Complex formation of cyclodextrins with some pharmacologically active 1,2,4-thiadiazole derivatives

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Complex formation of cyclodextrins with some pharmacologically active 1,2,4-thiadiazole derivatives : Thermodynamics and binding mode. / Chislov, Mikhail; Silyukov, Oleg; Kumeev, Roman; Proshin, Alexey; Perlovich, German; Terekhova, Irina.

In: Journal of Thermal Analysis and Calorimetry, Vol. 127, No. 2, 01.02.2017, p. 1797-1805.

Research output: Contribution to journal › Article › peer-review

Author

Chislov, Mikhail ; Silyukov, Oleg ; Kumeev, Roman ; Proshin, Alexey ; Perlovich, German ; Terekhova, Irina. / Complex formation of cyclodextrins with some pharmacologically active 1,2,4-thiadiazole derivatives : Thermodynamics and binding mode. In: Journal of Thermal Analysis and Calorimetry. 2017 ; Vol. 127, No. 2. pp. 1797-1805.

BibTeX

@article{1f98b406cd2f4e2fa5298ca27e848cbc,

title = "Complex formation of cyclodextrins with some pharmacologically active 1,2,4-thiadiazole derivatives: Thermodynamics and binding mode",

abstract = "Previously synthesized 1,2,4-thiadiazole derivatives displayed an activity in the treatment of Alzheimer{\textquoteright}s disease; however, these compounds are poorly soluble in aqueous solutions. Inclusion complex formation with cyclodextrins is proposed for the development of water-soluble dosage forms of 1,2,4-thiadiazoles under study. To this end, binding of 1,2,4-thiadiazole derivatives with α-, β- and γ-cyclodextrins as well as with modified β-cyclodextrins was investigated by isothermal titration calorimetry, 1H NMR and UV–Vis spectroscopy in aqueous buffered solution (pH = 7.4) at 298.15 K. The detailed analysis of the thermodynamic parameters of complex formation is presented. The structure of 1,2,4-thiadiazole/cyclodextrin complexes was evaluated on the basis of 2D 1NMR (ROESY) experiments. The influence of structural factor (dimensions of macrocyclic cavity, modification of the host external surface, structure of guest molecules) on the thermodynamics and binding mode was discussed.",

keywords = "H NMR, 1,2,4-Thiadiazole, Alzheimer{\textquoteright}s disease, Complex formation, Cyclodextrins, Isothermal titration calorimetry",

author = "Mikhail Chislov and Oleg Silyukov and Roman Kumeev and Alexey Proshin and German Perlovich and Irina Terekhova",

year = "2017",

month = feb,

day = "1",

doi = "10.1007/s10973-016-5929-1",

language = "English",

volume = "127",

pages = "1797--1805",

journal = "Journal of Thermal Analysis and Calorimetry",

issn = "1388-6150",

publisher = "Springer Nature",

number = "2",

}

RIS

TY - JOUR

T1 - Complex formation of cyclodextrins with some pharmacologically active 1,2,4-thiadiazole derivatives

T2 - Thermodynamics and binding mode

AU - Chislov, Mikhail

AU - Silyukov, Oleg

AU - Kumeev, Roman

AU - Proshin, Alexey

AU - Perlovich, German

AU - Terekhova, Irina

PY - 2017/2/1

Y1 - 2017/2/1

N2 - Previously synthesized 1,2,4-thiadiazole derivatives displayed an activity in the treatment of Alzheimer’s disease; however, these compounds are poorly soluble in aqueous solutions. Inclusion complex formation with cyclodextrins is proposed for the development of water-soluble dosage forms of 1,2,4-thiadiazoles under study. To this end, binding of 1,2,4-thiadiazole derivatives with α-, β- and γ-cyclodextrins as well as with modified β-cyclodextrins was investigated by isothermal titration calorimetry, 1H NMR and UV–Vis spectroscopy in aqueous buffered solution (pH = 7.4) at 298.15 K. The detailed analysis of the thermodynamic parameters of complex formation is presented. The structure of 1,2,4-thiadiazole/cyclodextrin complexes was evaluated on the basis of 2D 1NMR (ROESY) experiments. The influence of structural factor (dimensions of macrocyclic cavity, modification of the host external surface, structure of guest molecules) on the thermodynamics and binding mode was discussed.

AB - Previously synthesized 1,2,4-thiadiazole derivatives displayed an activity in the treatment of Alzheimer’s disease; however, these compounds are poorly soluble in aqueous solutions. Inclusion complex formation with cyclodextrins is proposed for the development of water-soluble dosage forms of 1,2,4-thiadiazoles under study. To this end, binding of 1,2,4-thiadiazole derivatives with α-, β- and γ-cyclodextrins as well as with modified β-cyclodextrins was investigated by isothermal titration calorimetry, 1H NMR and UV–Vis spectroscopy in aqueous buffered solution (pH = 7.4) at 298.15 K. The detailed analysis of the thermodynamic parameters of complex formation is presented. The structure of 1,2,4-thiadiazole/cyclodextrin complexes was evaluated on the basis of 2D 1NMR (ROESY) experiments. The influence of structural factor (dimensions of macrocyclic cavity, modification of the host external surface, structure of guest molecules) on the thermodynamics and binding mode was discussed.

KW - H NMR

KW - 1,2,4-Thiadiazole

KW - Alzheimer’s disease

KW - Complex formation

KW - Cyclodextrins

KW - Isothermal titration calorimetry

UR - http://www.scopus.com/inward/record.url?scp=84994423071&partnerID=8YFLogxK

U2 - 10.1007/s10973-016-5929-1

DO - 10.1007/s10973-016-5929-1

M3 - Article

AN - SCOPUS:84994423071

VL - 127

SP - 1797

EP - 1805

JO - Journal of Thermal Analysis and Calorimetry

JF - Journal of Thermal Analysis and Calorimetry

SN - 1388-6150

IS - 2

ER -

ID: 37016273