Research Institute for Basic Sciences and Department of Chemistry, College of Sciences, Kyung Hee University, Seoul 130-701, Republic of Korea.
Bioorg Med Chem Lett. 2013 Dec 15;23(24):6656-62. doi: 10.1016/j.bmcl.2013.10.049. Epub 2013 Oct 31.
The growth inhibition of human cancer cells via T-type Ca(2+) channel blockade has been well known. Herein, a series of new 3,4-dihydroquinazoline derivatives were synthesized via a brief SAR study on KYS05090 template and evaluated for both T-type Ca(2+) channel (Cav3.1) blockade and cytotoxicity on three human ovarian cancer cells (SK-OV-3, A2780 and A2780-T). Most of compounds except 6i generally exhibited more potent cytotoxicity on SK-OV-3 than mibefradil as a positive control regardless of the degree of T-type channel blockade. In particular, eight compounds (KYS05090, 6a and 6c-6h) showing strong channel blockade exhibited almost equal and more potent cytotoxicity on A2780 when compared to mibefradil. On A2780-T paclitaxel-resistant human ovarian carcinoma, two compounds (KYS05090 and 6d) were 20-fold more active than mibefradil. With respect to cell cycle arrest effect on A2780 and A2780-T cells, KYS05090 induced large proportion of sub-G1 phase in the cell cycle progression of A2780 and A2780-T, meaning the induction of cancer cell death instead of cell cycle arrest via blocking T-type Ca(2+) channel. Among new analogues, compounds 6g and 6h induced cell cycle arrest at G1 phase of A2780 and A2780-T cells in dose-dependent manner and exhibited strong anti-proliferation effects of ovarian cancer cells by blocking T-type Ca(2+) channel. Furthermore, 6g and 6h possessing strong cytotoxic effects could induce apoptosis of A2780 cells, which was detected by confocal micrographs using DAPI staining.
通过 T 型钙通道阻断抑制人类癌细胞的生长已为人熟知。在此,我们通过对 KYS05090 模板进行简要的 SAR 研究,合成了一系列新的 3,4-二氢喹唑啉衍生物,并对其进行了 T 型钙通道(Cav3.1)阻断和对三种人卵巢癌细胞(SK-OV-3、A2780 和 A2780-T)的细胞毒性评估。大多数化合物(6i 除外)通常对 SK-OV-3 的细胞毒性比米贝地尔作为阳性对照更强,而与 T 型通道阻断程度无关。特别是,有 8 种化合物(KYS05090、6a 和 6c-6h)表现出较强的通道阻断作用,与米贝地尔相比,对 A2780 的细胞毒性几乎相等且更强。对于紫杉醇耐药的人卵巢癌 A2780-T,两种化合物(KYS05090 和 6d)的活性比米贝地尔高 20 倍。关于 KYS05090 对 A2780 和 A2780-T 细胞的细胞周期阻滞作用,它诱导 A2780 和 A2780-T 细胞周期进展中较大比例的亚 G1 期,这意味着通过阻断 T 型钙通道诱导癌细胞死亡而不是细胞周期阻滞。在新的类似物中,化合物 6g 和 6h 以剂量依赖的方式诱导 A2780 和 A2780-T 细胞的 G1 期细胞周期阻滞,并通过阻断 T 型钙通道显示出对卵巢癌细胞的强烈增殖抑制作用。此外,具有强细胞毒性作用的 6g 和 6h 可以诱导 A2780 细胞凋亡,这可以通过 DAPI 染色的共聚焦显微镜观察到。