Detection and characterization of cyclodextrin complexes with β-carboline derivatives by spectroscopic techniques

Martín, Laura Serrano; León, Andrés G.; Martín, M. Antonia; Castillo, B. del; Menéndez, J. Carlos

doi:10.1016/s0731-7085(03)00201-2

Cited by 23 publications

(13 citation statements)

References 31 publications

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“…Negative values of complexation energies obtained for α‐, β‐, and γ‐CD complexes indicate the tendency of examined ligands toward complexation (Table ). Results of harmane‐β‐CD and harmine‐β‐CD complexes were in agreement with their complexation previously confirmed by 13 C‐NMR, 1 H‐NMR, infrared, and UV‐Vis absorption spectra . Further investigated thermochemistry of complexation process, enthalpy changes (ΔH°), entropy contribution (ΔSº), and Gibbs free energy changes (ΔG°) were calculated at 1 atm and 289.15 K by PM3 method.…”

Section: Resultssupporting

confidence: 80%

Quantitative structure‐mobility relationship analysis of imidazoline receptor ligands in CDs‐mediated CE

et al. 2013

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The performed quantitative structure-mobility relationship (QSMR) study has investigated relative migration times of 11 guanidine/imidazoline derivatives, imidazoline receptor ligands, in CE system containing one of CDs, α-, β-, or γ-CD, using linear and nonlinear modeling methods. The analyzed ligands and their inclusion complexes with CDs were fully examined and optimized at semiempirical parametrized model 3 level. The density functional theory, such as B3LYP/6-31G+(d,p)/3-21G(d)/STO-3G(d,p)/STO-3G(d), and ab initio theory, such as HF/3-21G(d)/STO-3G(d), were applied for molecular descriptors computation of the optimized ligands and their complexes. Predictive performances of the developed QSMR models were tested by use of the cross-validation and external test set prediction. Obtained results for Q(2) values (0.869, 0.911, and 0.966 for CE system containing α-, β-, and γ-CD, respectively) and root mean squared error of prediction (0.239, 0.242, and 0.288 for α-, β-, and γ-CD, respectively) were proved high predictive power of the proposed models. Finally, multitarget QSMR model, using the ligands descriptors (X) and the relative migration time in presence of α-CD (Y1), β-CD (Y2), and γ-CD (Y3), has been created. The multitarget QSMR model can be used as initial screening predictive tool for CE migration behavior of other related guanidine/imidazoline derivatives in presence of α-, β-, and γ-CD.

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Section: Resultssupporting

confidence: 80%

Quantitative structure‐mobility relationship analysis of imidazoline receptor ligands in CDs‐mediated CE

et al. 2013

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“…Also, the C-H bending of amine (1472 and 1364 cm −1 ) and C*-C stretching (1013 cm −1 ) were shifted to 1479, 1357 and 1006 cm −1 , respectively. The change in the intensity and shape of the bands for the complex revealed that the formation of a complex restricts the vibration and bending of the pheniramine molecule [21,46]. A similar feature was observed for the S-ClPha complexes.…”

Section: Quantum Chemical Calculationssupporting

confidence: 61%

“…X-ray diffraction [17], fluorescence [18,19], infrared (IR) [20,21], ultraviolet (UV) [22,23] and nuclear magnetic resonance ( 1 H, 13 C-NMR) [24][25][26] spectroscopy have enabled the structure, stoichiometry and binding constant of the supramolecular system to be investigated. Wenzel et al [13] adopted 1 H-NMR to gain information on the geometry of association between pheniramines and ␤-CD.…”

Section: Introductionmentioning

confidence: 99%

Halogenation effects of pheniramines on the complexation with β-cyclodextrin

Wang

2009

Journal of Pharmaceutical and Biomedical Analysis

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“…The THβC are pharmacologically active, characterized by presenting hypotensive, hallucinogenic, tremorogenic and anxiolytic properties in humans [14]. These alkaloids have high affinity by different types of the receptors, such as benzodiazepinics [15,16], imidazolynics [17] and serotonergics [18].…”

Section: Introductionmentioning

confidence: 99%

Effects of Spider Venom Toxin PWTX-I (6-Hydroxytrypargine) on the Central Nervous System of Rats

Cesar-Tognoli

Salamoni

Tavares

et al. 2011

Toxins

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The 6-hydroxytrypargine (6-HT) is an alkaloidal toxin of the group of tetrahydro-β-carbolines (THβC) isolated from the venom of the colonial spider Parawixia bistriata. These alkaloids are reversible inhibitors of the monoamine-oxidase enzyme (MAO), with hallucinogenic, tremorigenic and anxiolytic properties. The toxin 6-HT was the first THβC chemically reported in the venom of spiders; however, it was not functionally well characterized up to now. The action of 6-HT was investigated by intracerebroventricular (i.c.v.) and intravenous (i.v.) applications of the toxin in adult male Wistar rats, followed by the monitoring of the expression of fos-protein, combined with the use of double labeling immunehistochemistry protocols for the detection of some nervous receptors and enzymes related to the metabolism of neurotransmitters in the central nervous system (CNS). We also investigated the epileptiform activity in presence of this toxin. The assays were carried out in normal hippocampal neurons and also in a model of chronic epilepsy obtained by the use of neurons incubated in free-magnesium artificial cerebro-spinal fluid (ACSF). Trypargine, a well known THβC toxin, was used as standard compound for comparative purposes. Fos-immunoreactive cells (fos-ir) were observed in hypothalamic and thalamic areas, while the double-labeling identified nervous receptors of the sub-types rGlu2/3 and NMR1, and orexinergic neurons. The 6-HT was administrated by perfusion and ejection in “brain slices” of hippocampus, inducing epileptic activity after its administration; the toxin was not able to block the epileptogenic crisis observed in the chronic model of the epilepsy, suggesting that 6-HT did not block the overactive GluRs responsible for this epileptic activity.

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Detection and characterization of cyclodextrin complexes with β-carboline derivatives by spectroscopic techniques

Cited by 23 publications

References 31 publications

Quantitative structure‐mobility relationship analysis of imidazoline receptor ligands in CDs‐mediated CE

Quantitative structure‐mobility relationship analysis of imidazoline receptor ligands in CDs‐mediated CE

Halogenation effects of pheniramines on the complexation with β-cyclodextrin

Effects of Spider Venom Toxin PWTX-I (6-Hydroxytrypargine) on the Central Nervous System of Rats

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