Investigation of the complexation of (+)-catechin by 
b-cyclodextrin by a combination of NMR, microcalorimetry and
molecular modeling techniques

J 2003

Investigation of the complexation of (+)-catechin by b-cyclodextrin by a combination of NMR, microcalorimetry and molecular modeling techniques

KŘÍŽ, Zdeněk, Jaroslav KOČA, Anne IMBERTY, Aurelia CHARLOT, Rachel AUZELY-VELTY et. al.

Basic information

Original name

Investigation of the complexation of (+)-catechin by b-cyclodextrin by a combination of NMR, microcalorimetry and molecular modeling techniques

Authors

KŘÍŽ, Zdeněk (203 Czech Republic, guarantor), Jaroslav KOČA (203 Czech Republic), Anne IMBERTY (250 France), Aurelia CHARLOT (250 France) and Rachel AUZELY-VELTY (250 France)

Edition

Organic and Biomolecular Chemistry, Royal Society of Chemistry, 2003, 1477-0520

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10403 Physical chemistry

Country of publisher

Czech Republic

Confidentiality degree

není předmětem státního či obchodního tajemství

RIV identification code

RIV/00216224:14310/03:00009078

Organization unit

Faculty of Science

Keywords in English

NMR; cyclodextrin; catechin; molecular modeling

Abstract

V originále

(+)-Catechin is a polyphenolic compound of natural origin that presents anti-oxidant properties of interest for therapeutics or cosmetics uses. Preliminary studies on inclusion into cyclodextrin cavities yielded contradictory results both for the quantitative (a nity constant) and qualitative description of the interaction. By a combination of several experimental and theoretical methods, the present study resolved the previous ambiguities about the interaction between (+)-catechin and b-cyclodextrin. Thermodynamic data measured by isothermal titration calorimetry demonstrate that the binding is enthalpy driven. Excellent agreement has been obtained for the measurement of the association constant by NMR and microcalorimetry. The several docking modes obtained by systematic docking studies have been compared to intermolecular contacts measured by NMR and the overall geometry of the complex can be proposed.

Links

LN00A016, research and development project

Name: BIOMOLEKULÁRNÍ CENTRUM

Investor: Ministry of Education, Youth and Sports of the CR, Biomolecular Center

Citovat

KŘÍŽ, Zdeněk, Jaroslav KOČA, Anne IMBERTY, Aurelia CHARLOT and Rachel AUZELY-VELTY. Investigation of the complexation of (+)-catechin by b-cyclodextrin by a combination of NMR, microcalorimetry and molecular modeling techniques (Investigation of the complexation of (+)-catechin by b-cyclodextrin by a combination of NMR, microcalorimetry and molecular modeling techniques). Organic and Biomolecular Chemistry. Royal Society of Chemistry, 2003, vol. 1, No 14, p. 2590-2595. ISSN 1477-0520.

@article{490003,
   author = {Kříž, Zdeněk and Koča, Jaroslav and Imberty, Anne and Charlot, Aurelia and AuzelyandVelty, Rachel},
   article_number = {14},
   keywords = {NMR; cyclodextrin; catechin; molecular modeling},
   language = {eng},
   issn = {1477-0520},
   journal = {Organic and Biomolecular Chemistry},
   title = {Investigation of the complexation of (+)-catechin by b-cyclodextrin by a combination of NMR, microcalorimetry and molecular modeling techniques},
   volume = {1},
   year = {2003}
}

TY  - JOUR
ID  - 490003
AU  - Kříž, Zdeněk - Koča, Jaroslav - Imberty, Anne - Charlot, Aurelia - Auzely-Velty, Rachel
PY  - 2003
TI  - Investigation of the complexation of (+)-catechin by b-cyclodextrin by a combination of NMR, microcalorimetry and molecular modeling techniques
JF  - Organic and Biomolecular Chemistry
VL  - 1
IS  - 14
SP  - 2590-2595
EP  - 2590-2595
PB  - Royal Society of Chemistry
SN  - 14770520
KW  - NMR
KW  - cyclodextrin
KW  - catechin
KW  - molecular modeling
N2  - (+)-Catechin is a polyphenolic compound of natural origin that presents anti-oxidant properties of interest for therapeutics or cosmetics uses. Preliminary studies on inclusion into cyclodextrin cavities yielded contradictory results both for the quantitative (a nity constant) and qualitative description of the interaction. By a combination of several experimental and theoretical methods, the present study resolved the previous ambiguities about the interaction between (+)-catechin and b-cyclodextrin. Thermodynamic data measured by isothermal titration calorimetry demonstrate that the binding is enthalpy driven. Excellent agreement has been obtained for the measurement of the association constant by NMR and microcalorimetry. The several docking modes obtained by systematic docking studies have been compared to intermolecular contacts measured by NMR and the overall geometry of the complex can be proposed.
ER  -

KŘÍŽ, Zdeněk, Jaroslav KOČA, Anne IMBERTY, Aurelia CHARLOT and Rachel AUZELY-VELTY. Investigation of the complexation of (+)-catechin by b-cyclodextrin by a combination of NMR, microcalorimetry and molecular modeling techniques (Investigation of the complexation of (+)-catechin by b-cyclodextrin by a combination of NMR, microcalorimetry and molecular modeling techniques). \textit{Organic and Biomolecular Chemistry}. Royal Society of Chemistry, 2003, vol.~1, No~14, p.~2590-2595. ISSN~1477-0520.

Detailed Information on Publication Record