 μM
Compound: 1; DANA
|
Inhibition of human CathA-IRES-6His-tagged NEU1 expressed in HEK293T cells using 4MU-NANA as substrate preincubated for 15 mins followed by substrate addition measured after 30 mins by fluorescence based assay
Inhibition of human CathA-IRES-6His-tagged NEU1 expressed in HEK293T cells using 4MU-NANA as substrate preincubated for 15 mins followed by substrate addition measured after 30 mins by fluorescence based assay
|
[PMID: 29425031] |
| HEK-293T | IC50 |
50 μM
Compound: 2; DANA
|
Inhibition of human Neu1 expressed in HEK293T cells using 4MU-Neu5Ac as substrate incubated for 30 mins by HPLC analysis
Inhibition of human Neu1 expressed in HEK293T cells using 4MU-Neu5Ac as substrate incubated for 30 mins by HPLC analysis
|
[PMID: 27095056] |
| HEK-293T | IC50 |
50 μM
Compound: 2; DANA
|
Inhibition of human Neu2 expressed in HEK293T cells using 4MU-Neu5Ac as substrate incubated for 30 mins by HPLC analysis
Inhibition of human Neu2 expressed in HEK293T cells using 4MU-Neu5Ac as substrate incubated for 30 mins by HPLC analysis
|
[PMID: 27095056] |
| HEK-293T | IC50 |
50 μM
Compound: 2; DANA
|
Inhibition of human Neu3 expressed in HEK293T cells using GM3 as substrate incubated for 30 mins by HPLC analysis
Inhibition of human Neu3 expressed in HEK293T cells using GM3 as substrate incubated for 30 mins by HPLC analysis
|
[PMID: 27095056] |
| HEK-293T | IC50 |
50 μM
Compound: 2; DANA
|
Inhibition of human Neu4 expressed in HEK293T cells using 4MU-Neu5Ac as substrate incubated for 30 mins by HPLC analysis
Inhibition of human Neu4 expressed in HEK293T cells using 4MU-Neu5Ac as substrate incubated for 30 mins by HPLC analysis
|
[PMID: 27095056] |
| HEK-293T | IC50 |
50 μM
Compound: 2; DANA
|
Inhibition of human Neu4 expressed in HEK293T cells using GM3 as substrate incubated for 30 mins by HPLC analysis
Inhibition of human Neu4 expressed in HEK293T cells using GM3 as substrate incubated for 30 mins by HPLC analysis
|
[PMID: 27095056] |
In Vitro
N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid (Neu5Ac2en) (10-100 μM) signifcantly inhibits sialidase activity in INS-1D cells[4].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
In Vivo
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
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Animal Model:Mice (Mouse model of pulmonary fibrosis)[3]
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Dosage:10 mg/kg
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Administration:I.p.; daily (starting at day 10 after Bleomycin, and then euthanized at day 21)
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Result:Inhibition of sialidases starting at day 10 after bleomycin attenuates fibrosis.
Clinical Trial
| NCT Number | Sponsor | Condition | Start Date |
Phase
|
|---|---|---|---|---|
| NCT01329991 | Plexxikon| | 2011-05 | PHASE1 |
Chemical Information
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CAS No. 24967-27-9
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Appearance Solid
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Molecular Weight 291.25
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Formula C11H17NO8
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Color White to off-white
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SMILES
OC[C@@H](O)[C@H]([C@@]1([H])[C@@H]([C@H](C=C(O1)C(O)=O)O)NC(C)=O)O
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Synonyms
Neu5Ac2en; DANA
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Shipping
Room temperature in continental US; may vary elsewhere.
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Storage
Powder -20°C 3 years In solvent -80°C 6 months -20°C 1 month
Publications (4)
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Journal Impact Factor
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Most Recent
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Cancer Res
Targeting Sialylation Enhances the Therapeutic Efficacy of the Nectin-4-Targeted Antibody-Drug Conjugate Enfortumab Vedotin in Bladder Cancer. [Abstract]2025 Oct 9. PMID: 41066596
2,3-Dehydro-2-deoxy-N-acetylneuraminic acid purchased from MedChemExpress. Usage Cited in: Cancer Res. 2025 Oct 9. [Abstract]
Coimmunoprecipitation assays were performed to explore the Ub levels of exogenous Flag-tagged Nectin-4 in KU-19-19 cells with or without transfection of HA-tagged Ub and the treatment of MG132 (10 μmol/L), 2,3-Dehydro-2-deoxy-N-acetylneuraminic acid (Neu5Ac2en) (80 μmol/L), or P-3Fax-Neu5Ac (200 μmol/L). The expression and Ub levels of Flag-tagged Nectin-4 were detected by Western blot. All cell samples were treated with MG132 (10 μmol/L) before collecting cells. The results showed that after the addition of Neu5Ac2en to inhibit neuraminidases and enhance sialylation in bladder cancer cells, there was an increase in the ubiquitination levels of exogenous Nectin-4.
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J Cachexia Sarcopenia Muscle
Lactate promotes myogenesis via activating H3K9 lactylation-dependent up-regulation of Neu2 expression. [Abstract]2023 Dec;14(6):2851-2865. PMID: 37919243
2,3-Dehydro-2-deoxy-N-acetylneuraminic acid purchased from MedChemExpress. Usage Cited in: J Cachexia Sarcopenia Muscle. 2023 Dec;14(6):2851-2865. [Abstract]
After inhibit Neu2 function by 2,3-Dehydro-2-deoxy-N-acetylneuraminic acid (DANA, 50 μM), then cultured with 15 mM lactate and differentiation for 3 days. Then detected MyHC protein level by western blot. The results showed that DANA diminished MyHC protein expression despite lactate treatment.
2,3-Dehydro-2-deoxy-N-acetylneuraminic acid purchased from MedChemExpress. Usage Cited in: J Cachexia Sarcopenia Muscle. 2023 Dec;14(6):2851-2865. [Abstract]
Representative photographs of MyHC, immunofluorescence staining in C2C12 cells differentiated for 3 days under L-lactate (10 mM) and 2,3-Dehydro-2-deoxy-N-acetylneuraminic acid (DANA, 50 μM) treatment. The results showed that the growing number of myotubes induced by lactate treatment was decreased in the presence of DAN. Scale bar = 100 μm.
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Thromb Haemost
Fc-dependent and -independent Platelet Clearance Caused by Anti-CD36 IgG1 and IgG2 Subclasses. [Abstract]2026 Jan 29. PMID: 41610876 -
bioRxiv
Oseltamivir (Tamiflu), a Commonly Prescribed Antiviral Drug, Mitigates Hearing Loss in Mice. [Abstract]2024 May 8:2024.05.06.592815. PMID: 38765999
Solvent & Solubility
In Vitro:
H2O : 33.33 mg/mL (114.44 mM; Need ultrasonic)
DMSO : 1 mg/mL (3.43 mM; Need ultrasonic and warming; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.
Concentration (start) × Volume (start) = Concentration (final) × Volume (final)
Purity & Documentation
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Data Sheet (277 KB)
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SDS (252 KB)
- English - EN (252 KB)
- Français - FR (252 KB)
- Deutsch - DE (252 KB)
- Norwegian - NO (252 KB)
- Español - ES (252 KB)
- Swedish - SV (252 KB)
- Italian - IT (252 KB)
- Korean - KR (252 KB)
- Portuguese - PT (252 KB)
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Handling Instructions (2659 KB)
References
[1]. Magesh S, et al. 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. [Content Brief]
[2]. Xiao A, et al. Sialidase-catalyzed one-pot multienzyme (OPME) synthesis of sialidase transition-state analogue inhibitors. ACS Catal. 2018;8(1):43-47. [Content Brief]
[3]. Karhadkar TR, et al. Sialidase inhibitors attenuate pulmonary fibrosis in a mouse model. Sci Rep. 2017;7(1):15069. Published 2017 Nov 8. [Content Brief]
[4]. Minami A, et al. 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. [Content Brief]
Complete Stock Solution Preparation Table
Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 6 months; -20°C, 1 month. When stored at -80°C, please use it within 6 months. When stored at -20°C, please use it within 1 month.
| Optional Solvent | Concentration Solvent Mass | 1 mg | 5 mg | 10 mg | 25 mg |
|---|---|---|---|---|---|
| DMSO / H2O | 1 mM | 3.4335 mL | 17.1674 mL | 34.3348 mL | 85.8369 mL |
| H2O | 5 mM | 0.6867 mL | 3.4335 mL | 6.8670 mL | 17.1674 mL |
| 10 mM | 0.3433 mL | 1.7167 mL | 3.4335 mL | 8.5837 mL | |
| 15 mM | 0.2289 mL | 1.1445 mL | 2.2890 mL | 5.7225 mL | |
| 20 mM | 0.1717 mL | 0.8584 mL | 1.7167 mL | 4.2918 mL | |
| 25 mM | 0.1373 mL | 0.6867 mL | 1.3734 mL | 3.4335 mL | |
| 30 mM | 0.1144 mL | 0.5722 mL | 1.1445 mL | 2.8612 mL | |
| 40 mM | 0.0858 mL | 0.4292 mL | 0.8584 mL | 2.1459 mL | |
| 50 mM | 0.0687 mL | 0.3433 mL | 0.6867 mL | 1.7167 mL | |
| 60 mM | 0.0572 mL | 0.2861 mL | 0.5722 mL | 1.4306 mL | |
| 80 mM | 0.0429 mL | 0.2146 mL | 0.4292 mL | 1.0730 mL | |
| 100 mM | 0.0343 mL | 0.1717 mL | 0.3433 mL | 0.8584 mL |
* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.