First solid-state NMR spectroscopy evaluation of complexes of benznidazole with cyclodextrin derivatives

Priotti, Josefina; Ferreira, Maria João; Lamas, María Celina; Leonardi, Darío; Salomón, Claudio J.; Nunes, Teresa

doi:10.1016/j.carbpol.2015.05.045

Cited by 21 publications

(5 citation statements)

References 25 publications

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“…The complexation-induced chemical shift (Δδ) of H3 and H5 protons (Δδ = 0.077, 0.133) of β-CD are those expected as a result of interaction with those protons of the aspartame Ha, Hb, Hb′, Hc, Hc′, Hf (Δδ = 0.014, 0.025, 0.021, 0.008, 0.008, 0.188, respectively), which are oriented towards the β-CD cavity. This result is consistent with a previous investigation of aspartame and cyclodextrin by 1 H NMR and the interaction of benznidazole or albendazole with cyclodextrin derivatives 32,38 . FT-IR spectrum was further used to characterize the inclusion of aspartame by CDs (Fig.S2 in Supporting Information).…”

Section: Characterization Of the Inclusion Complexsupporting

confidence: 93%

Sweetness Enhancement of Aspartame in the Presence of Cyclodextrins and the Thermodynamics in Bindinge

Tiantian¹,

Xu²,

Bingqiang³

et al. 2016

Acta Physico-Chimica Sinica

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Current research on the effects of cyclodextrins (CDs) on the sweetness of aspartame (ASP) focuses on the stability of aspartame as protected by CDs. We propose a relationship between the sweetness intensity of aspartame and its thermodynamic binding affinity with CDs. In this paper, we describe the sensory evaluation of aspartame with the five CDs α-cyclodextrin (α-CD), β-cyclodextrin (β-CD), γ-cyclodextrin (γ-CD), hydroxypropylβ-cyclodextrin (HP-β-CD), and methyl-β-cyclodextrin (Met-β-CD). β-CD was found to significantly enhance the sweetness intensity of aspartame. The binding affinity of CDs with aspartame was then investigated using isothermal titration calorimetry (ITC) and fluorescence spectroscopy. The binding of aspartame with β-CD resulted in a free energy change with the largest binding constant. Differential scanning calorimetry (DSC), nuclear magnetic resonance (1 H NMR), and Fourier transform infrared (FT-IR) spectroscopy further revealed the mechanism behind the complexation. This research gives insight to the contribution of the thermodynamic binding affinity to the sweetness intensity of aspartame. It also provides an approach for screening flavorretention agents by measuring binding constants.

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Section: Characterization Of the Inclusion Complexsupporting

confidence: 93%

Sweetness Enhancement of Aspartame in the Presence of Cyclodextrins and the Thermodynamics in Bindinge

Tiantian¹,

Xu²,

Bingqiang³

et al. 2016

Acta Physico-Chimica Sinica

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“…Similar peaks were observed in previously reported solid-state 13 C NMR spectra of γ-CD/aromatic compound complexes. 37,38 These results suggest that the complex is in an amorphous state with guest molecules encapsulated within γ-CD. Because the anthracene derivative is insoluble in water, it was difficult to determine the stoichiometric ratio of the complexes using NMR measurements in aqueous solution.…”

Section: Resultsmentioning

confidence: 86%

Circularly polarised luminescence from excimer emission of anthracene derivatives complexed with γ-cyclodextrin in the solid state

et al. 2023

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“…Chemical shifts were measured relative to the peak at 4.80 ppm, due to the solvent (D 2 O). The ROESY spectrum was recorded applying a mixing time of 500 ms under spin lock condition, 256 increments were collected with 32 repetitions and the data matrix measured was processed as a matrix of 2 k (F2) by 1 k (F1) data points [35].…”

Section: Molecular Docking Between A- B-cd and Isopmentioning

confidence: 99%

Docking and physico-chemical properties of α- and β-cyclodextrin complex containing isopulegol: a comparative study

Menezes

Dória

Araújo

et al. 2016

J Incl Phenom Macrocycl Chem

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Isopulegol (ISOP) is a monoterpenoid alcohol presented in the essential oils of several plants that possesses therapeutic properties The aim of this work was prepare samples with ISOP and a-and b-cyclodextrins (aand b-CD) through three different methods: physical mixture, paste method (PC) and slurry complexation (SC). In order to evaluate the formation of inclusion complexes, the techniques of differential scanning calorimetry, thermogravimetry/derivative thermogravimetry, fourier transform infrared spectroscopy, X-ray diffractometry (XRD), gas chromatography-mass spectrometry analyses (GC/ MS), docking, nuclear magnetic resonance and scanning electron microscopy were considered. The analyses of the a-CD or b-CD/ISOP revealed the formation of a complex mainly through the PC and SC methods for a-CD and b-CD, respectively. XRD diffraction characteristics presented formation of a trend to new solid phase, which suggested the formation of inclusion complexes. The GC/MS demonstrated that the PC method was the best one to form complexation with a-CD (48.8 %). Concerning b-CD, the SC method exhibited the strongest complexation (68.3 %). Furthermore, the molecular theoretical docking study demonstrated that a-CD/ISOP inclusion complex formed a more stable complex than did the b-CD/ISOP inclusion complex.

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First solid-state NMR spectroscopy evaluation of complexes of benznidazole with cyclodextrin derivatives

Cited by 21 publications

References 25 publications

Sweetness Enhancement of Aspartame in the Presence of Cyclodextrins and the Thermodynamics in Bindinge

Sweetness Enhancement of Aspartame in the Presence of Cyclodextrins and the Thermodynamics in Bindinge

Circularly polarised luminescence from excimer emission of anthracene derivatives complexed with γ-cyclodextrin in the solid state

Docking and physico-chemical properties of α- and β-cyclodextrin complex containing isopulegol: a comparative study

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