Inclusion Interactions of Cucurbit[8]uril with Methotrexate

Chem. J. Chinese Universities ›› 2011, Vol. 32 ›› Issue (11): 2544.

• Articles • Previous Articles Next Articles

Inclusion Interactions of Cucurbit[8]uril with Methotrexate

MA Yan-Hui¹, HUANG Ying², ZHU Qian-Jiang^1*, ZHANG Jian-Xin³, XUE Sai-Feng¹, TAO Zhu¹

1. Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province,
2. Engineering and Research Center for Southwest Bio\|Pharmaceutical Resources of Ministry of Education,
3. Key Laboratory of Chemistry for Nature Products of Guizhou Province and Chinese Academy of Sciences, Guizhou University, Guiyang 550025, China

Received:2011-01-11 Revised:2011-05-24 Online:2011-11-10 Published:2011-10-14
Contact: ZHU Qian-Jiang E-mail:gzuzhuqj@163.net
Supported by:
国家自然科学基金(批准号: 20972034), 贵州省科技厅自然科学基金(批准号: 黔科合J字[2009]2288号), 贵州省教育厅自然科学研究项目(批准号: 黔教科2010013号)和贵州大学人才引进项目[批准号: 贵大人基合字(2009)023号]资助.

Abstract

Abstract: Cucurbit[n]urils(Q[n]) which have the unique structure with hydrophobic central cavity and hydrophilic carbonyl group portals, are a class of molecular containers that bind to a variety of cationic and neutral species with high affinity and therefore show great promise as a drug delivery system. In this paper, interactions of cucurbit[8]uril(Q[8]) with anti-cancer drug MTX in different proton forms were studied in details by UV absorption spectroscopy. The result shows that the inclusion ratio of Q[8] and MTX+ is 1:1, and the formation constant is (7.64±1.52)×104 L/mol. Moreover, the thermodynamic parameters of the complex formation were also determined, and it shows that the formation of the inclusion complexes between MTX and Q[8] is entropy controlled, suggesting that hydrophobic forces are the main driving forces. The inclusion complex was further proved by 1H NMR.

Key words: Cucurbit[8]uril, Methotrexate, Ultraviolet absorption spectroscopy, Thermodynamic stability

CLC Number:

TrendMD:

MA Yan-Hui, HUANG Ying, ZHU Qian-Jiang*, ZHANG Jian-Xin, XUE Sai-Feng, TAO Zhu. Inclusion Interactions of Cucurbit[8]uril with Methotrexate[J]. Chem. J. Chinese Universities, 2011, 32(11): 2544.

[1]	LI Lin, XU Xinru, LI Yingqi, ZHANG Caifeng. Preparation of Targeting Nanodiamond-metaminopterone Drug System and Its Interaction with MCF-7 Cells ^† [J]. Chem. J. Chinese Universities, 2019, 40(9): 1998.
[2]	SHI Zhanping, SHI Mai, ZHANG Wenhui, SHEN Shigang, YUE Zhilian, YANG Hui, DING Liang, PAN Xuefeng. Preparation, Characterization and Toxicological Analysis of Alginate-phospholipid Vesicle Composite Hydrogels^† [J]. Chem. J. Chinese Universities, 2017, 38(7): 1270.
[3]	HUANG Ying, WANG Juan, GUO Gai-Ying, TAO Zhu, XUE Sai-Feng, ZHU Qian-Jiang, ZHOU Qing-Di. Interaction of 6-Thioguanine with Cucurbit[7]uril and Bovine Serum Albumin by Spectroscopic Method [J]. Chem. J. Chinese Universities, 2013, 34(2): 375.
[4]	CHEN Rou, YANG Jin-Rong, YANG Xiao-Ying, WANG Yu-Mei, LI Rong-Shan, WANG Rui-Ling, WANG Yin-Song. In vitro Studies of Chitosan-based Multifunctional Drug Delivery Nanosystem [J]. Chem. J. Chinese Universities, 2012, 33(07): 1586.
[5]	HE Hai-Peng, CUI Zhong-Hua, DING Yi-Hong*. Theoretical Studies on the Structures and Stabilities of [MAl₅]⁺(M=Si,Ge,Sn,Pb) [J]. Chem. J. Chinese Universities, 2010, 31(4): 772.
[6]	SHI Guo-Sheng, DING Yi-Hong*. Theoretical Studies on the Conversion Mechanism Between Double-substituted Ammonium Oxides(R₂HNO) and Double-substituted Hydroxylamines(R₂NOH)——Electronegativity and Steric Effects of Substituents [J]. Chem. J. Chinese Universities, 2009, 30(5): 1010.
[7]	XI Cun-Xian, LIU Zhong-Fang, LIU Shao-Pu*, HU Xiao-Li, ZHENG Tian-Long. Resonance Rayleigh Scattering Spectra of the Interaction of Pd(Ⅱ)-Methotrexate Chelate with Methylene Blue and Their Analytical Application [J]. Chem. J. Chinese Universities, 2008, 29(3): 510.
[8]	WANG Yin-Song¹*, HAN Yue-Lian², LI Ying-Xia³, WANG Yu-Mei¹, LI Rong-Shan¹. Preparation and in vitro Experimental Study of Methotrexate-Lactosyl-Chitosan Conjugate [J]. Chem. J. Chinese Universities, 2007, 28(6): 1092.
[9]	YE Ling, JING Xiao-Zhou, YANG Hua, SU Jian-Ting, YUN Liu-Hong . Complex and in vitro Release of Methotrexate-PAMAM Dendrimer [J]. Chem. J. Chinese Universities, 2005, 26(2): 353.
[10]	GAO Dong-Zhao, GUO Yan-He, ZHU Shou-Rong, LIN Hua-Kuan, XU Xin-He . Thermodynamic Stability Studies on the N-[Bis(2-pyridyl)methyl] pyridine-2-carboxamide Metal Complexes [J]. Chem. J. Chinese Universities, 2004, 25(3): 493.
[11]	WANG Yin-Song, LI Ying-Xia, SONG Ni, ZHANG Hua . Preparation and in Vitro Stability of Targeting Antitumor Drug: Methotrexate-Succinyl-Chitosan Conjugate [J]. Chem. J. Chinese Universities, 2003, 24(11): 2103.
[12]	SUN Zi-Jie, HU Jin-Bo, QIAN Yong-Gui, LU Yi-Qiang, LI Qi-Long. Studies on the Electrochemical Behavior of Methotrexate and Its Applicationat Co/GC Ion Implantation Modified Electrode [J]. Chem. J. Chinese Universities, 2002, 23(4): 541.
[13]	SI Yu-Gui, GONG Yue-Fa, ZHANG Zheng-Bo . Synthesis and Spectroscopic Characterizations of Polyfluoroalkoxy Chlorophthalocyanines [J]. Chem. J. Chinese Universities, 1999, 20(3): 403.
[14]	CHENG Jin-Pei, LIU Bo, LU Yun, MI Jiang-Lin, HUAN Zhen-Wei. Homolytic and Heterolytic C-H Bond Dissociation Energies of a-V (or Ⅵ)-Group Cation-substituted Toluenes and Acetophenones [J]. Chem. J. Chinese Universities, 1997, 18(7): 1081.
[15]	FAN Chang-Lie, HU Bin, ZHUO Ren-Xi, DU Yang . Studies on the Tyrosine-Based Polyphosphate Antitumor Drugs [J]. Chem. J. Chinese Universities, 1997, 18(1): 149.

Inclusion Interactions of Cucurbit[8]uril with Methotrexate

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments