Silver(I)‐Mediated Base Pairs in DNA Sequences Containing 7‐Deazaguanine/Cytosine: towards DNA with Entirely Metallated Watson–Crick Base Pairs

DNA sequences comprising noncanonical 7‐deazaguanine (7CG) and canonical cytosine (C) are capable of forming Watson–Crick base pairs via hydrogen bonds as well as silver(I)‐mediated base pairs by coordination to central silver(I) ions. Duplexes I and II containing 7CG and C have been synthesized and...

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Published in:Chemistry : a European journal 2018-03, Vol.24 (18), p.4583-4589
Main Authors: Méndez‐Arriaga, José M., Maldonado, Carmen R., Dobado, José A., Galindo, Miguel A.
Format: Article
Language:English
Subjects:
7-deazaguanine
Base pairs
Bats
Chemical bonds
Chemical synthesis
Chemistry
Circular dichroism
Complementarity
Conformation
Cytosine
Deoxyribonucleic acid
Dichroism
DNA
Gene sequencing
Hydrogen bonding
Hydrogen bonds
Ions
metal-mediated base pairs
Nucleotide sequence
Silver
Spectroscopy
Temperature dependence
Thymine
Watson–Crick base pairing
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Summary:DNA sequences comprising noncanonical 7‐deazaguanine (7CG) and canonical cytosine (C) are capable of forming Watson–Crick base pairs via hydrogen bonds as well as silver(I)‐mediated base pairs by coordination to central silver(I) ions. Duplexes I and II containing 7CG and C have been synthesized and characterized. The incorporation of silver(I) ions into these duplexes has been studied by means of temperature‐dependent UV spectroscopy, circular dichroism, and DFT calculations. The results suggest the formation of DNA molecules comprising contiguous metallated 7CG‐AgI‐C Watson–Crick base pairs that preserve the original B‐type conformation. Furthermore, additional studies performed on duplex III indicated that, in the presence of AgI ions, 7CG–C and 7CA–T Watson–Crick base pairs (7CA, 7‐deazadenine; T, thymine) can be converted to metallated 7CG‐AgI‐C and 7CA‐AgI‐T base pairs inside the same DNA molecule whilst maintaining its initial double helix conformation. These findings are very important for the development of customized silver–DNA nanostructures based on a Watson–Crick complementarity pattern. Full metal packet: 7‐Deazaguanine and canonical cytosine are capable of forming Watson–Crick base pairs via hydrogen bonds and silver(I)‐mediated base pairs by coordination to a central silver(I) ion. This finding, establishes a methodology for the preparation of metallo‐DNA systems based on the metallization of the whole Watson–Crick base‐paring pattern (see figure).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201705131