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新型丁卡因酰肼腙的设计、合成及抗癌活性评价

Design, Synthesis, and Anticancer Evaluation of Novel Tetracaine Hydrazide-Hydrazones.

作者信息

Han M İhsan, İmamoğlu Nalan

机构信息

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Erciyes University, Kayseri 38039, Turkey.

Department of Basic Sciences, Faculty of Pharmacy, Erciyes University, Kayseri 38039, Turkey.

出版信息

ACS Omega. 2023 Feb 28;8(10):9198-9211. doi: 10.1021/acsomega.2c07192. eCollection 2023 Mar 14.

DOI:10.1021/acsomega.2c07192
PMID:36936335
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10018687/
Abstract

Tetracaine is an ester derivative used as a local anesthetic molecule. In this study, a series of novel Tetracaine derivatives bearing hydrazide-hydrazone moiety were designed, synthesized, and evaluated for anticancer activity. The structures of these compounds were characterized by spectral (H NMR,C NMR, FT-IR, and HRMS analyses) methods. All synthesized compounds were screened for anticancer activity against two different human cancer cell lines (Colo-205 and HepG2). Among the synthesized molecules, compounds and showed the most potent anticancer activity against the Colo-205 cell line (IC = 50.0 and 20.5 μM, respectively). Compounds , , and demonstrated the best anticancer activity against the HepG2 cell line (IC = 30.5, 35.9, and 20.8 μM, respectively). mRNA transcription levels of Bax and caspase-3 genes were determined by real-time polymerase chain reaction (qRT-PCR) analysis of both Colo-205 and HepG2 cell lines. Doxorubicin was used as a positive sensitivity reference standard. qRT-PCR analysis showed that there was a time-dependent rise in the expression levels of Bax and Caspase 3 on apoptosis. Inhibition of apoptotic proteins PI3K, Akt, PTEN, pPTEN, FoXO1, FoXO3a, TXNIP, and p27 was investigated in Colo-205 and HepG2 cells treated with compounds , and by using Western blotting.

摘要

丁卡因是一种用作局部麻醉分子的酯衍生物。在本研究中，设计、合成了一系列带有酰肼腙部分的新型丁卡因衍生物，并对其抗癌活性进行了评估。这些化合物的结构通过光谱（1H NMR、13C NMR、FT-IR和HRMS分析）方法进行了表征。对所有合成化合物针对两种不同的人类癌细胞系（Colo-205和HepG2）进行了抗癌活性筛选。在合成的分子中，化合物[具体化合物编号]和[具体化合物编号]对Colo-205细胞系表现出最有效的抗癌活性（IC50分别为50.0和20.5 μM）。化合物[具体化合物编号]、[具体化合物编号]和[具体化合物编号]对HepG2细胞系表现出最佳的抗癌活性（IC50分别为30.5、35.9和20.8 μM）。通过对Colo-205和HepG2细胞系进行实时聚合酶链反应（qRT-PCR）分析，测定了Bax和caspase-3基因的mRNA转录水平。多柔比星用作阳性敏感性参考标准。qRT-PCR分析表明，凋亡时Bax和Caspase 3的表达水平呈时间依赖性升高。通过蛋白质印迹法研究了用化合物[具体化合物编号]、[具体化合物编号]和[具体化合物编号]处理的Colo-205和HepG2细胞中凋亡蛋白PI3K、Akt、PTEN、pPTEN、FoXO1、FoXO3a、TXNIP和p27的抑制情况。

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