A1 Vertaisarvioitu alkuperäisartikkeli tieteellisessä lehdessä

Characterization of bile salt/cyclodextrin interactions using isothermal titration calorimetry




TekijätOllila F, Pentikainen OT, Forss S, Johnson MS, Slotte JP

KustantajaAMER CHEMICAL SOC

Julkaisuvuosi2001

JournalLangmuir

Tietokannassa oleva lehden nimiLANGMUIR

Lehden akronyymiLANGMUIR

Vuosikerta17

Numero22

Aloitussivu7107

Lopetussivu7111

Sivujen määrä5

ISSN0743-7463

DOIhttps://doi.org/10.1021/la0109258


Tiivistelmä
The interactions of cholate, deoxycholate, glycocholate, and taurocholate with methyl-beta -cyclodextrin and 2-hydroxypropyl-beta -cyclodextrin were studied by means of isothermal titration calorimetry and molecular modeling. The binding constants, standard molar enthalpy, Gibbs free energy, and entropy changes were determined for the formation of bile salt/cyclodextrin inclusion complexes. We observed a 1:1 stoichiometry for all inclusion complexes and could demonstrate marked differences in binding affinity between the different bile salt and cyclodextrin molecules. The dihydroxy bile salt deoxycholate showed significantly higher affinity toward methyl-beta -cyclodextrin (K = 6276 +/- 164 M-1) and 2-hydroxypropyl-beta -cyclodextrin (K = 4429 +/- 34 M-1) compared to the trihydroxy bile salt cholate (K = 2693 +/- 25 M-1 and K = 2510 +/- 98 M-1, respectively). The conjugation of cholate with glycine or taurine lowered its affinity markedly toward methyl-beta -cyclodextrin (K = 1958 +/- 178 M-1 and K = 2148 +/- 33 M-1, respectively). Our molecular modeling and docking data suggest that the most probable mode of binding would be by insertion of the bile salt A-ring into the rim of the cyclodextrin containing the secondary alcohol moieties. Our results show that bile salt binding to cyclodextrin is influenced both by the degree of bile salt hydroxylation and by bile salt conjugation.



Last updated on 2024-26-11 at 21:20