Theoretical investigation into the cooperativity effect between the intermolecular πâπ and H-bonding interactions in the curcuminâcytosineâH2O system.
J Mol Model
; 24(10): 298, 2018 Sep 28.
Article
en En
| MEDLINE
| ID: mdl-30267159
ABSTRACT
In order to reveal the mechanism of drug action and design of DNA/RNA-targeted drugs containing aromatic rings, the cooperativity effects between the intermolecular πâââπ and H-bonding interactions in curcumin(drug)âââcytosine(DNA/RNA base)âââH2O were investigated by the B3LYP-D3 and MP2(full) methods with the 6-311++G(2d,p) basis set. The πâââπ interaction plays an important role in stabilizing the linear ternary complexes with the cooperativity effects, and the cyclic structures suffer the anticooperativity effects. The cooperativity or anticooperativity effects are notable, which could lead to a possible significant change in drug activity. The hydration is essentially the cooperativity or anticooperativity effect. These results were confirmed by the atoms in molecules (AIM), reduced density gradient (RDG), and surface electrostatic potentials analyses. The cyclic complexes are more stable, from which it can be deduced that the drug always links with the DNA/RNA base and H2O by the πâââπ or H-bonding interactions, and only in this way can the drug activity be shown. Therefore, the designed DNA/RNA-targeted drugs should possess a certain number of hydrophilic groups in contact with the DNA/RNA base and H2O to reconcile drug activity by the cooperativity effect between the πâââπ and H-bonding interactions, as is in agreement with many of the drugs in use. Graphical abstract RDG isosurface of ternary complex.
Palabras clave
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Agua
/
Modelos Moleculares
/
Curcumina
/
Citosina
Idioma:
En
Revista:
J Mol Model
Asunto de la revista:
BIOLOGIA MOLECULAR
Año:
2018
Tipo del documento:
Article
País de afiliación:
China