Synthesis and Characterization of Host Guest Inclusion Complexes of Cyclodextrin Molecules with Theophylline by Diverse Methodologies

Ashutosh Dutta, Niloy Roy, Koyeli Das, Debadrita Roy, Raja Ghosh, Mahendra Nath Roy

Abstract


Steady host–guest inclusion complexes have been produced with medicinally important guest molecule theophylline within aqueous α-Cyclodextrin and HP-β-Cyclodextrin. α-and HP-β-Cyclodextrins have been established with favorable structural features for inclusion with Theophylline which include diversified applications in modern science such as controlled delivery in the field of pharmaceuticals, food processing, pesticides, foodstuffs etc. Theophylline is one of the most widely accepted drugs for the treatment of asthma and chronic obstructive pulmonary disease (COPD) worldwide, even if it has been used clinically for many years. With both α and HP-β-Cyclodextrins it is found that 1:1 hosts-guest inclusion complexes are formed with the guest molecule theophylline. The construction and quality of the inclusion complexes have been characterized by using conductivity measurement, surface tension study, and Job’s method. The inclusion phenomenon has been confirmed by FTIR spectroscopy, proton NMR study. Association constants and thermodynamic parameters have been evaluated for the created inclusion complexes by ultraviolet spectroscopy.


Keywords


Theophylline; Hydroxypropyl-β-Cyclodextrin; α-Cyclodextrin; Host–Guest Inclusion Complex; Non-Covalent Interaction.

References


Yoshida, Ken-ichi, Takeshi Shimomura, Kohzo Ito, and Reinosuke Hayakawa. “Inclusion Complex Formation of Cyclodextrin and Polyaniline.” Langmuir 15, no. 4 (February 1999): 910–913. doi:10.1021/la9812471.

Chiang, Po-Chiang, Yue Shi, and Yong Cui. “Temperature Dependence of the Complexation Mechanism of Celecoxib and Hydroxyl-β-Cyclodextrin in Aqueous Solution.” Pharmaceutics 6, no. 3 (August 13, 2014): 467–480. doi:10.3390/pharmaceutics6030467.

Saha, Subhadeep, Aditi Roy, Kanak Roy, and Mahendra Nath Roy. “Study to Explore the Mechanism to Form Inclusion Complexes of β-Cyclodextrin with Vitamin Molecules.” Scientific Reports 6, no. 1 (October 20, 2016). doi:10.1038/srep35764.

Hu, Liandong, Hailei Zhang, Weihua Song, Deliang Gu, and Qiaofeng Hu. “Investigation of Inclusion Complex of Cilnidipine with Hydroxypropyl-β-Cyclodextrin.” Carbohydrate Polymers 90, no. 4 (November 2012): 1719–1724. doi:10.1016/j.carbpol.2012.07.057.

Akhilesh, D., H. Mehta, P. Prabhakara, and J. V. Kamath. "Enhancement of Solubility by Complexation with Cyclodextrin and Nanocrystallisation." International Research Journal of Pharmacy 3, no. 5 (2012): 100-105.

Zhou, Qiuna, Xiaohui Wei, Wei Dou, Guixin Chou, and Zhengtao Wang. “Preparation and Characterization of Inclusion Complexes Formed Between Baicalein and Cyclodextrins.” Carbohydrate Polymers 95, no. 2 (June 2013): 733–739. doi:10.1016/j.carbpol.2013.02.038.

Roy, Kanak, Pranish Bomzan, Milan Chandra Roy, and Mahendra Nath Roy. “Inclusion of Tyrosine Derivatives with α-Cyclodextrin in Aqueous Medium of Various pH Conditions by Surface Tension, Conductance, UV–Vis and NMR Studies.” Journal of Molecular Liquids 230 (March 2017): 104–112. doi:10.1016/j.molliq.2016.12.104.

Gould, Sarah, and Robert C. Scott. “2-Hydroxypropyl-β-Cyclodextrin (HP-β-CD): A Toxicology Review.” Food and Chemical Toxicology 43, no. 10 (October 2005): 1451–1459. doi:10.1016/j.fct.2005.03.007.

Liu, Longxiao, and Suyan Zhu. “Preparation and Characterization of Inclusion Complexes of Prazosin Hydrochloride with β-Cyclodextrin and Hydroxypropyl-β-Cyclodextrin.” Journal of Pharmaceutical and Biomedical Analysis 40, no. 1 (January 2006): 122–127. doi:10.1016/j.jpba.2005.06.022.

Williams III, Robert O., Vorapann Mahaguna, and Mongkol Sriwongjanya. “Characterization of an Inclusion Complex of Cholesterol and Hydroxypropyl-β-Cyclodextrin.” European Journal of Pharmaceutics and Biopharmaceutics 46, no. 3 (November 1998): 355–360. doi:10.1016/s0939-6411(98)00033-2.

Wu, Huahua, Hao Liang, Qipeng Yuan, Tianxin Wang, and Xu Yan. “Preparation and Stability Investigation of the Inclusion Complex of Sulforaphane with Hydroxypropyl-β-Cyclodextrin.” Carbohydrate Polymers 82, no. 3 (October 2010): 613–617. doi:10.1016/j.carbpol.2010.05.020.

Ma, Y. J., D. Q. Jiang, J. X. Meng, M. X. Li, H. H. Zhao, Y. Wang, and L. Q. Wang. “Theophylline: a Review of Population Pharmacokinetic Analyses.” Journal of Clinical Pharmacy and Therapeutics 41, no. 6 (August 31, 2016): 594–601. doi:10.1111/jcpt.12435.

Fernandes, José A., Mariana Sardo, Luís Mafra, Duane Choquesillo-Lazarte, and Norberto Masciocchi. “X-Ray and NMR Crystallography Studies of Novel Theophylline Cocrystals Prepared by Liquid Assisted Grinding.” Crystal Growth & Design 15, no. 8 (June 29, 2015): 3674–3683. doi:10.1021/acs.cgd.5b00279.

Chang, Shao-Yu, and Changquan Calvin Sun. “Superior Plasticity and Tabletability of Theophylline Monohydrate.” Molecular Pharmaceutics 14, no. 6 (May 5, 2017): 2047–2055. doi:10.1021/acs.molpharmaceut.7b00124.

Shannon, Michael. “Predictors of Major Toxicity after Theophylline Overdose.” Annals of Internal Medicine 119, no. 12 (December 15, 1993): 1161. doi:10.7326/0003-4819-119-12-199312150-00002.

Roy, Mahendra Nath, Kanak Roy, Koyeli Das, and Biraj Kumar Barman. “Self-Assembly Inclusion of Green Solvent with Oligosaccharides.” Journal of Molecular Liquids 216 (April 2016): 132–136. doi:10.1016/j.molliq.2015.12.097.

Roy, Mahendra Nath, Deepak Ekka, Subhadeep Saha, and Milan Chandra Roy. “Host–guest Inclusion Complexes of α and β-Cyclodextrins with α-Amino Acids.” RSC Adv. 4, no. 80 (2014): 42383–42390. doi:10.1039/c4ra07877b.

Piñeiro, Ángel, Xavier Banquy, Silvia Pérez-Casas, Edgar Tovar, Abel García, Alessandra Villa, Alfredo Amigo, Alan E. Mark, and Miguel Costas. “On the Characterization of Host−Guest Complexes: Surface Tension, Calorimetry, and Molecular Dynamics of Cyclodextrins with a Non-Ionic Surfactant.” The Journal of Physical Chemistry B 111, no. 17 (May 2007): 4383–4392. doi:10.1021/jp0688815.

Saha, Subhadeep, Tanusree Ray, Saptarshi Basak, and Mahendra Nath Roy. “NMR, Surface Tension and Conductivity Studies to Determine the Inclusion Mechanism: Thermodynamics of Host–guest Inclusion Complexes of Natural Amino Acids in Aqueous Cyclodextrins.” New Journal of Chemistry 40, no. 1 (2016): 651–661. doi:10.1039/c5nj02179k.

Roy, Aditi, Subhadeep Saha, and Mahendra Nath Roy. “Study to Explore Host-Guest Inclusion Complexes of Cyclodextrins with Biologically Active Molecules in Aqueous Environment.” Fluid Phase Equilibria 425 (October 2016): 252–258. doi:10.1016/j.fluid.2016.06.013.

Roy, Mahendra Nath, Subhadeep Saha, Mitali Kundu, Binoy Chandra Saha, and Siti Barman. “Exploration of Inclusion Complexes of Neurotransmitters with β-Cyclodextrin by Physicochemical Techniques.” Chemical Physics Letters 655–656 (July 2016): 43–50. doi:10.1016/j.cplett.2016.05.031.

Qian, Tao, Chenfei Yu, Shishan Wu, and Jian Shen. “Gold Nanoparticles Coated Polystyrene/reduced Graphite Oxide Microspheres with Improved Dispersibility and Electrical Conductivity for Dopamine Detection.” Colloids and Surfaces B: Biointerfaces 112 (December 2013): 310–314. doi:10.1016/j.colsurfb.2013.08.005.

Ekka, Deepak, and Mahendra Nath Roy. “Conductance, a Contrivance To Explore Ion Association and Solvation Behavior of an Ionic Liquid (Tetrabutylphosphonium Tetrafluoroborate) in Acetonitrile, Tetrahydrofuran, 1,3-Dioxolane, and Their Binaries.” The Journal of Physical Chemistry B 116, no. 38 (September 14, 2012): 11687–11694. doi:10.1021/jp302465s.

Gao, Yan-An, Zhong-Hao Li, Ji-Min Du, Bu-Xing Han, Gan-Zuo Li, Wan-Guo Hou, Dong Shen, Li-Qiang Zheng, and Gao-Yong Zhang. “Preparation and Characterization of Inclusion Complexes of β-Cyclodextrin with Ionic Liquid.” Chemistry - A European Journal 11, no. 20 (October 7, 2005): 5875–5880. doi:10.1002/chem.200500120.

Bhattacharjee, Arijit, and Mahendra Nath Roy. “Ion Association and Solvation Behavior of Tetraalkylammonium Iodides in Binary Mixtures of Dichloromethane + N,N-Dimethylformamide Probed by a Conductometric Study.” Physical Chemistry Chemical Physics 12, no. 43 (2010): 14534. doi:10.1039/c0cp00532k.

Ekka, Deepak, and Mahendra Nath Roy. “Conductance, a Contrivance To Explore Ion Association and Solvation Behavior of an Ionic Liquid (Tetrabutylphosphonium Tetrafluoroborate) in Acetonitrile, Tetrahydrofuran, 1,3-Dioxolane, and Their Binaries.” The Journal of Physical Chemistry B 116, no. 38 (September 14, 2012): 11687–11694. doi:10.1021/jp302465s.

Gao, Yan-An, Zhong-Hao Li, Ji-Min Du, Bu-Xing Han, Gan-Zuo Li, Wan-Guo Hou, Dong Shen, Li-Qiang Zheng, and Gao-Yong Zhang. “Preparation and Characterization of Inclusion Complexes of β-Cyclodextrin with Ionic Liquid.” Chemistry - A European Journal 11, no. 20 (October 7, 2005): 5875–5880. doi:10.1002/chem.200500120.

Palepu, Ramamurthy, Joyce E. Richardson, and Vincent C. Reinsborough. “Binding Constants of .beta.-Cyclodextrin/surfactant Inclusion by Conductivity Measurements.” Langmuir 5, no. 1 (January 1989): 218–221. doi:10.1021/la00085a041.

Topchieva, Irina N., Alan E. Tonelli, Irina G. Panova, Elena V. Matuchina, Filipp A. Kalashnikov, Vasily I. Gerasimov, Cristian C. Rusa, Mariana Rusa, and Marcus A. Hunt. “Two-Phase Channel Structures Based on α-Cyclodextrin−Polyethylene Glycol Inclusion Complexes.” Langmuir 20, no. 21 (October 2004): 9036–9043. doi:10.1021/la048970d.

Job, Paul. "Job’s method of continuous variation." Ann. chim 9, no. 11 (1928).

Renny, Joseph S., Laura L. Tomasevich, Evan H. Tallmadge, and David B. Collum. “Method of Continuous Variations: Applications of Job Plots to the Study of Molecular Associations in Organometallic Chemistry.” Angewandte Chemie International Edition 52, no. 46 (October 24, 2013): 11998–12013. doi:10.1002/anie.201304157.

Caso, Jolanda Valentina, Luigi Russo, Maddalena Palmieri, Gaetano Malgieri, Stefania Galdiero, Annarita Falanga, Carla Isernia, and Rosa Iacovino. “Investigating the Inclusion Properties of Aromatic Amino Acids Complexing Beta-Cyclodextrins in Model Peptides.” Amino Acids 47, no. 10 (May 19, 2015): 2215–2227. doi:10.1007/s00726-015-2003-4.

Benesi, H. A., and J. H. Hildebrand. “A Spectrophotometric Investigation of the Interaction of Iodine with Aromatic Hydrocarbons.” Journal of the American Chemical Society 71, no. 8 (August 1949): 2703–2707. doi:10.1021/ja01176a030.

Cramer, F., W. Saenger, and H.-Ch. Spatz. “Inclusion Compounds. XIX.1aThe Formation of Inclusion Compounds of α-Cyclodextrin in Aqueous Solutions. Thermodynamics and Kinetics.” Journal of the American Chemical Society 89, no. 1 (January 1967): 14–20. doi:10.1021/ja00977a003.

Horvath, Gabriela, Thathan Premkumar, Ali Boztas, Eunhye Lee, Sangyong Jon, and Kurt E. Geckeler. “Supramolecular Nanoencapsulation as a Tool: Solubilization of the Anticancer Drug Trans-Dichloro(dipyridine)platinum(II) by Complexation with β-Cyclodextrin.” Molecular Pharmaceutics 5, no. 2 (February 19, 2008): 358–363. doi:10.1021/mp700144t.

Nurhayati, T, Yanti, I Royani, Widayani, and Khairurrijal. “Synthesis and Study of Guest-Rebinding of MIP Based on MAA Prepared Using Theophylline Template.” Journal of Physics: Conference Series 739 (August 2016): 012127. doi:10.1088/1742-6596/739/1/012127.

B. Chankvetadze, N. Burjanadze, G. Pintore, D. Strickmann, D. Bergenthal, G. Blaschke, Chiral recognition of verapamil by cyclodextrins studied with capillary electrophoresis, NMR spectroscopy, and electrospray ionization mass spectrometry. Chirality: The Pharmacological, Biological, and Chemical Consequences of Molecular Asymmetry, 1999, 11(8), pp.635-644. doi: 10.1002/(sici)1520-636x(1999)11:8<635::aid-chir5>3.0.co;2-d.

Sindelar, Vladimir, Mabel A. Cejas, Françisco M. Raymo, Weizhong Chen, Samantha E. Parker, and Angel E. Kaifer. “Supramolecular Assembly of 2,7-Dimethyldiazapyrenium and Cucurbit[8]uril: A New Fluorescent Host for Detection of Catechol and Dopamine.” Chemistry - A European Journal 11, no. 23 (November 18, 2005): 7054–7059. doi:10.1002/chem.200500917.

Wang, Ting, MingDong Wang, ChenDi Ding, and JiaJun Fu. “Mono-Benzimidazole Functionalized β-Cyclodextrins as Supramolecular Nanovalves for pH-Triggered Release of p-Coumaric Acid.” Chem. Commun. 50, no. 83 (2014): 12469–12472. doi:10.1039/c4cc05677a.

Sambasevam, Kavirajaa, Sharifah Mohamad, Norazilawati Sarih, and Nor Ismail. “Synthesis and Characterization of the Inclusion Complex of β-Cyclodextrin and Azomethine.” International Journal of Molecular Sciences 14, no. 2 (February 7, 2013): 3671–3682. doi:10.3390/ijms14023671.

Yang, Rui, Jing-Bo Chen, Xiao-Yang Dai, Rong Huang, Chuan-Fan Xiao, Zhan-Yong Gao, Bo Yang, et al. “Inclusion Complex of GA-13315 with Cyclodextrins: Preparation, Characterization, Inclusion Mode and Properties.” Carbohydrate Polymers 89, no. 1 (June 2012): 89–97. doi:10.1016/j.carbpol.2012.02.054.

Wang, Ting, MingDong Wang, ChenDi Ding, and JiaJun Fu. “Mono-Benzimidazole Functionalized β-Cyclodextrins as Supramolecular Nanovalves for pH-Triggered Release of p-Coumaric Acid.” Chem. Commun. 50, no. 83 (2014): 12469–12472. doi:10.1039/c4cc05677a.

Sindelar, Vladimir, Mabel A. Cejas, Françisco M. Raymo, Weizhong Chen, Samantha E. Parker, and Angel E. Kaifer. “Supramolecular Assembly of 2,7-Dimethyldiazapyrenium and Cucurbit[8]uril: A New Fluorescent Host for Detection of Catechol and Dopamine.” Chemistry - A European Journal 11, no. 23 (November 18, 2005): 7054–7059. doi:10.1002/chem.200500917.

Wang, Ting, MingDong Wang, ChenDi Ding, and JiaJun Fu. “Mono-Benzimidazole Functionalized β-Cyclodextrins as Supramolecular Nanovalves for pH-Triggered Release of p-Coumaric Acid.” Chem. Commun. 50, no. 83 (2014): 12469–12472. doi:10.1039/c4cc05677a.

Chen, Wen, Li-Juan Yang, Shui-Xian Ma, Xiao-Dong Yang, Bao-Min Fan, and Jun Lin. “Crassicauline A/β-Cyclodextrin Host–guest System: Preparation, Characterization, Inclusion Mode, Solubilization and Stability.” Carbohydrate Polymers 84, no. 4 (April 2011): 1321–1328. doi:10.1016/j.carbpol.2011.01.031.


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DOI: 10.28991/esj-2020-01210

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