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oai:riubu.ubu.es:10259/42822022-12-20T11:21:21Zcom_10259_3593com_10259_5086com_10259_2604com_10259_4365com_10259_4883com_10259_3596col_10259_3594col_10259_4366col_10259_4884col_10259_3597

Selectivity of a thiosemicarbazonatocopper(II) complex towards duplex RNA. Relevant noncovalent interactions both in solid state and solution Gil García, Rubén Ugalde, María Busto Vázquez, Natalia Lozano Ordóñez, Héctor J. Leal Villalba, José María Pérez, Begoña Madariaga, Gotzon Insausti, Maite Lezama, Luis Sanz Díez, Roberto Gómez Sainz, Lidia M. García Ruiz, Begoña García Tojal, Javier Chemistry, Organic Química orgánica Thiosemicarbazones and their metal derivatives have long been screened as antitumor agents, and their interactions with DNA have been analysed. Herein, we describe the synthesis and characterization of compounds containing [CuL]+ entities (HL = pyridine-2-carbaldehyde thiosemicarbazone) and adenine, cytosine or 9-methylguanine, and some of their corresponding nucleotides. For the first time, crystal structures of adenine- and 9-methylguanine-containing thiosemicarbazone complexes are reported. To the best of our knowledge, the first study on the affinity thiosemicarbazone–RNA is also provided here. Experimental and computational studies have shown that [CuL(OH2)]+ entities at low concentration intercalate into dsRNA poly(rA)·poly(rU) through strong hydrogen bonds involving uracil residues and π–π stacking interactions. In fact, noncovalent interactions are present both in the solid state and in solution. This behaviour diverges from that observed with DNA duplexes and creates an optimistic outlook in achieving selective binding to RNA for subsequent possible medical applications. Obra Social “la Caixa” (OSLC-2012-007), Ministerio de Economía y Competitividad and FEDER funds (CTQ2013-48937-C2-1-P, CTQ2015-70371- REDT, MAT2012-34740 and CTQ2014-58812-C2-2-R), Junta de Castilla y León (BU237U13), the Basque Government (IT-779- 13), Gerencia Regional de Salud, Consejería de Sanidad, Junta de Castilla y León (GRS 1023/A/14 and GR172). 2016-11-24T08:30:17Z 2017-12-07T03:45:06Z 2016-12 info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion 1477-9226 http://hdl.handle.net/10259/4282 eng Dalton transactions, 2016, n. 45, p. 45, 18704-18718 http://dx.doi.org/10.1039/C6DT02907H info:eu-repo/semantics/openAccess application/pdf Royal Society of Chemistry