Kukoamine A

Base Information

• Chemical Name: Kukoamine A
• CAS No.: 75288-96-9
• Molecular Formula: C28H42 N4 O6
• Molecular Weight: 530.665
• UNII: 9YM64FBW2R
• DSSTox Substance ID: DTXSID401318256
• Nikkaji Number: J11.311E
• Wikipedia: Kukoamine A
• Wikidata: Q27155166
• Metabolomics Workbench ID: 143494
• ChEMBL ID: CHEMBL79129
• Mol file: 75288-96-9.mol

Synonyms:kukoamine A;N(1),N(12)-bis(dihydrocaffeoyl)spermine

Chemical Property of Kukoamine A

Chemical Property:

• Boiling Point: 872.1±65.0 °C(Predicted)
• PKA: 9.48±0.10(Predicted)
• PSA: 163.18000
• Density: 1.213±0.06 g/cm3 (20 ºC 760 Torr)
• LogP: 3.61000
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 19
• Exact Mass: 530.31043507
• Heavy Atom Count: 38
• Complexity: 601

Purity/Quality:

≥98% ^*data from raw suppliers

Kukoamine A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1CCC(=O)NCCCNCCCCNCCCNC(=O)CCC2=CC(=C(C=C2)O)O)O)O
• Description: Kukoamine A is a spermine alkaloid originally isolated from L. chinense that has diverse biological activities, including anticancer, neuroprotective, and anti-inflammatory properties. Kukoamine A (5-20 μg/ml) inhibits colony formation of U251 and WJ1 glioblastoma cells in a concentration-dependent manner. It halts the cell cycle at the G0/G1 phase and induces apoptosis when used at concentrations of 60 and 80 μg/ml. Kukoamine A (20 and 40 μM) induces autophagy and increases cell viability in an SH-SY5Y cell model of MPP-induced injury. It increases the number of dopamine neurons in the substantia nigra and striatum, decreases α-synuclein expression, and improves motor function in an MPTP mouse model of Parkinson’s disease when administered at a dose of 20 mg/kg per day. Kukoamine A (10 and 20 mg/kg) decreases IL-1β, TNF-α, and COX-2 protein levels in the hippocampus and increases hippocampal neurogenesis in a rat model of radiation injury. It also selectively inhibits trypanothione reductase (Ki = 1.8 μM), an enzyme that protects certain parasites from oxidative stress, over human glutathione reductase (Ki = >10 mM).
• Uses: Kukoamine A is a neuroprotective agent which is used to prevent the loss of dopaminergic neurons in substantia nigra.

Technology Process of Kukoamine A

There total 19 articles about Kukoamine A which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

3-Benzo[1,3]dioxol-5-yl-N-(3-{4-[3-(3-benzo[1,3]dioxol-5-yl-propionylamino)-propylamino]-butylamino}-propyl)-propionamide (77485-31-5) → kukoamine A (75288-96-9)

Guidance literature:

With boron trichloride; In dichloromethane; for 18h; from 0 deg C to room temperature;

DOI:10.1016/0040-4039(81)80030-5

Reference yield: 82.0%

(E)-N-(3-{Benzyl-[4-(benzyl-{3-[(E)-3-(3,4-bis-benzyloxy-phenyl)-acryloylamino]-propyl}-amino)-butyl]-amino}-propyl)-3-(3,4-bis-benzyloxy-phenyl)-acrylamide → kukoamine A (75288-96-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; ethyl acetate; for 24h; Ambient temperature;

DOI:10.1016/S0040-4039(98)00940-X

Reference yield: 40.0%

C56H62N4O6 → kukoamine A (75288-96-9)

Guidance literature:

With palladium on activated charcoal; hydrogen; acetic acid; In methanol; at 20 ℃; for 6h;

upstream raw materials:

3-Benzo[1,3]dioxol-5-yl-N-(3-{4-[3-(3-benzo[1,3]dioxol-5-yl-propionylamino)-propylamino]-butylamino}-propyl)-propionamide

dihydrocaffeic acid

[4-({(4-{tert-Butoxycarbonyl-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-amino}-butyl)-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propyl]-carbamoyloxy}-methyl)-phenoxy]-acetic acid

Spermine