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Journal articles on the topic 'Caffeine cocrystals'

Author: Grafiati

Published: 4 June 2021

Last updated: 13 February 2022

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1

Mukherjee, Arijit, Robin D. Rogers, and A. S. Myerson. "Cocrystal formation by ionic liquid-assisted grinding: case study with cocrystals of caffeine." CrystEngComm 20, no. 27 (2018): 3817–21. http://dx.doi.org/10.1039/c8ce00859k.

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2

Xia, Yanming, Yuanfeng Wei, Hui Chen, Shuai Qian, Jianjun Zhang, and Yuan Gao. "Competitive cocrystallization and its application in the separation of flavonoids." IUCrJ 8, no. 2 (2021): 195–207. http://dx.doi.org/10.1107/s2052252520015997.

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Recently, cocrystallization has been widely employed to tailor physicochemical properties of drugs in the pharmaceutical field. In this study, cocrystallization was applied to separate natural compounds with similar structures. Three flavonoids [baicalein (BAI), quercetin (QUE) and myricetin (MYR)] were used as model compounds. The coformer caffeine (CAF) could form cocrystals with all three flavonoids, namely BAI–CAF (cocrystal 1), QUE–CAF (cocrystal 2) and MYR–CAF (cocrystal 3). After adding CAF to methanol solution containing MYR and QUE (or QUE and BAI), cocrystal 3 (or cocrystal 2) prefer

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3

Smit, Jared P., and Eric J. Hagen. "Polymorphism in Caffeine Citric Acid Cocrystals." Journal of Chemical Crystallography 45, no. 3 (2015): 128–33. http://dx.doi.org/10.1007/s10870-015-0573-3.

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4

Jetti, R. K. R., U. J. Griesser, S. Krivovichev, V. Kahlenberg, D. Bläser, and R. Boese. "Supramolecular synthesis of caffeine solvates and cocrystals." Acta Crystallographica Section A Foundations of Crystallography 61, a1 (2005): c286. http://dx.doi.org/10.1107/s0108767305087799.

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5

Budziak, Arczewska, and Kamiński. "Formation of Prenylated Chalcone Xanthohumol Cocrystals: Single Crystal X-Ray Diffraction, Vibrational Spectroscopic Study Coupled with Multivariate Analysis." Molecules 24, no. 23 (2019): 4245. http://dx.doi.org/10.3390/molecules24234245.

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Four novel xanthohumol (XN) cocrystals with pharmaceutically acceptable coformers, such as nicotinamide (NIC), glutarimide (GA), acetamide (AC), and caffeine (CF) in the 1:1 stoichiometry were obtained by the slow evaporation solution growth technique. The structure of the cocrystals was determined by single crystal X-ray diffraction. The analysis of packing and interactions in the crystal lattice revealed that molecules in the target cocrystals were packed into almost flat layers, formed by the O–HO, O–HN, and N–HO-type contacts between the xanthohumol and coformer molecules. The results prov

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6

Wang, Feng-Yuan, Qi Zhang, Zaiyong Zhang, Xiaoyi Gong, Jian-Rong Wang, and Xuefeng Mei. "Solid-state characterization and solubility enhancement of apremilast drug–drug cocrystals." CrystEngComm 20, no. 39 (2018): 5945–48. http://dx.doi.org/10.1039/c8ce00689j.

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7

Liu, Lili, Chenguang Wang, Jiangnan Dun, Albert H. L. Chow, and Changquan Calvin Sun. "Lack of dependence of mechanical properties of baicalein cocrystals on those of the constituent components." CrystEngComm 20, no. 37 (2018): 5486–89. http://dx.doi.org/10.1039/c8ce00787j.

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8

Verdugo-Escamilla, Cristóbal, Carolina Alarcón-Payer, Antonio Frontera, et al. "Interconvertible Hydrochlorothiazide–Caffeine Multicomponent Pharmaceutical Materials: A Solvent Issue." Crystals 10, no. 12 (2020): 1088. http://dx.doi.org/10.3390/cryst10121088.

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The design of new multicomponent pharmaceutical materials that involve different active pharmaceutical ingredients (APIs), e.g., drug-drug cocrystals, is a novel and interesting approach to address new therapeutic challenges. In this work, the hydrochlorothiazide-caffeine (HCT–CAF) codrug and its methanol solvate have been synthesized by mechanochemical methods and thoroughly characterized in the solid state by powder and single crystal X-ray diffraction, respectively, as well as differential scanning calorimetry, thermogravimetric analyses and infrared spectroscopy. In addition, solubility an

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9

Aitipamula, Srinivasulu, Joseph Cadden, and Pui Shan Chow. "Cocrystals of zonisamide: physicochemical characterization and sustained release solid forms." CrystEngComm 20, no. 21 (2018): 2923–31. http://dx.doi.org/10.1039/c8ce00084k.

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A multi-API cocrystal containing two anti-obesity drugs, zonisamide and caffeine, was found to be promising for the development of a sustained release fixed-dose combination drug for the treatment of obesity.

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10

Leyssens, T., N. Tumanova, K. Robeyns, N. Candoni, and S. Veesler. "Solution cocrystallization, an effective tool to explore the variety of cocrystal systems: caffeine/dicarboxylic acid cocrystals." CrystEngComm 16, no. 41 (2014): 9603–11. http://dx.doi.org/10.1039/c4ce01495b.

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11

Hawkins, Bryson A., Jaeyeon Han, Jonathan J. Du, et al. "Analyzing Hydration Differences in Cocrystal Polymorphs: High-Resolution X-ray Investigation of Caffeine–Glutaric Acid Cocrystals." Crystal Growth & Design 21, no. 8 (2021): 4456–67. http://dx.doi.org/10.1021/acs.cgd.1c00358.

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12

Souza, Matheus S., Luan F. Diniz, Lautaro Vogt, Paulo S. Carvalho, Richard F. D’vries, and Javier Ellena. "Avoiding irreversible 5-fluorocytosine hydration via supramolecular synthesis of pharmaceutical cocrystals." New Journal of Chemistry 42, no. 18 (2018): 14994–5005. http://dx.doi.org/10.1039/c8nj02647e.

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13

Gołdyn, Mateusz, Daria Larowska, Weronika Nowak, and Elżbieta Bartoszak-Adamska. "Theobromine cocrystals with monohydroxybenzoic acids – synthesis, X-ray structural analysis, solubility and thermal properties." CrystEngComm 21, no. 38 (2019): 5721–32. http://dx.doi.org/10.1039/c9ce01020c.

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Theobromine, a compound from the purine alkaloid group, is much less soluble in polar solvents than its analogues, i.e. caffeine and theophylline, that is why it was used as an active pharmaceutical ingredient (API) model in cocrystal preparation.

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14

Leyssens, Tom, Geraldine Springuel, Riccardo Montis, Nadine Candoni, and Stéphane Veesler. "Importance of Solvent Selection for Stoichiometrically Diverse Cocrystal Systems: Caffeine/Maleic Acid 1:1 and 2:1 Cocrystals." Crystal Growth & Design 12, no. 3 (2012): 1520–30. http://dx.doi.org/10.1021/cg201581z.

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15

Vigilante, Nicolas J., and Manish A. Mehta. "A 13C solid-state NMR investigation of four cocrystals of caffeine and theophylline." Acta Crystallographica Section C Structural Chemistry 73, no. 3 (2017): 234–43. http://dx.doi.org/10.1107/s2053229617000869.

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We report an analysis of the 13C solid-state NMR chemical shift data in a series of four cocrystals involving two active pharmaceutical ingredient (API) mimics (caffeine and theophylline) and two diacid coformers (malonic acid and glutaric acid). Within this controlled set, we make comparisons of the isotropic chemical shifts and the principal values of the chemical shift tensor. The dispersion at 14.1 T (600 MHz 1H) shows crystallographic splittings in some of the resonances in the magic angle spinning spectra. By comparing the isotropic chemical shifts of individual C atoms across the four c

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16

Palanisamy, Vasanthi, Palash Sanphui, Muthuramalingam Prakash, and Vladimir Chernyshev. "Multicomponent solid forms of the uric acid reabsorption inhibitor lesinurad and cocrystal polymorphs with urea: DFT simulation and solubility study." Acta Crystallographica Section C Structural Chemistry 75, no. 8 (2019): 1102–17. http://dx.doi.org/10.1107/s2053229619008829.

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Lesinurad (systematic name: 2-{[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetic acid, C17H14BrN3O2S) is a selective uric acid reabsorption inhibitor related to gout, which exhibits poor aqueous solubility. High-throughput solid-form screening was performed to screen for new solid forms with improved pharmaceutically relevant properties. During polymorph screening, we obtained two solvates with methanol (CH3OH) and ethanol (C2H5OH). Binary systems with caffeine (systematic name: 3,7-dihydro-1,3,7-trimethyl-1H-purine-2,6-dione, C8H10N4O2) and nicotinamide (C6H6N2O)

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17

Suresh Kumar, G. S., P. G. Seethalakshmi, N. Bhuvanesh, and S. Kumaresan. "Cocrystals of caffeine with formylphenoxyaliphatic acids: Syntheses, structural characterization, and biological activity." Journal of Molecular Structure 1034 (February 2013): 302–9. http://dx.doi.org/10.1016/j.molstruc.2012.10.033.

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18

Ghosh, Soumyajit, and C. Malla Reddy. "Elastic and Bendable Caffeine Cocrystals: Implications for the Design of Flexible Organic Materials." Angewandte Chemie International Edition 51, no. 41 (2012): 10319–23. http://dx.doi.org/10.1002/anie.201204604.

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19

Ghosh, Soumyajit, and C. Malla Reddy. "Elastic and Bendable Caffeine Cocrystals: Implications for the Design of Flexible Organic Materials." Angewandte Chemie 124, no. 41 (2012): 10465–69. http://dx.doi.org/10.1002/ange.201204604.

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20

Singaraju, Aditya B., Dherya Bahl, Chenguang Wang, Dale C. Swenson, Changquan Calvin Sun, and Lewis L. Stevens. "Molecular Interpretation of the Compaction Performance and Mechanical Properties of Caffeine Cocrystals: A Polymorphic Study." Molecular Pharmaceutics 17, no. 1 (2019): 21–31. http://dx.doi.org/10.1021/acs.molpharmaceut.9b00377.

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21

Cassidy, A. M. C., C. E. Gardner, and W. Jones. "Following the surface response of caffeine cocrystals to controlled humidity storage by atomic force microscopy." International Journal of Pharmaceutics 379, no. 1 (2009): 59–66. http://dx.doi.org/10.1016/j.ijpharm.2009.06.009.

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22

Abosede, Olufunso O., Allen T. Gordon, Tendai O. Dembaremba, et al. "Trimesic acid–Theophylline and Isopthalic acid–Caffeine Cocrystals: Synthesis, Characterization, Solubility, Molecular Docking, and Antimicrobial Activity." Crystal Growth & Design 20, no. 5 (2020): 3510–22. http://dx.doi.org/10.1021/acs.cgd.0c00301.

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23

Otsuka, Yuta, Akira Ito, Masaki Takeuchi, and Hideji Tanaka. "Dry Mechanochemical Synthesis of Caffeine/Oxalic Acid Cocrystals and Their Evaluation by Powder X-Ray Diffraction and Chemometrics." Journal of Pharmaceutical Sciences 106, no. 12 (2017): 3458–64. http://dx.doi.org/10.1016/j.xphs.2017.07.025.

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24

Suresh Kumar, G. S., P. G. Seethalakshmi, D. Sumathi, N. Bhuvanesh, and S. Kumaresan. "Syntheses, structural characterization, and DPPH radical scavenging activity of cocrystals of caffeine with 1- and 2-naphthoxyacetic acids." Journal of Molecular Structure 1035 (March 2013): 476–82. http://dx.doi.org/10.1016/j.molstruc.2012.12.022.

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25

Bučar, Dejan-Krešimir, Rodger F. Henry, Xiaochun Lou, Richard W. Duerst, Leonard R. MacGillivray, and Geoff G. Z. Zhang. "Cocrystals of Caffeine and Hydroxybenzoic Acids Composed of Multiple Supramolecular Heterosynthons: Screening via Solution-Mediated Phase Transformation and Structural Characterization." Crystal Growth & Design 9, no. 4 (2009): 1932–43. http://dx.doi.org/10.1021/cg801178m.

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26

Schultheiss*, Nate, Melanie Roe, and Stephan X. M. Boerrigter. "Cocrystals of nutraceuticalp-coumaric acid with caffeine and theophylline: polymorphism and solid-state stability explored in detail using their crystal graphs." CrystEngComm 13, no. 2 (2011): 611–19. http://dx.doi.org/10.1039/c0ce00214c.

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27

Peterson, Katherine E., Rodger F. Henry, Geoff G. Z. Zhang, and Leonard R. MacGillivray. "Reducing a cocrystal to nanoscale dimensions enables retention of physical crystal integrity upon dehydration." CrystEngComm 19, no. 27 (2017): 3723–26. http://dx.doi.org/10.1039/c7ce00826k.

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28

Kerr, Hannah E., Helen E. Mason, Hazel A. Sparkes, and Paul Hodgkinson. "Testing the limits of NMR crystallography: the case of caffeine–citric acid hydrate." CrystEngComm 18, no. 35 (2016): 6700–6707. http://dx.doi.org/10.1039/c6ce01453d.

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The effects of geometry optimisation on the ability to predict linewidths due to disorder and crystal packing energies is investigated on a previously unreported caffeine citric acid cocrystal system.

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29

Thakuria, Ranjit, Mihails Arhangelskis, Mark D. Eddleston, et al. "Cocrystal Dissociation under Controlled Humidity: A Case Study of Caffeine–Glutaric Acid Cocrystal Polymorphs." Organic Process Research & Development 23, no. 5 (2019): 845–51. http://dx.doi.org/10.1021/acs.oprd.8b00422.

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30

Sowa, Michał, Katarzyna Ślepokura, and Ewa Matczak-Jon. "Solid-state characterization and solubility of a genistein–caffeine cocrystal." Journal of Molecular Structure 1076 (November 2014): 80–88. http://dx.doi.org/10.1016/j.molstruc.2014.07.036.

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31

Hasa, Dritan, Marina Marosa, Dejan-Krešimir Bučar, et al. "Mechanochemical Formation and “Disappearance” of Caffeine–Citric-Acid Cocrystal Polymorphs." Crystal Growth & Design 20, no. 2 (2019): 1119–29. http://dx.doi.org/10.1021/acs.cgd.9b01431.

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32

Pal, Sharmistha, B. N. Roopa, Khalid Abu, Sulur G. Manjunath, and Sudhir Nambiar. "Thermal studies of furosemide–caffeine binary system that forms a cocrystal." Journal of Thermal Analysis and Calorimetry 115, no. 3 (2013): 2261–68. http://dx.doi.org/10.1007/s10973-013-3031-5.

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33

Duggirala, Naga Kiran, Amber Vyas, Joseph F. Krzyzaniak, Kapildev K. Arora, and Raj Suryanarayanan. "Mechanistic Insight into Caffeine–Oxalic Cocrystal Dissociation in Formulations: Role of Excipients." Molecular Pharmaceutics 14, no. 11 (2017): 3879–87. http://dx.doi.org/10.1021/acs.molpharmaceut.7b00587.

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34

Mishra, Manish Kumar, Kamini Mishra, Aditya Narayan, C. Malla Reddy, and Venu R. Vangala. "Structural Basis for Mechanical Anisotropy in Polymorphs of a Caffeine–Glutaric Acid Cocrystal." Crystal Growth & Design 20, no. 10 (2020): 6306–15. http://dx.doi.org/10.1021/acs.cgd.0c01033.

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35

Alsirawan, Mhd Bashir, Xiaojun Lai, Rafel Prohens, et al. "Solid-State Competitive Destabilization of Caffeine Malonic Acid Cocrystal: Mechanistic and Kinetic Investigations." Crystal Growth & Design 20, no. 12 (2020): 7598–605. http://dx.doi.org/10.1021/acs.cgd.0c01246.

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36

Aher, Suyog, Ravindra Dhumal, Kakasaheb Mahadik, Jarkko Ketolainen, and Anant Paradkar. "Effect of cocrystallization techniques on compressional properties of caffeine/oxalic acid 2:1 cocrystal." Pharmaceutical Development and Technology 18, no. 1 (2011): 55–60. http://dx.doi.org/10.3109/10837450.2011.618950.

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37

Ji, Canran, Mikaila C. Hoffman, and Manish A. Mehta. "Catalytic Effect of Solvent Vapors on the Spontaneous Formation of Caffeine–Malonic Acid Cocrystal." Crystal Growth & Design 17, no. 4 (2017): 1456–59. http://dx.doi.org/10.1021/acs.cgd.6b01164.

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38

Chow, Pui Shan, Grace Lau, Wai Kiong Ng, and Venu R. Vangala. "Stability of Pharmaceutical Cocrystal During Milling: A Case Study of 1:1 Caffeine–Glutaric Acid." Crystal Growth & Design 17, no. 8 (2017): 4064–71. http://dx.doi.org/10.1021/acs.cgd.6b01160.

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39

Moghimi, A., H. R. Khavasi, F. Dashtestani, D. Kordestani, E. Behboodi, and B. Maddah. "A cocrystal of caffeine and dipicolinic acid: synthesis, characterization, X-ray crystallography, and solution studies." Journal of Structural Chemistry 54, no. 5 (2013): 990–95. http://dx.doi.org/10.1134/s0022476613050247.

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40

Habgood, Matthew, and Sarah L. Price. "Isomers, Conformers, and Cocrystal Stoichiometry: Insights from the Crystal Energy Landscapes of Caffeine with the Hydroxybenzoic Acids." Crystal Growth & Design 10, no. 7 (2010): 3263–72. http://dx.doi.org/10.1021/cg100405s.

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41

Bučar, Dejan-Krešimir, Graeme M. Day, Ivan Halasz, et al. "The curious case of (caffeine)·(benzoic acid): how heteronuclear seeding allowed the formation of an elusive cocrystal." Chemical Science 4, no. 12 (2013): 4417. http://dx.doi.org/10.1039/c3sc51419f.

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42

Aher, Suyog, Ravindra Dhumal, Kakasaheb Mahadik, Anant Paradkar, and Peter York. "Ultrasound assisted cocrystallization from solution (USSC) containing a non-congruently soluble cocrystal component pair: Caffeine/maleic acid." European Journal of Pharmaceutical Sciences 41, no. 5 (2010): 597–602. http://dx.doi.org/10.1016/j.ejps.2010.08.012.

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43

Bučar, Dejan-Krešimir, Rodger F. Henry, Richard W. Duerst, Xiaochun Lou, Leonard R. MacGillivray, and Geoff G. Z. Zhang. "A 1:1 Cocrystal of Caffeine and 2-Hydroxy-1-Naphthoic Acid Obtained via a Slurry Screening Method." Journal of Chemical Crystallography 40, no. 11 (2010): 933–39. http://dx.doi.org/10.1007/s10870-010-9766-y.

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44

Ketkar, Sameer, Sudhir K. Pagire, N. Rajesh Goud, Kakasaheb Mahadik, Ashwini Nangia, and Anant Paradkar. "Tracing the Architecture of Caffeic Acid Phenethyl Ester Cocrystals: Studies on Crystal Structure, Solubility, and Bioavailability Implications." Crystal Growth & Design 16, no. 10 (2016): 5710–16. http://dx.doi.org/10.1021/acs.cgd.6b00759.

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45

Otsuka, Yuta, Akira Ito, Masaki Takeuchi, Tetsuo Sasaki, and Hideji Tanaka. "Effects of temperature on terahertz spectra of caffeine/oxalic acid 2:1 cocrystal and its solid-state density functional theory." Journal of Drug Delivery Science and Technology 56 (April 2020): 101215. http://dx.doi.org/10.1016/j.jddst.2019.101215.

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46

Yu, Yue-Ming, Ling-Yang Wang, Fan-Zhi Bu, et al. "The supramolecular self-assembly of 5-fluorouracil and caffeic acid through cocrystallization strategy opens up a new way for the development of synergistic antitumor pharmaceutical cocrystal." CrystEngComm 22, no. 45 (2020): 7992–8006. http://dx.doi.org/10.1039/d0ce01297a.

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47

Battini, Swapna, M. K. Chaitanya Mannava, and Ashwini Nangia. "Improved Stability of Tuberculosis Drug Fixed-Dose Combination Using Isoniazid-Caffeic Acid and Vanillic Acid Cocrystal." Journal of Pharmaceutical Sciences 107, no. 6 (2018): 1667–79. http://dx.doi.org/10.1016/j.xphs.2018.02.014.

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48

Dabir, Tasneem Omer, Vilas Gajanan Gaikar, Sujatha Jayaraman, and Shreya Mukherjee. "Thermodynamic modeling studies of aqueous solubility of caffeine, gallic acid and their cocrystal in the temperature range of 303 K–363 K." Fluid Phase Equilibria 456 (January 2018): 65–76. http://dx.doi.org/10.1016/j.fluid.2017.09.021.

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49

Acree, William E. "Comments on “Thermodynamic modeling studies of aqueous solubility of caffeine, gallic acid and their cocrystal in the temperature range of 303 K–363 K”." Fluid Phase Equilibria 463 (May 2018): 32–33. http://dx.doi.org/10.1016/j.fluid.2018.01.037.

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50

Verma, Priya, Anubha Srivastava, Karnica Srivastava, Poonam Tandon, and Manishkumar R. Shimpi. "Molecular Structure, Spectral Investigations, Hydrogen Bonding Interactions and Reactivity-Property Relationship of Caffeine-Citric Acid Cocrystal by Experimental and DFT Approach." Frontiers in Chemistry 9 (July 26, 2021). http://dx.doi.org/10.3389/fchem.2021.708538.

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The pharmaceutical cocrystal of caffeine-citric acid (CAF-CA, Form II) has been studied to explore the presence of hydrogen bonding interactions and structure-reactivity-property relationship between the two constituents CAF and Citric acid. The cocrystal was prepared by slurry crystallization. Powder X-ray diffraction (PXRD) analysis was done to characterize CAF-CA cocrystal. Also, differential scanning calorimetry (DSC) confirmed the existence of CAF-CA cocrystal. The vibrational spectroscopic (FT-IR and FT-Raman) signatures and quantum chemical approach have been used as a strategy to get i

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