Theoretical study on interactions of β-cyclodextrin with helicobacter pylori eradicating agent (TG44)

• Published in: Journal of molecular modeling Vol. 17; no. 4; pp. 913 - 920
• Main Authors: Jin, Xin, Wang, Xueye, Ren, Cuihuan, Miao, Yuan, Yi, Ling
• Format: Journal Article
• Language: English
• Published: Berlin/Heidelberg Springer-Verlag 01.04.2011
• Subjects: Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Benzoates - chemistry; Benzoates - pharmacology; Characterization and Evaluation of Materials; Chemistry; Chemistry and Materials Science; Computer Appl. in Life Sciences; Computer Applications in Chemistry; Computer Simulation; Cyclodextrins - chemistry; Guanidines - chemistry; Guanidines - pharmacology; Helicobacter pylori - drug effects; Models, Molecular; Molecular Medicine; Molecular Structure; Original Paper; Theoretical and Computational Chemistry; 44; Cyclodextrin; Density functional theory (DFT); Inclusion complex; PM3
• ISSN: 1610-2940; 0948-5023
• DOI: 10.1007/s00894-010-0781-x

The inclusion complex of β -cyclodextrin ( β -CD) and 4-methylbenzyl-4′-[trans-4- (guanidinomethyl)cylohexylcarbonyloxy]-biphenyl-4-carboxlylate monohydrochloride ( TG 44) had been investigated by using densify functional theory (DFT) and PM3 semiempirical method. The results indicate that the β -CD includes predominantly the biphenyl moiety of TG 44, and the inclusion complex formed by TG 44 entering into the cavity of β -CD from its narrow side (the primary hydroxyl group side) is more stable than that formed by TG 44 entering into the cavity of β -CD from its wide side (the secondary hydroxyl group side). The negative enthalpy changes calculated from the statistical thermodynamic calculations at 1 atm and 298.15 K suggest that the inclusion complexes are favored enthalpy-driven processes. The molecular modeling results are in good agreement with the experiment for 2D 1 H– 13 C H HETCOR spectroscopic and H-NMR spectroscopic observations. Figure β-cyclodextrin with helicobacter pylori eradicating agent (TG44)