75288-96-9

Usage

Uses

Used in Neuroprotection:
Kukoamine A is used as a neuroprotective agent for preventing the loss of dopaminergic neurons in the substantia nigra.
Used in Anticancer Applications:
Kukoamine A is used as an anticancer agent, inhibiting 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.
Used in Cell Viability and Autophagy:
Kukoamine A is used to induce autophagy and increase cell viability in an SH-SY5Y cell model of MPP-induced injury.
Used in Parkinson's Disease Treatment:
Kukoamine A is used to increase the number of dopamine neurons in the substantia nigra and striatum, decrease α-synuclein expression, and improve motor function in an MPTP mouse model of Parkinson’s disease when administered at a dose of 20 mg/kg per day.
Used in Anti-inflammatory Applications:
Kukoamine A is used to decrease IL-1β, TNF-α, and COX-2 protein levels in the hippocampus and increase hippocampal neurogenesis in a rat model of radiation injury.
Used in Parasite Infection Treatment:
Kukoamine A is used to selectively inhibit trypanothione reductase (Ki = 1.8 μM), an enzyme that protects certain parasites from oxidative stress, over human glutathione reductase (Ki = >10 mM).
Used in Hypotension:
Kukoamine A is used as a hypotensive agent, inducing hypotension in rats at a dose of 5 mg/kg when given intravenously.

Upstream product

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Relevant academic research and scientific papers

Method for synthesizing kukoamine A and analogue thereof

The invention relates to the technical field of medicines, and relates to a method for synthesizing a natural product kukoamine A and analogue thereof. The method comprises the following steps: (1) performing a nucleophilic reaction on hydroxyl, halogen or C1-C10 alkoxy or C1-C10 alkyl substituted or unsubstituted benzaldehyde and malonic acid to obtain a compound 1; (2) reacting the compound 1 in the step (1) with N-hydroxy succinimide to obtain a compound 2; (3) reacting the compound 2 with spermine to obtain a compound 3; and (4) reacting the compound 3 with hydrogen to reduce carbon-carbon double bond, and purifying. The preparation method is simple, and provides a compound base to pharmacological activity research of compounds with similar structures.

Optimising inhibitors of trypanothione reductase using solid-phase chemistry

A series of inhibitors of the enzyme trypanothione reductase has been identified using directed solid-phase chemistry. The compounds were based on a series of polyamine scaffolds and used the natural product kukoamine A as the lead structure. A compound with a K(i) of 76 nM was identified, although somewhat surprisingly the compound appeared to be noncompetitive in nature. (C) 2000 Elsevier Science Ltd.

The synthesis of symmetrical spermine conjugates using solid-phase chemistry

The utility of spermine, selectively functionalised and immobilised on a solid support by means of the Wang 'oxycarbonyl' linker is demonstrated by the solid-phase synthesis of a number of spermine conjugates including the natural product and potent antihypertensive agent kukoamine. The synthesis opens up the area of solid-phase spermine chemistry and library generation based on the symmetrical spermine scaffold.

Simple fragment syntheses of all four isomers of the spermine alkaloid kukoamine

All four isomers of the spermine alkaloid kukoamine were unambiguously prepared through diacylation with O,O'-dibenzylcasseyl chloride of suitably protected (benzyl and/or trityl groups) spermine derivatives, assembled on solid and/or in liquid phase using β-alanine and γ-aminobutyric acid, followed by simultaneous N- and O- deprotection and double bond reduction using catalytic hydrogenation.