kukoamine A Chemical Properties

Boiling point:

872.1±65.0 °C(Predicted)

Density 

1.213±0.06 g/cm3 (20 ºC 760 Torr)

storage temp. 

Store at -20°C

solubility 

DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 30 mg/ml; PBS (pH 7.2): 10 mg/ml

form 

A crystalline solid

pka

9.48±0.10(Predicted)

color 

Off-white to yellow

InChIKey

IOLDDENZPBFBHV-UHFFFAOYSA-N

SMILES

C(NCCCNC(=O)CCC1=CC=C(O)C(O)=C1)CCCNCCCNC(=O)CCC1=CC=C(O)C(O)=C1

CAS DataBase Reference

75288-96-9

kukoamine A Usage And Synthesis

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 (K_i = 1.8 μM), an enzyme that protects certain parasites from oxidative stress, over human glutathione reductase (K_i = >10 mM).

Chemical Properties

White crystalline powder, soluble in organic solvents such as methanol, ethanol, DMSO, etc., derived from the bark of Lycium bark.

Occurrence

The root bark of Lychium chinense yields this alkaloid. Kukoamine A possesses hypotensive activity inducing hypotension in rats at a dose of 5 mg/kg when given intravenously.

Uses

Kukoamine A is a neuroprotective agent which is used to prevent the loss of dopaminergic neurons in substantia nigra.

Definition

ChEBI: Kukoamine A is an amine.

IC 50

Trypanosoma

References

[1] SHINJI FUNAYAMA. Structure of kukoamine A, a hypotensive principle of Lycium chinense root barks1[J]. Tetrahedron Letters, 1980, 21 14: Pages 1355-1356. DOI: 10.1016/s0040-4039(00)74574-6
[2] QIAOPING WANG. Kukoamine A inhibits human glioblastoma cell growth and migration through apoptosis induction and epithelial-mesenchymal transition attenuation[J]. Scientific Reports, 2016, 6 1. DOI: 10.1038/srep36543
[3] XIAOLONG HU . Neuroprotective effects of Kukoamine A on neurotoxin-induced Parkinson’s model through apoptosis inhibition and autophagy enhancement[J]. Neuropharmacology, 2017, 117: Pages 352-363. DOI: 10.1016/j.neuropharm.2017.02.022
[4] YAQIONG ZHANG. Kukoamine A Prevents Radiation-Induced Neuroinflammation and Preserves Hippocampal Neurogenesis in Rats by Inhibiting Activation of NF-κB and AP-1[J]. Neurotoxicity Research, 2016, 31 1: 259-268. DOI: 10.1007/s12640-016-9679-4
[5] J A PONASIK. Kukoamine A and other hydrophobic acylpolyamines: potent and selective inhibitors of Crithidia fasciculata trypanothione reductase.[J]. Biochemical Journal, 1995, 311 ( Pt 2): 371-375. DOI: 10.1042/bj3110371

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