title: Theoretical study on interactions of β-cyclodextrin with Helicobacter pylori eradicating agent (TG44).
abstract: The inclusion complex of β-cyclodextrin (β-CD) and 4-methylbenzyl-4'-[trans-4- (guanidinomethyl)cylohexylcarbonyloxy]-biphenyl-4-carboxlylate monohydrochloride (TG44) 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 TG44, and the inclusion complex formed by TG44 entering into the cavity of β-CD from its narrow side (the primary hydroxyl group side) is more stable than that formed by TG44 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.
authors.affiliation: Key Laboratory of Environmentally Friendly Chemistry and Applications of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan, Hunan 411105, People's Republic of China.
authors.forename: Xin
authors.initials: X
authors.lastname: Jin
authors.forename: Xueye
authors.initials: X
authors.lastname: Wang
authors.forename: Cuihuan
authors.initials: C
authors.lastname: Ren
authors.forename: Yuan
authors.initials: Y
authors.lastname: Miao
authors.forename: Ling
authors.initials: L
authors.lastname: Yi
mesh_terms: D000900:Anti-Bacterial Agents / Q000737:chemistry* / Q000494:pharmacology; D001565:Benzoates / Q000737:chemistry* / Q000494:pharmacology; D003198:Computer Simulation; D003505:Cyclodextrins / Q000737:chemistry*; D006146:Guanidines / Q000737:chemistry* / Q000494:pharmacology; D016480:Helicobacter pylori / Q000187:drug effects; D008958:Models, Molecular; D015394:Molecular Structure
chemical_list: C510407:4-methylbenzyl 4'-(4-(guanidinomethyl)cyclohexylcarbonyloxy)biphenyl-4-carboxylate; D000900:Anti-Bacterial Agents; D001565:Benzoates; D003505:Cyclodextrins; D006146:Guanidines