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> N-Acetylneuraminic acid [131-48-6]

N-Acetylneuraminic acid [131-48-6]

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N-Acetylneuraminic acid (NANA; Lactaminic acid), a nonphenolic structure, is the predominant form of sialic from Collocalia esculenta. N-Acetylneuraminic acid plays a biological role in myocardial injury, melanoma and viral or bacterial infection. N-Acetylneuraminic acid inhibits melanogenesis by reducing tyrosinase activity and triggers myocardial injury in vitro and in vivo by activation of the Rho/Rho-associated signaling pathway through binding to RhoA and Cdc42. N-Acetylneuraminic acid may prevent high fat diet (HFD)-induced inflammation and oxidative stress, thereby prevents hyperlipidemia-associated inflammation and oxidative stress. N-Acetylneuraminic acid is promising for research in the field of melanoma, coronary artery, obesity-related diseases and hyperlipidemia.

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N-Acetylneuraminic acid Estructura química

N-Acetylneuraminic acid Estructura química

No. CAS : 131-48-6

This product is a controlled substance and not for sale in your territory.

Based on 3 publication(s) in Google Scholar

Other Forms of N-Acetylneuraminic acid:

  • N-Acetylneuraminic acid-13C Obtener un presupuesto
  • N-Acetylneuraminic acid-13C-1 Obtener un presupuesto
  • N-Acetylneuraminic acid-13C-2 Obtener un presupuesto
  • N-Acetylneuraminic acid-13C-3 Obtener un presupuesto

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Descripciòn

N-Acetylneuraminic acid (NANA; Lactaminic acid), a nonphenolic structure, is the predominant form of sialic from Collocalia esculenta. N-Acetylneuraminic acid plays a biological role in myocardial injury, melanoma and viral or bacterial infection. N-Acetylneuraminic acid inhibits melanogenesis by reducing tyrosinase activity and triggers myocardial injury in vitro and in vivo by activation of the Rho/Rho-associated signaling pathway through binding to RhoA and Cdc42. N-Acetylneuraminic acid may prevent high fat diet (HFD)-induced inflammation and oxidative stress, thereby prevents hyperlipidemia-associated inflammation and oxidative stress. N-Acetylneuraminic acid is promising for research in the field of melanoma, coronary artery, obesity-related diseases and hyperlipidemia[1][2][3][4][5].

IC50 & Target

Microbial Metabolite

 

Human Endogenous Metabolite

 

In Vitro

N-Acetylneuraminic acid (0 - 2 mg/mL, 2 days) has no effect on cell proliferation, but significantly decreases tyrosinase protein level, the number of melanosomes, p62 protein level and increases CCT3, CCT5, LC3-II protein level mRNA levels in B16 melanoma cells[1].
N-Acetylneuraminic acid (0 - 500 μM, 12 h) specifically binds to RhoA and Cdc42 and activates Rho/ROCK-JNK/ERK signaling in cardiomyocytes[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

N-Acetylneuraminic acid Related Antibodies

Immunofluorescence[1]

Cell Line: B16 melanoma cells
Concentration: 0 - 2 mg/mL
Incubation Time: 2 days
Result: Was colocalized in the presence of tyrosinase, LAMP-1 and cathepsin L2 at 1 and 2 mg/mL concentrations and reduced p62 levels in B16 melanoma cells.

Real Time qPCR[1]

Cell Line: B16 melanoma cells
Concentration: 0 - 2 mg/mL
Incubation Time: 2 days
Result: Significantly decreased tyrosinase protein level in a concentration-dependent manner and increased CCT3 and CCT5 mRNA levels in B16 melanoma cells.

Western Blot Analysis[1]

Cell Line: B16 melanoma cells
Concentration: 0 - 2 mg/mL
Incubation Time: 2 days
Result: Significantly increased the LC3-II protein level and decreased the p62 protein level at 1 and 2 mg/mL in B16 melanoma cells.

Cell Viability Assay[2]

Cell Line: Neonatal rat ventricular myocytes (NRVMs)
Concentration: 0.05 - 5 mM
Incubation Time: 12 h
Result: Decreased the NRVMs cells viability and increased the release of lactate dehydrogenase and creatine kinase-MB.

Western Blot Analysis[2]

Cell Line: NRVMs cells
Concentration: 0 - 500 μM
Incubation Time: 12 h
Result: Induced significant increase and activation in RhoA and Cdc42, also enhanced the phosphorylation of JNK and ERK in NRVMs cells.
In Vivo

N-Acetylneuraminic acid (0 - 20 mg/kg, i.p., twice a day for 6 weeks) triggers myocardial injury in healthy rats[2].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model: Healthy rats[2]
Dosage: 0 - 20 mg/kg
Administration: i.p., twice a day for 6 weeks
Result: Increased left ventricular end-diastolic pressure, -dP/dtmax and dp/dtmax, but showed no significant effects on left ventricular systolic pressure in rats.
Peso molecular

309.27

Fòrmula

C11H19NO9
No. CAS

131-48-6
Appearance

Solid

Color

White to off-white

SMILES

OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](NC(C)=O)[C@@H](O)CC(C(O)=O)=O
Structure Classification
  • Saccharides
  • Monosaccharides
Initial Source
  • Microorganisms
  • Endogenous metabolite
Envío

Room temperature in continental US; may vary elsewhere.
Almacenamiento

-20°C, stored under nitrogen

*In solvent : -80°C, 6 months; -20°C, 1 month (stored under nitrogen)

Solvente y solubilidad
In Vitro: 

H2O : 125 mg/mL (404.18 mM; Need ultrasonic)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 3.2334 mL 16.1671 mL 32.3342 mL
5 mM 0.6467 mL 3.2334 mL 6.4668 mL
View the 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 (stored under nitrogen). 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.

  • Calculadora de molaridad

  • Calculadora de dilución

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

Mass
=
Concentration
×
Volume
×
Molecular Weight *

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

Concentration (start)

C1

×
Volume (start)

V1

=
Concentration (final)

C2

×
Volume (final)

V2

In Vivo:

For the following dissolution methods, please prepare the working solution directly. It is recommended to prepare fresh solutions and use them promptly within a short period of time.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

  • Protocol 1

    Add each solvent one by one:  PBS

    Solubility: 100 mg/mL (323.34 mM); Clear solution; Need ultrasonic and warming and heat to 60°C

In Vivo Dissolution Calculator
Please enter the basic information of animal experiments:

Dosage

mg/kg

Animal weight
(per animal)

g

Dosing volume
(per animal)

μL

Number of animals

Recommended: Prepare an additional quantity of animals to account for potential losses during experiments.
Calculation results:
Working solution concentration: mg/mL
This product has good water solubility, please refer to the measured solubility data in water/PBS/Saline for details.
The concentration of the stock solution you require exceeds the measured solubility. The following solution is for reference only.If necessary, please contact MedChemExpress (MCE).
Pureza y Documentación

Purity: 99.90%

COA (247 KB) HNMR (260 KB) RP-HPLC (215 KB) LCMS (89 KB)

Instrucciones de manejo (2659 KB)
Referencias

  • [1]. Yoshikawa, K., et al. N-Acetylneuraminic Acid Inhibits Melanogenesis via Induction of Autophagy[J]. Cosmetics 2024, 11, 82.

    [2]. Zhang L, et al. Functional Metabolomics Characterizes a Key Role for N-Acetylneuraminic Acid in Coronary Artery Diseases[J]. Circulation. 2018 Mar 27;137(13):1374-1390.  [Content Brief]

    [3]. Yida Z, et al. High fat diet-induced inflammation and oxidative stress are attenuated by N-acetylneuraminic acid in rats[J]. J Biomed Sci. 2015 Oct 24;22:96.  [Content Brief]

    [4]. Kiefel MJ, et al. Synthesis and biological evaluation of N-acetylneuraminic acid-based rotavirus inhibitors[J]. J Med Chem. 1996 Mar 15;39(6):1314-20.  [Content Brief]

  • [1]. Yoshikawa, K., et al. N-Acetylneuraminic Acid Inhibits Melanogenesis via Induction of Autophagy[J]. Cosmetics 2024, 11, 82.

    [2]. Zhang L, et al. Functional Metabolomics Characterizes a Key Role for N-Acetylneuraminic Acid in Coronary Artery Diseases[J]. Circulation. 2018 Mar 27;137(13):1374-1390.

    [3]. Yida Z, et al. High fat diet-induced inflammation and oxidative stress are attenuated by N-acetylneuraminic acid in rats[J]. J Biomed Sci. 2015 Oct 24;22:96.

    [4]. Kiefel MJ, et al. Synthesis and biological evaluation of N-acetylneuraminic acid-based rotavirus inhibitors[J]. J Med Chem. 1996 Mar 15;39(6):1314-20.

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 (stored under nitrogen). 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
H2O 1 mM 3.2334 mL 16.1671 mL 32.3342 mL 80.8355 mL
5 mM 0.6467 mL 3.2334 mL 6.4668 mL 16.1671 mL
10 mM 0.3233 mL 1.6167 mL 3.2334 mL 8.0836 mL
15 mM 0.2156 mL 1.0778 mL 2.1556 mL 5.3890 mL
20 mM 0.1617 mL 0.8084 mL 1.6167 mL 4.0418 mL
25 mM 0.1293 mL 0.6467 mL 1.2934 mL 3.2334 mL
30 mM 0.1078 mL 0.5389 mL 1.0778 mL 2.6945 mL
40 mM 0.0808 mL 0.4042 mL 0.8084 mL 2.0209 mL
50 mM 0.0647 mL 0.3233 mL 0.6467 mL 1.6167 mL
60 mM 0.0539 mL 0.2695 mL 0.5389 mL 1.3473 mL
80 mM 0.0404 mL 0.2021 mL 0.4042 mL 1.0104 mL
100 mM 0.0323 mL 0.1617 mL 0.3233 mL 0.8084 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.

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N-Acetylneuraminic acid Related Classifications

  • Inflammation/Immunology Cardiovascular Disease Cancer
  • Cancer Targeted Therapy Cancer Immunotherapy Cancer Metabolism and Metastasis
  • MAPK/ERK Pathway GPCR/G Protein Anti-infection Metabolic Enzyme/Protease
  • Tyrosinase Ras Influenza Virus Endogenous Metabolite
Help & FAQs

Keywords:

N-Acetylneuraminic acid131-48-6NANA Lactaminic acidTyrosinaseRasInfluenza VirusEndogenous Metabolitesialicmelanogenesismyocardial injuryviral or bacterial infectionRhoACdc42melanomacoronary artery diseasesobesity-related diseasesinflammationoxidative stressInhibitorinhibitorinhibit

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