Intramolecular pi-stacks in mixed-ligand copper(II) complexes formed by heteroaromatic amines and antivirally active acyclic nucleotide analogs carrying a hydroxy-2-(phosphonomethoxy)propyl residue

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388963%3A_____%2F18%3A00496372" target="_blank" >RIV/61388963:_____/18:00496372 - isvavai.cz</a>

Result on the web

<a href="http://dx.doi.org/10.1080/00958972.2018.1490019" target="_blank" >http://dx.doi.org/10.1080/00958972.2018.1490019</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1080/00958972.2018.1490019" target="_blank" >10.1080/00958972.2018.1490019</a>

Result language

angličtina

Original language name

Intramolecular pi-stacks in mixed-ligand copper(II) complexes formed by heteroaromatic amines and antivirally active acyclic nucleotide analogs carrying a hydroxy-2-(phosphonomethoxy)propyl residue

Original language description

Acyclic nucleoside phosphonates (ANPs) are of medical relevance and deserve detailed chemical characterization. We focus here on 1-[2-(phosphonomethoxy)ethyl]cytosine (PMEC), (S)-1-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine (HPMPC), 9-[2-(phosphonomethoxy)ethyl]adenine (PMEA), and (S)-9-[3-hydroxy-2-(phosphonomethoxy)propyl]adenine (HPMPA) and include for comparison the nucleobase-free (phosphonomethoxy)ethane (PME) and (R)-hydroxy-2-(phosphonomethoxy)propane (HPMP). The acidity constants of H-3(ANP)(+) and H-2(NP) (NP2-=nucleoside phosph(on)ate derivative) are needed to understand the properties of the ternary neutral Cu(Arm)(ANP/NP) [Arm=2,2-bipyridine (Bpy) or 1,10-phenanthroline (Phen)] and the monoprotonated Cu(Arm)(H,ANP)(+) complexes. The Cu(Arm)(ANP) species are considerably more stable than the corresponding Cu(Arm)(R-PO3), where R-PO32- represents a phosph(on)ate ligand with a non-coordinating group R. The observed stability enhancements are due to intramolecular stack formation (st) between the aromatic rings of Arm and the nucleobase residues and also to the formation of five-membered chelates involving the ether oxygen of the -CH(R)-O-CH2-PO32- residue (cl/O) (R=H or CH2-OH). In intramolecular equilibria, three structurally different Cu(Arm)(ANP) isomers occur, for example, of Cu(Phen)(HPMPA) about 5% exist as an open (op) Cu(Phen)(HPMPA)(op) isomer, 17% as Cu(Phen)(HPMPA)(cl/O), and 78% as Cu(Phen)(HPMPA)(st). In Cu(Arm)(ANP) the stacking tendency decreases in the order PMEA(2-)>HPMPA(2-)>PMEC2->HPMPC2-. In monoprotonated Cu(Arm)(H,ANP)(+) both H+ and Cu(Arm)(2+) are at PO32- undergoing similar intramolecular equilibria as indicated above.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10401 - Organic chemistry

Project

—

Continuities

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Publication year

2018

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Journal of Coordination Chemistry

ISSN

0095-8972

e-ISSN

—

Volume of the periodical

71

Issue of the periodical within the volume

11/13

Country of publishing house

GB - UNITED KINGDOM

Number of pages

25

Pages from-to

1910-1934

UT code for WoS article

000448334400023

EID of the result in the Scopus database

2-s2.0-85055117394