TML-6 - ≥99% , CAS No.1462868-88-7

CAS: 1462868-88-7 Cat. No.: T646596 Molecular Weight: 523.62 PubChem CID: 72705569

GRADE & PURITY ≥99%

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

TML-6, an orally active curcumin derivative, inhibits the synthesis of the β-amyloid precursor protein and β-amyloid (Aβ) . TML-6 can upregulate Apo E, suppress NF-κB and mTOR , and increase the activity of the anti-oxidative Nrf2 gene. TML-6 has the potential for Alzheimer’s disease (AD) research

In Vitro

TML-6 (0.65-5.24 µg/mL; for 24 h) reduces the protein expression levels of APP and phospho-NF-κB, and induces the protein expression level of ApoE. TML-6 inhibits the mTOR signaling pathway through the suppression of phospho-mTOR. TML-6 (0.31, 0.63, 2.5, 5, 10, 20 μM; 24 h) reveals no cytotoxicity in Huh-7 cells at concentrations below 5 μM and has an IC 50 of 4.19 µg/mL (8 μM). TML-6 (1.05, 2.09, 3.14, 4.19 μg/mL; 24 h) reduces the production of Aβ40 and Aβ42 between 1.05, 2.09 and 3.14 μg/mL (equal to 2, 4 and 6 μM) in a dose-dependent manner in N2a/APPswe cell. TML-6 can exhibit transcriptional activation of the Nrf2 gene in a dose-dependent manner, with the highest activity at a concentration of 1.32 µg/mL. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Western Blot AnalysisCell Line: Huh-7 cells Concentration: 0.65, 1.31, 1.96, 2.61, 3.93, 5.24 µg/mL Incubation Time: For 24 hours Result: Reduced the amyloid precursor protein (APP) protein expression level by 60% and decreased the level of phosphorylated NF-κB by about 50% at a dose of 1.96 µg/mL after 24 h treatment. Induced the protein expression level of ApoE by approximately 44% at a dose of 2.62 µg/mL.

In Vivo

TML-6 (diet; 150 mg/kg/day; for four months) treatment results in significant improvement in learning, suppression of the microglial activation marker Iba-1, and reduction in Aβ in the brain . TML-6 (oral; 150 mg/kg) has a T 1/2 of 1.27 hours, a C max of 35.9 ng/mL and an AUC of 177 ng•hr/mL . MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Six-month-old 3xTg (mutations: APP KM670/671NL , MAPT P301L and PSEN1 M146V ) AD transgenic mice Dosage: 150 mg/kg Administration: Diet; daily; for four months Result: Improved the learning behaviors, significantly suppressed the Aβ levels and Iba-1 expression in the brain of 3xTg AD transgenic mice. Animal Model: SD rats Dosage: 150 mg/kg (Pharmacokinetic Analysis) Administration: Oral Result: Had a T 1/2 of 1.27 hours, a C max of 35.9 ng/mL and an AUC of 177 ng•hr/mL.

Form:Solid

IC50& Target:NF-κB mTOR

Specifications

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

TML-6, an orally active curcumin derivative, inhibits the synthesis of the β-amyloid precursor protein and β-amyloid (Aβ) . TML-6 can upregulate Apo E, suppress NF-κB and mTOR , and increase the activity of the anti-oxidative Nrf2 gene. TML-6 has the pote

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥99%

Names and Identifiers

• Canonical Smiles: CCN(CC)C(=O)CC(C)(C(=O)C=CC1=CC(=C(C=C1)OC)OC)C(=O)C=CC2=CC(=C(C=C2)OC)OC
• IUPAC Name: (E)-6-(3,4-dimethoxyphenyl)-3-[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]-N,N-diethyl-3-methyl-4-oxohex-5-enamide
• InChIKey: UWVCYNXVZRDWSD-UNZYHPAISA-N
• INCHI: 1S/C30H37NO7/c1-8-31(9-2)29(34)20-30(3,27(32)16-12-21-10-14-23(35-4)25(18-21)37-6)28(33)17-13-22-11-15-24(36-5)26(19-22)38-7/h10-19H,8-9,20H2,1-7H3/b16-12+,17-13+
• Isomeric SMILES: CCN(C(=O)CC(C(=O)/C=C/C1=CC(=C(C=C1)OC)OC)(C(=O)/C=C/C2=CC(=C(C=C2)OC)OC)C)CC
• PubChem CID: 72705569
• Molecular Weight: 523.62

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Diarylheptanoids
      • Subclass Linear diarylheptanoids

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Diarylheptanoids
• Subclass: Linear diarylheptanoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Curcuminoids
• Alternative Parents: Cinnamic acids and derivatives Dimethoxybenzenes Styrenes Phenoxy compounds Anisoles Alkyl aryl ethers N-acyl amines Tertiary carboxylic acid amides Enones Acryloyl compounds Ketones Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Curcumin - Cinnamic acid or derivatives - Dimethoxybenzene - O-dimethoxybenzene - Phenoxy compound - Phenol ether - Styrene - Anisole - Methoxybenzene - Alkyl aryl ether - Benzenoid - N-acyl-amine - Monocyclic benzene moiety - Tertiary carboxylic acid amide - Acryloyl-group - Alpha,beta-unsaturated ketone - Enone - Ketone - Carboxamide group - Carboxylic acid derivative - Ether - Organic nitrogen compound - Organooxygen compound - Carbonyl group - Hydrocarbon derivative - Organic oxide - Organonitrogen compound - Organic oxygen compound - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as curcuminoids. These are aromatic compounds containing a curcumin moiety, which is composed of two aryl buten-2-one (feruloyl) chromophores joined by a methylene group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: DMSO : 120 mg/mL (229.17 mM; Need ultrasonic)