2307-88-2

Usage

Type of compound

Derivative of acridine

Functional group

Dimethylaminopropyl group

Application

Fluorescent dye

Usage

Biochemical and pharmaceutical research

Purpose

Tracer and label for biomolecules, proteins, and DNA

Property

Strong absorption and emission in the visible range

Suitability

Ideal candidate for various fluorescence-based applications

Investigated activities

Potential antitumor and antimalarial properties

InChI:InChI=1/C18H20N2O/c1-19(2)12-7-13-20-16-10-5-3-8-14(16)18(21)15-9-4-6-11-17(15)20/h3-6,8-11H,7,12-13H2,1-2H3

Upstream product

• 109-54-6 3-(Dimethylamino)propyl chloride 
• 578-95-0 10H-acridin-9-one 
• 124-40-3 dimethyl amine 
• 427883-75-8 10-(3-bromopropyl) acridin-9(10H)-one 

Relevant academic research and scientific papers

Highly photoresistant chemosensors using acridone as fluorescent label

Highly photoresistant and selective chemosensors have been prepared using acridone as fluorescent label in combination with monoclonal antibodies.

Synthesis, cytotoxicity evaluation, and molecular modeling studies of 2,N10-substituted acridones as DNA-intercalating agents

Acridine-based compounds possess anticancer activities by intercalating to DNA. Although they have chemotherapeutic potential, acridine-based compounds are not used to treat cancer. In this study, 2,N10-acridone derivatives are designed and synthesized based on acridone, a ketone derivative of acridine. Herein, acridone is functionalized with alkyl side chains containing terminal nitrogen-based moieties at the N10-position and substituted at the C2-position. The products are evaluated for in vitro cytotoxicity against four cancer cell lines: Molt-3, HepG2, A549, and HuCCA-1. The derivative bearing two butyl piperidine side chains at the C2- and N10-positions is the most active, with IC50 values ranging from 2.96 to 9.46 μM. Molecular modeling studies supported the binding of the derivatives to DNA by intercalation, thereby confirming the observed cytotoxic effects.