Molecular Structure of Cefuroxime Axetil Complexes with α-, β-, γ-, and 2-Hydroxypropyl-β-Cyclodextrins: Molecular Simulations and Raman Spectroscopic and Imaging Studies
The formation of cefuroxime axetil+cyclodextrin (CA+CD) complexes increases the aqueous solubility of CA, improves its physico-chemical properties, and facilitates a biomembrane-mediated drug delivery process. In CD-based tablet formulations, it is crucial to investigate the molecular details of com...
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2021-05-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/22/10/5238 |
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| author | Barbara Gieroba Grzegorz Kalisz Anna Sroka-Bartnicka Anita Płazińska Wojciech Płaziński Małgorzata Starek Monika Dąbrowska |
| author_facet | Barbara Gieroba Grzegorz Kalisz Anna Sroka-Bartnicka Anita Płazińska Wojciech Płaziński Małgorzata Starek Monika Dąbrowska |
| author_sort | Barbara Gieroba |
| collection | DOAJ |
| description | The formation of cefuroxime axetil+cyclodextrin (CA+CD) complexes increases the aqueous solubility of CA, improves its physico-chemical properties, and facilitates a biomembrane-mediated drug delivery process. In CD-based tablet formulations, it is crucial to investigate the molecular details of complexes in final pharmaceutical preparation. In this study, Raman spectroscopy and mapping were applied for the detection and identification of chemical groups involved in α-, β-, γ-, and 2-hydroxypropyl-β-CD (2-HP- β-CD)+CA complexation process. The experimental studies have been complemented by molecular dynamics-based investigations, providing additional molecular details of CA+CD interactions. It has been demonstrated that CA forms the guest–host type inclusion complexes with all studied CDs; however, the nature of the interactions is slightly different. It seems that both α- and β-CD interact with furanyl and methoxy moieties of CA, γ-CD forms a more diverse pattern of interactions with CA, which are not observed in other CDs, whereas 2HP-β-CD binds CA with the contribution of hydrogen bonding. Apart from supporting this interpretation of the experimental data, molecular dynamics simulations allowed for ordering the CA+CD binding affinities. The obtained results proved that the molecular details of the host–guest complexation can be successfully predicted from the combination of Raman spectroscopy and molecular modeling. |
| first_indexed | 2024-03-10T11:22:35Z |
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| id | doaj.art-11a0b73fcb4946a39a63d4fa15ff6b0d |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-10T11:22:35Z |
| publishDate | 2021-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-11a0b73fcb4946a39a63d4fa15ff6b0d2023-11-21T19:53:45ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672021-05-012210523810.3390/ijms22105238Molecular Structure of Cefuroxime Axetil Complexes with α-, β-, γ-, and 2-Hydroxypropyl-β-Cyclodextrins: Molecular Simulations and Raman Spectroscopic and Imaging StudiesBarbara Gieroba0Grzegorz Kalisz1Anna Sroka-Bartnicka2Anita Płazińska3Wojciech Płaziński4Małgorzata Starek5Monika Dąbrowska6Department of Biopharmacy, Medical University of Lublin, ul. Chodzki 4a, 20-093 Lublin, PolandDepartment of Biopharmacy, Medical University of Lublin, ul. Chodzki 4a, 20-093 Lublin, PolandDepartment of Biopharmacy, Medical University of Lublin, ul. Chodzki 4a, 20-093 Lublin, PolandDepartment of Biopharmacy, Medical University of Lublin, ul. Chodzki 4a, 20-093 Lublin, PolandJerzy Haber Institute of Catalysis and Surface Chemistry, ul. Niezapominajek 8, 30-239 Krakow, PolandDepartment of Inorganic and Analytical Chemistry, Faculty of Pharmacy, Jagiellonian University Medical College, ul. Medyczna 9, 30-688 Kraków, PolandDepartment of Inorganic and Analytical Chemistry, Faculty of Pharmacy, Jagiellonian University Medical College, ul. Medyczna 9, 30-688 Kraków, PolandThe formation of cefuroxime axetil+cyclodextrin (CA+CD) complexes increases the aqueous solubility of CA, improves its physico-chemical properties, and facilitates a biomembrane-mediated drug delivery process. In CD-based tablet formulations, it is crucial to investigate the molecular details of complexes in final pharmaceutical preparation. In this study, Raman spectroscopy and mapping were applied for the detection and identification of chemical groups involved in α-, β-, γ-, and 2-hydroxypropyl-β-CD (2-HP- β-CD)+CA complexation process. The experimental studies have been complemented by molecular dynamics-based investigations, providing additional molecular details of CA+CD interactions. It has been demonstrated that CA forms the guest–host type inclusion complexes with all studied CDs; however, the nature of the interactions is slightly different. It seems that both α- and β-CD interact with furanyl and methoxy moieties of CA, γ-CD forms a more diverse pattern of interactions with CA, which are not observed in other CDs, whereas 2HP-β-CD binds CA with the contribution of hydrogen bonding. Apart from supporting this interpretation of the experimental data, molecular dynamics simulations allowed for ordering the CA+CD binding affinities. The obtained results proved that the molecular details of the host–guest complexation can be successfully predicted from the combination of Raman spectroscopy and molecular modeling.https://www.mdpi.com/1422-0067/22/10/5238cefuroxime axetilcyclodextrinsdrug deliveryinclusion complexesRaman spectroscopymolecular dynamics |
| spellingShingle | Barbara Gieroba Grzegorz Kalisz Anna Sroka-Bartnicka Anita Płazińska Wojciech Płaziński Małgorzata Starek Monika Dąbrowska Molecular Structure of Cefuroxime Axetil Complexes with α-, β-, γ-, and 2-Hydroxypropyl-β-Cyclodextrins: Molecular Simulations and Raman Spectroscopic and Imaging Studies International Journal of Molecular Sciences cefuroxime axetil cyclodextrins drug delivery inclusion complexes Raman spectroscopy molecular dynamics |
| title | Molecular Structure of Cefuroxime Axetil Complexes with α-, β-, γ-, and 2-Hydroxypropyl-β-Cyclodextrins: Molecular Simulations and Raman Spectroscopic and Imaging Studies |
| title_full | Molecular Structure of Cefuroxime Axetil Complexes with α-, β-, γ-, and 2-Hydroxypropyl-β-Cyclodextrins: Molecular Simulations and Raman Spectroscopic and Imaging Studies |
| title_fullStr | Molecular Structure of Cefuroxime Axetil Complexes with α-, β-, γ-, and 2-Hydroxypropyl-β-Cyclodextrins: Molecular Simulations and Raman Spectroscopic and Imaging Studies |
| title_full_unstemmed | Molecular Structure of Cefuroxime Axetil Complexes with α-, β-, γ-, and 2-Hydroxypropyl-β-Cyclodextrins: Molecular Simulations and Raman Spectroscopic and Imaging Studies |
| title_short | Molecular Structure of Cefuroxime Axetil Complexes with α-, β-, γ-, and 2-Hydroxypropyl-β-Cyclodextrins: Molecular Simulations and Raman Spectroscopic and Imaging Studies |
| title_sort | molecular structure of cefuroxime axetil complexes with α β γ and 2 hydroxypropyl β cyclodextrins molecular simulations and raman spectroscopic and imaging studies |
| topic | cefuroxime axetil cyclodextrins drug delivery inclusion complexes Raman spectroscopy molecular dynamics |
| url | https://www.mdpi.com/1422-0067/22/10/5238 |
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