Synthesis, characterization, anti-cancer evaluation, and DNA-binding study of new bay-substituted perylene derivatives

IF 2.5 3区 工程技术 Q2 BIOLOGY Yale Journal of Biology and Medicine Pub Date : 2023-07-21 DOI:10.17352/jbm.000039
Abourajab Arwa, Mostafanejad S Melika, Dinleyici Meltem, Al-Khateeb Basma, Kunter Imge, Tuzmen Sukru, Icil Huriye
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Abstract

Two new perylene derivatives 1,7-di(3,5-diamino-pyrimidoxyl) perylene-3,4,9,10- tetracarboxylic acid bisanhydride (4) and 1,7-di(2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]) ethoxyperylene-3,4,9,10-tetracarboxylic bisanhydride (6) have been synthesized. We aimed to study their interactions with G-quadruplex (G4) structures as potent G4 ligands and telomerase inhibitors. We used a PCR-amplified guanine-rich region from the human beta-globin gene, oligonucleotide from human telomeres (a-coreTT), an oncogene (c-kit), and SK-HEP-1 adenocarcinoma cells to characterize those compounds’ binding and stabilizing abilities to G4 structures and anti-cancer potential. All results obtained through UV-visible and fluorescence spectroscopies, agarose gel electrophoresis, and MTT assay on SK-HEP-1 adenocarcinoma cells were in good agreement. Compounds 4 and 6 are promising DNA-binding and cytotoxic compounds with a relatively antiproliferative effect on the selected tumour. In all studies, the formal positive charge carrier, compound 6, showed higher activity in terms of anti-cancer effects. These results may help elucidate the feasibility of the perylene derivatives as future chemo-therapeutic agents.
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新型海湾取代苝衍生物的合成、表征、抗癌评价及dna结合研究
合成了两个新的苝衍生物1,7-二(3,5-二氨基嘧啶)苝-3,4,9,10-四羧酸双酸酐(4)和1,7-二(2-[3-[(4-氨基-2-甲基嘧啶-5-基)甲基]-4-甲基-1,3-噻唑-3- -5-基])乙氧基苝-3,4,9,10-四羧酸双酸酐(6)。我们的目的是研究它们与g -四重体(G4)结构的相互作用,作为有效的G4配体和端粒酶抑制剂。我们使用pcr扩增的人β -珠蛋白基因富鸟嘌呤区、人端粒寡核苷酸(a- corett)、致癌基因(c-kit)和SK-HEP-1腺癌细胞来表征这些化合物与G4结构的结合和稳定能力以及抗癌潜力。通过对SK-HEP-1腺癌细胞的紫外可见光谱、荧光光谱、琼脂糖凝胶电泳和MTT分析,结果一致。化合物4和6是有希望的dna结合和细胞毒性化合物,对选定的肿瘤具有相对的抗增殖作用。在所有的研究中,形式正电荷载体化合物6在抗癌作用方面表现出更高的活性。这些结果有助于阐明苝衍生物作为未来化学治疗剂的可行性。
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来源期刊
Yale Journal of Biology and Medicine
Yale Journal of Biology and Medicine Biochemistry, Genetics and Molecular Biology-General Biochemistry,Genetics and Molecular Biology
CiteScore
5.00
自引率
0.00%
发文量
41
期刊介绍: The Yale Journal of Biology and Medicine (YJBM) is a graduate and medical student-run, peer-reviewed, open-access journal dedicated to the publication of original research articles, scientific reviews, articles on medical history, personal perspectives on medicine, policy analyses, case reports, and symposia related to biomedical matters. YJBM is published quarterly and aims to publish articles of interest to both physicians and scientists. YJBM is and has been an internationally distributed journal with a long history of landmark articles. Our contributors feature a notable list of philosophers, statesmen, scientists, and physicians, including Ernst Cassirer, Harvey Cushing, Rene Dubos, Edward Kennedy, Donald Seldin, and Jack Strominger. Our Editorial Board consists of students and faculty members from Yale School of Medicine and Yale University Graduate School of Arts & Sciences. All manuscripts submitted to YJBM are first evaluated on the basis of scientific quality, originality, appropriateness, contribution to the field, and style. Suitable manuscripts are then subject to rigorous, fair, and rapid peer review.
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