Theoretical investigation into the cooperativity effect between the intermolecular π∙π and H-bonding interactions in the curcumin∙cytosine∙H2O system

  • Jie PanEmail author
  • Duan-lin Cao
  • Fu-de Ren
  • Jian-long Wang
  • Lu Yang
Original Paper


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 π∙∙∙π and H-bonding interactions in curcumin(drug)∙∙∙cytosine(DNA/RNA base)∙∙∙H2O were investigated by the B3LYP-D3 and MP2(full) methods with the 6–311++G(2d,p) basis set. The π∙∙∙π 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 π∙∙∙π 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 π∙∙∙π and H-bonding interactions, as is in agreement with many of the drugs in use.

Graphical abstract

RDG isosurface of ternary complex


Cooperativity effect between the π∙π and H-bonding interactions Hydration Curcumin∙cytosine interaction MP2 Surface electrostatic potentials 


Compliance with ethical standards

Ethical statement

We allow the journal to review all the data, and we confirm the validity of the results. We have no financial relationships. The manuscript is not submitted to more than one journal, and it was not published previously. This work is not split up into several parts to submit. No data have been fabricated or manipulated.

Supplementary material

894_2018_3836_MOESM1_ESM.doc (33 mb)
ESM 1 (DOC 33799 kb)


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Copyright information

© Springer-Verlag GmbH Germany, part of Springer Nature 2018

Authors and Affiliations

  • Jie Pan
    • 1
    Email author
  • Duan-lin Cao
    • 1
  • Fu-de Ren
    • 1
  • Jian-long Wang
    • 1
  • Lu Yang
    • 2
  1. 1.School of Chemical Engineering and TechnologyNorth University of ChinaTaiyuanChina
  2. 2.Software School of North University of ChinaTaiyuanChina

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