Studies on the Protonation Structure of Ofloxacin in Concentrated Sulfuric Acid Solutions

Chem. J. Chinese Universities ›› 2010, Vol. 31 ›› Issue (9): 1747.

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Studies on the Protonation Structure of Ofloxacin in Concentrated Sulfuric Acid Solutions

LI Hui-Zhen^1,2, LIU Shao-Xuan¹, HUA Xiao-Hui¹, PAN Qing-Hua¹, YANG Zhan-Lan¹, GAO Xiu-Xiang¹, ZHU Xi³, XU Yi-Zhuang^1*, WU Jin-Guang¹

1. State Key Laboratory of Rare Earth Materials Chemistry and Applications, College of Chemistry and Molecular Engineering, Peking University, Beijing National Laboratory for Molecular Sciences, Beijing 100871, China;
2. College of Chemistry and Environmental Science, Henan Normal University, Xinxiang 453007, China;
3. Department of Critical Care Unit, Third Hospital of Peking University, Beijing 100191, China

Received:2010-01-22 Online:2010-09-10 Published:2010-09-10
Contact: XU Yi-Zhuang. E-mail: xyz@pku.edu.cn
Supported by:
国家自然科学基金(批准号: 50673005, 20671007, 50973003)和北京大学先进技术研究院培育项目资助.

Abstract

Abstract: Systematic NMR spectroscopic investigation on ofloxacin(OFL) in concentrated sulfuric acid solution was carried out via ¹⁹F NMR, ¹H NMR and ¹³C NMR experiments. Complete assignment on ¹⁹F NMR, ¹H NMR and ¹³C NMR of ofloxacin in sulfuric acid solutions were obtained. The chemical shift of H, F, C, and the J_FC of OFL molecule in sulfuric acid solutions of different concentrations were found to be very helpful for the identification the protonation structure of OFL molecule. According to the variation of the chemical shift of H, F, C, and the J_FC of OFL molecule in sulfuric acid solutions of different concentrations, we propose that the N_1′ is further protonated in concentrated sulfuric acid solutions. Additionally, a new hydrogen bond(N_1′—H⁺┈F₉) forms and the structure can be stabilized by a five-member ring and the conjugate system is distorted by the five-member ring. As a result, the emission peak, excitation peak in fluorescent spectra and absorption peak in UV spectra of OFL exhibit blue-shifted significantly. In addition, the proposed protonation structure was further supported by spectroscopic behavior of oxygen-fluorine acid and methyl-ofloxacin.

Key words: Ofloxacin, Quinolone, NMR, Protonation

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LI Hui-Zhen, LIU Shao-Xuan, HUA Xiao-Hui, PAN Qing-Hua, YANG Zhan-Lan, .... Studies on the Protonation Structure of Ofloxacin in Concentrated Sulfuric Acid Solutions[J]. Chem. J. Chinese Universities, 2010, 31(9): 1747.

References

[1]Hyoung R. P., Tae H. K., Ki M. B.. Eur. J. Med. Chem.[J], 2002, 37: 443—460 [2]Bolmstrom A., Karlsson A.. Diagn. Micr. Infec. Dis.[J], 2002, 42: 65—69 [3]Predrag T. D., Milena J. S.. J. Pharm. Biomed. Anal.[J], 1999, 19: 501—510 [4]Rodrigues C., Gameiro P., Reis S., Lima J. L. F. C., Castro B. D.. Langmuir[J], 2002, 18: 10231—10236 [5]Fasani E., Barberis N. F. F., Mella M., Monti S., Albini A.. J. Org. Chem.[J], 1999, 64: 388—5395 [6]Kapetanovic V., Milovanovik L., Erceg M.. Talanta[J], 1996, 43: 2123—2130 [7]Park H. R., Kim T. H., Bark K. M.. Eur. J. Med. Chem.[J], 2002, 37: 443—460 [8]Fang K. C., Chen Y. L., Sheu J. Y., Wang T. C., Tzeng C. C.. J. Med. Chem.[J], 2000, 43: 3809—3812 [9]LI Hui-Zhen(李慧珍), ZHANG Cheng-Feng(章成峰), GAO Xiu-Xiang(高秀香), HUANG Kun(黄昆), ZHAI Yu-Jing(翟羽京), XU Yi-Zhuang(徐怡庄), WU Jin-Guang(吴瑾光). Spectroscopy and Spectral Analysis(光谱学与光谱分析)[J], 2009, 29(5): 1308—1312 [10]LIU Cui-Ge(刘翠格), XU Yi-Zhuang(徐怡庄), WEI Yong-Ju(魏永巨), QI Jian(齐剑), XU Zhen-Hua(许振华), YE Fang(叶放), WU Jin-Guang(吴瑾光). Spectroscopy and Spectral Analysis(光谱学与光谱分析)[J], 2005, 25(4): 584—587 [11]LIU Cui-Ge(刘翠格), XU Yi-Zhuang(徐怡庄), WEI Yong-Ju(魏永巨), ZHAO Jing(赵晶), QI Jian(齐剑), WANG Xin-Hong(王新红), XU Zhen-Hua(许振华), WU Jin-Guang(吴瑾光). Spectroscopy and Spectral Analysis(光谱学与光谱分析)[J], 2005, 25(9): 1446—1450 [12]QI Jian(齐剑), GAO Xiu-Xiang(高秀香), ZHAO Mei-Xian(赵梅仙), XIANG Jun-Feng(向俊峰), LIN Chong-Xi(林崇熙), XU Yi-Zhuang(徐怡庄), WU Jin-Guang(吴瑾光). Chem. J. Chinese Universities(高等学校化学学报)[J], 2007, 28(5): 913—917 [13]GAO Xiu-Xiang(高秀香), QI Jian(齐剑), ZHAO Mei-Xian(赵梅仙), TU Guang-Zhong(涂光中), AN Dong-Ge(安东各), XU Yi-Zhuang(徐怡庄), WU Jin-Guang(吴瑾光). Spectroscopy and Spectral Analysis(光谱学与光谱分析)[J], 2008, 28(6): 1420—1425 [14]QI Jian(齐剑). A New Strategy to Bulid 2D Correlation Spectroscopy & Studies on the Spectroscopic Behavior of Quinolones[D], Peking University, 2007 [15]HE Li-Qin(何黎琴), CHEN Tian-Yu(陈天宇), XIAN Yu-Juan(见玉娟). Anhui Chemical Industry(安徽化工)[J], 2004, 131(6): 22 [16]ZHANG Li-Wei(张黎伟), ZHANG Xin-Xiang(张新祥). Chem. J. Chinese Universities(高等学校化学学报)[J], 2008, 29(4): 694—699 [17]ZENG Yan-Bo(曾延波), ZHAO Di-Hai(赵弟海), LI Lei(李蕾), WANG Lian(王练), SHEN Bing(沈兵), XI Qi-Hui(奚奇辉), ZHANG Meng-Meng(张萌萌). Chem. J. Chinese Universities(高等学校化学学报)[J], 2009, 30(10): 1956—1959

Studies on the Protonation Structure of Ofloxacin in Concentrated Sulfuric Acid Solutions

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