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Design, Synthesis, in Vitro Cytotoxic Activity Evaluation, and Apoptosis-Induction Study of New 9(10H-Acridinone-1,2,3-Triazoles Publisher Pubmed



Mohammadikhanaposhtani M1, 4 ; Safavi M2 ; Sabourian R3 ; Mahdavi M1, 4 ; Pordeli M5 ; Saeedi M6 ; Ardestani SK5 ; Foroumadi A1, 4 ; Shafiee A1, 4 ; Akbarzadeh T1, 3, 4
Authors
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Authors Affiliations
  1. 1. Department of Medicinal Chemistry, Tehran University of Medical Sciences, Tehran, Iran
  2. 2. Department of Biotechnology, Iranian Research Organization for Science and Technology, Tehran, Iran
  3. 3. Persian Medicine and Pharmacy Research Center, Tehran University of Medical Sciences, Tehran, Iran
  4. 4. Department of Medicinal Chemistry, Tehran University of Medical Sciences, Tehran, Iran
  5. 5. Institute of Biochemistry and Biophysics, Department of Biochemistry, University of Tehran, Tehran, Iran
  6. 6. Medicinal Plants Research Center, Tehran University of Medical Sciences, Tehran, Iran

Source: Molecular Diversity Published:2015


Abstract

A new series of 9(10H-acridinone-1,2,3-triazole derivatives were designed, synthesized and evaluated for their cytotoxic activity against human breast cancer cell lines. The acridone skeleton was prepared through the Ullman condensation of 2-bromobenzoic acid and anilines. Subsequently, it was functionalized with propargyl bromide. Then, a click reaction of the latter compound and in situ prepared 1-(azidomethyl)-4-methoxybenzene derivatives led to the formation of the desired triazole products. Finally, all products were investigated for their capability to cause cytotoxicity against MCF-7, T-47D, and MDA-MB-231 cell lines. Among them, 2-methoxy-10-((1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)methyl)acridin-9(10H-one 8c exhibited the most potency (\hbox {IC}_{50}\,{=}\,11.0\,{\pm }\, 4.8\, \upmu \hbox {M})(IC50=11.0±4.8μM) against MCF-7 cells, being more potent than etoposide (\hbox {IC}_{50}\,{=}\, 12.4\,{\pm }\, 4.7 \upmu \hbox {M})(IC50=12.4±4.7μM). Also, apoptosis induced by compound 8c was confirmed via acridine orange/ethidium bromide and Annexin V-FITC/propidium iodide (PI) double staining. © 2015, Springer International Publishing Switzerland.
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