N-acetyl-2,3-didehydro-2-deoxyneuraminic acid

Names

[ Name ]:
N-acetyl-2,3-didehydro-2-deoxyneuraminic acid

[Synonym ]:
5-acetamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galactonon-2-enonic acid
2,3,4-TRIMETHYL-3-PENTANOL
5-acetamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enoic acid
N-acetyl-2,3-didehydro-2-deoxyneuraminic acid
1,3-DEHYDRO-2-DEOXY-N-ACETYLNEURAMINIC ACID
2,3-DEHYDRO-2-DEOXY-N-ACETYLNEURAMINIC ACID
2,3-Dehydro-2-deoxy-N-acetylneuraminic AcidDANA
MFCD00057470
N-Acetyl-2,3-dehydro-2-deoxyneuraminic acid
2,3-didehydro-2-deoxy-N-acetylneuraminic acid
2-deoxy-2,3-dehydro-n-acetylneuraminicacid
EINECS 246-550-7

Biological Activity

[Description]:

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[1][2].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> Influenza Virus

Research Areas >> Infection

[In Vitro]

N-acetyl-2,3-dehydro-2-Deoxyneuraminic Acid (Neu5Ac2en) (10-100 μM) signifcantly inhibits sialidase activity in INS-1D cells[4].

[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]. 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.

[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.

Chemical & Physical Properties

[ Density]:
1.58g/cm3

[ Boiling Point ]:
773.4ºC at 760 mmHg

[ Melting Point ]:
227-228ºC

[ Molecular Formula ]:
C₁₁H₁₇NO₈

[ Molecular Weight ]:
291.25500

[ Flash Point ]:
421.6ºC

[ Exact Mass ]:
291.09500

[ PSA ]:
156.55000

[ Vapour Pressure ]:
1.27E-27mmHg at 25°C

[ Index of Refraction ]:
1.612

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Safety Phrases ]:
22-24/25

[ RIDADR ]:
NONH for all modes of transport

Precursor & DownStream

Precursor

DownStream

Articles

Chemistry, metabolism, and biological functions of sialic acids.

Adv. Carbohydr. Chem. Biochem. 40 , 131, (1982)

Identification of selective inhibitors for human neuraminidase isoenzymes using C4,C7-modified 2-deoxy-2,3-didehydro-N-acetylneuraminic acid (DANA) analogues.

J. Med. Chem. 56(7) , 2948-58, (2013)

In the past two decades, human neuraminidases (human sialidases, hNEUs) have been found to be involved in numerous pathways in biology. The development of selective and potent inhibitors of these enzy...

Elastin-derived peptides are new regulators of insulin resistance development in mice.

Diabetes 62(11) , 3807-16, (2013)

Although it has long been established that the extracellular matrix acts as a mechanical support, its degradation products, which mainly accumulate during aging, have also been demonstrated to play an...