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Article

Adsorption of Chiral [5]-Aza[5]helicenes on DNA Can Modify Its Hydrophilicity and Affect Its Chiral Architecture: A Molecular Dynamics Study

1
Department of Chemistry, Materials and Chemical Engineering “Giulio Natta”, Politecnico di Milano, Piazza L. Da Vinci 32, 20131 Milano, Italy
2
INSTM, National Consortium of Materials Science and Technology, Local Unit Politecnico di Milano, 20131 Milano, Italy
3
Dipartimento di Ingegneria e Scienze Applicate, Università degli Studi di Bergamo, 24044 Bergamo, Italy
*
Author to whom correspondence should be addressed.
Materials 2020, 13(21), 5031; https://doi.org/10.3390/ma13215031
Received: 14 September 2020 / Revised: 3 November 2020 / Accepted: 4 November 2020 / Published: 7 November 2020
(This article belongs to the Special Issue Chiral Materials)
Helicenes are interesting chiral molecules without asymmetric carbon atoms but with intrinsic chirality. Functionalized 5-Aza[5]helicenes can form non-covalent complexes with anticancer drugs and therefore be potential carriers. The paper highlights the different structural selectivity for DNA binding for two enantiopure compounds and the influence of concentration on their adsorption and self-aggregation process. In this theoretical study based on atomistic molecular dynamics simulations the interaction between (M)- and (P)-5-Aza[5]helicenes with double helix B-DNA is investigated. At first the interaction of single pure enantiomer with DNA is studied, in order to find the preferred site of interaction at the major or minor groove. Afterwards, the interaction of the enantiomers at different concentrations was investigated considering both competitive adsorption on DNA and possible helicenes self-aggregation. Therefore, racemic mixtures were studied. The helicenes studied are able to bind DNA modulating or locally modifying its hydrophilic surface into hydrophobic after adsorption of the first helicene layer partially covering the negative charge of DNA at high concentration. The (P)-enantiomer shows a preferential binding affinity of DNA helical structure even during competitive adsorption in the racemic mixtures. These DNA/helicenes non-covalent complexes exhibit a more hydrophobic exposed surface and after self-aggregation a partially hidden DNA chiral architecture to the biological environment. View Full-Text
Keywords: chirality; intrinsic chirality; helicenes; structural selectivity; adsorption; DNA recognition; molecular dynamics simulations; racemic mixture; cholesteric liquid crystals chirality; intrinsic chirality; helicenes; structural selectivity; adsorption; DNA recognition; molecular dynamics simulations; racemic mixture; cholesteric liquid crystals
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MDPI and ACS Style

Raffaini, G.; Mele, A.; Caronna, T. Adsorption of Chiral [5]-Aza[5]helicenes on DNA Can Modify Its Hydrophilicity and Affect Its Chiral Architecture: A Molecular Dynamics Study. Materials 2020, 13, 5031. https://doi.org/10.3390/ma13215031

AMA Style

Raffaini G, Mele A, Caronna T. Adsorption of Chiral [5]-Aza[5]helicenes on DNA Can Modify Its Hydrophilicity and Affect Its Chiral Architecture: A Molecular Dynamics Study. Materials. 2020; 13(21):5031. https://doi.org/10.3390/ma13215031

Chicago/Turabian Style

Raffaini, Giuseppina, Andrea Mele, and Tullio Caronna. 2020. "Adsorption of Chiral [5]-Aza[5]helicenes on DNA Can Modify Its Hydrophilicity and Affect Its Chiral Architecture: A Molecular Dynamics Study" Materials 13, no. 21: 5031. https://doi.org/10.3390/ma13215031

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