Design, synthesis, in vitro cytotoxic activity evaluation, and apoptosis-induction study of new 9(10H)-acridinone-1,2,3-triazoles

被引：44

作者：

Mohammadi-Khanaposhtani, Maryam ^{[1
]}

Safavi, Maliheh ^{[2
]}

Sabourian, Reyhaneh ^{[3
]}

Mahdavi, Mohammad ^{[1
,4
]}

Pordeli, Mahboobeh ^{[5
]}

Saeedi, Mina ^{[6
]}

Ardestani, Sussan Kabudanian ^{[5
]}

Foroumadi, Alireza ^{[1
,4
]}

Shafiee, Abbas ^{[1
,4
]}

Akbarzadeh, Tahmineh ^{[1
,3
]}

机构：

[1] Univ Tehran Med Sci, Fac Pharm, Dept Med Chem, Tehran, Iran

[2] Iranian Res Org Sci & Technol, Dept Biotechnol, Tehran, Iran

[3] Univ Tehran Med Sci, Persian Med & Pharm Res Ctr, Tehran, Iran

[4] Univ Tehran Med Sci, Pharmaceut Sci Res Ctr, Tehran, Iran

[5] Univ Tehran, Inst Biochem & Biophys, Dept Biochem, Tehran, Iran

[6] Univ Tehran Med Sci, Fac Pharm, Med Plants Res Ctr, Tehran, Iran

来源：

MOLECULAR DIVERSITY | 2015年 / 19卷 / 04期

关键词：

Acridone-1,2,3-triazoles; Cytotoxic activity; Click chemistry; Breast cancer; BIOLOGICAL EVALUATION; ACRIDONE DERIVATIVES; CANCER; 1,2,3-TRIAZOLE; INHIBITORS; CELL; ACETYLCHOLINESTERASE; RESISTANCE; CHEMISTRY; TOXICITY;

D O I：

10.1007/s11030-015-9616-0

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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 against MCF-7 cells, being more potent than etoposide . Also, apoptosis induced by compound 8c was confirmed via acridine orange/ethidium bromide and Annexin V-FITC/propidium iodide (PI) double staining.

引用

页码：787 / 795

页数：9

共 42 条

[11] Synthesis and antitumor activity of conjugates of muramyldipeptide, normuramyldipeptide, and desmuramylpeptides with acridine/acridone derivatives [J].