Structure and pharmacological studies of the anaesthetic 1-(3-n-butoxypropyl)-4-benzoyloxypiperidin hydrochloride and its complex with β-cyclodextrin in solution. NMR and IR-spectroscopy data

Kemelbekov, U. S.; Saipov, Amangeldi; Abdildanova, A. A.; Ospanov, I.; Luo, Ying; Guskov, Albert; Imachova, Sh. O.; Nasyrova, S. R.; Пичхадзе, Г.М.

doi:10.1007/s10847-012-0239-0

Cited by 8 publications

(15 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…According to [9], the 1 H NMR spectrum of β-CD, obtained in DMSO-d 6 , consists of six groups of signals in the range 3.23-3.32; 3.45-3.53; 3.56-3.60; 4.47-4.49; 4.77-4.78; 5.66-5.73 ppm. Herein, we study the formation of inclusion complexes of β-CD with APIs 1-3 by determining the difference in the values of 1 H and 13 C chemical shifts of substrates (1-3) and the receptor (β-CD) in the free state and as a part of complexes due to the intermolecular interaction. By the magnitude of the chemical shifts of the internal or external protons of β-CD, it is possible to reveal the formation of, respectively, internal, external, or mixed complexes.…”

Section: Introductionmentioning

confidence: 99%

“…By the magnitude of the chemical shifts of the internal or external protons of β-CD, it is possible to reveal the formation of, respectively, internal, external, or mixed complexes. Changes in the 1 H and 13 C chemical shifts in the spectra of the substrate make it possible to determine the direction of entry of the latter into the β-CD cavity or interaction with the outer segment of the cavity [12,13].…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

NMR study of the inclusion complexes of β-cyclodextrin with diphenhydramine, clonidine and tolperisone

Zhumakova¹,

Ten

Zharkynbek³

et al. 2022

SN Appl. Sci.

View full text Add to dashboard Cite

Forming complexes with β-cyclodextrin can enhance stability, dissolution rate, solubility, and bioavailability of an active pharmaceutical ingredient. In this study, the inclusion behavior between β-cyclodextrin (β-CD) and diphenhydramine, clonidine, and tolperisone in DMSO-d6 was investigated using NMR spectroscopy. 1H, 13C, COSY, HMQC, and ROESY data were applied to determine the structure of inclusion complexes, and molecular docking analysis was engaged to identify the most favorable host–guest interactions in the inclusion complexes. Complexation of β-CD with diphenhydramine, clonidine, and tolperisone is accompanied by the insertion of a molecular fragment of the guest molecule, one molecule of diphenhydramine and tolperisone, and two molecules of clonidine, into the inner sphere of one host molecule. The reported study provides useful information for the potential application of the complexation of β-CD with diphenhydramine, clonidine, and tolperisone. This may be a good strategy for the development of solid pharmaceutical dosage forms based on β-CDs as a drug delivery system. Article highlights The inclusion complexes of β-CD and diphenhydramine, clonidine, and tolperisone were synthesized and analyzed using 1Н, 13С, COSY, HMQC, and ROESY spectroscopy. Diphenhydramine, clonidine, and tolperisone interact with β-CD with the formation of stable 1:1 stoichiometric complexes for β-CD:diphenhydramine and β-CD:tolperisone, and 1:2 stoichiometric complex for β-CD:clonidine. Possible structures of the inclusion complexes between β-CD and diphenhydramine, clonidine, and tolperisone were determined using molecular docking in the software AutoDock 4.0.

show abstract

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

NMR study of the inclusion complexes of β-cyclodextrin with diphenhydramine, clonidine and tolperisone

Zhumakova¹,

Ten

Zharkynbek³

et al. 2022

SN Appl. Sci.

View full text Add to dashboard Cite

show abstract

“…The chemical shift changes were the most prominent in the cases of H 3 and H 5 atoms oriented towards the inner part of the cyclodextrin cone, evidencing about formation of the inner inclusion complexes [5,6]. The signals shift ∆δ of the H 3 and H 5 atoms ranged from -0.3 to 0.04 ppm in the cases of six-and eight-unit α-and γ-cyclodextrins.…”

mentioning

confidence: 95%

“…For instance, the change of chemical shift of the inner or outer protons upon the complex formation concludes about formation of the inner or outer complexes, respectively. Similarly, changes of the substrate atoms chemical shifts define the position of the complex forming site [5,6]. 1 Table 1.…”

mentioning

confidence: 99%

See 1 more Smart Citation

NMR study of supramolecular inclusion complexes of 7-[2-(morpholin-4-yl)ethyl]-3-(2-ethoxyethyl)-3,7-diazabicyclo[3.3.1]nonane with cyclodextrins

et al. 2015

View full text Add to dashboard Cite

Structures of 7-[2-(morpholin-4-yl)ethyl]-3-(2-ethoxyethyl)-3,7-diazabicyclo[3.3.1]nonane and its inclusion complexes with α-, β-, and γ-cyclodextrins have been studied by 1 H, 13 C, COSY, and HMQC NMR spectroscopy. The complexes are formed via entering of one morpholine fragment of the substrate into the inner sphere of a receptor molecule..1]nonane, α-, β-, and γ-cyclodextrin, inclusion complex, NMR spectroscopy NMR spectroscopy has been recognized among the most informative methods to investigate structure and intermolecular interactions in inclusion complexes [1]. Therefore, we have applied this method to study new drug formulations of pharmaceutically active 7-[2-(morpholin-4-yl)ethyl]-3-(2-ethoxyethyl)-3,7-diazabicyclo[3.3.1]nonane I with cyclodextrins.Compound I possesses a wide range of biological activity due to the presence of two piperidine rings in the structure; in particular, it displays a local anesthetic effect [2].Cyclodextrins are accessible compounds produced from renewable source (starch), the most widespread types of them being α-, β-, and γ-cyclodextrins containing 6, 7, and 8 glucopyranose units, respectively. Cyclodextrins are capable of hydrophobic binding of a guest molecule in their cavity in aqueous medium.

show abstract

The structure and pharmacological properties of the 4-acetoxy-1-(2-ethoxyethyl)-4-phenylpiperidine inclusion complex with β-cyclodextrin

Sharipov¹,

Sharapov

Kemelbekov³

et al. 2016

J Incl Phenom Macrocycl Chem

View full text Add to dashboard Cite

Structure and pharmacological studies of the anaesthetic 1-(3-n-butoxypropyl)-4-benzoyloxypiperidin hydrochloride and its complex with β-cyclodextrin in solution. NMR and IR-spectroscopy data

Cited by 8 publications

References 13 publications

NMR study of the inclusion complexes of β-cyclodextrin with diphenhydramine, clonidine and tolperisone

NMR study of the inclusion complexes of β-cyclodextrin with diphenhydramine, clonidine and tolperisone

NMR study of supramolecular inclusion complexes of 7-[2-(morpholin-4-yl)ethyl]-3-(2-ethoxyethyl)-3,7-diazabicyclo[3.3.1]nonane with cyclodextrins

The structure and pharmacological properties of the 4-acetoxy-1-(2-ethoxyethyl)-4-phenylpiperidine inclusion complex with β-cyclodextrin

Contact Info

Product

Resources

About