Silver(I)-mediated base pairing in parallel-stranded DNA involving the luminescent cytosine analog 1,3-diaza-2-oxophenoxazine
Schönrath I., Tsvetkov V. B., Zatsepin T. S., Aralov A. V., Müller J.
Journal of Biological Inorganic Chemistry
Vol.24, Issue5, P. 693-702
Опубликовано: 2019
Тип ресурса: Статья
DOI:10.1007/s00775-019-01682-1
Аннотация:
Abstract: 1,3-Diaza-2-oxophenoxazine (X) has been introduced as a ligand in silver(I)-mediated base pairing in a parallel DNA duplex. This fluorescent cytosine analog is capable of forming stabilizing X–Ag(I)–X and X–Ag(I)–C base pairs in DNA duplexes, as confirmed by temperature-dependent UV spectroscopy and luminescence spectroscopy. DFT calculations of the silver(I)-mediated base pairs suggest the presence of a synergistic hydrogen bond. Molecular dynamics (MD) simulations of entire DNA duplexes nicely underline the geometrical flexibility of these base pairs, with the synergistic hydrogen bond facing either the major or the minor groove. Upon silver(I) binding to the X:X or X:C base pairs, the luminescence emission maximum experiences a red shift from 448 to 460 nm upon excitation at 370 nm. Importantly, the luminescence of the 1,3-diaza-2-oxophenoxazine ligand is not quenched significantly upon binding a silver(I) ion. In fact, the luminescence intensity even increases upon format
Ключевые слова:
DNA; Metal-mediated base pair; Phenoxazine; Silver
1,3 diaza 2 oxophenoxazine; cytarabine derivative; DNA; silver; unclassified drug; 1,3-diaza-2-oxophenoxazine; DNA; oxazine derivative; phenoxazinone; silver; Article; base pairing; binding affinity; controlled study; DNA structure; hydrogen bond; ligand binding; luminescence; priority journal; process development; structure activity relation; ultraviolet spectroscopy; chemistry; temperature; DNA; Luminescent Measurements; Oxazines; Silver; Temperature
Язык текста: Английский
ISSN: 1432-1327
Schönrath I.
Tsvetkov V. B. Vladimir Borisovich 1964-
Zatsepin T. S.
Aralov A. V.
Müller J.
Счöнратх И.
Цветков В. Б. Владимир Борисович 1964-
Зацепин Т. С.
Аралов А. В.
Мüллер Й.
Silver(I)-mediated base pairing in parallel-stranded DNA involving the luminescent cytosine analog 1,3-diaza-2-oxophenoxazine
Текст визуальный непосредственный
Journal of Biological Inorganic Chemistry
Springer-Verlag GmbH
Vol.24, Issue5 P. 693-702
2019
Статья
DNA Metal-mediated base pair Phenoxazine Silver
1,3 diaza 2 oxophenoxazine cytarabine derivative DNA silver unclassified drug 1,3-diaza-2-oxophenoxazine DNA oxazine derivative phenoxazinone silver Article base pairing binding affinity controlled study DNA structure hydrogen bond ligand binding luminescence priority journal process development structure activity relation ultraviolet spectroscopy chemistry temperature DNA Luminescent Measurements Oxazines Silver Temperature
Abstract: 1,3-Diaza-2-oxophenoxazine (X) has been introduced as a ligand in silver(I)-mediated base pairing in a parallel DNA duplex. This fluorescent cytosine analog is capable of forming stabilizing X–Ag(I)–X and X–Ag(I)–C base pairs in DNA duplexes, as confirmed by temperature-dependent UV spectroscopy and luminescence spectroscopy. DFT calculations of the silver(I)-mediated base pairs suggest the presence of a synergistic hydrogen bond. Molecular dynamics (MD) simulations of entire DNA duplexes nicely underline the geometrical flexibility of these base pairs, with the synergistic hydrogen bond facing either the major or the minor groove. Upon silver(I) binding to the X:X or X:C base pairs, the luminescence emission maximum experiences a red shift from 448 to 460 nm upon excitation at 370 nm. Importantly, the luminescence of the 1,3-diaza-2-oxophenoxazine ligand is not quenched significantly upon binding a silver(I) ion. In fact, the luminescence intensity even increases upon format