Interaction Mode Between Q[8] and Feb †

doi:10.7503/cjcu20190380

Abstract

Abstract:

Ultraviolet absorption spectroscopy, fluorescence spectroscopy, nuclear magnetic resonance spectroscopy, infrared spectroscopy and other methods were used to investigate the inclusion of Q[8] on Feb. The effect of Q[8] on the physicochemical properties of Feb was studied by UV absorption spectroscopy. The influences of Q[8] on the physicochemical properties of Feb and the release of Q[8]/Feb inclusion solution at different pH values and the release of Q[8]/Feb inclusion in artificial intestinal and gastric juice were studied by UV-Vis absorption spectroscopy. The results showed that Q[8] and Feb can form a stable host-guest complex with a molar ratio of 1∶1 in a hydrochloric acid medium with a pH of 1.2. The binding constant was 4.20×10 ⁴ L/mol. At pH=1.2(artificial gastric juice), Feb can combined with Q[8], a stable complex can be formed. At pH=6.8(artificial intestinal juice), the Q[8]/Feb complex can release pure free Feb, which was stable in gastric juice and released in intestinal fluid. Q[8] may be used as a potential drug carrier for Feb to provide basic research data for alleviating the side effects of Feb vomiting, but the actual effect needs further experimental research. It may be due to the better solubility of Q[8] in acidic medium. The release of Q[8]/Feb solid inclusion compound in artificial gastric juice(pH=1.2) was greater than that of artificial intestinal juice(pH=6.8).

Key words: Q[8], Feb, Host-guest complex, Drug release

TrendMD:

JIANG Jing,CHEN Xiaoli,HUANG Yali,ZHANG Qilong,XU Hong,YANG Xiaosheng. Interaction Mode Between Q[8] and Feb ^†[J]. Chem. J. Chinese Universities, 2020, 41(2): 277.

Figures/Tables 10

Scheme 1 Structures of host Q[8](A) and guest β-dichroine(B)

Fig.1 UV spectra of Feb(A) and the absorbance intensity plot at 228 nm(B) of Feb at different pH values c(Feb)=20 μmol/L.

Fig.2 UV spectra of Feb with Q[8] at different pH values(A), trend chart of simple Feb solution and after addition the Q[8](B) and ΔA value(C) of AFeb and AFeb/Q[8] λ=228 nm; c(Feb)=20 μmol/L.

Fig.3 UV spectra(A) and Job’s plot(B) of Feb with Q[8] (A) c(Feb)=20 μmol/L; n(Q[8])/n(Feb), a—k: 0, 0.2, 0.4, 0.6, 0.8, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5. Inset of (A): absorption intensity plot at 228 nm of Feb upon addition of increasing concentrations of Q[8].

Fig.4 Fluorescence emission spectra(A), and Job’s plot(B) of Feb with Q[8] (A) c(Feb)=20 μmol/L; n(Q[8])/n(Feb), a—l: 0, 0.2, 0.4, 0.6, 0.8, 1.0, 1.5, 2.0, 2.5, 3.0, 3.5, 4.0. Inset of (A): the fluorescence intensity plot at 340 nm of Feb upon addition of increasing concentrations of Q[8].

Fig.5 1H NMR spectra of interaction between Q[8] and Feb(pH=1.2) a. Q[8]; b. n(Q[8])/n(Feb)=1:1; c. Feb.

Scheme 2 Interaction mode of Feb with Q[8]

Fig.6 IR spectra of Q[8] with Feb a. Feb; b. Q[8]; c. Feb/Q[8] physical mixture; d. Feb/Q[8] Inclusion complex.

Fig.7 Release of Feb at different pH values pH, a—f: 1.2, 2.0, 3.0, 4.0, 5.0, 6.8. Inset: absorbance intensity plot at 228 nm of Q[8]/Feb.

Fig.8 Release of Q[8]/Feb inclusion complex at pH=1.2(a) and 6.8(b)

References 23

[1]	Chinese Pharmacopoeia Commission, Chinese Pharmacopoeia 2015, Section One, China Medical Science and Technology Press, Beijing, 2015,313
	( 国家药典委员会. 中国药典2015年版一部, 北京: 中国医药科技出版社, 2015,313)
[2]	Li Y., Liu M. C., Jin L. H., Hu D. Y., Yang S., Guangzhou Chemical Industry, 2011,39(9), 7— 9
	( 李燕, 刘明川, 金林红, 胡德禹, 杨松 . 广州化工, 2011,39(9), 7— 9)
[3]	Guo Z. T., Liu X. L., Liang J. P., Shang R. F., Liu Y., Qiang Z., Journal of Traditional Chinese Veterinary Medicine, 2013,32(2), 17— 19
	( 郭志廷, 刘晓璐, 梁剑平, 尚若锋, 刘宇, 强哲 . 中兽医医药杂志, 2013,32(2), 17— 19)
[4]	Zhang J. Y., Liu X. Q., Yang L. X., Feng W. H., China Journal of Chinese Materia Medica, 2017,42(16), 3178— 3184
	( 张继远, 刘晓谦, 杨立新, 冯伟红 . 中国中药杂志, 2017,42(16), 3178— 3184)
[5]	Zhu S., Chandrashekar G., Meng L., Robinson K., Chatterji D., Bioorg. Med. Chem., 2012,20(2), 927— 932
[6]	Kaur K., Jain M., Kaur T., Jain R., Bioorg. Med. Chem., 2009,17(9), 3229— 3256 doi: 10.1016/j.bmc.2009.02.050 URL
[7]	Gao Z. R., Luo Y., Su K. X., Pan J. C., Xie X. Y., Gao Y. J., Chinese Journal of Practical Stomatology, 2018,11(6), 343— 346
	( 高峥嵘, 罗银, 苏楷欣, 潘军臣, 谢小燕, 高义军 . 中国实用口腔科杂志, 2018,11(6), 343— 346)
[8]	Jonge M. J. A. D., Dumez H., Verweij J., Yarkoni S., Snyder D., Lacombe D., Marréaud S., Yamaguchi T., Punt C. J. A., van Oosterom A., Eur. J. Cancer, 2006,42(12), 1768— 1764 doi: 10.1016/j.ejca.2005.12.027 URL
[9]	Guo Z. Y., Liang J. P., Wei X. B., Shang R. F., Guo W. Z., Wang X. H., Hao B. C., Chinese Journal of Veterinary Science, 2013,33(7), 1083— 1085, 1118
	( 郭志廷, 梁剑平, 韦旭斌, 尚若锋, 郭文柱, 王学红, 郝宝成 . 中国兽医学报, 2013,33(7), 1083— 1085, 1118)
[10]	Jiang W. D., Acta Physiologica Sinica, 1961,24(3), 180— 186
	( 江文德 . 生理学报, 1961,24(3), 180— 186)
[11]	Nanjing University Of Chinese Medicine, Chinese Medicine Dictionary Volume Ⅱ(Second Edition), Shanghai Scientific and Technical Publishers, Shanghai, 2006, 2942— 2944
	( 南京中医药大学. 中药大辞典下册(第2版), 上海: 上海科学技术出版社, 2006, 2942— 2944)
[12]	Assaf K. I., Nau W. M., Chem. Soc. Rev., 2014,44(2), 394— 418 doi: 10.1039/C4CS00273C URL
[13]	Mandadapu V., Day A. I., Ghanem A., Chirality, 2014,26(11), 712— 723 doi: 10.1002/chir.22363 URL
[14]	Day A. I. D., Blanch R. J. B., Arnold A. P., Lorenzo S., Lewis G. R., Dance I., Angew. Chem. Int. Ed. Engl., 2010,41(2), 275— 277 doi: 10.1002/1521-3773(20020118)41:2<275::AID-ANIE275>3.0.CO;2-M URL
[15]	Huang Y., Tao Z., Xue S. F., Zhu Q. J., Chem. J. Chinese Universities, 2011,32(9), 2022— 2031
	( 黄英, 陶朱, 薛赛凤, 祝黔江 . 高等学校化学学报, 2011,32(9), 2022— 2031)
[16]	Uzunova V. D., Cullinane C., Brix K., Nau W. M., Day A. I., Org. Biomol. Chem., 2010,8(9), 2037— 2042 doi: 10.1039/b925555a URL
[17]	Chen H., Chan J. Y. W., Xue Y., Wyman I. W., Bardelang D., Macartney D. H., Lee S. M. Y., Wang R., RSC Advances, 2015,5(38), 30067— 30074 doi: 10.1039/C5RA04335B URL
[18]	Fu Y. Z., Shen X. C., Huang Y., Tao Z., Xue S. F., Zhu Q. J., Journal of Guizhou University(Natural Sciences), 2007,24(6), 650— 652
	( 傅晓钟, 沈祥春, 黄英, 陶朱, 薛赛凤, 祝黔江 . 贵州大学学报(自然科学版), 2007,24(6), 650— 652)
[19]	Du P., Zhang Y. P., Journal of Guiyang University of Chinese Medicine, 2016,38(6), 9— 11
	( 杜鹏, 张永萍 . 贵阳中医学院学报, 2016,38(6), 9— 11)
[20]	Jiang J., Huang Y. L., Zhang Q. L., Xu H., Sun X. H., Chem. J. Chinese Universities, 2019,40(1), 76— 82
	( 蒋静, 黄亚励, 张奇龙, 徐红, 孙晓红 . 高等学校化学学报, 2019,40(1), 76— 82)
[21]	Held B., Tang H., Natarajan P., Da S. C., De O. S. V., Bohne C., Quina F. H., Photochem. Photobiol. Sci., 2016,15(6), 832— 832 doi: 10.1039/C6PP90018F URL
[22]	Basílio N., Petrov V., Pina F . ChemPlusChem, 2016,80(12), 1779— 1785 doi: 10.1002/cplu.201500304 URL
[23]	Chinese Pharmacopoeia Commission, Chinese Pharmacopoeia, 2015, Section Two, China Medicai Science and Technology Press, Beijing, 2015,119
	( 国家药典委员会. 中国药典 2015年版二部, 北京: 中国医药科技出版社, 2015,119)