Efficient Purification of Camptothecin via Aqueous Two-phase System Composed of 1,1,3,3-Tetramethylguanidinium Benzoate Ionic Liquid and K2CO3

doi:10.1007/s40242-016-5488-9

Abstract

Abstract:

After being hydrolyzed into corresponding hydrosoluble carboxylate by 1,1,3,3,-tetramethylguanidine (TMG), camptothecin was extracted via the aqueous two-phase systems composed of ionic liquid 1,1,3,3- tetramethylguanidinium(TMGM) carboxylate and K₂CO₃, and was regenerated at the final by dilute aqueous hydrochloric acid. Among the ionic liquids, TMGM benzoate showed the best effect, TMGM formate the worst, this results were consistent with the liposolubilities of different carboxylic acid components in the ionic liquids. Through two-step extraction of TMGM benzoate ionic liquid/K₂CO₃ aqueous two-phase under a favorable condition, camptothecin was obtained in a purity of 98.3% and a total yield of 85.1%, from the crude camptothecin extract with a purity of 14.2%.

Key words: Ionic liquid, Aqueous two-phase extraction, Camptothecin, 1,1,3,3-Tetramethylguanidine, Reversible hydrolysis

ZHU Jian, JIN Zhimin. Efficient Purification of Camptothecin via Aqueous Two-phase System Composed of 1,1,3,3-Tetramethylguanidinium Benzoate Ionic Liquid and K₂CO₃[J]. Chemical Research in Chinese Universities, 2016, 32(4): 630-633.

References

[1] Wall M. E., Wani M. C., Cook C. E., Palmer K. H., McPhail A. T., Sim G. A., J. Am. Chem. Soc., 1966, 88, 3888
[2] Zhang H., Tong M. R., Pan J. L., Yu Y. T., Wang Y. Y., Huang X. L., Huang J. D., Hu X. J., Ion Exch. Adsorp., 1995, 12, 145
[3] Guo Z. J., Ma C. J., Acta Chin. Med. Pharmacol., 2005, 4, 10
[4] Yan X. H., Hu X. Y., Tan F., Zhu S. Q., Li L. Q., Zhang L. L., Xie J., China J. Chin. Mater. Med., 2007, 32, 1598
[5] Han J., Wang Y., Yu C., Li C., Yan Y., Liu Y., Wang L., Anal. Chim. Acta, 2011, 685, 138
[6] Li Z. Y., Pei Y. C., Liu L., Wang J. J., J. Chem. Thermodyn., 2010, 42, 932
[7] Neves C. M. S. S., Ventura S. P. M., Freire M. G., Marrucho I. M., Coutinho J. A. P., J. Phys. Chem. B, 2009, 113, 5194
[8] Zeng Y. B., Zhao D. H., Li L., Wang L., Shen B., Xi Q. H., Zhang M. M., Chem. J. Chinese Universities, 2009, 30(10), 1956
[9] Freire M. G., Neves C. M. S. S., Marrucho I. M., Lopes J. N. C., Rebelo L. P. N., Coutinho J. A. P., Green Chem., 2010, 12, 1715
[10] Ma C. H., Wang L., Yan Y. S., Che G. B., Yin Y. S., Wang R. Z., Li D. Y., Chem. Res. Chinese Universities, 2009, 25(6), 832
[11] Deive F. J., Rodríguez A., Pereiro A. B., Araújo J. M. M., Longo M. A., Coelho M. A. Z., Marrucho I. M., Green Chem., 2011, 13, 390
[12] Fassberg J., Stella V. J., J. Pharm. Sci., 1992, 81, 676
[13] Underberg W. J. M., Goossen R. M. J., Smith B. R., J. Pharm. Biomed. Anal., 1990, 8, 681
[14] Wang Y., Yu T., Zang Y. H., Zu Y. G., Chin. Trad. Herb Drugs, 2001, 32, 882
[15] Hinz H. R., Method for Purifying Camptothecin Compounds, US5352789, 1994
[16] Ding X. Q., Wang Y. Z., Zeng Q., Chen J., Huang Y. H., Xu K. J., Anal. Chim. Acta, 2014, 815, 22
[17] Liu G. S., Dong Q. L., Yao Y. S., Yao Z. J., Org. Lett., 2008, 10, 5393
[18] Li C. Y., Lin C. H., Wu T. S., Chem. Pharm. Bullet., 2005, 53, 347

Efficient Purification of Camptothecin via Aqueous Two-phase System Composed of 1,1,3,3-Tetramethylguanidinium Benzoate Ionic Liquid and K₂CO₃

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	YU Fengli, CHI Yujie, GAO Chong, CHEN Ruirui, XIE Congxia, YU Shitao. Baeyer-Villiger Oxidation of Cyclic Ketones Catalyzed by Amino Acid Ionic Liquids [J]. Chemical Research in Chinese Universities, 2020, 36(5): 865-869.
[2]	ZHAO Qi, LIANG Xiaoxiao, YOU Yingxue, WANG Yuliang, DU Xinwei, LIU Baijun, HU Wei. Proton Conductivity Improvement Effect of Cellulose on SPEEKK Based PEM [J]. Chemical Research in Chinese Universities, 2019, 35(5): 916-923.
[3]	GUAN Lianyue, LUO Qiang, LIANG Na, YU Wei. Determination of Lignans in Schisandra sphenanthera and Schisandra chinensis Using Ionic Liquid-based Ultrasonic-assisted Extraction and High-performance Liquid Chromatography [J]. Chemical Research in Chinese Universities, 2018, 34(6): 887-892.
[4]	CHEN Siyan, GAO Zhenhai. Structure of a Mixture of Graphene Plates and Ionic Liquid 1-Octyl-3-methylimidazolium Hexafluoroborate [J]. Chemical Research in Chinese Universities, 2018, 34(4): 598-603.
[5]	ZHU Xuelin, YE Qinmei, WEN Chao, CHEN Liping, LIANG Guangping, ZENG Ting, ZHANG Dongmei, JIANG Renwang. Synthesis of Camptothecin-10-O-glucoside Using an Engineered Oleandomycin Glucosyltransferase [J]. Chemical Research in Chinese Universities, 2018, 34(3): 423-427.
[6]	XU Chao, YIN Xuhan, ZHANG Chuan, CHEN Hongyue, HUANG He, HU Yi. Improving Catalytic Performance of Burkholderiacepacia Lipase by Chemical Modification with Functional Ionic Liquids [J]. Chemical Research in Chinese Universities, 2018, 34(2): 279-284.
[7]	WANG Jingyang, ZHANG Meng, XU Xiaodong, FENG Jing, WANG Yanli, ZHANG Milin, HAN Wei, CHEN Yitung, TIAN Guoxin. Synthesis and Characterization of [Cu(N-MeIm)₄(BF₄)₂] in Ionic Liquid [J]. Chemical Research in Chinese Universities, 2018, 34(1): 8-12.
[8]	Ana Maria POPESCU, Kazimir YANUSHKEVICH, Vasile SOARE, Cristina DONATH, Elena Ionela NEACSU, Virgil CONSTANTIN. Recovery of Metals from Anodic Dissolution Slime of Waste from Electric and Electronic Equipment(WEEE) by Extraction in Ionic Liquids [J]. Chemical Research in Chinese Universities, 2018, 34(1): 113-118.
[9]	LI Shuang, LI Shuni, ZHAI Quanguo, JIANG Yucheng, HU Mancheng. Phase Behavior of Ionic Liquids-Cesium Carbonate-Water Aqueous Two-phase Systems and Their Extraction of L-Tryptophan [J]. Chemical Research in Chinese Universities, 2018, 34(1): 127-131.
[10]	BU Luxia, LIU Daying, WEI Zhen, MA Zhanlin. Physicochemical Properties of Bi-containing Ionic Liquid Analogs Based on Choline Chloride [J]. Chemical Research in Chinese Universities, 2017, 33(6): 929-933.
[11]	TONG Jing, ZHENG Xu, TONG Jian, QU Ye, LIU Lu, LI Hui. Molar Surface Gibbs Energy of the Aqueous Solution of Ionic Liquid[C₄mim] [OAc] [J]. Chemical Research in Chinese Universities, 2017, 33(5): 828-832.
[12]	ZHANG Lifeng, DU Suqing, SONG Qiaolan, LIU Yi, GUO Shouwu. Fluorine-free Ionic Liquid Based on Thiocyanate Anion with Propylene Carbonate as Electrolytes for Supercapacitors:Effects of Concentration and Temperature [J]. Chemical Research in Chinese Universities, 2017, 33(5): 779-784.
[13]	BIAN Min, TIAN Ling, YAO Cheng. An Improved Method of Simultaneous Determination of Four Bioactive Compounds in Evodiae Fructus Using Ionic Liquids as Mobile Phase Additives in High Performance Liquid Chromatography [J]. Chemical Research in Chinese Universities, 2017, 33(4): 552-558.
[14]	GAO Shenghan, GAO Ruichang. Antibacterial Cellulose Composite Membranes Prepared in Ionic Liquid via Phase Inversion Method [J]. Chemical Research in Chinese Universities, 2017, 33(4): 678-683.
[15]	LIU Lihong, WANG Chunfeng, ZHUO Kelei. Cetyltrimethylammonium Bromide(CTAB)-Ionic Liquid Composite Modified Electrode for Sensitive Cyclic Voltammetric Determination of Bisphenol A [J]. Chemical Research in Chinese Universities, 2016, 32(6): 992-995.