[CAS NO. 24967-27-9] 2,3-Dehydro-2-deoxy-N-acetylneuraminicacid
PRODUCTS SPECIFICATIONS [24967-27-9]
DESCRIPTION [24967-27-9]
Overview
| MDL | MFCD00057470 |
|---|---|
| Molecular Weight | 291.25 |
| Molecular Formula | C11H17NO8 |
| SMILES | OC(C1=C[C@H](O)[C@@H](NC(C)=O)[C@@]([C@H](O)[C@H](O)CO)([H])O1)=O |
Summary
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 IC 50 s of 143, 43, 61, and 74 μM for NEU1, NEU2, NEU3, and NEU4, respectively. Anti-influenza virus activity [1] [2] .
In Vitro
N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid (Neu5Ac2en) (10-100 μM) signifcantly inhibits sialidase activity in INS-1D cells [4] .
MCE has not independently confirmed the accuracy of these methods. They are for reference only.
In Vivo
N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid (Neu5Ac2en) (10 mg/kg; i.p.; daily) attenuates pulmonary fibrosis in a mouse model [3] .
MCE has not independently confirmed the accuracy of these methods. They are for reference only.
| Animal Model: | Mice (Mouse model of pulmonary fibrosis) [3] |
| Dosage: | 10 mg/kg |
| Administration: | I.p.; daily (starting at day 10 after Bleomycin, and then euthanized at day 21) |
| Result: | Inhibition of sialidases starting at day 10 after bleomycin attenuates fibrosis. |
Clinical Trial
| NCT Number | Sponsor | Condition | Start Date | Phase |
|---|---|---|---|---|
| NCT02903862 | AnthroTronix, Inc.|Bright Focus Foundation|Mindoula Health Inc.|21st Century Brain Trust|Geoffrey Beene Foundation |
Depression and Burden in Caregivers
|
July 2016 | Not Applicable |
| NCT01728129 | Henry M. Jackson Foundation for the Advancement of Military Medicine|U.S. Army Medical Research and Development Command |
Brain Concussion|Traumatic Brain Injury
|
January 2013 | Not Applicable |
| NCT01728142 | Henry M. Jackson Foundation for the Advancement of Military Medicine|U.S. Army Medical Research and Development Command |
Traumatic Brain Injury|Brain Concussion
|
January 2013 | Not Applicable |
| NCT05143333 | Johns Hopkins University|AnthroTronix, Inc. |
COVID-19
|
July 1, 2021 |
Appearance
Solid
Shipping
Room temperature in continental US; may vary elsewhere.
Storage
| Powder | -20°C | 3 years |
|---|---|---|
| In solvent | -80°C | 6 months |
| -20°C | 1 month |
Solvent & Solubility
H 2 O : 33.33 mg/mL ( 114.44 mM ; Need ultrasonic)
Stock Solutions
| Concentration Solvent Mass | 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 |
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.
- [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.
- [3] Karhadkar TR, et al. Sialidase inhibitors attenuate pulmonary fibrosis in a mouse model. Sci Rep. 2017;7(1):15069. Published 2017 Nov 8.
- [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.
Synonyms
