Lacto-N-neotetraose

Names

[ Name ]:
Lacto-N-neotetraose

[Synonym ]:
LACTO-N-NEOTETRAOSE
Lacto-N-neo-tetraose
beta-D-Gal-(1->4)-beta-D-GlcNAc-(1->3)-beta-D-Gal-(1->4)-D-Glc

Biological Activity

[Description]:

Lacto-N-neotetraose (LNnT) is an endogenous metabolite. Lacto-N-neotetraose can inhibit TNF-α induced IL-8 secretion in immature epithelial cells. Lacto-N-neotetraose has anti-inflammatory avtivity, and can improve the wound closure[1][2][4].

[Related Catalog]:

Research Areas >> Inflammation/Immunology

[Target]

Endogenous Metabolite[1], TNFR1[2].

[In Vitro]

Lacto-N-neotetraose (5 mg/mL, 24 h) induces IL-8 secretion in T84 cells[2]. Lacto-N-neotetraose (5 mg/mL, 24 h) reduces TNF-α induced IL-8-secretion with 38% in FHs 74 Int cells[2]. Lacto-N-neotetraose binds TNFR1 (Tumor necrosis factor receptor 1) with a Kd value of 900 ± 660 nM[2]. Lacto-N-neotetraose (5 mg/mL, 24 h) attenuates TNF-α induced inflammation by TNFR1 ectodomain shedding in FHs 74 Int cells[2].

[In Vivo]

Lacto-N-neotetraose (100 μM, intratracheal administration for 24 h) reduces the abundance of Streptococcus pneumonia in the lungs of pneumonia rabbits[3]. Lacto-N-neotetraose (100/200 μg, Intradermal injection, at 3, 7, 14, and 21 days post-surgery) increases the wound closure rate on day 7 post-wounding[4]. Animal Model: Rabbit model of pneumonia[3] Dosage: 100 μM Administration: Intratracheal administration for 24 h Result: Decreased by ~2 logs the bacterial load in the lung at 48 h after challenge. Eliminated the extensive, edematous right middle lobe lesion evident at 48 h in control animals. Animal Model: Mice with symmetric full-thickness wounds Dosage: 100, 200 μg Administration: Intradermal injection, at 3, 7, 14, and 21 days post-surgery. Result: Exhibited better healing score, follicle formation, and lower epidermal thickness index (H&E staining).

[References]

[1]. Xiaomin Dong, et al. CRISPRi-Guided Multiplexed Fine-Tuning of Metabolic Flux for Enhanced Lacto- N-neotetraose Production in Bacillus subtilis. J Agric Food Chem. 2020 Feb 26;68(8):2477-2484.

[2]. Lianghui Cheng, et al. The Human Milk Oligosaccharides 3-FL, Lacto-N-Neotetraose, and LDFT Attenuate Tumor Necrosis Factor-α Induced Inflammation in Fetal Intestinal Epithelial Cells In Vitro through Shedding or Interacting with Tumor Necrosis Factor Receptor 1. Mol Nutr Food Res. 2021 Apr;65(7):e2000425.

[3]. I Idänpään-Heikkilä, et al. Oligosaccharides interfere with the establishment and progression of experimental pneumococcal pneumonia. J Infect Dis. 1997 Sep;176(3):704-12.

[4]. Behrouz Farhadihosseinabadi, et al. The in vivo effect of Lacto-N-neotetraose (LNnT) on the expression of type 2 immune response involved genes in the wound healing process. Sci Rep. 2020 Jan 22;10(1):997.

Chemical & Physical Properties

[ Density]:
1.72g/cm3

[ Boiling Point ]:
1173.6ºC at 760mmHg

[ Molecular Formula ]:
C₂₆H₄₅NO₂₁

[ Molecular Weight ]:
707.63000

[ Flash Point ]:
663.6ºC

[ Exact Mass ]:
707.24800

[ PSA ]:
356.70000

[ Vapour Pressure ]:
0mmHg at 25°C

[ Index of Refraction ]:
1.668

[ Storage condition ]:
2-8°C

Safety Information

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

Articles

Chemo-enzymatic supported synthesis of the 3-sulfated Lewis a pentasaccharide on a multimeric polyethylene glycol.

Carbohydr. Res. 343(5) , 970-6, (2008)

The 3-sulfated Lewis(a) pentasaccharide was synthesized on multimeric-based polyethylene glycol support. Coupling of O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-(1-->3)-4,6-di-O-acetyl-2-deoxy-...

Enhanced factor H binding to sialylated Gonococci is restricted to the sialylated lacto-N-neotetraose lipooligosaccharide species: implications for serum resistance and evidence for a bifunctional lipooligosaccharide sialyltransferase in Gonococci.

Infect. Immun. 73(11) , 7390-7, (2005)

We isolated serologically identical (by serovar determination and porin variable region [VR] typing) strains of Neisseria gonorrhoeae from an infected male and two of his monogamous female sex partner...

Syntheses of a series of lacto-N-neotetraose clusters using a carbosilane dendrimer scaffold.

Carbohydr. Res. 341(4) , 467-73, (2006)

4-Pentenyl (2,3,4,6-tetra-O-acetyl-beta-d-galactopyranosyl)-(1-->4)-(3,6-di-O-acetyl-2-deoxy-2-phthalimido-beta-d-glucopyranosyl)-(1-->3)-(2,6-di-O-benzoyl-beta-d-galactopyranosyl)-(1-->4)-2,3,6-tri-O...

Related Compounds

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