title: How strong is the edge effect in the adsorption of anticancer drugs on a graphene cluster?
abstract: The adsorption of nucleobase-analog anticancer drugs (fluorouracil, thioguanine, and mercaptopurine) on a graphene flake (C54H18) was investigated by shifting the site at which adsorption occurs from one end of the sheet to the other end. The counterpoise-corrected M06-2X/cc-pVDZ binding energies revealed that the binding stability decreases in the sequence thioguanine > mercaptopurine > fluorouracil. We found that adsorption near the middle of the sheet is more favorable than adsorption near the edge due to the edge effect. This edge effect is stronger for the adsorption of thioguanine or mercaptopurine than for fluorouracil adsorption. However, the edge effect reduces the binding energy of the drug to the flake by only a small amount, <5 kcal/mol, depending on the adsorption site and the alignment of the drug at this site.
authors.affiliation: NANOTEC, National Science and Technology Development Agency (NSTDA), Pathum Thani, 12120, Thailand.
authors.forename: Chompoonut
authors.initials: C
authors.lastname: Rungnim
authors.affiliation: Metallurgy and Materials Science Research Institute (MMRI), Chulalongkorn University, Bangkok, 10330, Thailand.
authors.forename: Rungroj
authors.initials: R
authors.lastname: Chanajaree
authors.affiliation: Structural and Computational Biology Research Group, Department of Biochemistry, Faculty of Science, Chulalongkorn University, Bangkok, 10330, Thailand.|Program in Bioinformatics and Computational Biology, Faculty of Science, Chulalongkorn University, Bangkok, 10330, Thailand.
authors.forename: Thanyada
authors.initials: T
authors.lastname: Rungrotmongkol
authors.affiliation: Computational Chemistry Unit Cell, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, 10330, Thailand.
authors.forename: Supot
authors.initials: S
authors.lastname: Hannongbua
authors.affiliation: Department of Chemistry, Faculty of Science, Chiang Mai University, Chiang Mai, 50200, Thailand.
authors.forename: Nawee
authors.initials: N
authors.lastname: Kungwan
authors.affiliation: Computational Chemistry Unit Cell, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, 10330, Thailand.|Institute for Theoretical Chemistry, University of Vienna, Vienna, 1090, Austria.|Department of Pharmaceutical Technology and Biopharmaceutics, University of Vienna, Vienna, 1090, Austria.
authors.forename: Peter
authors.initials: P
authors.lastname: Wolschann
authors.affiliation: Institute for Theoretical Chemistry, University of Vienna, Vienna, 1090, Austria. alfred.karpfen@univie.ac.at.
authors.forename: Alfred
authors.initials: A
authors.lastname: Karpfen
authors.affiliation: Computational Chemistry Unit Cell, Department of Chemistry, Faculty of Science, Chulalongkorn University, Bangkok, 10330, Thailand. vudhichai.p@chula.ac.th.
authors.forename: Vudhichai
authors.initials: V
authors.lastname: Parasuk
mesh_terms: D000327:Adsorption; D000970:Antineoplastic Agents / Q000737:chemistry*; D005472:Fluorouracil / Q000737:chemistry*; D006108:Graphite / Q000737:chemistry*; D015122:Mercaptopurine / Q000737:chemistry*; D008956:Models, Chemical; D011789:Quantum Theory; D013816:Thermodynamics; D013866:Thioguanine / Q000737:chemistry*
chemical_list: D000970:Antineoplastic Agents; D006108:Graphite; D015122:Mercaptopurine; D013866:Thioguanine; D005472:Fluorouracil
keywords: Density functional theory; Graphene; Nucleobase-analog