NMR spectroscopy of inclusion complex of d-(-)-chloramphenicol with β-cyclodextrin in aqueous solution

Ali, Sk Ajim; Asmat, Fahmeena; Maheshwari, Arti

doi:10.1016/j.farmac.2004.05.009

Cited by 29 publications

(11 citation statements)

References 14 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In fact, as shown by the empty black circles in Figure S1A ( Supporting Information File 1 ), Δδ H7 followed a linear trend further downfield when the amount of CD was increased. As described in [ 10 ], the inclusion complex occurred under our conditions involving mainly the methyl group of the S 4 TdR. Indeed, the observed downfield shift in Figure S1A ( Supporting Information File 1 ) is related to changes in the polarity due to the inclusion of the S 4 TdR into the cavity of the CDs [ 59 ].…”

Section: Resultssupporting

confidence: 51%

“…Interesting results were obtained when the protons of the guest molecule were considered. The chemical shifts of the guest protons are often reported as an indication of the inclusion complex formation [ 10 ]. As reported in Figure S1A ( Supporting Information File 1 ), in which the observed Δδ values (see Eq.…”

Section: Resultsmentioning

confidence: 99%

“…The results are shown in Fig. 6 in which a modified B–H equation, as suggested by [ 10 ], was used both for DIMEB and TRIMEB CDs. In particular, by plotting Δδ H5 / Δδ H3 as a function of the ratio [H]/[G], a linear trend was observed supporting the formation of an inclusion complex with a 1:1 stoichiometry, as already observed for 2-HP-CDs.…”

Section: Resultsmentioning

confidence: 99%

“…While α-CD, characterized by a small cavity size, is hardly used and γ-CD is expensive, β-CD is extensively used because its cavity size is able to allocate a large number of guest molecules [ 9 ]. In fact, in the formation of inclusion complexes [ 10 – 12 ] the inner diameter of the cavity of the CDs and the size of the guest molecule play an important role.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Interactions between 4-thiothymidine and water-soluble cyclodextrins: Evidence for supramolecular structures in aqueous solutions

Rizzi¹,

Matera²,

Semeraro³

et al. 2016

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

SummarySince several years the inclusion of organic compounds (guests) within the hydrophobic cavity (host) of cyclodextrins (CDs) has been the subject of many investigations. Interestingly, the formation of inclusion complexes could affect the properties of the guest molecules and, for example, the influence of the delivery system can be a method to improve/change the photochemical behavior of the guest. In particular, very recent studies have shown the protective role of CDs preventing the degradation of the encapsulated guest. Starting from this consideration, in this work, only the structure and complexation mode of the inclusion complexes involving 4-thiothymidine (S4TdR, a known photosensitizer) and five CDs, namely 2-hydroxypropyl-α-cyclodextrin (2-HP-α-CD), 2-hydroxypropyl-β-cyclodextrin (2-HP-β-CD), 2-hydroxypropyl-γ-cyclodextrin (2-HP-γ-CD), heptakis-(2,6-di-O-methyl)-β-cyclodextrin (DIMEB CD) and heptakis-(2,3,6-tri-O-methyl)-β-cyclodextrin (TRIMEB CD) were investigated by different spectroscopic techniques (UV–vis, FTIR–ATR, 1H NMR) and cyclic voltammetry analysis (CV). This work is necessary for a prospective research on the photoreactivity of S4TdR in aqueous environment and in the presence of CDs to prevent its degradation under irradiation. UV–vis, FTIR–ATR and CV measurements suggested the formation of supramolecular structures involving the employed CDs and mainly the pyrimidine ring of S4TdR. 1H NMR analyses confirmed such indication, unveiling the presence of inclusion complexes. The strongest and deepest interactions were suggested when TRIMEB and DIMEB CDs were studied. The S4TdR affinity towards CDs was also evaluated by using the Benesi–Hildebrand (B–H) equation at 25 °C employing CV and 1H NMR methods. The stoichiometry of the interaction was also inferred and it appears to be 1:1 for all examined CDs.

show abstract

Section: Resultssupporting

confidence: 51%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Interactions between 4-thiothymidine and water-soluble cyclodextrins: Evidence for supramolecular structures in aqueous solutions

Rizzi¹,

Matera²,

Semeraro³

et al. 2016

Beilstein J. Org. Chem.

View full text Add to dashboard Cite

show abstract

“…This type of downfield shift is normally observed in CD inclusion complexes such as βCD–nicardipine hydrochloride, sodium picosulfate, and d (−)-chloramphenicol. 41 − 43 …”

Section: Resultsmentioning

confidence: 99%

Dramatically Increased Binding Constant of Water-Soluble Cyclodextrin Hyperbranched Polymers: Explored with Diffusion Ordered NMR Spectroscopy (DOSY)

Doan

Katsuki

et al. 2022

ACS Omega

View full text Add to dashboard Cite

We report that the polymerization of cyclodextrin (CD) with epichlorohydrin (ECH) dramatically increases the binding constant of CD to vanillin, from 55 to 8.4 × 10 3 M –1 , by approximately 100 times, as determined by diffusion ordered spectroscopy (DOSY)– 1 H NMR. The binding constant increased with an increase of the ECH content of the polymer, although ECH polymers without CDs showed no affinity at all, suggesting that the hydrophobicity of the ECH network outside of CDs helps to enhance the binding. This increased binding constant allows CD–ECH polymers to increase the drug loading ratio, which may be one of the most critical issues for drug delivery systems.

show abstract

Spectroscopic Study on Interaction of β‐Cyclodextrin with Triprolidine Hydrochloride

Ali¹,

Asmat

2006

Chin. J. Chem.

Self Cite

View full text Add to dashboard Cite

The complexation of triprolidine hydrochloride (TRP) and β-cyclodextrin (β-CD) in deuterium oxide was investigated by 400 MHz 1 H NMR spectroscopy. The 800 MHz 2D ROESY data revealed that two 1∶1 and one 2∶1 β-CD-TRP inclusion complexes were formed. Both aromatic moieties (p-tolyl and pyridyl ring) has entered into the β-CD cavity, confirming the existence of two different equilibria for 1∶1 inclusion complexes in which p-tolyl ring of the guest is more tightly held by the host cavity. The ROE intermolecular interactions provided the plausible structures of these 1∶1 and 2∶1 stoichiometric inclusion complexes of β-CD-triprolidine hydrochloride in solution.

show abstract

NMR spectroscopy of inclusion complex of d-(-)-chloramphenicol with β-cyclodextrin in aqueous solution

Cited by 29 publications

References 14 publications

Interactions between 4-thiothymidine and water-soluble cyclodextrins: Evidence for supramolecular structures in aqueous solutions

Interactions between 4-thiothymidine and water-soluble cyclodextrins: Evidence for supramolecular structures in aqueous solutions

Dramatically Increased Binding Constant of Water-Soluble Cyclodextrin Hyperbranched Polymers: Explored with Diffusion Ordered NMR Spectroscopy (DOSY)

Spectroscopic Study on Interaction of β‐Cyclodextrin with Triprolidine Hydrochloride

Contact Info

Product

Resources

About