Copyright (c) 2022 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Structural Studies of Inclusion Complexes of HP-β-CD and Cetirizine by Combination of ROESY and Molecular Modelling Methods
Corresponding Author(s) : Jagjeet Singh
Asian Journal of Chemistry,
Vol. 34 No. 12 (2022): Vol 34 Issue 12, 2022
Abstract
Cyclodextrin inclusion complexes (CD ICs) mimics the biological systems in molecular and chiral recognition mechanisms and therefore used as models in understanding molecular and chiral recognition because of their small size as compared to large biological systems. Cross peaks observed in the ROESY spectra of the mixture of cetirizine (CIT) and HP-β-CD demonstrate the portions of the guest encapsulated in the cavity that helped in establishing the probable orientations of complexes. Protons of both chlorobenzene and phenyl rings showed interactions with the cavity protons suggesting the formation of two complexes. Molecular mechanics (MM) and molecular dynamics (MD) studies were performed only from the wider end of the CD cavity because of steric hinderance of hydroxypropyl groups on the narrow side of CD cavity. Using the fusion of 2D ROESY and molecular modelling studies, the final structures of ensembles of the inclusion complexes were established.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- K. Uekama, F. Hirayama and T. Irie, Chem. Rev., 98, 2045 (1998); https://doi.org/10.1021/cr970025p
- H. Arima, K. Motoyama and T. Higashi, Chem. Pharm. Bull. (Tokyo), 65, 341 (2017); https://doi.org/10.1248/cpb.c16-00779
- M.E. Davis and M.E. Brewster, Nat. Rev. Drug Discov., 3, 1023 (2004); https://doi.org/10.1038/nrd1576
- D. Ma, G. Hettiarachchi, D. Nguyen, B. Zhang, J.B. Wittenberg, P.Y. Zavalij, V. Briken and L. Isaacs, Nat. Chem., 4, 503 (2012); https://doi.org/10.1038/nchem.1326
- S. Muzaffar, S. Imtiaz and S.M. Ali, J. Mol. Struct., 1217, 128419 (2020); https://doi.org/10.1016/j.molstruc.2020.128419
- R. Ficarra, S. Tommasini, D. Raneri, M.L. Calabrò, M.R. Di Bella, C. Rustichelli, M.C. Gamberini and P. Ficarra, J. Pharm. Biomed. Anal., 29, 1005 (2002); https://doi.org/10.1016/S0731-7085(02)00141-3
- A. Cid-Samamed, J. Rakmai, J.C. Mejuto, J. Simal-Gandara and G. Astray, Food Chem., 384, 132467 (2022); https://doi.org/10.1016/j.foodchem.2022.132467
- R. Zhao, C. Sandström, H. Zhang and T. Tan, Molecules, 21, 372 (2016); https://doi.org/10.3390/molecules21040372
- S.M. Ali, S. Muzaffar and S. Imtiaz, J. Mol. Struct., 1197, 56 (2019); https://doi.org/10.1016/j.molstruc.2019.06.080
- S.M. Ali and S. Muzaffar, J. Mol. Struct., 1176, 461 (2019); https://doi.org/10.1016/j.molstruc.2018.08.086
- M. Paczkowska, M. Mizera, K. Lewandowska, A. Miklaszewski, M. Kozak and J. Cielecka-Piontek, J. Incl. Phenom. Macrocycl. Chem., 91, 149 (2018); https://doi.org/10.1007/s10847-018-0808-y
- S. Imtiaz, S. Muzaffar and S.M. Ali, J. Incl. Phenom. Macrocycl. Chem., 100, 71 (2021); https://doi.org/10.1007/s10847-021-01047-9
- S. Imtiaz, S. Banoo, S. Muzaffar and S.M. Ali, Struct. Chem., 32, 1505 (2021); https://doi.org/10.1007/s11224-021-01727-9
- S. Imtiaz and S.M. Ali, J. Indian Chem. Soc., 99, 100299 (2022); https://doi.org/10.1016/j.jics.2021.100299
- M.V. Rekharsky, R.N. Goldberg, F.P. Schwarz, Y.B. Tewari, P.D. Ross, Y. Yamashoji and Y. Inoue, J. Am. Chem. Soc., 117, 8830 (1995); https://doi.org/10.1021/ja00139a017
- S. Khan, K. Fatma and S.M. Ali, J. Incl. Phenom. Macrocycl. Chem., 72, 413 (2012); https://doi.org/10.1007/s10847-011-0005-8
- N.L. Allinger, J. Am. Chem. Soc., 99, 8127 (1977); https://doi.org/10.1021/ja00467a001
- A. Fifere, N. Marangoci, S. Maier, A. Coroaba, D. Maftei and M. Pinteala, Beilstein J. Org. Chem., 8, 2191 (2012); https://doi.org/10.3762/bjoc.8.247
References
K. Uekama, F. Hirayama and T. Irie, Chem. Rev., 98, 2045 (1998); https://doi.org/10.1021/cr970025p
H. Arima, K. Motoyama and T. Higashi, Chem. Pharm. Bull. (Tokyo), 65, 341 (2017); https://doi.org/10.1248/cpb.c16-00779
M.E. Davis and M.E. Brewster, Nat. Rev. Drug Discov., 3, 1023 (2004); https://doi.org/10.1038/nrd1576
D. Ma, G. Hettiarachchi, D. Nguyen, B. Zhang, J.B. Wittenberg, P.Y. Zavalij, V. Briken and L. Isaacs, Nat. Chem., 4, 503 (2012); https://doi.org/10.1038/nchem.1326
S. Muzaffar, S. Imtiaz and S.M. Ali, J. Mol. Struct., 1217, 128419 (2020); https://doi.org/10.1016/j.molstruc.2020.128419
R. Ficarra, S. Tommasini, D. Raneri, M.L. Calabrò, M.R. Di Bella, C. Rustichelli, M.C. Gamberini and P. Ficarra, J. Pharm. Biomed. Anal., 29, 1005 (2002); https://doi.org/10.1016/S0731-7085(02)00141-3
A. Cid-Samamed, J. Rakmai, J.C. Mejuto, J. Simal-Gandara and G. Astray, Food Chem., 384, 132467 (2022); https://doi.org/10.1016/j.foodchem.2022.132467
R. Zhao, C. Sandström, H. Zhang and T. Tan, Molecules, 21, 372 (2016); https://doi.org/10.3390/molecules21040372
S.M. Ali, S. Muzaffar and S. Imtiaz, J. Mol. Struct., 1197, 56 (2019); https://doi.org/10.1016/j.molstruc.2019.06.080
S.M. Ali and S. Muzaffar, J. Mol. Struct., 1176, 461 (2019); https://doi.org/10.1016/j.molstruc.2018.08.086
M. Paczkowska, M. Mizera, K. Lewandowska, A. Miklaszewski, M. Kozak and J. Cielecka-Piontek, J. Incl. Phenom. Macrocycl. Chem., 91, 149 (2018); https://doi.org/10.1007/s10847-018-0808-y
S. Imtiaz, S. Muzaffar and S.M. Ali, J. Incl. Phenom. Macrocycl. Chem., 100, 71 (2021); https://doi.org/10.1007/s10847-021-01047-9
S. Imtiaz, S. Banoo, S. Muzaffar and S.M. Ali, Struct. Chem., 32, 1505 (2021); https://doi.org/10.1007/s11224-021-01727-9
S. Imtiaz and S.M. Ali, J. Indian Chem. Soc., 99, 100299 (2022); https://doi.org/10.1016/j.jics.2021.100299
M.V. Rekharsky, R.N. Goldberg, F.P. Schwarz, Y.B. Tewari, P.D. Ross, Y. Yamashoji and Y. Inoue, J. Am. Chem. Soc., 117, 8830 (1995); https://doi.org/10.1021/ja00139a017
S. Khan, K. Fatma and S.M. Ali, J. Incl. Phenom. Macrocycl. Chem., 72, 413 (2012); https://doi.org/10.1007/s10847-011-0005-8
N.L. Allinger, J. Am. Chem. Soc., 99, 8127 (1977); https://doi.org/10.1021/ja00467a001
A. Fifere, N. Marangoci, S. Maier, A. Coroaba, D. Maftei and M. Pinteala, Beilstein J. Org. Chem., 8, 2191 (2012); https://doi.org/10.3762/bjoc.8.247