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SML1686

Sigma-Aldrich

Neoseptin-3

≥98% (HPLC)

Synonym(s):

(αS)-α-[[4-Amino-3-[2-(4-hydroxyphenyl)ethyl]benzoyl]amino]-benzenebutanoic acid 1,1-dimethylethyl ester

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About This Item

Empirical Formula (Hill Notation):
C29H34N2O4
CAS Number:
1622863-21-1
Molecular Weight:
474.59
UNSPSC Code:
12352200
PubChem Substance ID:
329826015
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

optical activity

[α]/D 37 to 45°, c = 0.1 in chloroform

color

white to beige

solubility

DMSO: 15 mg/mL, clear

storage temp.

−20°C

SMILES string

NC1=CC=C(C(N[C@@H](CCC2=CC=CC=C2)C(OC(C)(C)C)=O)=O)C=C1CCC3=CC=C(O)C=C3

Biochem/physiol Actions

Neoseptin-3 is a highly efficacious and specific agonist of the mouse TLR4 (mTLR4)/myeloid differentiation factor 2 (MD-2) complex. Neoseptin-3 binds to MD2, changes the conformation of MD-2 and facilitates active TLR4/MD-2 dimer formation. Neoseptin-3 exhibits no structural similarity to lipid A.
Neoseptin-3 stimulates the activity of mouse TLR4 (mTLR4)/myeloid differentiation factor 2 (mTLR) independently of CD14 (cluster of differentiation 14). This activated mTLR4/ mTLR promotes canonical myeloid differentiation primary response gene 88 (MyD88) and toll-interleukin(IL) 1 receptor (TIR) domain-containing adaptor inducing interferon (IFN)-β (TRIF)-dependent signaling. In addition, neoseptin-3 also stimulates tumor necrosis factor α (TNF-α), IL-6 and IFNβ production in a dose-dependent manner.

Hazard Statements

H413

Precautionary Statements

P273 - P501

Hazard Classifications

Aquatic Chronic 4

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Ying Wang et al.
Proceedings of the National Academy of Sciences of the United States of America, 113(7), E884-E893 (2016-02-03)
Structurally disparate molecules reportedly engage and activate Toll-like receptor (TLR) 4 and other TLRs, yet the interactions that mediate binding and activation by dissimilar ligands remain unknown. We describe Neoseptins, chemically synthesized peptidomimetics that bear no structural similarity to the

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