[1] Ge Yuhua, Sun Hui, Wang Mingliang,. Crystal structure and fluorescence property of antofloxacin [J]. Journal of Southeast University (English Edition), 2011, 27 (4): 449-451. [doi:10.3969/j.issn.1003-7985.2011.04.020]
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Crystal structure and fluorescence property of antofloxacin(
)
安妥沙星晶体结构及荧光性能
)Journal of Southeast University (English Edition)[ISSN:1003-7985/CN:32-1325/N]
- Volumn:
- 27
- Issue:
- 2011 4
- Page:
- 449-451
- Research Field:
- Mathematics, Physics, Mechanics
- Publishing date:
- 2011-12-31
Info
- Title:
- Crystal structure and fluorescence property of antofloxacin
- 安妥沙星晶体结构及荧光性能
- Author(s):
- Ge Yuhua, Sun Hui, Wang Mingliang
- School of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, China
- PACS:
- O723
- DOI:
- 10.3969/j.issn.1003-7985.2011.04.020
- Abstract:
- Antofloxacin free base is prepared from antofloxacin hydrochloride by removing hydrogen chloride. Its crystal is obtained by slow evaporation of an acetonitrile-methanol mixed solution. Single-crystal X-ray diffraction reveals that the crystallography belongs to a triclinic P1- space group with cell parameters: a=0.66307(13)nm, b=0.89839(18)nm, c=1.5690(3)nm, α=75.12(3)°, β=87.92(3)°, γ=77.57(3)°. Antofloxacin shows no fluorescence in solution, but the crystalline state emits strong green light at 510 nm under the excitation of 360 nm, indicating a fluorescence enhancement induced by aggregation. It demonstrates that intermolecular packing and interaction in the crystal lead to the improved fluorescence quantum yield. These results provide important information for the further exploration of the structure-activity relationship of antofloxacin and the development of new drugs.
- 以盐酸安妥沙星为原料, 通过脱HCl反应制备了安妥沙星游离碱, 在乙腈-甲醇混合溶剂中培养出单晶, 经单晶X衍射测得其晶体结构属于三斜晶系, 空间群为P1-, 晶胞参数:a=0.66307(13)nm, b=0.89839(18)nm, c=1.5690(3)nm;α=75.12(3)°, β=87.92(3)°, γ=77.57(3)°.安妥沙星的溶液无荧光, 但其晶体在360 nm波长光激发下发射较强的绿光, 最大发射波长位于510 nm, 存在明显的聚集诱导荧光增强效应, 表明晶体内分子间的堆积及其相互作用有效地提高了荧光量子产率.该研究为进一步探索安妥沙星的构效关系及同类结构新药的设计提供了重要的参考.
References:
[1] Hooper D C, Wolfson J S. Mode of action of the quinolone antimicrobial agents: review of recent information [J]. Rev Infect Dis, 1989, 11(Sup 5): 902-911.
[2] Chu D T W, Fernandes P B. Recent developments in the field of quinolone antibacterial agents [J]. Adv Drug Res, 1991, 21(1): 39-144.
[3] Yao W. Recent advances of fluorescence spectrometric methods for the studies of quinolone drugs[J]. Journal of Huangshan University, 2004, 6(3):67-70.(in Chinese)
[4] Du L M, Jin W J, Dong C, et al. Studies on correlation between protonation and tautomerism and luminescence characteristics of quinolone [J].Spectroscopy and Spectral Analysis, 2001, 21(4):518-520.(in Chinese)
[5] Qi X J, Wang J X, Liu Z R. Fluorescent spectrometry of balofloxacin [J]. Chinese Journal of Analytical Chemistry, 2006, 34(7):1047-1048.(in Chinese)
[6] Wang Y, Li S W, Wu X M, et al. Study on fluorescence spectra of four quinolones [J]. Journal of Sichuan Normal University: Natural Science, 2003, 26(6): 617-619.(in Chinese)
[7] Mei Y J. The novel high efficient and broad-spectrum drug-antofloxacin[J]. Anhui Medical and Pharmaceutical Journal, 2010, 14(2):229-231.(in Chinese)
[8] Hong J W, Hu C Q. Determination of enantiomeric impurity of antofloxacin hydrochloride by high-performance liquid chromatography [J]. Chinese Journal of Antibiotics, 2004, 29(6): 349-353.(in Chinese)
[9] Mei Y J, Chen X M, Song C W, et al. Content determination of main components in antofloxacin hydrochloride tablets by ultraviolet spectrophotometry [J]. Anhui Medical and Pharmaceutical Journal, 2011, 15(5):573-574.(in Chinese)
[10] Li X M. Improvement and clinical evaluation of fluoroquinolone[J]. Evaluation and Analysis of Drug-Use in Hospital of China, 2003, 3(2):83-86.(in Chinese)
[11] Wang G P, Cai G Q, Zhu L G. Synthesis and crystal structure of fluoroquinolone complex of copper with two-dimension network [J]. Chinese Journal of Inorganic Chemistry, 2000, 16(6):987-989.(in Chinese)
[12] Yuan R X, Xiong R G, Zhang Z E, et al. Preparation, characterization, and X-ray crystal structure of a one-dimensional calcium-based coordination polymer with strong blue fluorescent emission[J]. Inorg Chem Commum, 2001, 4(8):430-433.
Memo
- Memo:
-
Biography: Ge Yuhua(1966—), male, doctor, associate professor, Geyuhua@263.net.
Citation: Ge Yuhua, Sun Hui, Wang Mingliang. Crystal structure and fluorescence property of antofloxacin[J].Journal of Southeast University(English Edition), 2011, 27(4):449-451.[doi:10.3969/j.issn.1003-7985.2011.04.020]