Department of Chemistry, National Institute of Technology , Hamirpur , Himachal Pradesh , India.
J Biomol Struct Dyn. 2019 Oct;37(17):4465-4480. doi: 10.1080/07391102.2018.1552198. Epub 2019 Jan 16.
1, 4 and 5, 8-Positions as well as type of functionalities on these positions at anthraquinone-9, 10-dione are proposed to be significant for anticancer activity. Therefore, keeping this into consideration, a series of 1-substituted anthraquinone-based compounds are designed, synthesized, characterized and biologically evaluated for anticancer activity. The structure of synthesized compounds is confirmed by spectroscopic analysis, i.e. 1D (H and C) nuclear magnetic resonance (NMR), electrospray ionization-mass spectrometry (ESI-MS) studies and Fourier transform infrared (FT-IR) tools. Synthesized 1-substituted anthraquinone compounds showed cytotoxic effect against human breast cancer cell line (MCF-7), human prostate cancer cell line (PC-3) and Hela derivative human cell line (Hep 2C) (Hela derivative) cell lines. All the compounds showed mild antibacterial property in comparison to standard antibiotic streptomycin against Gram + ve and -ve bacteria. They also exhibit mild antifungal activity. calf thymus (ct)-DNA binding studies of synthesized series using UV-visible absorption spectra measurement and fluorescence tools indicate partial intercalative mode of binding. Electronic properties of synthesized analogues and mitoxantrone are compared using highest occupied molecular orbital-lowest occupied molecular orbital (HOMO-LUMO) calculation. Low energy gap between HOMO and LUMO of 1-substituted anthraquinone compounds indicates the highly charged structure of the molecules in comparison to mitoxantrone, and the same is proposed to be responsible for comparable cytotoxic activities of the synthesized 1-substituted anthraquinone molecules. Docking interaction of synthesized 1-substituted anthraquinone compounds and i-motif sequence indicates intercalative mode of binding of compounds with telomeric junction. Communicated by Ramaswamy H. Sarma.
1、4 和 5、8 位以及蒽醌-9、10-二酮这些位置上的功能类型被认为对抗癌活性很重要。因此，考虑到这一点，设计、合成、表征了一系列 1-取代蒽醌类化合物，并对其抗癌活性进行了生物评价。通过光谱分析，即一维（H 和 C）核磁共振（NMR）、电喷雾电离质谱（ESI-MS）研究和傅里叶变换红外（FT-IR）工具，确认了合成化合物的结构。合成的 1-取代蒽醌化合物对人乳腺癌细胞系（MCF-7）、人前列腺癌细胞系（PC-3）和 Hela 衍生人细胞系（Hep 2C）（Hela 衍生）具有细胞毒性作用。与标准抗生素链霉素相比，所有化合物对革兰氏阳性菌和革兰氏阴性菌均表现出轻微的抗菌活性。它们还表现出轻微的抗真菌活性。用紫外可见吸收光谱测量和荧光工具研究合成系列与小牛胸腺（ct）-DNA 的结合，表明部分为嵌入结合模式。用最高占据分子轨道-最低占据分子轨道（HOMO-LUMO）计算比较了合成类似物和米托蒽醌的电子性质。与米托蒽醌相比，1-取代蒽醌化合物的 HOMO 和 LUMO 之间的低能隙表明分子的高度带电结构，这被认为是合成 1-取代蒽醌分子具有相当的细胞毒性活性的原因。合成的 1-取代蒽醌化合物与 i-motif 序列的对接相互作用表明化合物与端粒连接的嵌入结合模式。由 Ramaswamy H. Sarma 传达。
