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Are the Absorption Spectra of Doxorubicin Properly Described by Considering Different Tautomers?
Journal of Chemical Information and Modeling ( IF 5.6 ) Pub Date : 2020-01-09 , DOI: 10.1021/acs.jcim.9b00785 Edvonaldo Florêncio E Silva 1 , Edna S Machado 1 , Iane B Vasconcelos 2 , Severino A Junior 2 , José Diogo L Dutra 1 , Ricardo O Freire 1 , Nivan B da Costa 1
Journal of Chemical Information and Modeling ( IF 5.6 ) Pub Date : 2020-01-09 , DOI: 10.1021/acs.jcim.9b00785 Edvonaldo Florêncio E Silva 1 , Edna S Machado 1 , Iane B Vasconcelos 2 , Severino A Junior 2 , José Diogo L Dutra 1 , Ricardo O Freire 1 , Nivan B da Costa 1
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The elucidation of the action of doxorubicin (DOX) has been considered a challenge for cancer therapy. Using theoretical approaches, we investigated the structure and electronic properties of DOX as a function of pH, which we thought likely to be related to the influence of its tautomers. Regarding the relative stabilities among the tautomers, the results obtained from PM6 were the most similar to those obtained from DFT. The theoretical absorption spectrum for each tautomeric species simply showed a single absorption peak located around 400 nm, in contrast to the experimental absorption spectra in the literature that showed four absorption bands. The experimental evidence was properly explained by considering four tautomeric conformers of DOX. The spectroscopic study of the deprotonated tautomers also suggested the presence of four deprotonated tautomers at more basic pH values. The spectrum at pH 10.08 can be explained by the presence of protonated and deprotonated doxorubicin species.
中文翻译：
通过考虑不同的互变异构体是否正确描述了阿霉素的吸收光谱？
阐明阿霉素（DOX）的作用已被认为对癌症治疗构成挑战。使用理论方法，我们研究了DOX的结构和电子性质随pH的变化，我们认为这可能与其互变异构体的影响有关。关于互变异构体之间的相对稳定性，从PM6获得的结果与从DFT获得的结果最为相似。每个互变异构物质的理论吸收光谱仅显示了一个位于400 nm附近的单个吸收峰，而文献中的实验吸收光谱显示了四个吸收带。通过考虑DOX的四个互变异构构象体，可以正确解释实验证据。对去质子化互变异构体的光谱研究还表明，在更碱性的pH值下存在四种去质子化互变异构体。pH 10.08的光谱可以用存在质子化和去质子化的阿霉素物质来解释。
更新日期：2020-01-10
中文翻译：
通过考虑不同的互变异构体是否正确描述了阿霉素的吸收光谱？
阐明阿霉素（DOX）的作用已被认为对癌症治疗构成挑战。使用理论方法，我们研究了DOX的结构和电子性质随pH的变化，我们认为这可能与其互变异构体的影响有关。关于互变异构体之间的相对稳定性，从PM6获得的结果与从DFT获得的结果最为相似。每个互变异构物质的理论吸收光谱仅显示了一个位于400 nm附近的单个吸收峰，而文献中的实验吸收光谱显示了四个吸收带。通过考虑DOX的四个互变异构构象体，可以正确解释实验证据。对去质子化互变异构体的光谱研究还表明，在更碱性的pH值下存在四种去质子化互变异构体。pH 10.08的光谱可以用存在质子化和去质子化的阿霉素物质来解释。
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