Solution environment effects on the photo-physical behavior of Daunorubicin and Mitoxantrone: Anthraquinone-based drugs

• Published in: Journal of molecular structure Vol. 1310; p. 138317
• Main Authors: Mehnati, P., Khoshsima, H., Zakerhamidi, M.S., Kian, R., Sahrai, M.
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 15.08.2024
• Subjects: Anthraquinone; Dipole moment; Intermediate resonance form; Polarity; Solvatochromism; Solvent accessible surface; Solvatochromism; Polarity; Solvent accessible surface; Anthraquinone; Intermediate resonance form; Dipole moment
• ISSN: 0022-2860
• DOI: 10.1016/j.molstruc.2024.138317

•Absorbance and fluorescence spectral shifts of Anthraquinone drugs are complex.•The spectral features of Anthraquinone drugs depend on the solvent media interactions.•SAS control dipole moment of Anthraquinone drugs molecules•The obtained effective molecular interactions and dipole moments show applicability of Anthraquinone drugs in biological environments.•Both drugs show high polarity in the excited state and show an excited state intra-molecular proton transfer (ESIPT) mechanism. Anthraquinone-based drugs are the focus of the pharmaceutical industry today due to their wide range of therapeutic applications and investigation of the electronic structure and intermediate resonance forms of these materials in different solvent environments can help to understand their photo-physical behavior in practical and functional environments. Considering the importance of this issue, the drugs Daunorubicin and Mitoxantrone were dissolved in different solvent environments with varying polarities, and their absorption and fluorescence spectra were investigated. The results of the spectroscopic data were evaluated with solvent polarity parameters, and the dipole moment of these drugs was obtained. Finally, by summarizing all the results, the resonance structures of Daunorubicin and Mitoxantrone were presented in ground- and excited-state. Both substances show high polarity in the excited state as well as an excited state intra-molecular proton transfer mechanism. The findings can pave the way for scientists and pharmacists to evaluate the effectiveness, efficiency of drugs and improve their function. [Display omitted]