Adsorption of cytarabine and gemcitabine anticancer drugs on the BNNT surface: DFT and GD3-DFT approaches
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Adsorption of cytarabine and gemcitabine anticancer drugs on the BNNT surface: DFT and GD3‑DFT approaches Hossein Roohi1 · Ahmad Facehi2 · Katereh Ghauri1 Received: 6 June 2019 / Revised: 5 December 2019 / Accepted: 2 July 2020 © Springer Science+Business Media, LLC, part of Springer Nature 2020
Abstract In this work, at first, in order to find the most stable conformers of the two types of anticancer cytarabine (CYT) and gemcitabine (GEM) drugs, the potential energy curves for rotation around the C1′-N bond were explored at M06-2X/6–311 + + G(2d,2p) level of theory. Adsorption of the most stable conformers of CYT and GEM drugs on the BNNT surface was explored. Depending on the orientation of CYTand GEM drugs on the outside surface of the BNNT, two different types of drug-BNNT adsorption complexes (A and B) were found on the potential energy surface. Dispersion corrected adsorption energies at M06-2X/6–31 + G(d)-GD3 level were in the range − 19.7 to − 26.1 kcal mol−1 for A1–A4 and − 21.7 to − 24.6 kcal mol−1 for B1–B4. The results show that adsorptions of CYTand GEM drugs on the BNNT surface in the water solvent are energetically favorable process. The structural and electronic density properties, charge transfer values, global reactivity descriptors and the molecular electrostatic potential maps of the drug-BNNT complexes were evaluated. It is anticipated that the complex formation accompanied by charge transfer between BNNT and drugs and the decrease in the HOMO − LUMO energy gap. The NCI (non-covalent interaction) analysis shows the role and importance of the cooperative π − π stacking and H-bonding interactions on the adsorption of drugs on the BNNT surface. Keywords BNNT · Anticancer drugs · CYT · GEM · Adsorption · M06-2X
1 Introduction The use of free nano-materials (NMs) as the carriers of therapeutic molecules has been extensively explored with the aim of improving the drug efficacy, reduction of overall drug dosages, protecting the drugs from the biological environment, an extension of drug lifetime in the bloodstream and increasing the drug solubility (Tacar et al. 2013; Lim et al. 2013a, 2013b; Aires et al. 2016; Latorre et al. 2014; Hosseinzadeh et al. 2012; Kurzątkowska et al. 2017). Carbon nanotubes (CNTs) have been widely used in the biological applications including biosensing (Star et al. 2016), intracellular delivery (Chen et al. 2007; Kostarelos et al. 2007), imaging (Wong et al. 1998) and cancer cell targeting (Kam et al. 2005). On the other hand, the intrinsic * Hossein Roohi [email protected] 1
Department of Chemistry, Faculty of Science, University of Guilan, Rasht, Iran
Department of Chemistry, University of Guilan, University Campus 2, Rasht, Iran
2
cytotoxicity of CNT has executed the restrictions on their applications as biological probes and in therapeutic composites (Sato et al. 2005; Bottini et al. 2006; Cui et al. 2005; Magrez et al. 2006). Although the cytotoxicity of CNTs can be reduced by surface functionalization (Kam et al. 2005; Chen et al. 2006; Sayes et
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