1-Amino-4-hydroxy-9,10-anthraquinone - An analogue of anthracycline anticancer drugs, interacts with DNA and induces apoptosis in human MDA-MB-231 breast adinocarcinoma cells: Evaluation of structure-activity relationship using computational, spectroscopic and biochemical studies.
1-Amino-4-hydroxy-9,10-anthraquinone - An analogue of anthracycline anticancer drugs, interacts with DNA and induces apoptosis in human MDA-MB-231 breast adinocarcinoma cells: Evaluation of structure-activity relationship using computational, spectroscopic and biochemical studies.
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DOI：
10.1016/j.bbrep.2015.10.008
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发表时间：
2015-12
影响因子：
2.7
通讯作者：
Guin PS
中科院分区：
文献类型：
--
作者：
Mondal P;Roy S;Loganathan G;Mandal B;Dharumadurai D;Akbarsha MA;Sengupta PS;Chattopadhyay S;Guin PS
采用实验和计算相结合的方法，研究了蒽环类化疗药物的简单类似物1-氨基-4-羟基-9，10-蒽醌（1-AHAQ）的X射线衍射和光谱性质。从计算方法得到的优化的几何参数进行了比较与X射线衍射分析的结果，两者被发现是在合理的良好协议。X射线衍射、密度泛函理论和自然键轨道分析表明分子中存在两种氢键。用振动能量分布分析（VEDA）和势能分布分析（PED）研究了1-AHAQ的红外光谱。用TDDFT计算了电子光谱，并与实验结果进行了比较。实验结果和理论结果在相当程度上相互印证。为了了解1-AHAQ的生物学功效，使其与小牛胸腺DNA和人乳腺癌细胞MDA-MB-231相互作用。发现该分子在该腺癌细胞中诱导凋亡，在HBL-100正常乳腺上皮细胞中几乎没有细胞毒性作用（如果有的话）。
The X-ray diffraction and spectroscopic properties of 1-amino-4-hydroxy-9,10-anthraquinone (1-AHAQ), a simple analogue of anthracycline chemotherapeutic drugs were studied by adopting experimental and computational methods. The optimized geometrical parameters obtained from computational methods were compared with the results of X-ray diffraction analysis and the two were found to be in reasonably good agreement. X-ray diffraction study, Density Functional Theory (DFT) and natural bond orbital (NBO) analysis indicated two types of hydrogen bonds in the molecule. The IR spectra of 1-AHAQ were studied by Vibrational Energy Distribution Analysis (VEDA) using potential energy distribution (PED) analysis. The electronic spectra were studied by TDDFT computation and compared with the experimental results. Experimental and theoretical results corroborated each other to a fair extent. To understand the biological efficacy of 1-AHAQ, it was allowed to interact with calf thymus DNA and human breast adino-carcinoma cell MDA-MB-231. It was found that the molecule induces apoptosis in this adinocarcinoma cell, with little, if any, cytotoxic effect in HBL-100 normal breast epithelial cell.