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SML1443

Sigma-Aldrich

L48H37

≥98% (HPLC)

Sinônimo(s):

(3E,5E)-1-ethyl-3,5-bis[(2,3,4-trimethoxyphenyl)methylidene]piperidin-4-one, 1-Ethyl-3,5-bis(3,4,5-trimethoxybenzylidene)piperidin-4-one, 1-Ethyl-3,5-bis[(2,3,4-trimethoxyphenyl)methylene]-4-piperidinone

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About This Item

Fórmula empírica (Notação de Hill):
C27H33NO7
Número CAS:
Peso molecular:
483.55
Código UNSPSC:
12352200
ID de substância PubChem:
NACRES:
NA.77

Nível de qualidade

Ensaio

≥98% (HPLC)

forma

powder

cor

white to beige

solubilidade

DMSO: 2 mg/mL, clear (warmed)

temperatura de armazenamento

2-8°C

cadeia de caracteres SMILES

O=C(/C(CN(CC)C/1)=C/C2=C(OC)C(OC)=C(OC)C=C2)C1=C\C3=CC=C(OC)C(OC)=C3OC

InChI

1S/C27H33NO7/c1-8-28-15-19(13-17-9-11-21(30-2)26(34-6)24(17)32-4)23(29)20(16-28)14-18-10-12-22(31-3)27(35-7)25(18)33-5/h9-14H,8,15-16H2,1-7H3/b19-13+,20-14+

chave InChI

XLPNFINERWLGNC-IWGRKNQJSA-N

Aplicação

L48H37 has been used as a myeloid differentiator protein 2 (MD2) antagonist/inhibitor:
  • to investigate intracellular signaling of LPS in signal transduction pathways via endosomic toll-like receptor 4 (TLR4) in colonic epithelium
  • to determine its anti-cancer effects in pancreatic ductal adenocarcinoma (PDAC)
  • to study its effects on lipopolysaccharide (LPS) and palmitate CC chemokine ligand 2 (CCL2) responses in normal kidney proximal tubule cells

Ações bioquímicas/fisiológicas

L48H37 can stimulate apoptosis and prevent proliferation in pancreatic cancer cells, especially in the absence of histone-lysine N-methyltransferase 2D (KMT2D). It has an unsaturated monoketone structure, which helps to enhance its stability and anti-cancer effects. L48H37 may possess an anti-neoplastic effect on human pancreatic ductal adenocarcinoma (PDAC) cells.
L48H37 is a potent and chemically stable anti-inflammatory curcumin analog that inhibits LPS-induced inflammation through the myeloid differentiation 2 (MD-2) and toll-like receptor 4 (TLR4) complex. L48H37 is a potent MD2 inhibitor that binds to the hydrophobic region of MD-2 and blocks the interaction between MD2 and LPS. L48H37 significantly improves survival and protected lung injury in LPS-induced septic mice.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable


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Si-Si Li et al.
World journal of gastrointestinal oncology, 11(8), 599-621 (2019-08-23)
Novel therapeutic strategies are urgently needed for patients with a delayed diagnosis of pancreatic ductal adenocarcinoma (PDAC) in order to improve their chances of survival. Recent studies have shown potent anti-neoplastic effects of curcumin and its analogues. In addition, the
Charles C Okechukwu et al.
Peptides, 136, 170436-170436 (2020-11-13)
The renin-angiotensin system (RAS) plays a critical role in the regulation of blood pressure. Inappropriate activation of the RAS, particularly stimulation of the ACE-Ang II-AT1 receptor axis is a key factor in hypertension and AT1R antagonists (ARBs) are first line
Ravi Holani et al.
Gut microbes, 12(1), 1785802-1785802 (2020-07-14)
We hypothesized that the antimicrobial peptide cathelicidin has a physiological role in regulating gut inflammatory homeostasis. We determined that cathelicidin synergizes with LPS to facilitate its internalization and signaling via endosomic TLR4 in colonic epithelium, evoking synthesis of the human

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