|
|
|
|
|
|
| Detection of Polymorphs of Nalidixic Acid by Terahertz Spectroscopy |
| XIAO Tian-tian, ZHANG Zhuo-yong, GUO Chang-bin, WANG Guo*, LIAO Yi* |
| Department of Chemistry, Capital Normal University, Beijing 100048, China |
|
|
|
|
Abstract Terahertz spectroscopy can provide the lattice vibration information of solid materials, which is different from previous measuring methods. And particularly, it is suitable to test polymorphs. Thus it has an important meaning for controlling and detecting the polymorphs of drugs. The polymorphs should affect the properties, such as stability,of the drugs in storage. Nalidixic acid, the earliest quinolone antibacterials used, was investigated in this work. Two polymorphs NA-Ⅰ and NA-Ⅱ were synthesized and were confirmed by X-ray powder diffraction experiments. Different absorption spectra in the range of 0.2~2.4 THz of two synthesized polymorphs of nalidixic acid were obtained with terahertz time-domain spectroscopy at room temperature. Significant differences existed in the terahertz spectra of NA-Ⅰ and NA-Ⅱ. Five characteristic absorption peaks observed in the terahertz spectrum of NA-Ⅰ were at 0.94, 1.41, 1.88, 2.05, and 2.16 THz, while six peaks of NA-Ⅱ were at 0.72, 0.96, 1.38, 1.80, 2.04 and 2.16 THz. The most obvious difference was that there was a shoulder peak at 2.04 THz for NA-Ⅱ, while the intensity of the peak at 2.05 THz for NA-Ⅱ was much larger. Unlike other spectroscopies, such as infrared spectroscopy, the characteristic peaks in terahertz spectra were not related to specific functional groups. Thus the assignment of the characteristic peaks in terahertz spectra was essential. Theoretical calculations for the two polymorphs were performed based on density functional theory. The calculated characteristic peaks were in accord with those in the experiments. The vibrational modes in this low frequency region were mainly skeletal vibrations. Also the difference of the two spectra was explained by the different packing modes of the two crystals. This work provides evidence for identification of drug polymorphs using terahertz spectroscopy.
|
|
Received: 2017-12-03
Accepted: 2018-04-24
|
|
|
|
Corresponding Authors:
WANG Guo, LIAO Yi
E-mail: wangguo@mail.cnu.edu.cn; 5732@cnu.edu.cn
|
|
[1] Threlfall T L. Analyst, 1995, 120(10): 2435.
[2] Talham D R. Cryst. Growth Des., 2002, 2(6): 675.
[3] Kprpinski P H. Chem. Eng. Technol., 2006, 29(2): 233.
[4] Wang H R, Zhang L T, Wang Q, et al. J. Chromatogr. B, 2006, 835(1-2): 71.
[5] McIntosh A I, Yang B, Goldup S M, et al. Chem. Soc. Rev., 2012, 41(6): 2072.
[6] Zhang F, Wang H W, Keisuke T, et al. J. Phys. Chem. B, 2016, 120(8): 1698.
[7] ZHAO Rong-jiao, HE Jin-long, LI Jing, et al(赵荣娇，何金龙，李 璟，等). Acta Phys.-Chim. Sin.(物理化学学报), 2011, 27(12): 2743.
[8] Sasaki T, Kambara O, Sakamoto T, et al. Vib. Spectro., 2016, 85: 91.
[9] LIU Jian-wei, SHEN Jing-ling, ZHANG Bo(刘建伟，沈京玲，张 波). Spectroscopy and Spectral Analysis(光谱学与光谱分析), 2015, 35(11): 3041.
[10] Gangavaram S, Raghavender S, Sanphui P, et al. Cryst. Growth. Des., 2012, 12(10): 4963.
[11] Kresse G, Furthmuller. J. Phys. Rev. B: Condens. Matter Mater. Phys., 1996, 54(16): 11169.
[12] Klimeš J, Bowler D R, Michaelides A. J. Phys. Cond. Matt., 2010, 22(7): 22201.
[13] Klimeš J, Bowler D R, Michaelides A. Phys. Rev. B, 2011, 83(19): 772.
[14] Giannozzi P, Baroni S. J. Chem. Phys., 1994, 100(11): 8537.
[15] Karhánek D, Bucko T, Hafner J. J. Phys. Condens. Matter., 2010, 22(26): 265006.
[16] Shen Y C, Upadhya P C, Linfield E H, et al. Appl. Phys. Lett., 2003, 82(14): 2350.
[17] Gerber R B, Brauer B, Gregurick S K, et al. Phys. Chem. Commun., 2002, 5(21): 142. |
| [1] |
BAI Xi-lin1, 2, PENG Yue1, 2, ZHANG Xue-dong1, 2, GE Jing1, 2*. Ultrafast Dynamics of CdSe/ZnS Quantum Dots and Quantum
Dot-Acceptor Molecular Complexes[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2024, 44(01): 56-61. |
| [2] |
WAN Mei, ZHANG Jia-le, FANG Ji-yuan, LIU Jian-jun, HONG Zhi, DU Yong*. Terahertz Spectroscopy and DFT Calculations of Isonicotinamide-Glutaric Acid-Pyrazinamide Ternary Cocrystal[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(12): 3781-3787. |
| [3] |
ZHANG Yan-dong1, WU Xiao-jing1*, LI Zi-xuan1, CHENG Long-jiu2. Two-Dimensional Infrared Spectroscopic Study of Choline
Chloride/Glycerin Solution Disturbed by Temperature[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(10): 3047-3051. |
| [4] |
YU De-guan1, CHEN Xu-lei1, WENG Yue-yue2, LIAO Ying-yi3, WANG Chao-jie4*. Computational Analysis of Structural Characteristics and Spectral
Properties of the Non-Prodrug-Type Third-Generation
Cephalosporins[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(10): 3211-3222. |
| [5] |
LI Yang1, LI Xiao-qi1, YANG Jia-ying1, SUN Li-juan2, CHEN Yuan-yuan1, YU Le1, WU Jing-zhu1*. Visualisation of Starch Distribution in Corn Seeds Based on Terahertz Time-Domain Spectral Reflection Imaging Technology[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(09): 2722-2728. |
| [6] |
WANG Yi-ru1, GAO Yang2, 3, WU Yong-gang4*, WANG Bo5*. Study of the Electronic Structure, Spectrum, and Excitation Properties of Sudan Red Ⅲ Molecule Based on the Density Functional Theory[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(08): 2426-2436. |
| [7] |
LIU Guo-peng1, YOU Jing-lin1*, WANG Jian1, GONG Xiao-ye1, ZHAO Yu-fan1, ZHANG Qing-li2, WAN Song-ming2. Application of Aerodynamic Levitator Laser Heating Technique: Microstructures of MgTi2O5 Crystal and Melt by in-situ Superhigh Temperature Raman Spectroscopy[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(08): 2507-2513. |
| [8] |
TANG Yan1, YANG Yun-fan1, HU Jian-bo1, 2, ZHANG Hang2, LIU Yong-gang3*, LIU Qiang-qiang4. Study on the Kinetic Process and Spectral Properties of the Binding of Warfarin to Human Serum Protein[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(07): 2099-2104. |
| [9] |
SUN Zhi-shen1, LIU Yong-gang2, 3, ZHANG Xu1, GUO Teng-xiao1*, CAO Shu-ya1*. Study on the Near-Infrared Spectra of Sarin Based on Density
Functional Theory[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(06): 1765-1769. |
| [10] |
ZHENG Zhi-jie1, LIN Zhen-heng1, 2*, XIE Hai-he2, NIE Yong-zhong3. The Method of Terahertz Spectral Classification and Identification for Engineering Plastics Based on Convolutional Neural Network[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(05): 1387-1393. |
| [11] |
LIANG Xiao-rui1, CONG Jing-xian2, LI Yin1, LIU Jie1, JIN Liang-jie1, SUN Xiao-wei1, LI Xiao-dong3. Study on Vibrational Spectra of Cypermethrin Based on Density Functional Theory[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(05): 1381-1386. |
| [12] |
CI Cheng-gang*, ZANG Jie-chao, LI Ming-fei*. DFT Study on Spectra of Mn-Carbonyl Molecular Complexes[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(05): 1434-1441. |
| [13] |
WANG Yu-ye1, 2, LI Hai-bin1, 2, JIANG Bo-zhou1, 2, GE Mei-lan1, 2, CHEN Tu-nan3, FENG Hua3, WU Bin4ZHU Jun-feng4, XU De-gang1, 2, YAO Jian-quan1, 2. Terahertz Spectroscopic Early Diagnosis of Cerebral Ischemia in Rats[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(03): 788-794. |
| [14] |
AN Huan1, YAN Hao-kui2, XIANG Mei1*, Bumaliya Abulimiti1*, ZHENG Jing-yan1. Spectral and Dissociation Characteristics of p-Dibromobenzene Based on External Electric Field[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(02): 405-411. |
| [15] |
XU Meng-lei1, 2, GAO Yu3, ZHU Lin1, HAN Xiao-xia1, ZHAO Bing1*. Improved Sensitivity of Localized Surface Plasmon Resonance Using Silver Nanoparticles for Indirect Glyphosate Detection Based on Ninhydrin Reaction[J]. SPECTROSCOPY AND SPECTRAL ANALYSIS, 2023, 43(01): 320-323. |
|
|
|
|
