Effect of preparation method on complexation of Cefdinir with β-cyclodextrin

Vij, Mohit; Garse, Harshal; Neha, Dand; Kadam, Vilasrao; Hirlekar, Rajashree

doi:10.1007/s10847-009-9666-y

Cited by 14 publications

(5 citation statements)

References 20 publications

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“…In the pharmaceutical formulation studies, CDs have mostly been applied as complexing compounds to increase the water solubility and to improve the bioavailability and stability of poorly soluble drugs, for example, cephalosporins [ 24 ], including cefuroxime. Cefuroxime axetil (CA), an 1-acetoxyethyl ester of cefuroxime (prodrug), is a broad spectrum second-generation semisynthetic cephalosporin comprising a β-lactam ring [ 25 ], being effectively absorbed from the gastrointestinal tract due to its lipophilicity and subsequently de-esterified to cefuroxime [ 26 ].…”

Section: Introductionmentioning

confidence: 99%

Molecular Structure of Cefuroxime Axetil Complexes with α-, β-, γ-, and 2-Hydroxypropyl-β-Cyclodextrins: Molecular Simulations and Raman Spectroscopic and Imaging Studies

Gieroba

Kalisz

Sroka-Bartnicka

et al. 2021

IJMS

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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.

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Section: Introductionmentioning

confidence: 99%

Molecular Structure of Cefuroxime Axetil Complexes with α-, β-, γ-, and 2-Hydroxypropyl-β-Cyclodextrins: Molecular Simulations and Raman Spectroscopic and Imaging Studies

Gieroba

Kalisz

Sroka-Bartnicka

et al. 2021

IJMS

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“…In this paper, we describe the microwave-assisted synthesis of Fc@CBn inclusion compounds (n = 7, 8) and the characterisation of these materials by several solid-state techniques. Although microwave synthesis has been shown to provide an efficient and cost-effective method for the isolation of CD inclusion compounds 10,[61][62][63] and also for the large-scale production of CBn, 64 we are not aware of any reports describing its use for the isolation of CBn inclusion compounds.…”

Section: Introductionmentioning

confidence: 99%

Solid-state study of the structure and host–guest chemistry of cucurbituril-ferrocene inclusion complexes

et al. 2016

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Inclusion complexes of ferrocene (Fc) with cucurbit[n]urils (n = 7, 8) have been prepared via a rapid microwave-assisted hydrothermal approach. Solids were isolated and characterised by elemental analysis, powder X-ray diffraction (PXRD), spectroscopic, and thermoanalytical methods. The UV-Vis spectra support the presence of Fc in Fc@CB7 and a mixture of Fc and ferrocenium ions in Fc@CB8. Partial oxidation of Fc to Fc takes place in situ mainly due to the presence of acid of crystallisation in CB8. On the basis of PXRD, the complex Fc@CB8 is classified into an isostructural series that is formed by several CB8-containing compounds that crystallise in the space group I4/a and have similar unit cell dimensions and CB8 packing motifs. The FT-IR and Raman spectra of Fc@CB7 are compared with those of the CB7 host and the Fc guest starting materials, revealing significant frequency shifts of some Fc-centered vibrational modes upon complexation. Blueshifts of the Fe-Cp stretching and ring tilt bands are attributed to encapsulation of Fc monomers in a constrained environment, leading to restricted motion effects and/or a change in the Fc conformation from staggered to eclipsed. The absence of comparable shifts for Fc@CB8 point to a weaker host-guest interaction as a consequence of the larger cavity size. The different host-guest interactions are also evident through a comparison of the C{H} CP MAS NMR spectra. Thermogravimetric analysis for the inclusion compounds reveals that sublimation of Fc is inhibited by molecular encapsulation to the extent that oxidative decomposition of the organoiron species takes place concurrently with cucurbituril decomposition, leading to the formation of hematite, α-FeO.

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“…There are various methods of forming inclusion complexes and the physico-chemical properties of the complexes are strongly dependent on the method of preparation. 32 Therefore, it would be interesting to nd out whether the method of preparation of inclusion complex will inuence the drug release process from hydrogels. For this reason the solid inclusion complexes of DX with CD were prepared by two commonly used methods; co-precipitation and freeze-drying.…”

Section: Introductionmentioning

confidence: 99%

Controlled delivery of dexamethasone to the intestine from poly(vinyl alcohol)–poly(acrylic acid) microspheres containing drug-cyclodextrin complexes: influence of method of preparation of inclusion complex

Das

Subuddhi

2014

RSC Adv.

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Effect of preparation method on complexation of Cefdinir with β-cyclodextrin

Cited by 14 publications

References 20 publications

Molecular Structure of Cefuroxime Axetil Complexes with α-, β-, γ-, and 2-Hydroxypropyl-β-Cyclodextrins: Molecular Simulations and Raman Spectroscopic and Imaging Studies

Molecular Structure of Cefuroxime Axetil Complexes with α-, β-, γ-, and 2-Hydroxypropyl-β-Cyclodextrins: Molecular Simulations and Raman Spectroscopic and Imaging Studies

Solid-state study of the structure and host–guest chemistry of cucurbituril-ferrocene inclusion complexes

Controlled delivery of dexamethasone to the intestine from poly(vinyl alcohol)–poly(acrylic acid) microspheres containing drug-cyclodextrin complexes: influence of method of preparation of inclusion complex

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