Abstract
With the aim to improve the hygroscopic stability of palmatine chloride (PMTCl), an unreported single crystal of PMT–SSA (C21H20NO4·C7H5O6S·H2O) is prepared by the solvent evaporation method and characterized. A comprehensive analysis of the structure and Hirshfeld surface reveals that π–π stacking plays a crucial role in accumulating PMT–SSA. As expected, the hygroscopic stability of PMT–SSA is significantly improved compared with that of PMTCl. This may be due to the presence of π–π stacking in the structure of PMT–SSA which improves the hygroscopic stability. The present work inaugurates an avenue for improving the hygroscopic stability of active pharmaceutical ingredients and provides a novel crystalline product with a bright commercial prospect. Unfortunately, the maximum solubility of PMT–SSA is lower than that of PMTCl. How to improve its solubility will be explored in subsequent studies. However, it is surprising that PMT–SSA shows advantages with regard to antibacterial properties in comparison to PMTCl.
Similar content being viewed by others
REFERENCES
A. W. Newman, S. M. Reutzel-Edens, and G. Zografi. J. Pharm. Sci., 2008, 97, 3. https://doi.org/10.1002/jps.21033
L. J. Mauer and L. S. Taylor. Annu. Rev. Food Sci. Technol., 2010, 1, 41. https://doi.org/10.1146/annurev.food.080708.100915
A. Jayasankar, L. Roy, and N. Rodríguez-Hornedo. J. Pharm., 2010, 99, 3977. https://doi.org/10.1002/jps.22245
Z. M. Jiang, L. N. Bai, N. Yang, Z. B. Feng, and B. Tian. J. Biomed. Biotechnol., 2017, 18, 867. https://doi.org/10.1631/jzus.B1700082
A. M. Abdul-Fattah, D. S. Kalonia, and M. J. Pikal. J. Pharm. Sci., 2010, 96, 1886. https://doi.org/10.1002/jps.20842
O. Bley, J. Siepmann, and R. Bodmeier. J. Pharm. Sci., 2009, 98, 651. https://doi.org/10.1002/jps.21429
O. Bley, J. Siepmann, and R. Bodmeier. Eur. J. Pharm. Biopharm., 2009, 73, 146. https://doi.org/10.1016/j.ejpb.2009.05.001
O. Bley, J. Siepmann, and R. Bodmeier. Int. J. Pharm., 2009, 378, 59. https://doi.org/10.1016/j.ijpharm.2009.05.036
M. J. Peres-Filho, M. Gaeti, S. Oliveira, R. N. Marreto, and E. M. Lima. J. Therm. Anal. Calorim., 2011, 104, 255. https://doi.org/10.1007/s10973-010-1245-3
E. Sjögren, B. Abrahamsson, P. Augustijns, D. Becker, M. B. Bolger, M. Brewster, J. Brouwers, T. Flanagan, M. Harwood, C. Heinen, R. Holm, H. P. Juretschke, M. Kubbinga, A. Lindahl, V. Lukacova, U. Münster, S. Neuhoff, M. A. Nguyen, A. Peer, C. Reppas, A. R. Hodjegan, C. Tannergren, W. Weitschies, C. Wilson, P. Zane, H. Lennernäs, and P. Langguth. Eur. J. Pharm. Sci., 2014, 57, 99. https://doi.org/10.1016/j.ejps.2014.02.010
J. Long, J. Song, L. Zhong, Y. Liao, L. Liu, and X. Li. Biochimie, 2019, 162, 176. https://doi.org/10.1016/j.biochi.2019.04.008
Y. J. Hu, O. Yang, C. M. Dai, Y. Liu, and X. H. Xiao. Biomacromolecules, 2010, 11 106. https://doi.org/10.1021/bm900961e
D. Tarabasz and K. K. Wirginia. Phytother. Res., 2020, 34, 33. https://doi.org/10.1002/ptr.6504
Y. N. Zhang, D. Zhang, Y. Zhang, L. Liu, X. Zhang, L. Zhang, and J. Xi. New J. Chem., 2017, 41, 13268. https://doi.org/10.1039/C7NJ02423A
L. X. Liu, D. Y. Zou, and Y. Zhang. New J. Chem., 2019, 43, 4886. https://doi.org/10.1039/C9NJ00131J
Y. N. Zhang, Y. F. Zhang, and L. Chang. J. Mol. Struct., 2021, 1230, 129631. https://doi.org/10.1016/j.molstruc.2020.129631
S. Yilmaz and F. Unal. Toxicol. Ind. Health, 2014, 30, 926. https://doi.org/10.1177/0748233712466132
E. Lok, F. Iverson, and D. B. Clayson. Cancer Lett., 1982, 16, 163. https://doi.org/10.1016/0304-3835(82)90057-X
C. J. Bailey, C. Day, J. Knapper, S. L. Turner, and P. R. Flatt. Br. J. Pharmacol., 2010, 120, 74. https://doi.org/10.1038/sj.bjp.0700871
Y. N. Zhang, H. M. Yin, Y. Zhang, D. J. Zhang, X. Su, and H. X. Kuang. J. Mol. Struct., 2017, 1130, 199. https://doi.org/10.1016/j.molstruc.2016.10.034
Y. N. Zhang, Y. L. Liu, L. X. Liu, Y. R. Feng, and D. J. Zhang. J. Mol. Struct., 2019, 1197, 377. https://doi.org/10.1016/j.molstruc.2019.07.075
Y. N. Zhang, D. J. Zhang, Y. Zhang, L. X. Liu, and X. Su. New J. Chem., 2017, 41, 13268. https://doi.org/10.1039/C7NJ02423A
L. Y. Liu, D. Y. Zou, Y. N. Zhang, D. Zhang, Y. Zhang, and Q. Zhang. New J. Chem., 2019, 43, 4886. https://doi.org/10.1039/C9NJ00131J
X. Su, Y.-N. Zhang, H.-M. Yin, L.-X. Liu, Y. Zhang, L.-L. Wu, Q. Zhang, C.-X. Wang, L. Zhang, Y.-J. Zhang, and Y.-X. Zhang. J. Mol. Struct., 2019, 1177, 107. https://doi.org/10.1016/j.molstruc.2018.09.050
R. Nongrum, G. S. Nongthombam, M. Kharkongor, N. Rahman, C. Kathing, B. Myrboh, and R. Nongkhlaw. RSC Adv., 2016, 6, 108384. https://doi.org/10.1039/C6RA24108E
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. Howard, and H. Puschmann. J. Appl. Crystallogr., 2010, 42, 339. https://doi.org/10.1107/S0021889808042726
L. J. Bourhis, O. V. Dolomanov, R. J. Gildea, J. Howard, and H. Puschmann. Acta Crystallogr., Sect. A, 2015, 71, 59. https://doi.org/10.1107/S2053273314022207
C. F. Macrae, I. J. Bruno, J. A. Chisholm, P. R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, J. van de Streek, and P. A. Wood. J. Appl. Crystallogr., 2008, 41, 466. https://doi.org/10.1107/S0021889807067908
M. S. Jasani, D. P. Kale, I. P. Singh, and A. K. Bansal. Mol. Pharmaceutics, 2019, 16, 151. https://doi.org/10.1021/acs.molpharmaceut.8b00923
Q. Tao, J. M. Chen, L. Ma, and T. B. Lu. Cryst. Growth Des., 2012, 12, 3144. https://doi.org/10.1021/cg300327x
S. K. Seth, D. Sarkar, and T. Kar. CrystEngComm, 2011, 13, 4528. https://doi.org/10.1039/c1ce05037k
S. K. Seth. Cryst. Growth Des., 2015, 11, 4837. https://doi.org/10.1021/cg2006343
M. A. Spackman and D. Jayatilaka. CrystEngComm, 2009, 11, 19. https://doi.org/10.1039/B818330A
D. M. Yong, C. Y. Min, and K. H. Lee. Arch. Pharm. Res., 2006, 29, 757. https://doi.org/10.1007/BF02974076
Funding
This work was supported by Joint Guidance Project of the Natural Science Foundation of Heilongjiang Province (No. LH2019H059).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare that they have no conflict of interests.
Additional information
Russian Text © The Author(s), 2022, published in Zhurnal Strukturnoi Khimii, 2022, Vol. 63, No. 1, pp. 30-32.https://doi.org/10.26902/JSC_id85852
Supplementary material
Rights and permissions
About this article
Cite this article
Zhang, Y.N., Duan, Y., Liu, L.X. et al. ON IMPROVING THE HYGROSCOPIC STABILITY OF PALMATINE CHLORIDE WITH CRYSTALLINE PALMATINE SULFOSALICYATE PHARMACEUTICAL SALT. J Struct Chem 63, 52–61 (2022). https://doi.org/10.1134/S0022476622010061
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0022476622010061