title: Molecular recognition of a lipophilic guanosine derivative in Langmuir films at the air-water interface.
abstract: Molecular recognition of a lipophilic deoxyguanosine derivative at the air-water interface was investigated by film balance experiments and Brewster Angle Microscopy. Results showed that guanosine, despite strong tendency towards self-assembly, interacts with both complementary and noncomplementary liponucleosides (lipophilic derivatives of deoxycytidine and deoxythymidine). At surface pressures below 17mN/m, attractive and repulsive interactions were present in case of both mixed monolayers and were the strongest at guanosine molar fractions of 0.5 and 0.75. At higher values of surface pressure, deoxyguanosine-deoxycytidine interactions were strictly attractive and were present only for monolayers with guanosine molar fraction of 0.75. On the contrary, attractive and repulsive interactions remained present in case of deoxyguanosine-deoxythymidine mixed monolayers. This indicates that interactions between guanosine and cytidine are much stronger than guanosine-thymidine interactions. Interactions for none of the nucleoside pairs, however, are specific and π-stacking interactions between the aromatic planes of liponucleoside derivatives probably dominate over hydrogen bonding interactions. This article is part of a Special Issue entitled "G-quadruplex" Guest Editor: Dr. Concetta Giancola and Dr. Daniela Montesarchio.
authors.affiliation: Faculty of Mathematics and Physics, University of Ljubljana, Jadranska 19, 1000 Ljubljana, Slovenia.
authors.forename: Lucija
authors.initials: L
authors.lastname: Čoga
authors.affiliation: Faculty of Mechanical Engineering, University of Maribor, Smetanova ulica 17, 2000 Maribor, Slovenia; Jožef Stefan Institute, Jamova 39, 1000 Ljubljana, Slovenia. Electronic address: lea.spindler@um.si.
authors.forename: Lea
authors.initials: L
authors.lastname: Spindler
authors.affiliation: Alma Mater Studiorum - Università di Bologna, Dipartimento "Giacomo Ciamician", Via San Giacomo 11, I-40126 Bologna, Italy.
authors.forename: Stefano
authors.initials: S
authors.lastname: Masiero
authors.affiliation: Faculty of Mathematics and Physics, University of Ljubljana, Jadranska 19, 1000 Ljubljana, Slovenia; Jožef Stefan Institute, Jamova 39, 1000 Ljubljana, Slovenia.
authors.forename: Irena
authors.initials: I
authors.lastname: Drevenšek-Olenik
mesh_terms: D000388:Air; D000399:Air Pressure; D003839:Deoxyadenosines / Q000737:chemistry; D003841:Deoxycytidine / Q000031:analogs & derivatives / Q000737:chemistry*; D003849:Deoxyguanosine / Q000737:chemistry*; D006860:Hydrogen Bonding; D057927:Hydrophobic and Hydrophilic Interactions; D008055:Lipids / Q000737:chemistry*; D008956:Models, Chemical; D013499:Surface Properties; D013936:Thymidine / Q000031:analogs & derivatives / Q000737:chemistry*; D014867:Water / Q000737:chemistry*
chemical_list: D003839:Deoxyadenosines; D008055:Lipids; D014867:Water; D003841:Deoxycytidine; D003849:Deoxyguanosine; D013936:Thymidine
keywords: Intermolecular recognition; Langmuir monolayer; Liponucleoside