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Extent of Intramolecular pi Stacks in Aqueous Solution in Mixed-Ligand Copper(II) Complexes Formed by Heteroaromatic Amines and 1-[2-(Phosphonomethoxy)ethyl]cytosine (PMEC), a Relative of Antivirally Active Acyclic Nucleotide Analogues (Part 72)
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SYSNO ASEP 0424812 Druh ASEP J - Článek v odborném periodiku Zařazení RIV J - Článek v odborném periodiku Poddruh J Článek ve WOS Název Extent of Intramolecular pi Stacks in Aqueous Solution in Mixed-Ligand Copper(II) Complexes Formed by Heteroaromatic Amines and 1-[2-(Phosphonomethoxy)ethyl]cytosine (PMEC), a Relative of Antivirally Active Acyclic Nucleotide Analogues (Part 72) Tvůrce(i) Blindauer, C. A. (CH)
Sigel, A. (CH)
Operschall, B. P. (CH)
Holý, Antonín (UOCHB-X)
Sigel, H. (CH)Celkový počet autorů 5 Zdroj.dok. Zeitschrift für anorganische und allgemeine Chemie. - : Wiley - ISSN 0044-2313
Roč. 639, 8-9 (2013), s. 1661-1673Poč.str. 13 s. Jazyk dok. eng - angličtina Země vyd. DE - Německo Klíč. slova nucleotide analogues ; antivirals ; complex stabilities ; isomers ; equilibria ; mixed ligand complexes Vědní obor RIV CC - Organická chemie Institucionální podpora UOCHB-X - RVO:61388963 UT WOS 000330180900048 EID SCOPUS 84880535321 DOI 10.1002/zaac.201300095 Anotace Stability constants of the ternary Cu(Arm)(H;PMEC)(+) and Cu(Arm)(PMEC) complexes were measured by potentiometric pH titrations and compared with those of Cu(Arm)(H;PMEA)(+) and Cu(Arm)(PMEA) {PMEA(2-)} and related species. The basicity of the terminal phosphonate group is similar in PMEC2- and PMEA(2-). Stability-constant comparisons reveal, that in the monoprotonated ternary u(Arm)(H;PMEC)(+) complexes H+ is at the phosphonate group, that the ether oxygen atom of the -CH2-O-CH2-P(O)(2)(-) (OH) residue participates, next to the P(O)(2)(-)(OH) group, in Cu(Arm)(2+) coordination. The Cu(Arm)(PMEC) complexes are considerably more stable than the corresponding Cu(Arm)(R-PO3) species. The stability enhancements are mainly attributed to intramolecular stacks and to the formation of five-membered chelates involving the ether oxygen atom of the -CH2-O-CH2-P(O)(3)(2-) residue of PMEC2-. Analysis of the intramolecular equilibria reveals that ca. 10% of the isomeric ternary complexes exist with Cu(Arm)(2+) solely coordinated to the phosphonate group, ca. 25% as a five-membered chelate involving the ether oxygen, and ca. 65% with an intramolecular pi-pi stack between the pyrimidine moiety of PMEC2- and the rings of Bpy or Phen. It seems feasible that the reduced stacking intensity of PMEC2- and a different hydrogen bonding, leads to a different orientation of the cytosine (compared to adenine) in the active site of the nucleic acid polymerases, resulting in a reduced antiviral activity of PMEC compared to PMEA. Pracoviště Ústav organické chemie a biochemie Kontakt asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434 Rok sběru 2014
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