| Title | Hydrogen Bonding and Stacking pi-pi Interactions in Solid 6-Thioguanine and 6-Mercaptopurine (Antileukemia and Antineoplastic Drugs) Studied by NMR-NQR Double Resonance Spectroscopy and Density Functional Theory. | | Author(s) | Latosińska JN, Seliger J, Žagar V, Burchardt DV | | Institution | Faculty of Physics, Adam Mickiewicz University, Umultowska 85, 61-614 Poznan, Poland. | | Source | J Phys Chem A 2009 Jul 2. | | Abstract | A chemotherapeutic drug 6-thioguanine (2-amino-1,7-dihydro-6H-purine-6-thione, 6-TG) has been studied experimentally in the solid state by NMR-NQR double resonance and theoretically by the density functional theory. Fourteen resonance frequencies on (14)N have been detected and assigned to particular nitrogen sites in the 6-TG molecule. A valid assignment of NQR frequencies for 6-mercaptopurine (6-MP) has been proposed. The effects of molecular aggregations, related to intermolecular hydrogen bonding and stacking pi-pi interactions on the NQR parameters have been analyzed within the DFT and AIM (atoms in molecules) formalism for 6-TG and 6-mercaptopurine (6-MP). The so-called global reactivity descriptors have been calculated to compare the properties of molecules of 6-TG and 6-MP, to check the effect of -NH(2) group as well as to identify the differences in crystal packing. | | Language | ENG | | Pub Type(s) | JOURNAL ARTICLE
| | PubMed ID | 19572681 |
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