Infrared Spectroscopy Study on Temperature Characteristics of Several Common Antibiotics and Therapeutic COVID-19 Drugs
WANG Fang1, 3, ZHU Nan2, CHEN Jing-yi1, ZAN Jia-nan3, XIAO Zi-kang1, LIU Chang1, LIU Yun-fei3*
1. College of Electronic Engineering, NanJing XiaoZhuang University, Nanjing 211171, China
2. Nanjing Institute of Product Quality Inspection, Nanjing 210019, China
3. College of Information Science and Technology, Nanjing Forestry University, Nanjing 210037, China
Abstract：The far infrared (1~10 THz) and mid-infrared (400~4 000 cm-1) spectra of six common antibiotics (Ofloxacin capsules, Ofloxacin tablets, Norfloxacin capsules, Azithromycin tablets, Roxithromycin tablets and Levofloxacin hydrochloride tablets), three antiviral drugs for COVID-19 (Ribavirin tablets, Abidol hydrochloride tablets and Chloroquine phosphate tablets) and an expectorant drug (Ambroxol hydrochloride tablets) within shelf-life were studied. The effects of vehicles and another high temperature environment (65 ℃) on the structure and crystal form of drugs were simulated and fed back to the changes in infrared spectra. After two months of continuous experiments, it was found that the structure and crystal form of other drugs had hardly changed except in ambroxol hydrochloride tablets. When capsule drugs were placed in high-temperature environment for a long time, the epidermis would become brittle and easy to rupture, but the efficacy of internal drugs had hardly changed. Taking fluoroquinolone antibiotics (Ofloxacin and Norfloxacin) as examples, combined with density functional theory (DFT) and the potential energy distribution (PED) method, the theoretical infrared spectra of the two antibiotics monomers, polymers and crystals were calculated by Crystal 14 and Gaussian 16 software with B3LYP/6-311++G(d,p) basis set. The vibrational modes and their contribution rates corresponding to all characteristic peaks were obtained, and the experimental spectrum was accurately identified. It was also found that from monomer to polymer and then to crystal, the stacking force (π—π interaction) between lattices accounted for the largest proportion of inter-molecular interaction, more than 90%. Therefore, the theoretical calculation was more consistent with the experimental results only when the crystal with periodic boundary conditions was taken as the initial configuration. The vibrational modes in the far infrared band mainly came from the collective vibration of molecules (vibration accounts for more than 99%, rotation and translation account for less than 1%), and the out-of-plane bending caused by inter-molecular hydrogen bond and Van der Waals force contributes the most, more than 90%. In the mid-infrared band, there were also a certain proportion of inter-molecular interactions. For example, the peaks of norfloxacin at 1 440 cm-1 and ofloxacin at 1 524 cm-1 can only be reproduced in the theoretical spectrum with the crystal as the configuration, respectively, from the collective vibration and the stretching of O—H…O bonds.
Key words：Infrared spectrum; Drugs; Temperature characteristics; Density functional theory; Vibrational modes
王 芳，朱 南，陈靖奕，昝佳男，肖子康，刘 畅，刘云飞. 几种常见抗生素及治疗COVID-19药物温度特性红外光谱表征研究[J]. 光谱学与光谱分析, 2022, 42(12): 3719-3729.
WANG Fang, ZHU Nan, CHEN Jing-yi, ZAN Jia-nan, XIAO Zi-kang, LIU Chang, LIU Yun-fei. Infrared Spectroscopy Study on Temperature Characteristics of Several Common Antibiotics and Therapeutic COVID-19 Drugs. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2022, 42(12): 3719-3729.
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